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Girlstuff
celandine
Registered User regular
Registered User regular
I am a girl. I am not a very girly girl. I don't really have clothes and makeup and hair figured out, and I have shitty posture and no 'grace.' Also, if any of y'all remember me, I am all about the math and the nerdiness and the gym and so on.
But. I recently co-founded a tech company. So now when my friends tell me I should dress better, get a makeover, stand up straighter, etc, I'm starting to think, "Hey, shit, if I want to succeed at this thing that means EVERYTHING to me, maybe I really do have to make a better impression on people."
Except that being feminine kind of freaks me out. I am, in some ways, a very independent person, and a part of me emphatically does not want to be anybody's bitch. And on some (probably irrational) level I feel like if I dress up and people perceive me as pretty I will not be treated as a legitimate human being any more. I don't like the prospect of "selling myself" with beauty. It's probably an issue about my mom (who is very pretty and graceful, and has spent most of her life doing things for other people and being walked all over.)
So. What kind of advice am I looking for?
General appearance advice; where do you shop if you are not super-rich but want to look decent; etc.
Also: is anybody else a not-girly girl? Did anybody become more comfortable with girly stuff over time? Is there a way to make a good first impression on people I meet professionally without making me feel trapped in the kind of gender role that really bothers me?
But. I recently co-founded a tech company. So now when my friends tell me I should dress better, get a makeover, stand up straighter, etc, I'm starting to think, "Hey, shit, if I want to succeed at this thing that means EVERYTHING to me, maybe I really do have to make a better impression on people."
Except that being feminine kind of freaks me out. I am, in some ways, a very independent person, and a part of me emphatically does not want to be anybody's bitch. And on some (probably irrational) level I feel like if I dress up and people perceive me as pretty I will not be treated as a legitimate human being any more. I don't like the prospect of "selling myself" with beauty. It's probably an issue about my mom (who is very pretty and graceful, and has spent most of her life doing things for other people and being walked all over.)
So. What kind of advice am I looking for?
General appearance advice; where do you shop if you are not super-rich but want to look decent; etc.
Also: is anybody else a not-girly girl? Did anybody become more comfortable with girly stuff over time? Is there a way to make a good first impression on people I meet professionally without making me feel trapped in the kind of gender role that really bothers me?
I write about math here:
http://numberblog.wordpress.com/
http://numberblog.wordpress.com/
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If your build allows, you may want to actually look at mens shops for suits and shirts. I get a bit frustrated with the womens suits in that they veryveryvery rarely have pockets with the pants or suit jackets, just faux pockets. Mens clothes do tend to cost a bit more though.
I already look *normal* and have plenty of dressy office-type clothes that are appropriate for more formal environments. (And I am polite to people in general.) My issue isn't so much appropriateness as the level above that -- looking Really Awesome, as opposed to just presentable. My (female) friends keep telling me I should make an effort to look Drop-Dead Gorgeous, and I don't want to.
http://numberblog.wordpress.com/
As far as general appearance advice goes: I try to hit the big department stores (Nordstroms, Macy's, etc.) during sales for nice dress shirts and slacks, though I did splurge on a nice suit jacket from Ann Taylor for dressier occasions.
Ages ago, and after some prodding from a relative, I had some sort of "makeup consultation" done at a department store where I basically sat in a chair for half an hour while someone from the cosmetics department dolled me up and gave me pointers on what kind of makeup looked good on me. The well-meaning relative bought me a bunch of stuff that I ended up hardly using, and the whole thing felt like a series of sales pitches (though I did get some good advice out of it). If you have friends that can give you that kind of advice for free then I'd definitely consider asking for their assistance.
Edit: Since you mentioned it, I would try to improve your posture, if only to save yourself from future pain (I say this as someone who also struggles with maintaining good posture and is already starting to pay for it). I don't know what your work environment is like, but it might be worth looking into ergonomics to see if you can implement any of those suggestions.
Well, I might be reading this wrong but being feminine doesn't mean you're automatically someone's bitch. I mean, if that's what you think, then you should let that one go. Be independent, go to the gym and enjoy math and nerdiness. Maybe that is what femininity is to you. Society's opinion of what is and isn't feminine doesn't always match up with individual's takes on femininity.
I'm just me. I enjoy things that some view as girly and some view as masculine but I don't stop and think about it in that way. I just do it.
