The Best Fun Socks for Men to Spruce Up Your Footwear Game

It goes against every men’s style manual ever written. In an attempt to keep men sophisticated, well-dressed, and attractive, tastemakers and style gurus have long decreed that socks should be simple and understated. Plain or subtly patterned versions in neutral colors have always assured a certain nonchalance, conferring a classic expression of ease and savoir faire on the modern gentleman. Even a chunky oatmeal hiking or plain white gym sock adds just the right touch of panache to work boots and jeans. Many men forgo them completely in favor of an elegant flash of tanned ankle. 

But no. When corporate wardrobes became more restricted, there was always that one guy in the boardroom wearing bright pink socks as an expression of his individuality. When dress codes relaxed, the lack of a necktie as a further means of unspoken commentary left men with little to do but “head south,” dressing their ankles in the sartorial equivalent of a flashy gown at a beauty pageant. 

Quoting that late, great man of style, George Michael: “If you’re gonna do it, do it right.” We’ve gathered some of our favorite “fun” socks below. Get ‘em now to throw on with slides or sandals and shorts — driving that elegant knife even deeper — as we tick off the last few unofficial days of summer. Keep ‘em around to wear with slightly shorter cut chinos, or rolled selvage-edged jeans and classic dress shoes. Be the rebel you’ve always wanted to be. 

Happy Socks Rolling Stones Box Set

Happy Socks Rolling Stones Box Set

Get all the satisfaction you need with this three-pair boxed set of Rolling Stones-themed socks featuring the bands iconic “lip & tongue” logo. The set includes “bottom” hits like “Paint It Bright,” “Stripe Me Up” and “I Got The Blues.” The black, blue, green, red, and yellow palette will coordinate with your rock-and-roll style, and generate plenty of reaction.  

Hot Sox Pool Floats

Hot Sox Pool Floats

Long after your suntan fades and the swimming pool is closed down for the season, these socks will keep your spirits up with their festive summery pattern. They’re just as fun paired with a pair of shorts as they are with casual trousers later in the year. The cotton blend fabric will keep feet comfy and cozy.

The British Apparel Group Artistic & Architecturally Inspired Abstract

The British Apparel Group Artistic & Architecturally Inspired Abstract

Bring out your inner architect. This abstract print has a bit of Bauhaus inspiration, the influential German design movement that’s celebrating its 100th anniversary this year. The combination of geometric shapes is reminiscent of the works of the group’s artist Wassily Kandinsky. They’re made in Peru, the home of luxury knitted cotton. 

Stance Reservoir Dogs

Stance Reservoir Dogs

It’s a big year for Quentin Tarantino with his hit movie “Once Upon A Time … in Hollywood.” Celebrate the work of this blockbuster auteur with this pair inspired by his 1992 classic “Reservoir Dogs.” The crisp black and white graphics — with a dash of blood-red at the top — would look great paired with, say,  a classic black suit, white shirt, and skinny black tie. 

Richer Poorer Coaster Crew

Richer Poorer Coaster Crew

Brevity is the soul of wit, and we like the minimalism of this pair that offers just a hint of tropical swagger with its palm tree silhouette on a white ribbed ground. Richer Poorer’s “Silver Lining Blend” sees cotton blended with silver fibers for odor control and added comfort. 

Arvin Goods Crew Socks

Arvin Goods Crew Socks

More sedate than some of the other socks in our category, for sure, but we like the classic double-striped, sporty nature of this classic, especially in this clean Capri blue. They’re also made from a durable upcycled cotton, so by buying a pair, you’ll be doing something that feels good inside and out. 

Chatty Feet Artists Sock Set

Chatty Feet Artists Sock Set

Sometimes even museums have to indulge a wry sense of humor. In this case, New York’s legendary Museum of Modern Art features a sock tribute to some of the great artists of its collection; including Andy Sock-Hole, Frida Callus, Feetasso, and Vincent Van Toe. 

Top & Derby Think Tank

Top & Derby Think Tank

Besides a powerful punch of color, these multi-striped socks also pack a wallop of therapy with unexpected compression power. These comfortable cotton blend socks offer graduated compression to help stimulate blood flow through the circulatory system, reducing leg pain and recovery time for sore muscles. They’re perfect to throw on after a solid leg-day workout, or for long airplane flights. 

Serendipity Custom Pet Socks

Serendipity Custom Pet Socks

If the point of wearing novelty socks is to express your personality, then perhaps nothing could be more expressive than these custom numbers featuring the faces of your very own furry family.  Just upload a picture of your pet’s face that clearly shows both ears, choose from eight background colors, and select your size. In about a week or so you’ll have a pair of socks that will turn heads everywhere from the dog run to the veterinarian’s office. 

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