10 Men's Dress Sock Rules You Should Never Break

There are a lot of rules in fashion. Like don’t wear white after Labor Day. Don’t mix stripes and plaids. Don’t button the bottom button of a suit jacket for some reason. It’s hard to keep up.

Well, grab your pencils because we’re about to add 10 dress sock rules to the list to help you avoid common dress sock mistakes. Even if you like to artistically break fashion rules from time to time, there’s some dress sock etiquette even rebels like us should stick to. 

Don’t worry, most of these end up being common sense for how to wear men's dress socks, and fortunately, our timeless durability and Lifetime Guarantee have you covered.

Wait, Why Does This Matter?

Dress socks can make a big difference — whether that’s in professional settings, on first dates, or at formal occasions like weddings. Dialing in your socks can complete a polished look, highlight your attention to detail, and most importantly, allow you to have comfortable feet in otherwise uncomfortable dress shoes.

10 Dress Sock Rules for Men

Here are 10 easy-to-follow sock style rules for how to not wear dress socks that will help you avoid common fashion mistakes with socks while elevating your style to a new level.

#1 Don't Wear Cotton Socks with Dress Shoes

Maybe you’ve heard how cotton is rotten for hiking and running, but that holds true for all situations where you’re on your feet for a long time or walking around all day.

With minimal venting and a high chance of walking in the rain to lunch, dress shoes are a recipe for trench foot, especially when worn all day and paired with the wrong socks. Cotton gets damp, stays damp, and holds onto odors like leftover food in a hot car. Merino Wool, on the other hand, wicks moisture and stays odor free — making it the perfect material for no-sweat dress socks.

#2 Toss the Holey Socks

Sometimes even the most beloved, durable socks can meet an otherwise unceremonious end. It takes acceptance and will power to pull the plug and start anew, because there’s no need to wear holey socks. Especially with our Unconditional Lifetime Guarantee.

But beyond that, even the smallest tears can open a rift in your fashion space-time continuum, made even more noticeable while sitting or crossing your legs. Invest in some high-quality, Merino Wool socks and stride through years of enjoyment while avoiding what might by the worst sock style mistake.

#3 Just Say No to White Socks with Dark Suits

It’s not the 1980s. White socks may fit right in at the gym, but they can quickly clash with formal and semi-formal attire.

Instead of giving wedding goers and colleagues reasons to pick apart the rest of your outfit and discover those actually are black sweatpants paired with a suit jacket, blend in with some legitimate dress socks.

Feel free to go dark-colored or even wear a fun pattern. Just skip the white socks (unless they match your light-colored suit pants).

#4 Don’t Let Your Socks Pool Around Your Ankles

The only pools you should be worried about are the fantasy football jackpot, your next vacation, and betting on Tim from accounting reheating white fish in the microwave. If your socks are pooling, you might as well just head home early because it can look sloppy and unprofessional.

Darn Tough dress socks feature a no-slip performance fit. Our complementary blend of the natural elasticity of Merino wool with the natural elasticity with Lycra Spandex prevents pooling, bunching, and slipping.

#5 Why Are You Wearing Socks That Are Too Short?

No need to wish your socks were a little bit taller, wish you were a baller, or wish you had a good dog so you could call her (shoutout Skee-Lo.) Flashing bare ankles can easily undermine the purpose of dress socks and end up looking unfinished.

There are times when this works — with cuffed chinos for example — but in those cases, you also need to make sure your socks are not too tall. They’re called no-show socks for a reason.

#6 Go Easy on the Patterns

It’s one thing to purposefully create fashion chaos with bold, funky patterns, but this strategy can get out of hand in a hurry. Loud socks are great, but paired with equally loud ties or shirts, they can leave you looking more like you got dressed in the dark than the perfectly curated look you were going for.

Create harmony and balance by practicing restraint. Pick a statement piece to focus on and take it easy with the rest of your outfit.

#7 Too Much Clash Is Not a Good Thing

The Clash is an iconic band, but it’s not a good ethos to live by for styling outfits. Rocking a loud look can be a fun complement to any fashion show, but this is a public service announcement — trying to play every instrument all at once is overwhelming and hectic. This is why bands have lead singers and backup singers. Let your socks do the talking and your shirt or tie stick to the harmony.

#8 Leave Stained Socks at Home (or in the Trash)

We’re not even going to bother making a music reference here, because this should go without saying. Don’t show up with stained socks, pretty much anywhere. Even if the rest of your outfit is freshly washed, steamed, ironed, or dry cleaned, dirty or discolored socks are an immediate dealbreaker, a men's dress sock faux pas.

If it’s been a while since you’ve done laundry... you’re an adult; you can figure it out.

#9 Straight Up Skipping Socks Altogether

Unless you’re a venture capitalist living in Ojai with your own brand of organic honey, just keep your socks on. Besides comfort and style, one of the biggest benefits of wearing socks (especially Merino Wool socks) is that they absorb moisture. Without that, where do you think all your foot sweat ends up? In your stinky shoes.

If you want the no sock look, check out our no-show sock selection for all the style points of bare ankles with the function of quality socks.

#10 Pay Attention to the Dress Code

Summer wedding on Cape Cod? Sure, go crazy with some wild print socks, no-shows, or even mismatch them to really stand out. But if you’re showing up to court as a character witness — maybe stick with something more professional or else Judge Judy is going to rip into you.

Lucky for you, we make our dress socks in a range of colors and patterns because we’re trying to set you up for successes, promotions, and dance battles, not contempt of court.

How to Avoid Sock Style Mistakes

While it may seem like there are tons of rules and delicate balances to strike with dress sock fashion, it can be made simple.

For one, invest in a versatile sock wardrobe full of patterns for different occasions. Whether you’re keeping it casual, have a formal event coming up, or just need to embrace the office rat race, having a variety of socks to choose from will give you some options.

Other easy steps to take are keeping tabs on the quality of your socks (no need to wait until the holidays to hope someone buys you a new pair) and being sure to do laundry before you want specific socks.

Some Rules Are Meant to be Broken

If there’s one thing we love more than making socks, it’s challenging the status quo and breaking sock rules. Why else would we guarantee our socks for life? But you need to know what the rules are before you can successfully break them successfully.

Parties, weddings, and all-inclusive cruises are the perfect time to get creative with your fashion, take risks with sock patterns, and live a little on the edge. Regardless, there are still some rules that shouldn’t be broken, some style mistakes with socks to always avoid (looking at you, cotton socks…).

It’d be easy to brush off dress sock fashion tips in lieu of being your own boss, but paying attention to proper etiquette is a sure-fire way to keep you looking your best, no matter the situation. If you felt inspired, enlightened, or personally attacked by these tips, take a few minutes to explore our men's dress sock collection and update your wardrobe.