10 Style Mistakes I Wish I Learned Long Ago

Learn from our mistakes: Dress your best by ridding your style of these 10 common errors.

Being virile young men, we are somewhat expected to be reckless in our nature. Perhaps we don't think everything through before we do it. Or maybe we do things in excess. But if there's something a well-dressed young man who at least looks put together can do, it's get away with most anything he desires.

There are, however, universal rules. While we individually may not be guilty of these infractions, we collectively as young men have experienced them. This goes beyond wearing socks with sandals, gentlemen.

1. Size Matters

The golden rule. There's too big, too small, and just right. If a man was to wear clothes too big for him, it looks sloppy. And because I assume none of us are looking to be in a Cash Money Records music video, it just doesn't make sense. The same can be said of wearing clothes too small. I hope all of us are finished with scream-o band T-shirts and lip rings, because no woman can take us seriously if we're pulling at everything we have on just so we have enough room to breathe. Plus, it's hard to have a conversation when you're trying not to stare at how tight someone's pants are.

READ MORE: How Your Suit Should Fit, A Visual Guide

2. The Hat as an Accessory

There are times when a hat is necessary: when it's sunny, when it's cold, when you're a NASCAR driver or Indiana Jones, and when you go back in time to the '40s and '50s. Other than that, wearing a hat is mostly useless and, honestly, tasteless. Unless you're hiding a bad haircut or something incriminating, being a young man and wearing a hat immediately screams unnecessary. And by that, I mean the guys who wear flat-billed, backward hats with sunglasses on. This in itself is a paradox. Now, as a Twins fan—well, a Kirby Puckett fan, mostly—I did enjoy my time with my Twins hat. But you don't want to be the guy whose hair flares out where the hat ends even if he isn't wearing the damn thing. It’s not a hard thing to learn: wear a hat when it’s sunny out. With purpose.

3. Brand Name Idolization

Aside from Alan Rickman in the original “Die Hard,” I've never seen anyone able to specifically point out the maker or brand name of a solid garment. Although this is something about fashion mistakes of times long past, the gut-wrenching explosion of both Ed Hardy and Affliction has prompted me to take into account two things: Not a lot of people are MMA fighters. Not a lot of people are tattoo artists, either. But, from what's impossible not to see, a lot of guys want to be. Wearing a shirt with a huge design or brand name logo on it distracts people from what you want them to see—your smiling, beautiful face.

4. Fan Shirts

All right, look. I love The Rock and Stone Cold as much as you do. But there comes a time when a man must draw the line. Those YouTube highlight videos are all that's left. We must move on, sadly. For those shirts featuring still-prominent figures, it's the same as the logo. You don't want to be remembered by someone as, “You know, what's his name? That guy with the Young Jeezy shirt.”

5. Socks, Socks, Socks

It's important to stress this point. Hosiery is an oft-neglected part of a man's wardrobe. It is, however, a medium to express yourself—for better or worse. Although it has been explained in detail—and something you should know already—do not, I repeat, do not wear athletic socks with anything but an athletic get-up. There are certain implications of a man who wears ankle socks or white tube socks with nice shoes. Socks are socks, sure, but, as with most things we wear, there are times and places for everything. And it's not when you're wearing a suit.

6. Wrinkles

It's like putting a bow tie on a trash bin. Wearing a wrinkled shirt—and this doesn't apply to the whole “distressed” thing I never understood—is instantly a cue that you're wearing something only because you have to. Every man should know how to iron a shirt. The point is, if you wear a wrinkled shirt to an interview or a date or something where you are being at least partially judged by the way you look, go the extra mile. Not even. Hell, go the extra inch, and iron your shirt. Even if you don’t think you need to, do it. A shirt always looks more dignified freshly ironed or pressed.

7. Embellished Shirts

It's cool in a sort of hot-rod kind of way. But, unless you're Ricky from “Trailer Park Boys,” those short-sleeved button-up shirts with the flames, dice and skulls on it are just synonymous with being a d-bag. And just to show how, how should I say, “versatile,” those Ed Hardy shirts are, I would put them into this category, too, although they're not technically embellished. So, unless you're looking to go out as a character from a certain shore from a certain state this Halloween, it's best if we all join forces to finally deep-six these obscenities for good.

