Having Fun with Socks

Apart from masturbation,  there are a bunch of ways that you can have fun with socks, classic menswear included.  We just happen to prefer the solid, colorful ones over the obnoxious novelty ones.  

The regular world always tries to find ways to make menswear “cool”; whether they achieve that or not is up to you.  I mean we all remember skimpy lapels and skinny suits, which was done to modernize and separate yourself  from your dad’s work attire.  Skinny ties and monkstraps soon followed, but the one I think that blew up most was the “fun sock” trend, as it was relatively easy to buy into (and capitalize on).

Image result for fun dress socks

I wasn’t immune to its charms as it was one of the best ways to say “hey look, I like being classy and fun at the same time”.   The world shared this sentiment as you could soon find these fun dress socks everywhere, from Banana Republic/J. Crew to your local Target. They made especially easy fodder for packing your monthly subscription boxes (looking at you Sprezza-Box).

While I didn’t wear these fun socks with my vintage attire, I definitely wore them a lot in my regular Ben Wyatt-esque clothing.  You could probably see some wild polka dots, random moose, and crazy block stripes if you look back in far enough on this blog.  I finally had to stop when I realized that I had just bought teal socks with sushi rolls on them.

It also doesn’t help that these socks are often worn with other bad items like cheap looking shoes and overtly “dapper” outfits like a tweed suit and super cropped trousers.  Sometimes it’s made even worse by guys who try and echo the colors in their shirts/pocket square/tie combos, making it seem more tacky than interesting.  It just screams “2010s wedding”, which is a look I definitely want you all to steer away from.

These fun socks really became the Bugs Bunny tie of our generation.

Image result for fun dress socks

Image result for novelty dress  socks

Image result for red socks and suit

I actually don’t mind this one that much, but tying it into the shirt and tie is little too much.

I think that my dislike for these types socks is that they’re way too loud.  It’s different than my stripe shirt + patterned tie mantra (which can be seen by others as “bold”), since most of these socks just come out of no where. More often than not, these socks are worn with rather simple/basic outfits, which marks a huge disconnect.  Granted some of these pictures only shoe the foot portion of the outfit, it’s still too much.  I soon began to see them as a mark of iGents and  #menswear rather than the classic look I was after.

I corrected hard, and soon began to wear navy and charcoal socks exclusively.  It was nice for a time, feeling a bit more elegant and minimal, but I felt that I was losing the fun. Those solid, dark socks were a great match for full suits, but it felt a little weird wearing them with separates and denim.   I didn’t want to go back to having dogs and food on my socks, but thanks to Drake’s (and a few others) I did find a work around to have fun with my hosiery.

While I haven’t gone back to patterned socks, I’ve been sort of obsessing over colorful socks for a little while now.  You might think that there isn’t a real difference between these and the ones I posted earlier, but that’s where you’re wrong.

Right away, you’ll notice that they aren’t multi colored or patterned.   Being completely solid removes any room for major mistakes.  I also like that the ones frequented by classic menswear enthusiasts are a darker compared to the examples we had earlier.  Don’t get me wrong, they’re still saturated, but when done in a slightly more somber tone, comes off as a “conservative yet fun” choice.

Drake’s has been a huge proponent of the colorful sock trend, of course doing it within the guidelines I stated above.  It’s probably a case of marketing done well (since it’s a part of their signature look), but it’s really their images that struck a cord with me, though it didn’t happen overnight. I remember only liking a select few (namely the green ones since they’re close to blue), but I eventually succumbed to the love.  It’s a great way to make a sartorial outfit less stuffy without having to go as far as wearing pac-man socks or even sockless.

It helps that Drake’s tends to go for solid and dark conservative hues in their tailoring (browns, greys, greens) which lets the socks shine through without being out of place. They even wear these fun socks with suits, though their suits are made from “casual fabrics” like cotton and linen rather than superfine worsteds. Like their affinity for fun ties, you can’t have a Drake’s look without a colorful sock.   Overall, you can just see how well these guys pull it off.  Its definitely an intentional choice (as navy or grey would be the “normal” thing to do), but it doesn’t scream dandy or bad to me.   It’s like the right amount of personality, drawing a bit of attention when worn with classic attire, but not too much.  Again, it could just be my bias.