Just look clean and friendly when you meet new people. Posture can help and you should definitely work on it. As for dressing better, you can shop anywhere really. It's most about what is attractive to you and what fits your body. Some things can be found at thrift stores or wal-mart or Neiman Marcus. If you feel good in it and look good in it while not breaking the bank, then get it.
Mim's got it down, there's no one definition of "femininity" and if you feel confident with the way you look then don't change just because other people are telling you to. If you look at yourself in the mirror and think "Yeah I'm pretty great and I look like myself today!" then you're doing awesome. There are TONS of people who struggle every day to feel comfortable with themselves, especially when they have these ridiculous and unrealistic standards to live up to
But if you like the way you look but there's a little voice in your head that wishes you could be "prettier" (I put this in quotes because I'm sure you're already pretty) or "more feminine" then for sure there's stuff you can do.
If you want to wear make-up, I would start slow. Go to nordstrom or sephora and ask for some help, let them know what you just want a little bit of makeup, maybe foundation and mascara. There's no need to cake anything on, a lot of girls look amazing with just a small amount that accentuates their features. Have who ever's working there put it on you but make sure they're showing you how to do and not just applying in silence. In my experience, the people who work there are so nice and extremely helpful so don't be shy to. Don't buy something dirt cheap but there's no need to spend $50 either.
It sounds like you already have a handle on great clothes, but for sure work on your posture. It always bugs me when I meet someone who's slouching! Its distracting.
I can empathize with the idea that being beautiful is synonymous with selling yourself. Its so, so, so easy to get sucked into the beauty and fashion industry and totally lose yourself, and look at beautiful girls in magazines and feel like shit about yourself. I've been there, its not a fun place to be. But the important thing is that is doesn't have to be like that. The key is so have confidence in yourself and feel great about you even when you're wearing sweats and haven't put on any make-up and haven't put a lick of effort on your hair. I think that's when putting time into your appearance actually makes a difference
Are your female friends drop-dead gorgeous and/or put in a lot of effort? You could always go shopping with them and get their opinions! (in fact, I'd recommend it)
If you'd like to dabble in how to apply foundation or eyeshadow or get new shoes or whatever (idk, at 27, having just gotten married, I still don't know how to do my own makeup), by all means, ask your girlier friends to show you; it wouldn't make you some kind of spineless sellout. On the other hand, if you're clean, dressed professionally, and feel that you're presenting a good image to yourself and whoever you're working with, don't let your friends bug you about it not being Good Enough. I am decidedly ungirly, but by wearing some nice, simple earrings and a bit of lip gloss to go with my office clothes, I fit in just fine at nice social events, when I was working for a law firm, etc. I don't feel the need to spend 20 minutes in the bathroom every day making myself look like something out of a magazine.
Friends and advice givers tend to try to be as nice and helpful as they can, but most times people say something, its for a serious reason. For example: People well tell you not to slouch because it'll give you back problems, well that's true, but even more true is the fact that people with bad posture look like unappealing slobs and people expect decision makers to carry themselves well.
Is it nice, no... is it fair to people who may have back problems that developed, no. Does it suck for people with no knowledge of fashion, of course. In the end though the benefits tend to be worth it, and anybody wanting to go with the "People should accept me for who I am" line, I have heard the same thing time and time again by perpetually unemployed 30 year-olds who spend all their time playing games and live with their parents.
I work at a company with a female CEO and the vast majority of upper management is female, and all of them dress well,care about how they look, and carry themselves with confidence and purpose. None of them are anyone's bitch.
From the sounds of your post, you are on a successful road and can do a lot in life, so don't let some kind of stubbornness that demands you never be found attractive get in your way.
About fifty percent of looking done up is the fancy hair. The problem is that it really does take an obnoxiously long time to get ready in the morning if you spend forty-five minutes getting fancy hair every day, but if you can figure out some multi-tasking and efficiency time-savers it's worth it.
As for some of the girly girl things, perspective is key.
Like the posture thing. Yeah, posture can be a way for flirty girls to show themselves off. But it's also the way we communicate confidence and authority, no matter our gender. Try looking for women in the public sphere that project themselves with a presence and confidence you admire, and emulate their posture. It isn't about being girly in a way that isn't you, it's about telegraphing your good traits.
