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Should Men Wear Socks With Shorts? More Fashion Help for Clueless Men Over 40

read about men's clothing

by Tina Boomerina (Christina Gregoire)

Can men wear socks with shorts? Well, it depends. The answer is yes... if the man is a German tourist over 40 or 50. And, the answer is yes if the man is engaging in a sport that requires shorts and socks (hiking, jogging, tennis, etc.). However, the answer is no... if the man doesn't want to look like a clueless dork.

I mean... if you're George Clooney or Brad Pitt you can wear socks and shorts. But, if you're not... pay attention. Most men and women don't look like movie stars, so they need a tiny bit of advice.

Why are Older Men So Freaking Clueless When it Comes to Fashion?

How did I get to the point where I decided to write about men's clothing again?

Answer: My husband, Genghis Gregoire (Mr. Boomerina), got up this morning and decided he wanted to wear a T-shirt and shorts along with A PAIR OF SUSPENDERS to keep his shorts up.

mens fashion article

Genghis in Shorts, Suspenders & Socks - Plus 2 Guys in Lederhosen

Men Should NOT Wear Socks (or Suspenders) With Shorts

I explained to Genghis that he could wear whatever he wanted when I wasn't around, however he had to look somewhat presentable if he wanted me to accompany him.

  • I have put up with his everyday outfit, consisting of a T-shirt, a pair of jeans, and a pair of suspenders, for quite some time.
  • However, a T-shirt, a pair of shorts, and a pair of suspenders is beyond the pale unless my husband is planning to learn how to yodel and he's planning to hang out with a bunch of folk-dancing Bavarian friends in Lederhosen.

Well, the moment I told Genghis that his suspenders would not work with shorts, he went into a major sulky temper tantrum. I told him that my critique was a fashion thing and not a personal attack, but it took Genghis about an hour to calm down. And, then... since he seemed almost reasonable at that point, I decided to go for broke and tell him something that I didn't think he would ever comprehend... I told him that:

  • Men should not wear socks with shorts.

Then Genghis said, "I don't know if it's an old wives tale, but I was told as a child that white stockings absorb the moisture and keep you from getting athletes foot. Plus your feet stay clean in a dusty environment. And, white socks annoy you (Tina Boomerina) and I want to annoy you."

Well, how could I argue with that? And, if my husband doesn't care if he has "style" or not... there's not much I can do. However, I think most men would rather risk the possibility of athletes foot than risk being considered an uneducated, unemployed, possum-eating bumpkin from a cave in Arkansas. But, I could be wrong. Men are something of a mystery to me.

read about men's fashion

Don't Wear Socks With Shorts - Men's Style

Men Should Not Wear Socks With Shorts:

Look at the photo above. What do you think? I say all three of these guys look hot. (Of course, they're male models so they're probably gay... but they're still hot.)

It doesn't matter whether the guy is wearing sneakers or boaters or loafers or whatever... socks look dorky with shorts. If you can't handle going sockless, wear long pants like a big boy.

read about clueless men's fashion

No Socks With Sandals for Men

Men Should Not Wear Socks With Sandals:

I doubt I need to tell any of you fashion conscious people, but men should not wear socks with sandals. Normally, I would not even bother explaining this, but I've been on several cruises where I've seen men wearing shorts, sandals, and socks. Sometimes, the socks are black. Sometimes, the socks are white. I don't know which is worse.

Tip for Guys: If your sandals (or shoes) bother you when you don't wear socks, it's because you haven't broken in your shoes properly. Try wearing your sandals with socks inside your house until the leather conforms to your feet. Just take the freaking socks off before going out the front door.

read about men's fashion

Do Men Need to Wear Socks With Long Pants?

Should Men Wear Socks With Trousers?

OK. This is where it starts to get into the tricky zone.

I once dated a cute guy ...a little bit psycho... but very tall and cute... who wore loafers with no socks. Mr. Cute Guy felt he had to explain his quirky sense of fashion to me, so he told me he didn't wear socks because going without stockings was more comfortable... like I really cared. (The guy was from the Midwest. I guess people in Michigan have fashion rules and regulations that people must follow. And, you my dear reader-friend may be from a time in the distant past where socks were required... that's why I'm going off on this tangent.)

Anyway, it turns out that the Michigan guy was ahead of his time. These days, a lot of young, hip men don't wear socks, even when they're wearing long pants.

