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Help me not dress like a hobo...

SentrySentry Registered User regular
edited October 2012 in Help / Advice Forum
Actually, I think hobo's probably dress way better then I do. I need help here.

Backstory: So, I've lost a lot of weight in the last two years, as I've mentioned here before... something to the tune of like, 190 lbs. Back then, I really didn't care how I dressed, or really about much of anything at all, and considering I had to go to a "special store" to buy clothes, it was really just a hodgepodge of crappy tent sized items.

Now: So, I've lost a ton of weight, feeling pretty good about myself, not exactly where I want to be weight/muscle wise but light years ahead of where I was, but I still find I'm dressing like I did back then. Most of my clothes are ironic t-shirts from Threadless or stuff off the bargain rack at Target. Since I'm actually looking to start dating, I'd like to know what I should be getting. I've included some photos from today... I'm actually not dressed terribly today, but this is well outside the norm.

Okay H/A... dress me like I was a slightly more anatomically correct Ken doll... then, next time, I can post a thread asking for relationship advice after I've done something stupid. Help me be that guy!

http://imgur.com/a/akbQm

please forgive the image quality... taking pictures of yourself is harder then I would have thought...

[SIGPIC][/SIGPIC]
wrote:
When I was a little kid, I always pretended I was the hero,' Skip said.
'Fuck yeah, me too. What little kid ever pretended to be part of the lynch-mob?'
Sentry on

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    PantshandshakePantshandshake Registered User regular
    I had more to say, but then I realized that I'm wearing a t-shirt from Threadless right now... so maybe I skip all that.

    How about this: Are you looking for casual? Business? Shorts? Pants? Just as a starting point, I think figuring out an outfit or two to start with is a good idea, rather than letting the internet en masse fill up your closet.

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    bowenbowen How you doin'? Registered User regular
    edited October 2012
    You look in pretty good shape sentry, I assume these are just old clothes you haven't updated in a while (I'm guilty of this).

    http://www.reddit.com/r/malefashionadvice/

    might be of help until someone here that looks really good gets back to you. If you want business, I imagine finding some khakis that are less relaxed fit would do wonders itself.

    bowen on
    not a doctor, not a lawyer, examples I use may not be fully researched so don't take out of context plz, don't @ me
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    SentrySentry Registered User regular
    Thanks Bowen, I will definitely check that site out. I guess I'm just looking for essential items every guy should have. Casual mostly, my job is very business casual so I'm not really needing suits for it or anything, although I would like to start dressing nicer for work. But mostly I'm looking for advice on how to dress casually for going out to bars, or dates, or things of that nature. I find myself buying clothes I think are cool, but then being incredibly self conscious when I wear them out. I have zero concept of color combinations, fit, or anything... like, I have no idea why those khaki's look like clown pants.

    [SIGPIC][/SIGPIC]
    wrote:
    When I was a little kid, I always pretended I was the hero,' Skip said.
    'Fuck yeah, me too. What little kid ever pretended to be part of the lynch-mob?'
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    bowenbowen How you doin'? Registered User regular
    They look like my old husky pants with "relaxed fit." They're comfortable around the butt, but look like I'm smuggling hula-hoops around my waist.

    Should be some semi decent advice there.

    Avoid skinny jeans. Also don't fret too much about the shoes. Focus entirely on shirts/sweaters and pants.

    http://i.imgur.com/P5YkO.jpg

    Don't look like that guy.

    not a doctor, not a lawyer, examples I use may not be fully researched so don't take out of context plz, don't @ me
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    BurtletoyBurtletoy Registered User regular
    Actually, shoes are one of the first things noticed, and are extremely important.

    Those khakis look like they're too big because, they're too big. Avoid relaxed fit and boot-cut on pants.

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    EggyToastEggyToast Jersey CityRegistered User regular
    If you've lost weight and want to look good, go to Express. You don't have to buy from them necessarily, but their nice pants and button up shirts are designed with slimmer, in-shape males in mind. Try on a bunch of shirts and talk to them about sizing.

    You can then go buy things at Macy's or a store that has generally cheaper prices. The reason you to to Express first is that the majority of their "nice" clothes look really sharp and will give you a solid idea of how you COULD look with the right clothes. If you just go to Macy's, you may still shop with the idea of buying for your old body, and they have many more options that are not flattering for a young, slimmer guy.

    Some basic advice: Pleated pants are for bigger men; button-up shirts should be fitted in some way or else they'll look overly baggy on a slimmer body; don't be afraid to ask for advice from the people at the stores; you can look good in a t-shirt and jacket/full-zip sweater, but it's hard to look good in cargo pants and hoodies.

    || Flickr — || PSN: EggyToast
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    bowenbowen How you doin'? Registered User regular
    Burtletoy wrote: »
    Actually, shoes are one of the first things noticed, and are extremely important.