--LeVar Burton
Same deal with shoes. A good pair of shoes will do wonders for your overall look and you will walk with much more confidence. Heel height is a matter of personal comfort. Some women can't or won't wear heels and that is perfectly okay. I personally like being taller and I like the way a higher heel makes me strut. The authoritative clack it makes on hard floors is nice too. But I am also very picky about my heels, I will not wear anything that makes me feel vulnerable or hurts my feet. I don't like kitten heels and I am very careful with spikes, and I don't like wedges because I feel like I am wearing hooves. But a solid, well-made heel with just the right amount of arch to the sole, that's magic. Heel or no heel, get a quality pair of shoes you love. If they are made of decent materials you can take 'em to the cobbler when they start to show wear.
As far as makeup goes, it doesn't take much. All those makeover shows, that is makeup for TV. You gotta cake it on to show up well on camera. In real life, all you usually need is decent spot concealer and a wee bit of eyeliner. Depending on your complexion and coloring, you may want a mascara and some lipcolor too. The younger you are, the less you need. Go consult with the lady at the mall if you like, it's one of those things that's kinda good to do once for fun. Just remember that her job is to sell you lots and lots of makeup. She may have good color advice and she may teach you a thing or two about application, but you do not need and will never use 90% of the products she recommends.
In the end, true confidence transcends gender roles. Do you have a good handshake? Can you look a new acquaintance in the eye? Can you be polite and cordial even in a situation that is new or awkward for you and/or the other person? These are not things that are gendered. These are things that other humans will be attracted to.
I was very not-girly for a very long time. As in, cargo shorts and flannels not-girly. It took me many years to embrace the more stereotypically feminine side of myself, and I'm very glad I did. Now I am equally as comfortable in Ferragamos and a skirt as I am in Doc martens with paint under my nails. I feel like my options are limitless and I can make whatever first impression I want. I control how I look and I control how it makes me feel. I am most definitely nobody's bitch.
I am not a girly-girl, but I have found a balance between strength and being feminine. For my charity organizations there is a formal dress code, but even then I have found dresses that are formal and beautiful, but that I feel still represent the strength of my character. I don't think I could pull off frills or ruffles or flowers - not that they aren't beautiful on others, just not right on me. So find what YOU think you look good in, and are comfortable in, and so long as it fits the dress code you need, you're fine.
As for makeup - if you can live without it, why bother? I rarely wear makeup, usually just special occasions, and even then it's a bit of foundation/powder, some eyeshadow, and lipstick or gloss. I'm lucky to have dark eyelashes so don't need mascara, and anything more than that feels like there is too much "gunk" on my face. I discovered a very lightweight foundation by CoverGirl, it's like a light whipped creme foundation that evens out your complexion without feeling like you've got layers on your face.
But the posture thing I'm in agreement with, although that is the hardest part of it all. Improving your posture isn't just an aesthetic thing, it's a life thing - you'll be better off in the long run if you can improve your posture now! Yoga or back exercises and generally being conscious about it helps - I also recommend back massage if you have the opportunity/budget for it, as it will help loosen the built up tissue in your shoulders from slouching.
If yoga isn't your thing (it sure isn't mine), you might think about taking a modern dance class for help with the posture. Modern dance isn't super-gendered like social/classical dance can be, but a good teacher will put a lot of emphasis on stance basics like keeping your shoulders back and tucking your tailbone under. It's definitely something you'll have to practice, but something about that stance gives a shot of automatic confidence that feels good.
Like a lot of other posters have said, confidence is key, not adherence to whoever's random gender norms. Be yourself... your best yourself, and practice business stuff like a good firm handshake, public speaking, and active listening. Take a look at the wide variety of women who are leaders in the tech industry and you'll see just about every kind of dress preference, from the super-glam to the very unisex. Rock whatever you prefer and concentrate on kicking ass and taking names. That's what people will remember.
I work in the consulting industry. As someone who has first-hand experience with moneyed investors and "c-suite" executives, I can tell you up front that looks count for a lot. Unless you are older and have a significant amount of proven experience with a long list of credentials after your name, there's basically no excuse to be under 40 and not look good. At the start-up level, you need to impress people, and being attractive is a big part of that, because you're being asked to make a good impression in a very short amount of time. This is true whether you're selling used cars or a multi-million dollar engagement. Excluding the necessary legal and procurement hoops everyone has to jump through, buying/investing decisions are made within a very small circle (if not a single person), who place a great deal of emphasis on personal relationships. If they have to work with you or build a business with you, they want to be certain that they can get along with you and, most importantly, that they can trust you. Looking like they expect and presenting yourself confidently is a large part of that.
