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How to Wear Fun Dress Socks - A Guide to Men’s Novelty Socks Fashion

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How to Wear Fun Dress Socks - A Guide to Men’s Novelty Socks Fashion


If you have a serious job, your wardrobe is probably equally serious. You’re all work and no play from head to toe, but it doesn’t have to be this way.  Fun dress socks can provide the tiny injection of humor, personality and edge you need to make your work outfits exciting again.  You don’t have to rage against the dress code to make a statement.  Instead, you can slide on a pair of fun socks to turn up the fashion factor without distracting from the rest of your look.

 Socks Types, Lengths & Styles

Types: Socks Fabrication

Unlike your standard issue dress socks, fun novelty socks come in a multitude of types, lengths and styles.  Before you can choose the pair that best suits you, you need to know what’s out there.

Dress sock types are mainly defined by fabrication.  There are five main fabrics you’ll encounter and the one you choose depends on your individual needs.  Cotton is the one you’ll run into the most because it’s the cheapest to produce, it’s extremely lightweight, it’s comfortable and it’s durable.  In casual socks, you’ll find versions made of 100% cotton, but in dress socks, it’s normal to find pairs that combine cotton with other fine fabrics.

If you live in a cold climate, you know all too well how it feels to have cold feet despite wearing socks and shoes.  While cotton is widely available and easily accessible, you need some reinforcement for the winter.  Wool socks cost a bit more but they provide the perfect insulation for those blustery days.


Like any other menswear category, fun dress socks also come in luxury types.  Silk is a go-to for men’s ties, but it also works for socks. Silk socks are expensive, and they’re nowhere near as durable as cotton or wool.  It’s best to reserve these for formal occasions only.  Cashmere offers warm qualities like wool, but it’s delicate.  Delicacy comes at a high price and it’s high maintenance when it comes to cleaning.

Lastly, there are synthetics.  Most socks you’ll find are crafted from a blend of synthetic fibers and cotton or wool.  The combination creates a durable sock that offers comfort and longevity.  Swaggy Socks offers all its cool socks in a high-grade cotton poly blend fabric complete with a cushioned heel.  If you want fun dress socks that will last through the work year, this is the blend you want.  Synthetics by themselves are a hard sell—they’re too soft and too flimsy.

Sock Lengths

Length is a simple matter.  There are three sock lengths on the market, only two of which are in dress socks.  Your gym socks are probably ankle socks.  These are the athletic cotton socks that hit right at your ankle bone.  They’re as casual as you can get and should never be worn to your place of business.


Most dress socks, including your fun patterned design socks, will be mid-calf socks.  The name is self-explanatory—these socks rise to your mid-calf.  They’re just high enough to keep your ankles and lower leg covered when your pant leg rises.  Occasionally, you’ll come across a knee-length pair but this is very old school.  And not just your dad’s definition of old school.  Knights from medieval times wore these under their armor to protect against disease.  Unless you live in the frozen tundra, there’s no reason to buy these.  Mid-calf should be your length of choice for novelty fun dress socks.

Socks Styles

In general, the dandy gentleman invests heavily in neutral socks. These are the navy, black and charcoal gray varieties you see on everyday businessmen. They’re common but they’re also boring. If you want your socks to stand out, you should aim for pop colors (also known as bright solids), intricate patterns or some good old fashioned novelty.  We’ll dive deeper into each category but first it’s important to know when crazy fun socks for men are acceptable.


Where You Should Wear Your Fun Dress Socks

The great news about fun dress socks is there aren’t many places where they’re restricted.  If you’re attending a black-tie fundraiser or a traditional wedding, it’s best to leave your American Flag Socks at home.  It’s acceptable to go for a bold pattern like polka dots or stripes if the rest of your outfit is toned down.  Get a feel for the event first before deciding how bold you want to be.  However, it’s usually a safe bet to skip novelty socks for these occasions.