In case you live in Nebraska, men's fashion has been changing quite a bit in the past few years due to the influence of the hipsters. Dapper dandies have come up with a new set of fashion "rules" or "non-rules". So, if you're the kind of guy who loves to be on the cutting edge, you now have the choice of wearing socks with long pants or going barelegged and showing off your sexy, hairy ankles.

read about men's socks

Can Men Wear Suits Without Socks?

Do Men Need to Wear Socks With Suits and Other Formal Wear?

If you work at an accounting office, you should wear socks with your suits. If you work in the entertainment industry, you can do whatever you want. I actually think it's kind of sexy to not wear socks with a suit. It takes a supremely formal look and turns it somewhat casual.

On the other hand, I also love patterned socks with suits. They're so veddy, veddy British. And, I happen to believe that men in London are the best dressed fellas in the world. Well... I've also seen a few cool dudes in Paris and Rome. So, all you fashionably clueless men should sit up and pay attention 'cause every girl crazy 'bout a sharp dressed man.

What color socks should your man wear?

Colored Socks, Patterned Socks for Men

Your Socks Should Match Your Trousers:

You can never go wrong when you match your socks to your trousers.

This creates a long, unbroken line, which makes you look slightly taller in some instances. However, once you've reached the point in your life when you're ready to experiment with different kinds of stocking styles... in order to create a unique look that makes you look better than you really do... you can throw this color rule out the window.

Listen to Your Wife or Girlfriend (or Boyfriend) When it Comes to Fashion:

If you're not sure whether to wear socks or not, or if you're not sure if your bright red or colorfully patterned socks are right for you ... and your outfit ... ask someone. If you're a guy over 40, 50, 60, or so, ask your wife or girlfriend.

Personally, I don't care if you wear socks with shorts or not, but your wife might. However, I DO care if MY husband wears socks with his shorts. So, I'm very happy when I see an older man wearing something smart. That way I can tell my husband, "See, that guy isn't wearing socks with shorts. "And, sometimes, if I'm really lucky, I get to say, "See, none of these guys are wearing shorts."

Soooooooooo, I guess I do care what you wear.

A Happy Ending to the Story:

Most of the time, my husband doesn't pay much attention to what I write. He thinks I'm making all this crap up. I assure you... I'm not. I do research and I use common sense.

But... this time there's a happy ending to the story.... My husband, Genghis Gregoire, stopped wearing white socks with his white sneakers. He also started wearing REAL shirts with his shorts... you know... the kind of shirt with buttons and a collar. AND he stopped wearing suspenders with his shorts. THIS is a HUGE breakthrough.

So, there's hope for all you unfashionable men out there. And, even more importantly, there's hope for all the wives and girlfriends of all the clueless fashion-zombie-men out there.

A Note to All the Older Men Stuck in a Fashion Time Warp:

We don't care what Eddie Haskell wore in the 1950s.

Unless you're a modern day beat-hipster, and you know what you're doing, you might want to pay attention to the advice in this article. You will never go wrong following these timeless fashion tips about not wearing shorts and socks. And... in so doing, you will be a good fashion role model for cluelessly unfashionable American men. However, I also believe in creating your own style. So, wear what looks good on YOU.

More Fashion Articles for American Men & Their Chic Wives:

What is Smart Casual for Women on Cruises?

7 Florals for Spring & Summer - Color Your Wardrobe

How to Manage Multiple Pills & Medications

Lace is Still Hot: Modern Ways to Wear Lace for Spring & Summer

 

read about men's fashion for dorky guys

Main Photo - Men's Fashion (for those on mobile phones)

Photo Credits: Prshots.com.

  • Main Photo: Men's at Dune.
  • Genghis in Shorts, Suspenders & Socks - Plus 2 Guys in Lederhosen: Christina Gregoire, Wikimedia Commons, Wikimedia Commons.
  • Don't Wear Socks With Shorts - Men's Style: Matalan, Crew Clothing, M&Co.
  • No Socks With Sandals for Men: Men's at Dune, House of Fraser.
  • Do Men Need to Wear Socks With Pants? Men's at Dune, Men's at Dune, Matalan.
  • Can Men Wear Suits Without Socks? Men's at Dune, Debenhams, Burton Menswear London.
  • Colored Socks, Patterned Socks for Men: Marks&Spencer, Next, Marks&Spencer.

What do you think of this article? If you're a woman with a boyfriend or husband who wears something you hate, let me know... send me a photo... and I'll put his picture on this article. You can do it anonymously (or not). Leave a comment at the bottom of the article.

Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

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14 Comments

  1. Martine

    AW. He looks cute with his suspenders and socks. Let him be, and give him a hug. Its Normcore.

    • Tina-Boomerina

      Martine, thanks for making me double-check the meaning of NormCore. (I don't watch telly.)

      If I win the lottery, I'm sending you to London. I want you to check out the difference between London hipsters and my husband.

      I will give my hubster a hug, but I will not let him be. NormCore is for ER docs in scrubs, military people in ugly ill-fitting uniforms, women weeding their backyards, and retro Chinese folks who like to carry little red books everywhere they go. I have nothing against wearing crazy combos of thriftshop clothing... a la hipsters and such... but I have to walk around with that guy in the photo (my husband). I was a hippie. I'm anti-label. I don't care what you wear. I don't care what your man wears.

      And, my husband has tried the line that he's a "hipster". Haha.

      Actually, all of you people reading this should go NormCore, and I will wear stuff that's somewhat flattering... and you will make me look just a tad bit better than I really do. Actually, I think all women (except me) should be forced to wear tees, shorts, suspenders, socks, and tennies. I need all the help I can get as I get older.

      NormCore is hip & trendy. Forget everything else you've ever read on this site.

      Tina

  2. Antome

    Hi.
    Well of course not all male models are gay, but it's funny nontheless (not in a gay=funny way, but in a Murphy law "all nice and handsome guys are gay" ^_^).
    Well socks are a subtle detail, they have a function but we have to know when they have to go, like all useful things.
    Once it's hot enough to wear shorts and discover the legs, the same goes with uncovering feet or part of them.
    It's important to premise though that in such cases shoes have to be light as well, or being sockless will have an opposite and not quite desirable effect on barefeet :).
    So the best kind would be loafers, boat shoes or canvas, preferably very low cut ones, (similar to the loafer of the model of your pic), made of good quality leather (or suede) or canvas for that matter.
    But most kind of shoes would be heavier and need at least some ankle socks.
    But even in said light shoes, I have the problem of properly breaking them off, I guess, so they irritated me when I tried them sockless.
    That's why I'm mostly going for sandals, when in shorts, it's just easier :). Currently I only have some birkenstock like kind, backless, moreover I find they look better than many shoes being somehow more "appropriate" for someone in shorts. That said, it's not a trivial matter finding some decent ones, but I liked this pair
    http://www.fantasticman.com/blog/wp-content/uploads/2010/05/HERMESSANDAL.jpg.

    • Tina-Boomerina

      Antome,

      Thanks for all the tips. You know WAY more about men's fashion than I... and your comment is spot on.

      Whenever you're wearing "light" summery clothes (shorts), your footwear should be low cut and "light" to go with your shorts (... unless you're going for whatever backwards style is the latest hipster look and you know what you're doing.)

      And... of course... the part about all male models being gay was supposed to be funny. I am SURE they're not all gay. Some of them are bi. (yes, joke... don't want tons of hatemail)

      Well, as I am a female, I have worn lots of shoes without socks throughout my life. The easiest way to break in shoes (or sandals) is to wear them around the house (with or without socks) for several short periods of time (half hour increments or something like that) throughout the day -- or throughout the week. You can spend part of this time sitting at your desk... but you have to walk a little to make sure your shoes stretch. (Be careful how long you wear the socks. Sometimes, you can stretch out your shoes too much and you might get blisters when your shoes are too loose... the extra movement.)

      If wearing your shoes around the house doesn't work, you've got the wrong shoes or the wrong size. Canvas and fabric shoes don't stretch, so that could be the problem. Leather and suede (especially suede) should end up stretching in the right places and fitting your tootsies perfectly.

      Manmade leather and fabrics are tricky. They usually don't stretch as well as suede or leather. The older you get, the more you will appreciate natural materials. Anyway, don't get canvas or faux leather shoes unless they fit really well.

      I love your tips! Thanks.

      Tina

  3. Antome

    Thank you for your kind reply and appreciation of my style and tips. Almost unexpected cause I keep it pretty much simple most of the times.

    Oh, and the sandals of the link are not my current ones, but a pair I'd want to shop. I got from your reply, but from your article as well, that you liked that style of sandals, but not sure. I do cause they are one of the few non bulky and sleek/elegant models of sandals for guys (flip flops don't count).

