Should You Wear Crazy Socks?

Should You Wear Crazy Socks?

Learn all about crazy socks, the pros and cons, and whether you should wear them or not. Some of you may wonder, do I actually wear these socks?

The answer is, unequivocally, NO!

Assortment of crazy socks as you can find them in many places these days

Assortment of crazy socks as you can find them in many places these days

What Are Crazy Socks?

They are socks that have bold colors, bold patterns, and whimsical motifs such as footballs, baseballs, or a solar panel.

You can find them in nearly every color under the sun and sometimes they have comical motifs or serious motifs or just something that an artist came up with.

In the last three years, they have almost become mainstream amongst casual business cultures. Maybe inspired by Silicon Valley or just a start-up culture where formal traditional dress codes are not enforced.

Many people think crazy socks are a good way to express their unique style and personality.

Interesting socks, not too crazy but pants too short by a long chalk

Interesting socks, not too crazy but pants too short by a long chalk

Pros & Cons Of Wearing Crazy Socks

A crazy sock really makes a statement and you’re definitely different that you stand from a crowd.

If that’s your ultimate goal, crazy socks are a good way to achieve that.

Now, standing out could also mean being the odd one out or being weird and crazy socks have that potential because they’re just so bold and outlandish that they don’t work with anything. They’re just contrasting and make an extreme statement. There’s no room for subtlety at all.

I think all the men gravitate towards them because it’s relatively easy to pick up a pair of socks and then think, you’re done with your outfit. However, if you want to have an elegant stylish outfit, just changing the socks is not enough.

More Taco Socks

More Taco Socks

“Do I want to identify as a well-dressed gentleman?” If the answer is yes, you should probably not wear crazy socks because they’re simply over the top. A simple bold obnoxious accessory won’t make or break the look instead, it draws the attention to itself and so people would look at your feet rather than your eyes. You want them to look at your face and not at your feet.

A gentleman can be eccentric and you can create an entire outfit that frames you as a person even using some louder accessories but if there are two out there, it just destroys the overall harmony. Would you wear tacos, beer mugs, or dinosaurs on your ties? Probably not and therefore you also shouldn’t wear them on your socks.

It’s a cry for attention. It basically says you can’t get people to look at you or get an interest in any other way,  that’s why you choose something that’s so overly bold and out there because it’s your last resort.

They are often of low quality. In order to keep the price low, you have to go with low-quality materials that mean a lot of nylon that means a very limited range of sizes because that way you can stock more and it’s easier and requires a lower capital investment.

Bold socks in oversized classic pattern - kind of crazy

Bold socks in oversized classic pattern – kind of crazy

While doing research for this video on crazy socks, we actually found, that often times they only come in short lengths and never over the calf and they have a lot of nylon and come in very limited sizes. Most of the time it’s one size fits it all or they have three sizes at the most.
So the problem is, those socks will slide down inevitably and expose your ankles which is not something you want to show to others.

The cotton used is of lower quality. It’s stretched with nylon and polyester to keep the price point down and basically what you pay for is the design or the eccentricity. In theory, you should be able to find quality crazy socks but in reality, it’s super difficult and it’s just not the case.

Extremely short pants with paisley crazy socks

Extremely short pants with paisley crazy socks

In essence, crazy socks are a disposable fashion item and it’s part of a throwaway culture because it won’t stand the test of time. It’s not something you can wear on and on and on. It’s not just something that combines very easily with other items in your wardrobe and for that reason, we suggest not to wear them.

Of course, the choice is entirely up to you. If you want to send a statement that way, go for it. If you want to be a well-dressed gentleman with a timeless wardrobe that is elegant and highlights the person behind it, avoid them.

Instead, go with solid color socks or maybe two-tone socks such as the shadow stripe socks.That way, you still can add some personality and color to your outfit without going overboard and looking obnoxious. Also, bear in mind that if you have crazy socks, you are less likely to be taken seriously. Usually, those socks are associated with teenagers or hipsters but not with men who work in office environments or professionals.