For work, the rules are a little more relaxed.  If you work in a painfully traditional workplace, learn how to read the room.  While it’s great to stand out, novelty socks may not go over well with your conservative bosses.  Guys who work in storied industries like banking or law may not get a ton of leeway.  But guys who work for startups, specifically in the tech space, and smaller companies won’t have a strict dress code.  In these offices, feel free to express your personality.

Semi-formal gatherings like summer weddings, happy hour, dates, dinners with friends and nights out at the movies or concerts are great places to break out fun dress socks.  

The less stuffy the environment, the more you can play.

The Rules for Bright Colorful Socks

One of the key styles in fun dress socks is the statement color.  Bright colorful socks are meant to be seen and instantly draw attention downward.  Since people will be sizing up your sock game, it’s important to pull off this style move correctly.

 Don’t go rogue and randomly select whatever color your spirit is leading you toward when you get dressed in the morning.  There are rules about wearing these socks.  The guiding force in matching your brightly colored socks to the rest of your look is the color wheel.  The color wheel should be your best friend for every part of your wardrobe but especially for men's fun socks.  The wheel is essentially broken up into warm and cool colors.  The warm colors are the reds, yellows and oranges; the cool ones are the greens, blues and purples.  If you’re going to choose a contrasting bright sock color, it should complement the rest of your outfit.  Greens complement reds, oranges complement blues, purples complement yellows, so on and so forth.


For example, let’s say you’re wearing a navy suit and you pull on a pair of purple socks.  This look doesn’t achieve the level of contrast you were hoping for.  Purple and blue are from the same side of the color wheel and thus cancel each other out.  If you want to make a statement, travel across the wheel for an orange or yellow sock.  These bright hues stand out against your navy suit while also complementing it.

 The only time you can wear blue on blue (or any similar color on top of similar color) is when you wear tonal socks.  That means you’re wearing a pair of socks that’s a different blue than your navy suit.  It’s not as bold as a yellow or orange pair, but it creates a contrast.

Go Bold with Patterned and Polka Dotted Socks

You should keep the bright color rules in mind when you’re selecting prints and patterned socks, but there are some other things to keep in mind specific to patterns.  Unlike solid colors, these fun dress socks are in a class all their own.  


If you’re going really bold, like a Green Apple Polka Dot socks, do so in moderation.  This shouldn’t be the day you decide to show off your new cropped suiting pants.  You want to wear a pair of pants with a classic or medium break, which rests atop your shoe when you’re standing.  When you sit down, only a sliver of bold pattern will show through to the rest of the office.  Anything more and it’ll be distracting for all the wrong reasons. 

Another way to ensure you’re on the right track is to make sure your novelty socks have at least one color from the rest of your outfit.  Let’s say you’re wearing a charcoal gray suit.  You can pair them back to purple socks if you like but they should have a pattern with a gray base or at least some hint of gray to keep things cohesive.

Fun Food Socks

Food socks are reserved for the most fun-loving guys out there.  This means you’ve got a fun personality and you spend your days in environments where your sense of fun is greatly appreciated.  If you’re a hedge fund manager for a 200-year-old company, this might not be you.  But if you just got hired as an engineer at Facebook, this could easily be your go-to move.


Food patterned socks occupy a different space than the previous styles we’ve discussed.  They’re the perfect combination of personality, adventure and kitsch.  They can add a level of intrigue to your look that screams fun.  The previous rules apply though.  So be sure to avoid any clashing between your Morning Coffee socks and the rest of your look.  Also, it’s best to reserve food patterned socks for less formal looks.  Gents who spend the day suited up in the boardroom should avoid them.  But for guys who rub elbows with their peers in a co-working space, mens food socks are perfect.  

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Funny dress socks are the perfect way to keep your look interesting without being too trendy or over the top.  You don’t need to spend thousands or consult a stylist to stand out.  You just need to heed a few simple rules and choose a pair of socks that you identify with. 


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