by Nathan James March 18, 2022

Let’s start with a story. Before joining the family business here at Boardroom Socks, I sold commercial insurance in the Mid-Atlantic. A colleague and I had spent months working on a large proposal for a prospective client. We walked into their office, exchanged pleasantries, then took our seats to get down to business. As my colleague sat down, he crossed his legs and revealed-to my horror-a pair of hot pink and yellow socks emblazoned with tacos. Yes, tacos.

This garish combination caught the prospective client’s eye as well. As he stared at them with a quizzical expression, I sensed our credibility slipping away. How could we be taken seriously if we showed up for a presentation looking like this? But, reverting to navy, grey, and khaki to match my trousers just isn’t a look I go for all the time, regardless of circumstance. Part of connecting with a client is showing a little personality, too.

So, let’s discuss what ‘fun’ dress socks are not. Then, we’ll cover five easy ways to style these socks-without going overboard.

What Fun Dress Socks Are Not- and Why

Socks with tacos, primates, or sea-dwelling animals may be fodder for your weekend Fun Run- but please, leave them out of the office. While, at one time, they may have crept into cubicles along with cropped, extreme tapered trousers and skinny braces, hosiery like this appears more a plea for attention than an indicator of being tragically hip.

Thankfully, this fleeting fancy seems to be on the downward spiral. Men are realizing, as The Wall Street Journal once put it, “crazy socks are passé- relying on them as your trademark has become cliché.”

Why is this, though? Is it that what was once reserved for the quirky character tapping away in the finance department suddenly so saturated the office hosiery market it became the norm? Or, have men begun to evolve sartorially? I’d like to hope it’s the latter.

Five Ways to Wear Fun Dress Socks

1. Light Pattern, Conservative Background

fun black dress socks with red dots


Dots or small squares are unobtrusive, but will still get plenty of notice. So, a pair featuring light pink dots with a neutral background like charcoal, or a primary color background (navy) with a complementary color (like orange) are excellent ways to introduce a pop of color into an otherwise conservative outfit.


2. Bolder, Solid Colors

fun solid red dress socks for men


Business doesn’t have to be stuffy. You can introduce bolder colors into your wardrobe. Bolder shades of blue and even shades of red can be exciting, but tasteful enough to wear to a business lunch. Colors and shades like these are also quite easy to pair with some fitted denim if it happens to be a casual Friday.


3. Subtly Sophisticated

solid burgundy dress socks for men


Darker, regal colors like burgundy or purple are excellent to pair with grey or olive trousers. Keeping a solid base for these colors can also accentuate a suit or set of trousers and help herringbone or (especially) a glen check pattern to pop.


4. Stripes

red and grey striped merino wool dress socks for men


Stripes are an integral pattern in classic menswear for a reason- they work! However, it’s easy to cross into ‘crazy sock’ territory when playing with stripes, so tread carefully. Instead of striped socks that look like a roll of LifeSavers stacked on your ankle, seek out a pair with a neutral or primary color base- like navy. Then, have the stripe act as an accent color- like red or sky blue.


5. Texture and Material

close up image showing texture of merino wool dress socks


We’ve waxed poetic about color and pattern, but some of the best upgrades are often the hardest to spot until you get closer. Instead of standard cotton (even our extra long staple cotton)- try merino wool dress socks. They’re an excellent complement to tweed suits and flannels in winter- and offer fantastic breathability in the summer heat.


Shop Boardroom Socks


A Paradigm Shift in Menswear

The Buffalo Springfield once sang about ‘something happening here. What it is ain’t exactly clear.’ While Stephen Stills was almost certainly referring to something other than menswear, he was nonetheless writing about a paradigm shift. Indeed, I think there is one happening now- and it can be identified in three primary ways.

First, men are learning the importance of harmony in an outfit. The hosiery is intended to complement rather than shout. Few will notice you’re wearing an impeccably tailored suit if you’ve selected a pair of socks with rubber chickens on them. Second, men are placing an increasing premium on materials and quality of construction. Those rubber chickens, like many fast fashion items, are made overseas cheaply and with inferior materials and artificial dyes. They’re a trend- and the manufacturers themselves know it. Third, as we move toward a more ecological and sustainable clothing industry, men are recognizing the importance of where something is made.

Here at Boardroom, we’re the antithesis of fast fashion. Every pair of socks we make is with versatility and applicability in mind. Every pair we make is with quality yarns, whether it be merino wool or long-staple cotton. And, we value manufacturing and producing something here in America.

Thanks for your support.


Yours in Style,


Nathan James

CEO, Boardroom Socks



 Other Helpful Articles on Sock Style:
How to match socks, shoes and pants.
How to wear colorful dress socks.
What are the best dress socks?

Nathan James
Nathan James

CEO, Boardroom Socks

Nathan is an eighth generation textile professional, passionate about producing quality hosiery right here in North Carolina. His favorite dress socks are our burgundy merino wool socks. You will also frequently find him wearing our no-show socks. Outside of the office he enjoys fishing, reading and exploring Charlotte with his wife, son and Golden Retriever.



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