8. Wearing Suits With Sneakers

I remember long, long ago when a game called “Tony Hawk's Pro Skater” came out, there was an option to wear a slim-fitting suit with sneakers as an outfit. Now, this was a shameful, shameful part of my past, so I thought, “Man, that's really stickin' it to those Wall Street suits.” Luckily, I've since shed that mentality and have actually adopted the nickname Wall Street. Funny how that worked out. Anyway, stick with this adage, gents: Your hair tells people how you want to be perceived, but your shoes show how you actually are.

9. Tank tops

You're ripped. It's hot outside. Too hot for anything with sleeves and not ribbed. However, wearing the ole ‘beater outside, regardless of the weather and how ripped you are, makes everyone uncomfortable. People may think “Did… did he just forget to put a shirt on over that?” And while you may be the talk of the town for your free tickets to the gun show, wearing a tank top while not in the gym or before you put on another shirt should very well be counted as public indecency. Four words, men: Think about the children.

10. Tight, Deep V-Necks

This final part may be somewhat biased. I met someone, a person who couldn't have been more than two years younger than I was, who called me a suit. A suit. Of course, he was wearing girl pants, a beanie when it was at least 65 degrees outside, a lip ring and a V-neck shirt at least two sizes too small. The modern-day hipster has destroyed so much of what we've worked so damn hard to achieve. Hipsters have a funny thing about them. They can take things like the V-neck, which, if worn properly, is always a good basic addition, and wrong them. Burn it with fire and dance on the ashes.

Gin Ando is a news junkie and coffee addict. He currently works in advertising and cannot stop writing. As a post-college twentysomething, he too is navigating the adult world. And he needs friends. Follow him on Twitter @GinAAndo.

  • Andrew

    I really liked the article. Solid advice for sure.

    As a young guy I must admit I have wanted to one day try the suit with sneakers look. Maybe its best if I just leave it to GQ.

    What does “senior” year at Cinci mean? What’s with the quotes?

    I ask becuase I’m a senior (no quotes) at Syracuse.

  • http://mytakeradio.com Rich

    100% Truth

  • http://ExceedandLead.com Fearless

    The deep V needs to die, won’t come soon enough I fear.

  • Peacekeeper

    I agree with everything… bar the wrestling t-shirts! I love to rock a CM-Punk shirt under a blazer.

  • Kory

    I appreciate the Twins refferal (I cannot wait until it warms up again to wear my AE Twins boat shoes.) You missed the boat a little on rule two, that is a cap, not a hat. A hat has a brim all the way around whereas a cap’s brim is only on the “front”.

    • Fred

      I think rule two is discussable. First, there are people who just look good with a head. Maybe it can be a little eccentric, but if it fits their personalities… (You should be a country musican or an artists.)
      Secondly, wear a cap as part of a casual outfit (like a baseball cap) is no big problem. But don’t wear it every day. Don’t make the casual cap outfit your daily fashion statement.

  • http://powerstylist.com/ Aydika

    Great article – and VERY well written! Thanks for pointing out the “not-so-obvious” in a fun, direct way. (Re: Tank Tops = Hilarious. And agreed.)

  • http://www.itsamiracletheyaintdeadyet.com Kenneth

    guilty of wearing my Austin 3:16 shirt in the gym.

  • Gin A. Ando

    A collective thanks to everyone. But for some individual business: Andrew, I put senior in quotes because at UC have asked me if I’m as old as 38 once. Although I don’t necessarily look 38, I think, it made me rethink why I was still in school. Peacekeeper and Kenneth—I’m sure my Triple H T-shirt will surface again some day. I do have a life-size The Rock cardboard cutout I got for a birthday present. And last, but not least, Kory, thank you for the clarification, my friend. I’m not a hat or cap person, so I apologize for my ignorance. All in all, thanks for reading, gents!

  • http://www.primermagazine.com Andrew

    Kory, The definition of a hat is simply a head covering. Even a balaclava is a hat (as well as baseball caps).

  • Freddy Lift

    Let me tell you something about this article: You could have fit another Die Hard reference in the “Tank tops” section… Actually, you SHOULD have fit another Die Hard reference in the “Tank tops” section.

  • Tom Connolly

    Most of this is great, save the hat. Now I’m not talking about ball caps, but men’s hats; driving caps, fedoras, even panamas. Maybe it’s an age thing, but men should wear the right hat for the right reason. See The Art of Manliness for more (artofmanliness.com). The rest, well said.