    It would defeat the purpose, if I want bulky footwear I might as well wear shoes and socks. If I ask that it's just to exchange opinion or tips if you don't mind, of course. Btw, there is a X variable in many guys, the higher it is the bulkier the sandals, shoes, the baggier or longer or ill fitted or the short and clothes have to be, to not look "feminine" preferably plain looking :).

    What this X variable is, is unknown to me, maybe the Q.I, but most probably it's the upbringing, environment, life experience etc. It's mostly guys who think this, apparently, but also some (much fewer) women.
    You are right, socks are much rarer with women, when in light clothes like shorts, dresses, but in general with warmer weather, some take it too far freezing in winter, though. That's among the many details I appreciate and seems like a key for the outfit to be flattering. I often noticed and wondered why many of us guys don't and are always in socks even with shorts.

    I think it's in part because even the shoes or some sandals like slingbacks, that they wear barefoot, are in general much lighter and airier than what guys wear in general wear, even if "closed" they basically only cover the toe area.

    The fit is much uncomfier the higher the heel is, but that's another matter. But generally with higher cut more "unisex" shoes, (converse, sneakers or with laces in general) they wear socks as well, I think. But I agree they also generally look at least bit classier with said lighter footwear :)

    Back to us guys and me ^_^, sandals with shorts are all about fine, but I want to go for loafers.

    I tried them rarely though, because I'm afraid I'll rot them, even after breaking in them, which anyway is a good tip. Is consistent hygiene, deodorant enough? I found that their leather or suede quality is crucial in that regard as an old pair was perfectly fine and comfy without needing socks, but that was years ago, maybe I'm just too used to socks (I also stopped wearing shorts until recently, I was a bit shy about it) and have to get a new pair of loafers using them at home from time to time.

    Oh about the shirt I mostly go for t-shirts, if in shorts, sometimes with buttons (but short sleeved) as well, though. I'm 28 and Italian, btw.
    Sorry for the long post, just exchanging some tips.

  4. Tina-Boomerina

    Antome,

    I'm sure the sandals in the link are perfect, but they're Hermes... so they're crazy, ridiculously expensive. However, those sandals (or a similar pair of cheaper, knockoff sandals) would look perfect with shorts or jeans or anything.

    I like most men's sandals... Tevas (sporty) or elegant leather styles. I think it depends on the outfit and the environment and what you're doing, like hiking vs going out to a club. (Flip flops are mostly for the beach.)

    I think I know what you mean about the X factor - X variable.

    Some men look better in bulkier shoes and sandals. Some men look better in lightweight, elegant shoes and sandals. Some men have no clue and don't care what they look like... and they would probably go to work in their underwear if someone didn't stop them.

    I don't know if you mean you're Italian from Italia or US-born Italian (like from Hoboken, New Jersey ... like Frank Sinatra). Either way, all 28-year-old Italian males are gorgeous. You will look hot no matter what you wear. You could probably wear cowboy boots with a swimsuit and look good... joke... please don't try that.

    I love hearing from you. You have good ideas.

    Tina

    • Tina-Boomerina

      Antome,

      The more I look at those Hermes sandals, the more I think every man should have a pair. Those are a great design. Maybe you can find something similar (a knock off).

      T

      • Antome

        Oh, I didn't know it was such an expensive brand, but that's exactly what I meant spot on, it's the model that I

        like and wanna to shop, definitely not the brand. So yeah, let's go for a similar knockoff, even if not

        identical, with the same base outline, maybe a taller sole and heel back and front or even a tiny bit larger

        straps, but same structure.
        " the more I think every man should have a pair." Ditto, goes without saying :).

        "with shorts or jeans or anything." Indeed, most guys seem to wear them with shorts, generally, myself included.

        If I wear trousers, shoes and socks follow. So I semiconsciously associate them with shorts, probably because of

        summer in general or the inverse rule "if it's warm enough for sandals I'm also in shorts", but why not try them

        with jeans one day.

        I share that bulkier ones can look great too, with chunkier legs and or thicker ankles or maybe bigger feet. Just

        an impression, there are not definite rules in stone ;).

        Haha, yeah I'm Italian and living in Italy. Thanks for the guess about handsomeness, but don't worry I'm not

        gonna try that, though maybe, I often thought about pairing shorts with Doc Martens or some other ankle boots in

        a sort of rock - punkish hip style, just for the sake of it and because I like, to an extend those range of

        "alternative" outfits not for who know what statement.