    Those khakis look like they're too big because, they're too big. Avoid relaxed fit and boot-cut on pants.

    In fashion and hipster circles. Not in your day to day. Aside from the CEO taking a dump in the bathroom.

    Last thing I notice is someone's shoes in a personal setting. It should not be his focus for "looking good."

    not a doctor, not a lawyer, examples I use may not be fully researched so don't take out of context plz, don't @ me
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    supabeastsupabeast Registered User regular
    Go to Bloomingdale’s. The nice people there will be happy to dress you up.

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    DjeetDjeet Registered User regular
    What kind of a look are you going for? What kind of budget are you looking at for: a pair of pants, a shirt, a pair of shoes, etc.?

    If you're not comfortable with your casual wear picks, beef up or modernize your dress wear and then just dress it down for social occasions. For example I wear long sleeve button down shirts (tucked), over a a black or grey undershirt, non-denim trousers, and semi-dressy shoes for work. When I leave work I might: roll up the shirt cuff twice and unbutton top few shirt buttons, roll the cuff and untuck shirt and unbutton shirt entirely, change into jeans, change into less dressy shoes. To dress up I might add a blazer or coat of some kind, or change into slacks, or add a tie. Since you're wearing the same clothes as you do all day at work you shouldn't feel too self conscious, or at least it's not the clothes fault unless you feel under/over-dressed (IMO).

    More important than color pairing or styles is picking clothes that fit you right. You need to figure that out on your own or bring a friend, personally I don't trust sales people very much when it comes to clothing selection. When clothes shopping it's OK to try on lots of stuff and not even buy anything, and maybe that's what you need to do to figure out what feels right for fit. When picking shirt colors, look in the mirror, then put on the shirt and look in mirror again. A good color/texture is one that makes your complexion and skin tone look nicer or at least doesn't make you look too sallow, pale, ruddy, or whatever you personally consider to be off-putting.

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    BurtletoyBurtletoy Registered User regular
    bowen wrote: »
    Burtletoy wrote: »
    Actually, shoes are one of the first things noticed, and are extremely important.

    Those khakis look like they're too big because, they're too big. Avoid relaxed fit and boot-cut on pants.

    In fashion and hipster circles. Not in your day to day. Aside from the CEO taking a dump in the bathroom.

    Last thing I notice is someone's shoes in a personal setting. It should not be his focus for "looking good."


    You are incorrect.

    http://www.sciencedirect.com/science/article/pii/S0092656612000608
    Participants provided photographs of their shoes, and during a separate session completed self-report measures. Coders rated the shoes on various dimensions, and these ratings were found to correlate with the owners’ personal characteristics. A new group of participants accurately judged the age, gender, income, and attachment anxiety of shoe owners based solely on the pictures. Shoes can indeed be used to evaluate others, at least in some domains.

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    Gilbert0Gilbert0 North of SeattleRegistered User regular
    Burtletoy wrote: »
    Actually, shoes are one of the first things noticed, and are extremely important.

    Those khakis look like they're too big because, they're too big. Avoid relaxed fit and boot-cut on pants.

    I agree with this. I'm 6'3 and now about 240. I was always tall and buying clothes to make me fit, I always got the looser fitting stuff in sizes that were actually too small for me. When I went up a size, went to a tighter fit, it looked like I lost weight. Cut and style is important and forget the size.

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    AkilaeAkilae Registered User regular
    It doesn't really matter what "look" you're going for, there are a few essentials every guy should go by (Disclaimer: I'm more of a continental dresser. A lot of American style dressers would disagree with what I am about to say):

    1) Shoes. They really are an important part of impression management. A pair of well polished black leather bluchers will go with anything. If you don't wear suits much then go dark brown/cordovan, which IMHO is a more versatile color. If you just want something for date night with jeans, then maybe a pair of Frye pull-on brown harness or engineer boots? Socks should match your shoe color.

    2) Shirts. Buy properly fitted dress shirts. Unless you're one of the rare few that fit the cut of <insert_mass_produced_brand_name_here>, you're better off just figuring out your collar size and sleeve length, and going from there. Want to be a bit more formal? Button down sports shirts. If you still want to go with <insert_mass_produced_brand_name_here>, then at the very least steer clear of so-called "classic fit", and go for "slim cut" or "custom fit", as these tend to be cut closer to the torso and look much better. Something with vertical stripes and darker hue, more slimming.

    3) Doesn't matter what pants you get, just make sure they're of the correct waist/length. Don't guess, get measured. Depends on you where you want your pants to sit at, but for date night low hanging jeans might not be a good idea, and pants that sit at the natural waist might not look too fashionable these days. Somewhere in between. Also up to you what kind of you break you want in your pants. Light khakis are universal (I personally love pleats, but only classic European-style pleats, not American-style reverse pleats. Some people hate them with a passion.). Darker jeans are more formal, lighter jeans are more casual. Don't wear skinny jeans that are tighter than your date's...