    • Fred

      It is only fair to point out that artofmanliness is a little backward directed. It is about the good old days (that were not perfect as well). Even though a hat can look good, you will definitely look a little out of time wearing one in an old fashioned way today. But if you don’t have a problem with that, great.

  • Jeff Ehmann

    learning how to iron is a plus & girls dig a guy that can iron. It’s a good mindless task to loose yourself in…like mowing the grass.

  • http://twitter.com/mattpooch Matt

    Realizing that socks are a medium to express yourself is huge. When that day comes for you, the rest of your wardrobe will benefit for the rest of your life.

    • Fred

      But don’t make sport socks your statement.

  • Kevin

    The Tenth Doctor wore sneakers with his suits…but then again he is The Doctor…

  • http://www.kangalex.com Alex


  • Liam

    Right along with ironing your shirt is tucking it in. Real attention to detail includes making the button seam of your shirt match the seam of your pants in one continious line. That’s sharp, and 100’s of 1,000’s of men and women hold themselves to that standard everyday. The widths will match, and if you look at any formally dressed military or police officer; they will be in “gig” line. At the low end of expectations includes tucking the damn thing in for your own dignity. Women look hot in your dress shirt b/c untucked, it practically looks like a dress. The worst is if you are wearing a sweater and you have this little diaper chute hanging out over your d!ck and a$$. Your collar and cuffs look fine, your shirt tails just make you look like you forgot to tuck in, zip up and wash off the last time you micturated poor Lebowski’s rug.

  • Fazel

    You nailed it!

  • Richard

    Agree with everything EXCEPT the hats. Men should be getting back to wearing hats – not caps, but hats. Of course the other half of the story is men need to learn hat etiquette, when to take them off, when to tip them, etc. Also, the hat must be appropriate for the outfit and the outfit appropriate to the occasion.

  • Gin A. Ando

    Richard—I wrote that part out of anger.

    Indeed, if hats come back and people understand the responsibility that comes with wearing them, I would be one of the first to wear one again.

    But I suppose the movement has to start somewhere!

  • Pingback: The Best of the Web for Grooms – January 12, 2012 | GroomsAdvice.com()

  • CS

    Also a fan of hats, specifically a wool flat cap. It keeps my head warm and dry, shades my eyes and sets me apart from chumps wearing ballcaps and beanies.

  • Roger

    Good list, but what about being bald for number 2. It’s either hat or hair piece, tough choice.

  • Gin A. Ando

    Roger, being bald isn’t a bad thing. At UC, one of the best dressed guys I’ve ever seen was bald… it’s about being able to embrace it, I think.

    Look at Jason Statham and Stone Cold, man. Those guys pull off their respective looks absolutely flawlessly.

  • Greg

    On any fashion test, Ricky’s shirts pass with flyin carpets!

  • TrixieinDixie

    Yes, yes, a million times, yes to everything in this article (with the clarification that baseball and trucker caps are not suave, whereas a proper hat certainly can be, as others have mentioned).

    I detest seeing adult men wearing athletic shoes (like running shoes) with everyday clothes as if all shoes were equal. Nothing looks dorkier. Now, some cool Chucks or similar sneaker type shoe can look fine with jeans.

    Also, flip flops. I don’t care what designer name is on them – if you are not near a body of water or at a picnic or something, don’t. Just don’t. Men’s feet are almost always unpleasant to look at. (Lots of women too, but that’s another article.)

    For me, that college frat boy is a huge turn off. Once you are out in the real world, you should dress like an adult, wear pants that reach the ground, leave home the t-shirts and the flip-flops and the backward caps. Ugh. I don’t care how hot you might be – if you’re dressed like some A&F wannabe, you look like a douche.

  • JoeBoxer

    I can understand how the points you made apply in many instances – bad taste always shows. However, articles like this seem to lean towards forcing conformity, like in Maoist China, and use too many “shoulds”. I’d rather see diversity.
    It also reveals some juvenile insecurity about male beauty. A hot guy with a hot body can wear anything and still look good. If you get uncomfortable seeing a man’s nipples peek out from a tank top, that’s your issue, not his.