Don't get me wrong, when I say "looking good" and "attractive", I don't mean that you have to be a model (although I would be lying if I didn't say that base aesthetics don't play a part). What I do mean is that you have to fit a certain mold - professional, confident, and comfortable. You can be confident and comfortable wearing t-shirts or turtleneck sweaters, but short of Silicon Valley it's hard to get away with that kind of look unless you want to send the message to everyone else that you don't care (i.e., "I know everyone took an extra hour to get ready but I just threw on this t-shirt and expect you to take me seriously lol."). Remember, people will judge how you look as a proxy for everything they're looking for (not just the physical, but the psychological).
It sounds shallow and vapid, but it's very, very true. Don't dismiss the "optics" of how you come across, because it will be a big part of how successful you are. Just think of it as another aspect of your job. You are expected to actually know what you're talking about, right? The business model, your overall timeline, projected obstacles and how you will overcome them, etc. etc. etc. Well, no one cares how great your business is unless you can convince them that it's great. If putting on make-up and speaking with conviction helps, why not do it? You wouldn't show up smelling like you haven't taken a shower in two weeks and with old, raggedy clothes, right? This is just another point along that spectrum.
Business is selling. Selling is convincing. Convincing is presentation. Presentation is perception.
You aren't making yourself anyone's bitch. You're performing very simple, easy adjustments in order to get them to do what you want. No one is asking you to change who you are - they're asking you to change how you present yourself in specific circumstances. You may find that it will help you in other aspects of your life, as well... Take it from a short, paunchy Asian guy with one ear. How you do something is just as important as what you're doing. And you don't have to be perfect to get the job done well.
Also having nice hair doesn't have to take 45 minutes or some ridiculous amount of time. Go to a nice, professional salon and ask how to get a great look with lower effort. Its possible
No wait, how people perceive you is 90% down to how you carry yourself, and how you behave. Work on your posture, be self-assured and confident (don't act cocky though, obviously), and try to remain relaxed and composed even if shit gets real running your company. You don't have to be a girly girl to gain respect as a woman. Looking pretty (and feeling pretty) is nice and all, but at the end of the day ought not to matter to the people you will be doing business with.
As SwashbucklerXX said, "concentrate on kicking ass and taking names. That's what people will remember." You want people to go to your company because you get shit done, and done right, and are pleasant and efficient to deal with.
You probably do want to take some time to examine your thoughts on looking pretty, gender roles and subservience - but it has nothing to do with how you want to dress. Do you look down on other women when they are dressed in a feminine manner?
Really late edit: Also, talk to your friends some more. By saying you should look "gorgeous", do they have some issues around gender roles and want you to look feminine? Or, is that their polite way of saying, yes, you have a suit and professional clothes, but the color or the cut isn't quite right and you could look a lot better with a few changes.
Interesting Article: http://www.nytimes.com/2011/10/13/fashion/makeup-makes-women-appear-more-competent-study.html?_r=1&WT.mc_id=ST-D-I-NYT-MOD-MOD-M225-ROS-1111-HDR&WT.mc_ev=click
It's not the case, in a business setting, dressing up can show attention to detail. Think about it if you were hiring someone, if there were two equally qualified candidates would you hire the one dressed great or the one dressed average?
Secondly, no one ever should feel bad about wanting to look nice. I mean I came from traditional black shirt teenage nerd to someone who ended up with a tailor. The main issue I overcame was that if I didn't make an effort, it didn't matter that people that people thought I looked dumb because I didn't try.
I realize to an extent that these are conflicting statements, but it's because it's a balancing act. It's ok to look nice, but looking nice doesn't have to define you.
Satans..... hints.....
Satans..... hints.....
I'm in the unpopular boat that the left picture looks the most attractive. I hate makeup. Always have.
I am not a girly-girl, nor do I wear make-up a lot. I will wear some for work, but that is because I'm going for an elegant and clean look ("polished", as someone else put it), and for this particular look I think it has to do with the fact that the people I admired growing-up had a striking, simple elegance to complement their personality (and they were usually much older!). Make-up isn't something you have to do too much of, but if you're going for "professional" you should look clean and not try to distract.