Crazy socks with pinrolled chinos to show them off even more

Crazy socks with pinrolled chinos to show them off even more

Who could wear crazy socks?

It’s perfect for people who want to be outlandish, geeks, or artists who have the Mona Lisa on their socks.

For example, if you have orange and gray, it has a brown tone so you could wear it with brown tones. You could wear it with a pair of denim, and they’re colorful so you could pick up an accessory like your tie or your pocket square and combine it in a way that’s meaningful, stylish, and it will earn you compliments.

Moonphase socks

Moonphase socks


It’s okay to go with bolder socks, try to either stick to solid colors, or patterns, don’t combine them. Otherwise, it’s over the top.

Should You Wear Crazy Socks?
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Should You Wear Crazy Socks?
Learn all about crazy socks; the pros and cons, and whether you should wear them or not.
Gentleman's Gazette LLC
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32 replies
  1. David Kindred says:

    Although I agree with almost all you wrote, I still choose to wear crazy socks. No, not the ones with dinosaurs and the like on them, but I do enjoy bright bands of color and vibrant patterns. My favorites are the ones that have the foot in a solid color, so the bright colors are only revealed when legs are crossed, or otherwise exposed.These look “normal” while walking, so the fun part of the sock is almost a secret that you can choose to expose, or not, depending upon posture. Why do I enjoy these socks? Well, I have a slightly quirky personality, and they’re a minor reflection of it. The rest of my outfit is generally termed “dapper” by my blue-chip company colleagues, but they universally love the socks I wear, and now (perhaps to your horror?) I’ve influenced at least a couple dozen other gentlemen to wear them. I consider it a very tiny way to add some extra flavor to a generally bland environment. So, yes, I agree with you, but…

    • Charlie fortune says:

      Good notes, i recently began wearing colorful socks, the kind that complement the colors of my outfit. It is an inexpensive way to have some fun with your wardrobe.

  2. Andrew Gregg says:

    Crazy socks can make an instant, positive impact, and break the ice in an unexpected way.

    Once, I was at a Middle School in my usual quiet suit, sincere tie, and brogues. When I crossed my legs, Scooby Doo socks, a gift from my sweet niece, an elementary teacher, were suddenly in evidence.

    “Ruh-roh!” was the chorus from the eighth graders, and the old bald guy in the suit was immediately accepted.


    Andy Gregg.

  3. Chris says:

    Sven! Question for you. As I near 40, I realize jeans and a t-shirt, while socially-acceptable, isn’t the Gentleman’s way. However, I find I’m losing my individuality by turning away from that look. I don’t just want to be an individual; I want my interests known. For instance, if I wear a Doctor Who t-shirt, people know a general idea of my interests, and I like that it already promotes a general knowledge of who I am in some ways. How can I get that same kind of “advertising” in a suit? I looked at comic book cuff links and ties, but they almost all look cheap. I’ve found a few decent watches and belt buckles, but those are actually too subtle. Am I just relegated to moving on from that in my life?

    • Christopher Lee says:

      Not Sven, but my personal take is that people will get to know who you are by deeper conversation and actually knowing you rather than seeing a t-shirt or accessory. It depends on whether you think it’s important to advertise your interests and values externally, similar to having a bumper sticker on a car. The latter seems to be a particularly American thing as well. In Europe and elsewhere in the world, it doesn’t seem as important to avertise one’s affiliations and interests to strangers.

    • David Kindred says:

      I agree with Christopher. At best, a T-shirt might serve as a conversation-starter on a particular topic. But that would be most valuable for impromptu meetings with new people. Anyone with whom you regularly converse is likely to learn of your interests through normal conversation, just as you might already know that Joe likes to fish and Bob likes photography, without either of them having first work hobby-themed clothing. Just be your genuine self, and people will want to know more about you, at a natural pace–no props needed! (FWIW: Tom Baker all the way)

      • Sven Raphael Schneider says:

        I find slogan t-shirts off-putting myself. If you want people to know you are into photography, have a camera, if you want them to know you are into clothes, wear tasteful outfits…

  4. Alexander_F says:

    I guess all of us will agree that socks with legged tacos on them should rather not be worn by adult men, and it is right to underline this.
    But finding a balance between all-gray-and-black and such obnoxious nuisances is part of becoming proficient in style, I guess.