    • Fred

      I get your point, but I think there is enough space for diversity even if you avoid many of the obvious style failures. Diversity through imagination, individuality and cool ideas is great. But diversity through not good looking styles (that too many people wear) is not really diversity.

      Don’t know if rules should depend on the ‘hotness’ of a person. They should be general and suit everybody. A ‘hot guy’s can wear anything and still look good? I doubt that. But more importantly, a hot guy can look more than good with the right clothes on, he can look great.

      We didn’t talk about colours or other fashion rules, that might have been a little too restrictive. This rules have really been the basics. And maybe breaking a rule, intentionally, is a good idea every now and then. But it is a difference to know you ‘break’ a rule and just to think it really is the coolest look to wear a tank top every day. If you do construction work on a hot day, fine. But it is not always a hot day and sometimes a T-shirt or long sleeves might be the best ‘every day’s option.

  • Gin A. Ando

    JB, this is far from an urging for people to move toward a Maoist mentality. This isn’t so much about conformity as it is just hopefully doing away with some things from our shameful past.

    I never mentioned anything about nipples, either. However, regardless of hot of a guy he is and how hot of a body he has, he will always look better in a well-fitting suit—Maybe one that’s velour or one that’s paisley or a deconstructed one or how about a polka dot bow tie? There are ways to be “nonconformist” and still wear what some people consider “dressy.”

  • Chandan


    I am Chandan, 28 years of age, 5ft11inches and slim figured and fair. I am going to marry on 24th of feb. I have purchased a black suit for the reception party and a blackish red shirt as a inner. I just need to know whether the blackish red shirt is a right choice to wear as a groom? Lso please advice me what are the other things that I should take care e.g wrist watch, shoes, belt,tie (whether its mandetory or not?).

    Please help me out:(


  • http://www.stylegirlfriend.com Megan

    These are great tips for all guys, and especially agree with the warning about suits with sneakers; that’s definitely a move with a higher degree of difficulty! You’ve got to master the basics (suits with actual dress shoes) before graduating to the more advanced stuff.

  • http://colebradburn.com Cole Bradburn

    I think the long sleeve T-shirt under the short sleeve T-shirt belongs on this list.

  • http://www.manshway.com Casey McGoff

    Great article. Its about time somebody said that about the vnecks AND sneakers with a suit. But about the hat, what is your opinion on this article from ArtOfManliness? http://artofmanliness.com/2008/03/01/bringing-back-the-hat/

    • http://www.primermagazine.com Andrew


      The dress hat is one of those things you have to do confidently to pull off. Having a modern style hat also helps. I think realistically, the dress hat in modern times is tough for most men in their 20s.

  • James Tollison

    I agree with what you said (but I’m still going to wear a hat, and by a hat, I mean a HAT, not a cap.)

  • http://www.manshway.com Casey @ Manshway

    Every one of these instantly contributes to one’s style and class. Death to the deep V-Neck. I think the first one is my favorite though, buying clothes that fit right will make anyone look infinitely better and you don’t have to spend a whole lot of money on name brand clothing

  • JD

    Standing ovation.

  • Marco

    I think only half of these are true no nos. What I mean by that is many of these are really only fashion mistakes now. No hats. No tank top. No sneakers with suits. Size matters. These all come in and out of fashion.
    For example wrinkled shirts are in by way of linen shirts….

    • Fred

      Size comes out of fashion?

      Well, that’s the problem with fashion, it only lasts for a season.

      Size always mattered. If you wear an Italian style suit or an English style one, size or fit will be different. But to wear totally oversized clothes never looked good. And totally ‘under’sized cloths are only short term fashion and no long lasting style.

  • Pingback: 50 Tips on Grooming, Style, and Living a Better Life - Primer()

  • Ben Flanders von Elgk

    this is just awful… in every sordid way… sigh! you mean you don’t learn this at home or in boarding school?

  • Jason

    Love #8. Well said.

  • Fred

    The basic message: Don’t care about fashion and concentrate on style.

    Style is what lasts for decades. Fashion is what comes and goes.
    Maybe you can use a certain fashion as a temporary highlight. But don’t concentrate on solely on fashion.

    Of course many things depend on the environment you live in. But don’t think sneakers with a suit make you look younger (or fresher or the like). Even if your favourite sport presenter on TV wears sneakers.