Here’s some examples from different inspirations.  I only wish I was able to take more pictures of myself (or Spencer) wearing some.  Oh well! I think you’ll get the point.


Green is a great color for socks.  Like I said earlier, it was one of my first forays into color socks since it was so similar to blue.  Works really well with navy and brown (which is like 75% of my wardrobe), which makes it a good choice.  Like most of the other colors here, you can always start with the deeper version first before experimenting with the brighter shades.

You can see how well green goes with both loud and subdued outfits.  You can’t really go wrong!


Yellow and orange are some bright colors.  They’re a bit out there compared to the rest, but I’m starting to like them a lot.   Naturally, they work best in fall but I wouldn’t mind seeing them with some navy or brown chinos in the spring.  For the most part, these examples don’t really play off any other piece in an outfit; I would advise against wearing an orange or yellow tie, as it would be too obvious of a match since the colors are so vibrant.  I don’t actually own any true yellow or orange socks, but if I did, I’d wear them with more subdued outfits, that way the socks could peek out brightly.  

Light & Dark Brown

Brown isn’t exactly a “colorful” sock but it’s something different than what most people wear.  Due to it’s plain appearance, I consider it my old man sock and wear it delightfully so.  It’s built for more subdued days but I especially love it for spring attire, since it’s a mature match for light colored trousers.  It’s a “mature choice”, especially when you feel like you’re going a bit bold with your other pieces.  It’s really my go to for denim, when I don’t feel like wearing anything too flashy.

Light brown works best as a neutral, almost rustic approach to the white sock while darker shades of brown does the same as a replacement for the navy sock.


We can’t talk about colorful socks without mentioning the infamous purple socks from Drake’s, as it’s been featured in almost every damn lookbook since they started expanding beyond neckwear.   I can’t help but love it, as it seems to be a perfect match for anything they pair it with; it especially looks smashing with brown trousers or denim.  If you took a shot every time you saw their infamous purple socks, you’d be dead of alcohol poisoning before you got to the end of the article.

I’m not sure what exactly the appeal is. It’s kinda/sorta similar to a navy sock in that it’s related to blue and it’s dark, but it’s got all the vibrance of a yellow/orange piece.  The fact that it’s darker allows it to be a more rakish (rather than overtly dandy) choice, making it appropriate for grey trousers.



Red is such a bold color.  Hell, I think it’s even bolder than yellow from earlier due to how bright it can be!  It’s a bit hard to wear due to the vibrance of the color, but thats all a part of the appeal.  Personally, it gives me preppy (or even slightly regal) connotations, making it probably the most rakish and dandy option depending on what you wear it with.  Its probably best to wear them with separates if you’re not sold on them just yet.

Burgundy is a good way to try out the color without being too bold.


We couldn’t forget white socks! Like I said in that previous article, white is a pretty underrated color for socks due to its old school vibes. While the original white sock was athletic (worn by lazy ivy students), you can find them in normal dress sock fabric for an elevated look.  I love it with casual separates (chinos/denim) but I’ve worn them with more formal fabrics like worsted or flannel.  Light shades of grey (like tan) also achieve a similar affect without going too hard into the vintage look.

On Us

While we would like to get socks from Drake’s or Pantherella, Spencer and I get ours from Uniqlo.  We’re not sponsored by them at all, but it just happens that they make some decent socks that work with our style.  At 4 for $10 for their standard selection, it’s really a no brainer.   Obviously the colors will be slightly different than the Drake’s ones you see in this article, but that’s really okay; we aren’t sticklers for how purple something should be, we just care that we have a fun sock that we like to wear.  The Uniqlo socks get the job done and they’re a great way to experiment with the colorful sock look without having to spend too much on a single pair.  Then when you feel like upgrading, Drake’s, Pantherella, or Brescani will be waiting for you.