  5. trackhorse says:

    Not only do I wear them, I sometimes mix them up. Last week, I wore a very loud pair to a black-tie event.

  6. Christopher Lee says:

    I tried bright, contrasting socks and for the most part have abandoned them as I don’t want the focus of attention to be on my ankles. If I dress well, I’d prefer notice of my tie or of the coherent whole, not my socks.

  7. David says:

    I tend to have a very serious personality while at the same time the majority of the thoughts that run through my head are not serious. With that said both my wife and a friend of ours have encouraged me over the past 5 years to start wearing more “fun socks.” After reading this article I believe that there is a difference between crazy and fun. The socks I wear now are a bit more bold than what I used to wear. They are still stylish with classic patterns, yet they just happen to be bold. It took me awhile to warm up to wearing fun socks, and now that I have warmed up to them I have found that when I wear fun socks I am more relaxed because I don’t take myself so seriously. It also helps others to relax around me. I don’t consider myself an intimidating person, but I have been told many times over the years by a variety of men that they find me intimidating. I have found that fun socks help to curb this persona.

  8. Terry says:

    My sister gave me a six-month subscription to a wild sock company for Father’s Day two years ago. I even bought a few more! I wear them with casual outfits (khakis and polos, etc.) on very informal occasions, but wouldn’t consider them with a tie. However, as has been mentioned before in this column, on the California Casual Coast most anything goes.

  9. Al R says:

    Sorry, the premise behind this article is mostly hocum! The psychology & reasoning is nonsensical!…I ‘ve been wearing ‘crazy’ socks probably before you were born!?…I’ve never received negative reactions from wearing them. I’ve been considered a neo classical elegant dresser by the peer group (tribe?) I’ve associated w for decades. This was in the service of engaging in Christian volunteer activities. I’ve chosen to wear them because I enjoy them & I like the wimsical quality to them. I personally have no need to attract attention by wearing them!? The way I dress & comport myself, generally garners very positive reactions from folks. If one knows the rules of the game, one can successfully & tastefully negotiate sartorial greatness!…

    • I J Black says:

      How very unChristian a response. Also, illogical. You dismiss the premise as “mostly hocum”, without either defining “hocum” or identifying what wasn’t. Because you’ve been wearing ‘crazy socks’ etc, doesn’t automatically mean that whoever disagrees with you is nonsensical. It just means you’ve been in taste or out of it longer than Sven. And I’ve been in and out of it longer that either of you. Time is irrelevant — bad taste is still bad taste, however long its beard. Likewise, that you’ve never received negative reactions means only that no-one gave you a negative reaction response.
      “Taste” does have self-defining parameters which do transcend peer group identities. A group of doctors may properly define the criteria for good medical practice. It is not, however, automatically the arbiter of sartorial or culinary standards. That your peer group considers you “a neo-classical elegant dresser” is only relevant if it has exhibited its own standards of taste. Do such empirical criteria pertain to Christian volunteers, as for example, following the teachings of Jesus, vis a vis, how we treat each other? If indeed it considers you “a neo-classical elegant dresser” only shows it doesn’t know what it’s talking about. “Neo-classical”? “Elegant dresser”? What do those terms really mean?
      That you choose to wear the socks because you enjoy them and like their whimsical nature, is entirely valid. I wear what I do for much the same reason. But I really don’t care much for what people think. Considering the vituperative nature of your reply, I would guess you’re more interested in garnering “very positive reactions from other people.” Sounds like the defensiveness of someone who’s gotten one too many negative comments and doesn’t like it.
      I’m still trying to figure out your last sentence. I agree with it completely. I just haven’t got a clue what it is doing here.