I think of make-up as an art; it's an opportunity to assert your creativity and your skill in the visual arts. You can use it to highlight one or some of your favorite features. For example, if you have striking eyes, use a bit of mascara or eye liner/shadow to frame them, but don't overdo it; and if you have great cheek bones, use a bit of blush (have someone at the mall help you pick the right color). You need to find what works for you and highlight your best features. Make-up is a custom thing; don't think you need to use too much of it, even. You don't want to distract people too much from your personality. :-)
I don't know what kind of tech company you started, but in the tech industry (as a whole) there is a bonus: you can look gorgeous in your own way, without looking "normal." I've known girls who were very high up in tech firms who were all about soft sweaters and wholesomeness, and others who were all about red lipstick and jet black hair and exquisitely tailored clothing with goth touches.
One way to make looking gorgeous and very put together feel special is to find a style you actually love, something that it makes you feel good to wear, and wear that (or a variation on that). One of my favorite girls in small publishing is Kaja Foglio, who manages to look gorgeous while wearing sort of vaguely-but-not-explicitly-steampunk things all the time (Yes, there are also pics of her wearing things that are explicitly steampunk, but her fancier day-to-day outfits are what I'm talking about here.)
Xeni Jardin is also a good example. I'm mostly naming people in publishing and media because that's what pops into my mind, but I've seen people with similar aesthetics all over the game-related regions of the tech industry, and even outside of those particular disciplines.
I'd say that if there's a celebrity whose makeup or style you admire, or a style of clothing you're particularly fond of, base a look off of that. If you need help with makeup there are a lot of good video tutorials on the net (I'm at the same place you are, makeup-wise... fortunately I'm not leading a company, I'm just a workaday dev.) You can also just walk up to any makeup counter and says "I want you to teach me makeup. I have all this money." and they will be glad to help you get set up with something you like.
I'm a huge tomboy in many ways (as a kid I caught frogs and went caving long after most girls had quit those classes at the local nature center), but I've always had a bit of a soft spot for dresses (many of my dresses when I was a kid had to be retired on account of grass stains or huge tears.) I was raised in a very (perhaps overly) progressive house, and so I didn't realize that wearing a dress or being a girl meant there was anything I couldn't do, until much much later. Without the stigma, a dress just becomes something you wear sometimes. Makeup is war paint. Shoes are... pretty. Like polished granite or a garter snake.
I'm not a girly girl now, but I sort of wish I could be. I've got bad feet so I can only wear flats, and I'm farsighted so I suck at applying makeup (Especially eye makeup. try doing that when you can't see. It isn't fun!). Every once in a while I try, but I just can't manage it, so I envy you your canvas of possibilities.
Think of your "presentation look" as a transformation, or an illusion, or a disguise (I'm not sure you're that kind of nerd, but stay with me.) It's a special ability that you are deploying to get people to serve your ends. Think of it like an art project, or a costume... a form of personal expression that also makes people look at you in a new light.
Depending on what kind of style you're looking for, I can recommend places to shop. Mostly, you can just go to any major mall and walk around. If you like something on display, go in and try it on. If you have a more specific fashion aesthetic you're looking for, you may have to specialize a bit more, and go catalogue shopping, shop online, or go to the big city to find a specialty shop.
Triwizard Drinking Tournament - '09 !Hufflepuff unofficial conscript, '10 !Gryffindor
Nerd blog at culturalgeekgirl.com
I agree with everything here. I hate to say it, but first impressions do count. Though if you dress well in a professional yet flattering manner, I'm not sure what else your friends could be hinting you do. Improving your posture can only be a good thing, so I agree with them there, it can make you look as if you're stood to attention and that you're proud of who you are.
I'd say though that if you don't want to wear make-up and don't need it, then don't do it just because you feel you have to. I wear a fair bit myself, I so look better with it and I feel more like myself with it. But thats not for everyone, and I get the impression thats not what you want, that you just feel a bit peer-pressured. If you want, start of small with a bit of mascara and foundation, ask the ladies at the cosmetics counters. If you're the lucky type that only needs a bit of make-up to emphasise their features then I'd just experiment bit by bit.
If you'd rather go dramatic, I have friends who have had good luck at MAC.
Triwizard Drinking Tournament - '09 !Hufflepuff unofficial conscript, '10 !Gryffindor
Nerd blog at culturalgeekgirl.com
(Example: A surgeon approved a website that the very beautiful marketing director had presented to him. 6 months later the marketing director went on leave. When the surgeon found out that I was in charge, he told the directors that he hated the website and hated working with me, even though I had never had any contact at all with him).
I really just shop for cosmetics and clothes at Target. They seem to have a good selection in make up and all that jazz. Clothing can get to a nice level of business casual.