    4) Jacket. We're entering fall/winter. A nice sports jacket will go well with everything from T-shirts and jeans to shirts and slacks. That and you can drape it over the lady when she gets cold. Chivalry is not dead! Dark navy is the classic color, but makes me think of conferences and conventions. Ask your salesperson if you're not sure what color/pattern to get.

    5) Iron and board. Helps a lot. Part of the reason you pants look like clown pants is because there's no longer any crease on them (that I can see from the photo).

    6) Bring a lady friend when you go shopping. Mother, sister, cousin, co-worker, doesn't really matter. I find most women just have a good natural intuition for what looks good on a guy.

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    GrisloGrislo Registered User regular
    supabeast wrote: »
    Go to Bloomingdale’s. The nice people there will be happy to dress you up.

    Or any local clothes store that has a somewhat wide selection. There's bound to be someone there who'd be happy to help you, and it's fine to tell them that you're on a budget, if that's the case.

    This post was sponsored by Tom Cruise.
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    DjeetDjeet Registered User regular
    Regarding fitment (of pants in particular) there's a whole sliding scale of vanity sizes. I think an Old Navy set of 36" pants is more like 40-41", so try on sizes above and below your actual size before buying. Get what fits, not which ones have the right number on them that match to your measurements.

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    JasconiusJasconius sword criminal mad onlineRegistered User regular
    avoid loose fitting stuff. you got a body now that you don't need to hide under cotton parachutes (like Target so often stocks)

    I'm a pretty thin dude and a lot of my old clothes is from Target, and that stuff just ends up making you look like a frumpy hobo (which is what I dress like most of the time anyway because I haven't replaced all my wardrobe from my awkward college years)

    I'm not sure what kind of work dress codes you have to abide by, but in my limited fashion experience, high quality casual clothing >>>>>>>>>> low quality (read: target) business casual

    Don't wear chinos if you don't gotta


    My favorite store in the universe is Lucky which you can find in some nicer malls. Aesthetically conservative casual clothing that will pass in most business casual environments... form fitting without being skin tight european nonsense (like, say, Deisel)

    I recommend just finding a nice mall and look EVERYWHERE, and try and find the style you like, and just buy one or two outfits maximum at a time, wear them, decide how you like them, and then repeat


    In terms of shoes: Doc Martens are A+, Clarks are a nice, dressier alternative without being formalwear

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    schussschuss Registered User regular
    1 - Use your iron. Even from that terrible picture I could tell the shirt wasn't terribly well ironed.
    2 - Get some good jeans. Go to Nordstrom or similar, preferably with a fashion-conscious woman. Make sure you look good by THEIR standards, not yours. Don't go too tight, skinny jeans are dumb.
    3 - Shirts - get some nice button downs and form fitting tight knits/sweaters. If you're worried about "pulling it off", get some nice plaids that complement your eyes to break up your profile.
    4 - Shoes - good leather shoes. Get comfy ones, but make sure they're more sleek than they are chunky.

    The other things to understand:
    1. Colors - Find yours. I have some red hair and freckles with grey/blue eyes, therefore I work best with Green, Orange and light blues as my dominant palette
    2. Fit - What are your best features? Mine are my legs and my eyes, so the main lesson was to wear better fitting pants and wear things that bring out the color (my eyes change color based on what I'm wearing).
    3. Confidence - Have it. This is the #1 thing when it comes to rolling around to bars/clubs etc. Remember that you are a bad-ass motherfucker, no matter what anyone else tells you.

    Don't go too trendy with your choices, as you'll want to first build up a more classic set of looks that you can riff on. There's a reason certain things like nice t-shirt and jeans, suits etc. have never gone out of style. Once you get the staples down, start interpreting in ways you enjoy.

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    Centipede DamascusCentipede Damascus Registered User regular
    Personally, I recommend visiting Put This On, the premier men's style blog on the internet.

    Let me quote a couple of important posts:

    Start by simplifying
    Do you want to know how to start looking better? Simplify.

    Stop wearing clothes with logos, prints and crazy details.

    Instead, focus on great basics. When I say basics, I mean basics. White t-shirt. Blue dress shirt. White oxford. Blue jeans. Gray wool pants. Khaki chinos. Blue blazer. Gray suit. Great boots. Basic shoes. Focus on blue, white, gray. Buy good clothes that fit.

    Minimalize.

    It’s OK for your clothes to be a simple frame for what’s important: you.

    The Essential Man's Wardrobe
    25 Things to Know

    They also have a video series you can watch here.