        Back to loafers.
        Maybe I got influenced by reading all aroung the net that whatever we do we're gonna quickly rot them if we don't

        have socks on.
        But then I wonder if they think women all around them who do it all the time are somehow non human etheareal

        people immune to all kind of sweat and magically clean :D
        https://s-media-cache-ak0.pinimg.com/236x/7d/a5/a1/7da5a1f1155c65866d0649d468547f9d.jpg like this one.
        I think you have your secret to prevent that and be comfy (unless in high heels, of course), because as you said,

        one should be comfier without them in summer than with, and it's a matter of habit.

        Of course it's not that important, but while we're discussing tips, why not? cya and thanks.

  5. Antome

    Oh, I didn't know it was such an expensive brand, but that's exactly what I meant spot on, it's the model that I like and wanna to shop, definitely not the brand. So yeah, let's go for a similar knockoff, even if not identical, with the same base outline, maybe a taller sole and heel back and front or even a tiny bit larger straps, but same structure.
    " the more I think every man should have a pair." Ditto, goes without saying :).

    "with shorts or jeans or anything." Indeed, most guys seem to wear them with shorts, generally, myself included. If I wear trousers, shoes and socks follow. So I semiconsciously associate them with shorts, probably because of summer in general or the inverse rule "if it's warm enough for sandals I'm also in shorts", but why not try them with jeans one day.

    I share that bulkier ones can look great too, with chunkier legs and or thicker ankles or maybe bigger feet. Just an impression, there are not definite rules in stone ;).

    Haha, yeah I'm Italian and living in Italy. Thanks for the guess about handsomeness, but don't worry I'm not gonna try that, though maybe, I often thought about pairing shorts with Doc Martens or some other ankle boots in a sort of rock - punkish hip style, just for the sake of it and because I like, to an extend those range of "alternative" outfits not for who know what statement.

    Back to loafers.
    Maybe I got influenced by reading all aroung the net that whatever we do we're gonna quickly rot them if we don't have socks on.
    But then I wonder if they think women all around them who do it all the time are somehow non human etheareal people immune to all kind of sweat and magically clean :D
    https://s-media-cache-ak0.pinimg.com/236x/7d/a5/a1/7da5a1f1155c65866d0649d468547f9d.jpg like this one.
    I think you have your secret to prevent that and be comfy (unless in high heels, of course), because as you said, one should be comfier without them in summer than with, and it's a matter of habit.

    Of course it's not that important, but while we're discussing tips, why not?

    • Tina-Boomerina

      Antome,

      I'm so sorry it took forever to approve your comment. Life and tech problems got in the way... website is working again but a whole backlog of comments to find in the website.

      Hey, I think Docs and shorts would look totally hip on a guy your age... or something like that. Totally punkish or hipsterish. I like street fashion. I just wish more American guys would take it to the next level.

      I've been to Italy a few times and Italian men always look great (the guys AND their clothes). Love Italy. Love it. Love it. Love the history. Love the architecture. Love the beauty. Love the wine. Love Rome... except for the transit strikes... and trying to cross the streets. Love Piza. Love Florence. Love Venice... which I thought would be corny. Love all the little towns that no one knows. Want to visit Milan. Want to see Sicily. Want to stay longer than a week and explore Italy by train.

      Fortunately, my husband knows French and Spanish, so he can pick up the language. Me... I only speak English, read French, and speak a few phrases of German.

      I love all of Italy... even the factories. Even the parts no one else cares about... that don't make the tourist maps. I come from a European family (grandparents from Germany), so I feel more at home in Europe than I do in the US.

      Now, I want to go back to Italy. Every area is different. Italy is a whole little continent and it's warmer than Germany. If you're still around, tell me what places I should visit. I like art museums... every time I've been to Florence the museum has been closed or under renovation or it's had a line that's gone around the block. I want to see the real David. I love the piazzas.

      In my next life, I'm going to live in Italy (or Talinn Estonia). I want to run away to Italy and become a painter, but there are already so many good ones, they don't need another. Maybe someday.

      Anyway, I'm glad you left another comment. It took me all this time to fix problems with my website and I just saw your comment.

      Tina

  6. Tina-Boomerina

    ps You don't need to spend a fortune to get something like a cute Hermes knockoff. And, you're right... you probably need socks in a hot climate. I'm no fashion expert... especially when it comes to men's shoes.

    Where I've just moved to, the high desert in Eastern Oregon, guys wear low hiking boots (we're up in the mountains) with short socks that just barely come above the boot, but you could wear anything with docs. Yeah, go punk. Make up your own style. That's what street style is... finding what looks good on YOU and making it trendy.

