A Guide to Wearing Fun & Funky Men's Dress Socks

Over the years, dress socks have transformed from functional basics in a narrow color range barely worth considering to powerful fashion statements. If you’re asking yourself right now, “what even are dress socks?” Then this is for you. If you already own dress socks and are just wondering what color men's dress socks should be to match the rest of your outfit, this is still for you.

Thanks to this cultural shift, we now have a wide breadth of options available for work, casual situations, special occasions, and more — whether you like to stick to the classics or mix things up with funky dress socks for men. When you add in comfortable, moisture-wicking Merino Wool, you have the ultimate selection of dress socks for any event.

Why Fun & Funky Dress Socks Are a Must-Have 

If you’re looking to express individuality, elevate your style, and add some versatile flair to your wardrobe, then colorful dress socks are the way to go. Fun dress socks for men can add a subtle amount of flavor to any outfit while simultaneously showing restraint.

A yin to the yang of solid-color ties. A much-needed pop to otherwise neutral outfits. With the right dress sock lineup, you can be ready for everything from brainstorming sessions to destination weddings with just a few pairs.

Choosing Fun & Funky Dress Socks 

Sure, there are some unique dress socks for men out there, but you can’t just throw on any and expect to wow. Start by trying to match your socks to your personality. Be honest with yourself.

Are you bold and adventurous? Go quirky with food and animal print options. If you keep things more buttoned up but still want to flex your wild side, try some stripe patterns or vibrant colors. If you find yourself alternating back and forth between a free spirit and toned down, then check out a pair like the Oxford Crew sock or Druid sock for the best of both worlds.

Material choice also plays a big part. First off, say no to cotton – it holds onto moisture like a sponge. We’re talking moisture-wicking, thermoregulating Merino Wool here. Merino fibers can absorb up to 30% of their weight in water without even feeling wet, for dress socks that effectively manage sweat and odor. This versatile material helps keep feet cool when it’s hot and warm when it’s cold.

We make thinner dress socks for daily wear as well as thicker dress socks for when life takes you to colder regions. No matter which style you go with, Darn Tough has high quality men’s novelty socks that are guaranteed for life.

Styling Tips for Fun & Funky Socks 

It's one thing to take a risk and liven up your outfit. It’s another to go overboard and start clashing. The goal is to look like you know what you’re doing, not like you got dressed in the dark.

Two of the most important clash-siderations to take into account are your pants and your shoes. If you’re already wearing patterned or heavily textured pants, then stick to solid color socks. If your pants are neutral/solid then feel free to go with patterned socks. The same principle goes for shoes, suits, shirts, and ties. Neutral solid outfit = funky socks. And vice versa. We’re trying to strike a balance.

For all you rebels and rule breakers out there — listen up. Mixing patterns and unexpected colors can work. Start by pairing highly contrasting patterns and colors first then see where it takes you. At the end of the day, confidence is king. If you feel good, you’ll look good.

Just think about those red-carpet celebrities wearing crazy dress socks and crazier outfits. They know it’s ridiculous, but they rock it with confidence. That’s how new trends start.

The Best Fun Dress Socks for Weddings, Work, & Beyond

There are plenty of places where you can wear fun or colorful dress socks and no one will bat an eye, and other times when showing restraint is the name of the game. But yes, crazy dress socks for work can be cool, just know your audience. From office holiday parties and quarterly sales meetings to outdoor weddings and first dates, here are some occasion-based dress sock Dos and Don’ts.

Office Holiday Party

Do:

• Go wild with your sock choice
• Match the event theme if there is one 

Don’t:

• Don’t remove any article of clothing other than jackets or sweaters
• Don’t forget you’re still at a work event, keep things appropriate 

Office Meetings 

Do:

• Mind the company dress code
• Pay extra attention to not clashing your socks with the rest of your outfit
• Remember the whole balance thing 

Don’t:

• Don’t make your socks a conversation piece
• Don’t leave people questioning your professionalism by wearing mis-matched, flashy socks 

Weddings

Do:

• Wear something fun (bonus points for matching the wedding color theme if you know it)
• Make sure to wear breathable Merino Wool socks for all the dancing you’ll be doing
• Ask permission to go crazy with your socks if you’re in the wedding party 

Don’t:

• Don’t outshine the groom, fashion-wise
• Don’t make your wedding speech all about your cool socks
• Don’t wear funky socks to a formal wedding 

First Date

Do:

• Wear socks that show off your personality
• Use your socks as an easter egg to start conversations
• Feel confident in your sock choice – you got this! 

Don’t:

• Don’t forget to ask some questions
• Don’t bring up your ex
• Don’t wear socks with holes in them 

Top Recommendations

With a lifetime guarantee and made-in-the-USA pedigree, along with super unique and fun prints, Darn Tough offers a wide range of socks for every level of funkiness. From men’s novelty dress socks to colorful dress socks to funny dress socks to flashy dress socks, we have something for everyone.

While not definitive by any means, here’s our official Dress Sock Funkiness Power Rankings, based on the North American Newtonian Funk Scale.

Funkiness Power Rankings (1 is most funky)

1. Animal Haus Crew Lightweight Sock. With imagery of otters rowing boats to gorillas eating ketchup, these are a real conversation-starter.
2. Wild Life Crew Lightweight Sock. These range from dialed back to wacky, depending on how high your pant cuffs go.
3. Spey Fly Crew Lightweight Sock. Starting to move more into all-over prints, which are a little less flashy. If something feels a little fishy, point to your socks.
4. Strut Crew Lightweight Sock. This all-over pattern is a little subtler while still providing some nuggets of fun.
5. Duck Duck Moose Crew Lightweight Sock. An all-over pattern in a darker, more neutral color. Still fun but blends in more.
6. Druid Crew Lightweight Sock. Striped socks are a little more traditional, but these add in some fun colors that bump up the funk. 
7. Oxford Crew Lightweight Sock. With a name like Oxford, this is an Ivy League choice that stays versatile enough for formal and casual occasions.
8. The Standard Crew Lightweight Sock. While neutral and solid, these socks can balance out patterned and loud outfits, and at the same time look professional in the workplace. 
9. Solid Crew Lightweight Sock. Nothing flashy, nothing fancy. These socks mean business when you need them but also make a great neutral to balance brighter outfits.
10. The Standard Mid-Calf Lightweight Sock. Get the job done, then go home. Plus, these come in your 4 favorite colors: black, charcoal, medium gray, and navy. 

To Sum Up

Fortunately, for as many tips as we’ve listed for how to wear colorful dress socks, there are really only a few to truly burn into your brain.

1. Go for Merino Wool.
2. Stay away from pattern clashing.
3. Know when to flex and know when to stay in your lane. 

So, whether you travel professionally for work or are just a professional partygoer, funky Merino Wool men's dress socks are a must-have for anyone who wants to show off their personality, add a little flair to the mundane, and skip out on swampy feet. Because at the end of the day, what you wear reflects yourself and you should do what you can to embrace your personal style. Check out our Men's Dress Socks: A Complete Guide for more guidance on choosing the right pair for you.