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    SilverEternitySilverEternity Registered User regular
    Jasconius wrote: »
    avoid loose fitting stuff. you got a body now that you don't need to hide under cotton parachutes (like Target so often stocks)

    If you're looking for casual things to wear on dates I would go for a pair of darker jeans that fit you very well (not skinny jeans, but jeans that show the shape of your leg when you move). I don't know if guys do this like girls do, but check out your butt in the jeans. I've noticed a lot of guys buy/wear jeans that give them a saggy butt look; being able to see the contours in a guy when he walks is nice. Personally I think a pair of jeans that fit well can look incredibly good when paired in the right way. Also I agree with what people said above that a slim/athletic fit button down shirt with shoes that fit your personality is a good choice. I do think shoes are noticed and different types of shoes can give off different vibes. I think the type of shoe you wear should be determined by what you're comfortable with, what type of people you are trying to attract and what the location/situation is.

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    EshEsh Tending bar. FFXIV. Motorcycles. Portland, ORRegistered User regular
    edited October 2012
    I really wish you people would get over your irrational skinny jean/hipster wharble garble. If you have the body, they look great. I wear Levi's 511s and I get compliments all the time. They're well worth checking out at the store.

    Esh on
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    schussschuss Registered User regular
    I think skinny jeans are dumb, personally, but I don't have anything against them. They should not be your 1 nice pair of jeans though.

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    EshEsh Tending bar. FFXIV. Motorcycles. Portland, ORRegistered User regular
    schuss wrote: »
    I think skinny jeans are dumb, personally, but I don't have anything against them. They should not be your 1 nice pair of jeans though.

    Why not? Maybe it's just a regional thing? I see people here in Portland, SF, and up in Seattle (and in France when I was there) using them as dress jeans all the time.

    I think maybe your problem is that you're thinking of the skin tight jeans that taper down sharply. My jeans fit, and fit well, but I can breath in them. They're not the "ex-girlfriend" jeans which look more like jeggings.

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    BagginsesBagginses __BANNED USERS regular
    Esh wrote: »
    schuss wrote: »
    I think skinny jeans are dumb, personally, but I don't have anything against them. They should not be your 1 nice pair of jeans though.

    Why not? Maybe it's just a regional thing? I see people here in Portland, SF, and up in Seattle (and in France when I was there) using them as dress jeans all the time.

    I think maybe your problem is that you're thinking of the skin tight jeans that taper down sharply. My jeans fit, and fit well, but I can breath in them. They're not the "ex-girlfriend" jeans which look more like jeggings.

    I think they're thinking of the hipster skinny jeans with the straight legs set as ankle width. They always make lower bodies look like fatty sausages hanging from diapers.

    For pleats, reverse pleats seem to be coming back into style, particularly single pleats, which I haven't seen before this year but are probably the best style for most men (from reading, they disappeared during the excessive pleating era of the eighties and were skipped when people switched to flat fronts).

    I'm not sure what's wrong with chinos, and I've recently become fond of a pair of navy corduroys I received after my parents cleaned their attack. Pretty sure they were my dad's (apparently he was fond of the material in college, even wearing a corduroy suit he got on discount for a while before realizing why it had been on discount).

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    mtsmts Dr. Robot King Registered User regular
    but you are a hipster esh, you have to love skinny jeans

    you just need clothes that fit you, that will solve 99 percent of your issues

    camo_sig.png
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    EshEsh Tending bar. FFXIV. Motorcycles. Portland, ORRegistered User regular
    mts wrote: »
    but you are a hipster esh, you have to love skinny jeans

    This is true...
    :D

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    schussschuss Registered User regular
    Esh wrote: »
    schuss wrote: »
    I think skinny jeans are dumb, personally, but I don't have anything against them. They should not be your 1 nice pair of jeans though.

    Why not? Maybe it's just a regional thing? I see people here in Portland, SF, and up in Seattle (and in France when I was there) using them as dress jeans all the time.

    I think maybe your problem is that you're thinking of the skin tight jeans that taper down sharply. My jeans fit, and fit well, but I can breath in them. They're not the "ex-girlfriend" jeans which look more like jeggings.

    Tight jeans != Skinny Jeans

    Looking at the pants you linked, those are almost between skinny and normal and probably suit your body type well. That said, the fashion hobos of major metro areas aren't necessarily where some random guy should take his cues from for normal wear. You start with the classics, then go towards the directions you suit you. You don't start with wayfarers, skinny jeans, those silly leather boot things and a fashion plaid, because that's not you yet, you're just a person in a costume. Eventually that may be your go-to, but as the first step? Nah.
    You also realize you mentioned the top 4 hipster areas other than NYC, right?

    If it makes you feel any better, I can't physically fit into skinny jeans due to being a skier/bicyclist.

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