While they are generally good, these socks aren’t as fine or thin as a true dress pair.  They also don’t stay smooth, since they aren’t over the calf socks, so they can tend slide down.  But that’s okay; it’s all about sprezzatura right?  We even wear these socks with everything from full suits and separates to our most casual (and seldom seen) attire.  And out of all of them, we mainly wear purple or white.  It’s probably because we love Drake’s a little too much.





















There’s nothing wrong with having fun with socks.  It’s just pretty hard to wear the mainstream “fun socks” (and by extension, pocket squares, ties, etc) in a classic menswear way.

Overcorrecting is something that everyone goes through in their menswear journey. When they first get in, it’s all about looking dapper and fancy all the time, with little eccentricities to prove that it’s fun (perhaps a little too fun).  Then you decide that your wardrobe isn’t as classic or versatile as you want it to be (perhaps you’re leaning toward #fuckyeahmenswear a bit too much) and so overcorrect and only wear plain colored ones.  Finally, you realize that it’s still fashion whether you like it or not, and you should have fun with it!   That’s exactly what happened to me and my socks.

I’m not trying to hate too much on the “fun socks” that you can get at Urban Outfitters, Sprezzabox, and Banana Republic.   But I believe that there is a more “subtle” and more classic alternative.  Hopefully you’ll be able to gather that from the inspiration images that I’ve compiled here.  Drake’s seriously makes a good case for it, proving that you can still have fun with classic menswear.  You’ll also note that these colorful socks aren’t trying “too hard”; by that I mean that they aren’t overly printed while simultaneously saturated.

To me each of these colors give off different vibes, which I then employ into my outfit thought process.  More often than not, they are my final choice (along with my shoes), as they can dictate what I’m going for. For examples, white socks and penny loafers give me a trad-ivy outfit, while purple and spit toes give a decidedly Drake’s look.  There really isn’t a go-to sock color as everyone’s tastes are different.  Pick which ever one you think works for you! And at Uniqlo prices, you can afford to have one or two outside of your comfort zone, because that way you have it.  You can always upgrade (as you should) when you get more confident in your choices!

I realize that this really left out patterned socks, but that’s because I haven’t fully gone back in that camp.  I’ve definitely seen a lot of great variatons of stripes and argyles that still work in classic menswear without being overtly dandy or #fuckyeahmneswear; it usually has to do more with the overall outfit at that point.  Perhaps we will see a follow-up in the future?

Always a pleasure,

Ethan W.


Street x Sprezza


  1. Pingback: Having Fun with Socks in Classic Menswear « Fashion
  2. EvanEverhart · June 18, 2018

    Hi Ethan,

    I highly and I mean Extremely Highly recommend Mes Chaussettes Rouges to you as a source of excellent men’s hosiery of exceptional quality, class, and style.

    I have been procuring mine from them exclusively for close to 3 years now.

    I would also recommend that you try hot pink and burgundy socks as well as pale corn-flower blue ones as they are quite classic amd elegant, and I mean sincerely elegant, not igent #elegant/dapper. Another trusty sidekick is olive green. Woolen socks and cashmere or silk blends give the best color saturation and look the most lush and luxe, while linen socks or honeycomb knit cotton socks are of course the best for our current weather.

    The average price dor socks at Mes Chaussettes Rouges is around $20-$35 per pair.

    For white or rather off-white socks, I’d recommend Wigwam woolen socks in natural; they’re the real deal ivy league sock of choice from the “hey day” and still available and rise to your knee. They’re also reasonably soft and run $20-$30.


  3. EvanEverhart · June 18, 2018

    P.S. the hot pink socks are always worn with an olive green or charcoal gray suit with a pale blue or white shirt, or occasion ally with a purple university striped shirt with any of the above or even a brown or golden rod colored suit. I mention it as out of context, the hot pink aocks aound outlandiah amd vulgarly loud.


  4. Pingback: Having Fun with Socks in Classic Menswear -
  5. Steve Morrisette · June 20, 2018

    Nice read – great photos. I am simple happy to see men wearing socks at all these days. And DO hope the “bugs Bunny” type are relegated to the dust bins of history.


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