In regards to gender roles, we as women are just stuck for the time being. There was a study published recently (I'm sure you could find it in a google search) that documented how appearance mattered a great deal when it came to income and success. The only thing that could trump that would be intelligence (this applied to both men and women).
Use gender roles to your advantage. As time goes on I'm learning the game. Not everyone who flirts and plays up their image are incompetent. I recently closed a deal with an law office by pretending like I was going to take a personal lunch with one of the attorneys. That didn't mean that I didn't sell my ideas to the guys, but it meant that we were one step closer to getting what we wanted simply because I dressed up that day and flirted.
I like to think of it as a tool, or a role I play as an actor. That way I can return to my normal self and feel comfortable.
I have a sudden windfall of disposable income, so I may as well go shopping.
My main clothing problem is fit -- most things I own are too baggy. Either because they're the wrong size, or they're not cut close to the body in the first place. I used to have a problem with being too exposed, and when I started grad school I didn't want to look like a ho, so I just erred in the other direction.
I would be tempted to just give up, and stick with my Shlub Life, but at the moment there are people who're depending on me; I can't just Drop Out Of Everything, because I have partners who quit their jobs for this, and it wouldn't be fair to them. And because I'm really lucky to have this opportunity. Right? Right.
But...yeah. We'll see how it goes. I may have another full-day catatonic freakout when I see myself in new clothes/hair/makeup. It's depressing as fuck. I don't actually look nice. I do not have one photo of myself that isn't ugly. I suppose I could try losing weight, but the thing is I'm not actually overweight, I'm a (US) size 4-6, I just have a face shaped like a potato. Dressing up will not make me less potato-like. Also, I don't have to worry about making people like me if I don't even try to make them like me, you know? Just be the growly hermit type. Except, for aforementioned reasons, it isn't fair for me to be giving anything less than my best...
I guess it's the same old Nerd Comfort Zone. I don't have to lose if I don't play the game. I really don't want to play the fucking game. I lost it at fourteen. It's not like I'm going to win now.
http://numberblog.wordpress.com/
Regardless of sex, appearance matters. Especially when you are trying to develop client relationships and things. The only real exception to this rule is if you know somebody or have very good networking already established. This isn't to say that you need to significantly alter the way you look to the point where it makes you feel uncomfortable (as this feeling can subconsciously manifest itself in your posture and demeanor). But yea, there's a balance.
And pretending like you're going to take a personal lunch with somebody (particularly potential clients) is an easy way to run into problems via conflict of interest...
If you don't like the clothes your friends pick out for you, go to a big department store like Nordstroms or Macys or Lord and Taylors and ask a sales-person for help. See what types of clothes they pick out for you. Try anything on even if it looks ugly on the hanger or is a different size than you normally wear.
You already look presentable and feel some resistance to your friends' suggestions, yet you posted here. If you're anything like me, it sounds like you're at a point where either a) you are seeking support from others on why not to change or b) you might be vaguely curious about changing certain aspects about yourself but are hesitant for several reasons.
I hope you know that changing your appearance will not change who you are, but feeling prettier is all coming from inside you to a great extent. If you buy a pair of pumps and they make you feel sexy and powerful, sweet. If those pumps make you all wobbly and unfocused, don't bother. Some things, in my experience, are out of your control, but just a few: don't go blonde if you can avoid it because people will treat you like an idiot and don't show cleavage because people will treat you like a stripper with a heart of gold and a head full of rocks.
You just started a company and you obviously know your shit, so I am guessing you present yourself confidently in your current attire. Posture, as everyone has said, can greatly improve the appearance of confidence, but good luck with changing that especially if you're particularly buxom. I've been trying to fix mine for years, but I have terrible back problems and no pointers here, sorry.
Maybe if you want to test the bounds of your comfort, go out shopping (to Kohl's if you have one nearby; they're cheap and the returns are relatively easy). Get some jewelry, nice skirts, whatever your ladygals tell you to get. Since they're urging you, I'm sure they'll be ecstatic to help. Try stuff on in the store, purchase some things if you feel okay with them in the store. If you get them home and never feel the urge to wear them out, return them. They won't be doing you any favors if you don't feel excited to wear them - you'll be uncomfortable and always fidgeting with something, which does not communicate confidence to others.