    T

  7. Antome

    Thanks for your reply, I was actually wondering if I did something wrong, so I didn't insiste hehe. It's no problem, I suspected you simply didn't see it.
    "ps You don't need to spend a fortune to get something like a cute Hermes knockoff." I knew that, but I wondered where to find them, at least on the net, do you have some example. My current sandals are all about ok, anyway, no hurry.
    "you probably need socks in a hot climate." in shorts? You gotta be kidding, I'm not falling for it ;). I still wear them with most shoes, when in trousers.
    The occasional problems I have, barefoot are not much due to the temperature, I think, rather, until june it's on average too cold to lose sock too often, at least for me, same goes for shorts.
    As for shoes without socks, can I bring up the example of your husband.
    You told, on the tips for men over 40, that you eventually made him lose the socks, when wearing his shorts ^_^. Depending on which kind of shoes they were, boat shoes, loafers, etc was him uncomfy at first?
    Maybe it's not that hard to get used to it.
    As you said you wear heels (btw, you don't need to), so ours it's not that big of a "price" to wear shorts, lol.
    Extra tip to men, also groom your feet and nails, for shorts, not assuming most don't, but it's not unmanly at all.
    P-s I'll respond also to that about the Italy, nice that you love it, but I'm not jealous of other place mind it.

    • Tina-Boomerina

      Antome,

      Hi again. You did not do anything wrong. You did everything right.

      My husband refuses to wear sandals... but I'm working on him... so I don't know where to get Hermes knockoffs. I don't have time to look for them right now, but I might later. Actually, you could just try googling something like "fake Hermes sandals for men" and something will probably pop up.

      Antome, I'm so happy to read your comment about how you're not "falling" for the idea of wearing socks with sandal and shorts. Good for you. I said that men could wear them... just to be nice. I didn't really mean it.

      Well, if you're jogging or riding a bike in shorts, it's fine to wear socks... but not for walking around the city. I don't know much about what men wear in Italy in the summer (I've only been there during colder months), but I know in Paris, no one wears shorts... however all men wear shorts everywhere in America. (I guess the hipster guys wear shorts in Paris... but I've never seen adult Parisians in shorts.) And, I doubt people in the bigger cities of Italy wear shorts... but who knows.

      Americans can be such slobs. It's a BIG DEAL for a man to wear a shirt with buttons when he's not forced to (for work). Buttons! Men in the states wear T-shirts everywhere. Well, not all men... but a lot of them. How hard is it to button up a shirt?

      I'm sorry you don't find Italy charming... if I understand your sentence correctly. I suppose anyplace is charming when you're on vacation and you have the hotel maid to make your bed each morning. I'm sure it's different when you live in a small expensive apartment and you have to work every day... not quite so charming. Are you in the north? You say it's cold in June.

      Anyway, I'm glad you responded. And, I'm glad you told men to groom their feet. You can tell them more ideas. American men are not like Europeans. Many Americans are barbarians. That's why their ancestors were kicked out of Europe... joke... but true joke.

      Tina

      • Antome

        "I'm sorry you don't find Italy charming" Never said that, only joked about not being jealous if you also liked other countries, because you seemed to sincerely like Italy.
        I'm from the southern main island of Italy, though, Sardinia, which I can advertise as a pretty awesome place I'm lucky I'm living in.
        But yeah, Venice, Rome, Napoli.
        "Hey, I think Docs and shorts would look totally hip on a guy your age... or something like that. Totally punkish or hipsterish. I like street fashion. I just wish more American guys would take it to the next level."
        Even if you might be chuckling bout it, I love the punk-chic whatever look :D. Can be tricky to pull of without coming off as either pretentiously chic or unharmoniously punk, but it's not that difficult, the rest of the outfit should match but not be excessively stereotypical, if you like spiked bracelets, not more than one. Well taylored shirts and some accessories.
        Some Americans do it, to those who don't and might like to try, I'm afraid they'll stop right at the idea of "look how women do it", if they are already on a given mind frame :D.
        I say that because some women pull perfectly off a similar outfit, made of pretty much unisex clothes, in an elegant way. They simply have nice accessory and less baggy clothes, when "baggyness" is there is intentional and the shirt is "flowy".
        While some women err on the side of following fashion too much, without a personal taste or style, many men err to the opposite side, and feel threatened in their gender roles by too many taboos. They should let themselves go a little on their artistic side ^_^.