  10. John Greyson says:

    I agree wholeheartedly. Wear them with jeans or casual pants. And puh-leeze don’t go bare-ankled when wearing a suit or a tie and jacket. Terrible trend!

  11. Mark says:

    Dear Rafael,

    I confess to wearing bright or bold socks both with denim and with a suit, though less often. I also enjoy using colored laces on my dress shoes. So I will match laces and socks to mark a holiday or special occasion; green and red at Christmas with red socks; Purple laces and socks on Mardi Gras, Green socks and laces on St. Patrick’s, and Pink on Easter, etc. Although I agree they can be over the top, I also like the bit of whimsy they impart. Like anything, if done with taste and intent it can work well. If there is no sense to it, then it compromises a look. Of course, I live in California so it is possible that local culture is more permissive. I do agree the bright socks are often not well made, but their intent isn’t classic style, but passing fancy. If you wear both well made dress and fun socks the people around you will know that you know the difference. Which also means it should be avoided if it is an occasion to make certain first impressions.

  12. BRENT SMITH says:

    I think it was Beau Brummell who said something along the lines of, “If a gentleman is remarked upon in the street he is invariably ill-dressed.” Beavis and Butthead socks would doubtless have offended him, as they do me.

  13. Randolph Belle says:

    I started wearing distinct socks as a teen, which was 30 years ago. Fo me it was a great and inexpensive retail therapy. I also maintain a pretty strict classic attire- suit, hat, boutonniere… which I believe I’ve managed to pull off. So I guess I’m saying, if you can get away with it, go for it.

  14. Tim Cogswell says:

    Probably not a good idea for conventional or traditional business dress; but seems perfectly suited for wear with an open collar shirt and blazer when having evening drinks at the pub.

  15. Andrew Rogers says:

    I’ve been a dedicated “crazy sock” wearer for 30 years, but I think there’s much wisdom in what Sven writes. Part of the problem, I think, is that with today’s styles for lower vamp shoes and higher pants legs, as in the rigs pictured above, there much more real estate for sock display than in classic tailoring. My theory has always been that nobody should be able to tell what color your socks are when you’re standing. When you sit, they can be a little flash of color or whimsy to be enjoyed by the observant. Wearing “crazy socks” with the intent of having them seen by everyone so you can stand apart somehow is, as Sven says, garish attention-seeking.

    (I should add that I’ve recently rediscovered the beauty of a well-made pair of absolutely plain black socks. Someone once wrote William F. Buckley to complain about a cliché appearing in the pages of his magazine. His response, basically, was, “When you write as well as we do, if we use a cliché, you can be sure we’re doing it on purpose.” Similarly, when a three-decade “crazy sock” wearer wears a pair of plain black socks, he’s doing it on purpose.)

  16. Phillip says:

    As with psychiatric examinations, I am not sure when a pair of socks should be certified as “crazy” or just an indication of an off-beat or mildly eccentric character. In years past I would never have considered wearing anything that hinted of most of the kind of garish hosiery mentioned here, but in these past few months my taste has taken a surprising turn in favor of some socks recently on the market displaying a certain traditional panache of frivolity or the absurd, and I find that the ordinary dress code with somber dark socks could do with a little jolting on occasion. I do like polka dots and muted red or green stripes (horizontal as well as vertical) on a dark ground and the traditional Argyles. They are just under the threshold, I believe, of what constitutes dressing “over the top,” or showing off, because the picture presented may remind one of a comic strip cartoon character, and so there follows the realization by anyone in their right mind that the wearer’s intent cannot be taken seriously. And what about the single “clock” stripe you see in men’s socks in some of Alan Flusser’s photos of the 1920s and ’30s? It’s the place and occasion where this kind of hosiery is worn that makes the style difference between the buffoonish and the elegant (with a twist).

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