Oh, and clothing tip: No one can see the number on the tag inside your pants, so buy a 10 instead of an 8 if it fits better. People *can* see a muffin top. (Courtesy: Lizbot's harsh life lessons)
Even if it's just to start wearing eyeliner or put your hair in a french twist (plenty of youtube videos on makeup and hair, by the way), maybe you'll see that slowly incorporating girlier items into your appearance makes you feel good, and you'll see how each thing affects your self-esteem and how people deal with you. If nothing seems like you, oh well, you've been perfect all along.
If you want to be "schlubby" as you put it, fancy sweaters may be your answer. They look expensive and pretty, are very comfortable, and can be sexy if they fit. The same is true for super cute jackets over nice shirts of various varieties. It's hard to feel exposed when you have a turtleneck on under a fluffy cable sweater, but the look can be quite attractive if it fits properly. Every single one of my "nice" outfits involves a sweater or jacket.
For advice on where to shop, it depends on how "cheap" you're trying to be. I like Marshall's/Ross/TJMaxx, because they often have higher end clothes at a serious discount - a word of warning, though: since those stores get what's left over, sometimes the stuff in there is horribly unflattering. You have to have a high tolerance for digging through crap to find the deals. Thrift stores in upscale areas can also be a godsend: I once found a $300 coat for $30 in one. If you're really uncertain, though, try going to a mid-range clothing store (like Talbots) and asking if someone can help you find something that fits/suits you. Don't feel obligated to buy anything they show you unless you love it, but they'll be happy to help you out.
If you are a 4-6, you do NOT need to lose weight! If you get clothes that actually fit you, you may soon develop a more positive opinion of your appearance (any time you try on clothes, try one size down, and see if they look better. This is something a friend can really help you with. If you have one female friend who you trust to be honest, patient, and kind, take her shopping with you.
You may also find that a good haircut (Spend $40-100) makes your face shape look better. Makeup may help as well. You can't "shop around" as well with a haircut, but if you find someone who is highly recommended and ask them to pick something out they think will suit, you will likely be pleased by the results. If you can afford to eventually spend $80-100 or so on makeup, you can go to several makeup counters and ask if they do sample makeovers. Explain your circumstances (new professional, looking to start using makeup, looking to make a big initial investment), then let them do you up. Don't let them pressure you to buy the same day if you aren't completely wowed (though I usually buy at least a small item like an eyeshadow or lip gloss because I am weak.)
I'm sometimes shocked at how much different girls I know look without makeup. You may be shocked at how good you look with it on, if it is properly done.
Edit: if it helps, don't think of it as a game. Think of it as an art you have yet to master. Do it for YOURSELF, do it in a way that will result in you enjoying the way you look more than you do now. Consider the fact that it will make better impressions on others an advantageous side benefit.
It's like your house. Sometimes you buy some towels that look nice, maybe? Or hang up a picture? You do that because it makes you smile when you see it, because having pretty or meaningful things around you makes you happy. Clothes and makeup can do the same thing. My tail coat and pocketwatch make me as happy as my Twisp and Catsby cell.
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Go shopping with your friends and buy some new clothes (that fit, someone also mentioned a tailor, this is truth). Have them help you pick out cute outfits, it doesn't have to be girly! Like I said, menswear for women can be amazing! Just get stuff that you feel good in, and let your friends push you a little to try stuff on that you normally wouldn't.
If you aren't already, try exercising a little more. Personally, I feel a lot better about myself when I'm in a routine of working out. I'll look at myself in the mirror and be like "oh yeeeeah. I'm in shape, look how in shape I am -flex- hey that's a muscle there! I'm so fit". If you're like me and think exercising is kind of the devil, then find a buddy to help motivate you!
You said earlier that you look decent, and then you said you look like a slob. If you feel crummy about yourself, new clothes and make-up isn't gonna do much. You could end up feeling even worse! Again, I've been there. Focus on gaining a better self image (like instead of having a "potato face" you have a adorable round face! Or instead of being at a "maybe I could lose some weight size 4-6" you've got a "curvy healthy figure size 4-6").
and you probobly will be, as long as you keep doing crap like this:
Anyway Calendine, as long as you look presentable I see no reason to conform to any fashion you feel uncomfortable in. If you focus on being polite and confident in demeanor, any business associates worth having will focus on that too.
An ex of mine was a bra fitter at Nordstrom. Its amazing how many women wear the wrong bra. Also, go to Nordstrom to get fitted. They are seriously the best, they have training and certification and everything for their boobie touchers. Even Oprah loves them!