Pairing socks with shoes and the rest of the outfit is something I haven’t thought about for a while because it comes naturally.

But, I understand there are a bunch of guys still unsure about which socks to choose when figuring out what to wear for the day.

Some questions you may have: Do I match them to my shoes or my pants? What about my shirt, can I match my socks to that? Should my socks match my underwear? Since my belt and shoes match, should I match my socks to those?

Okay, I was exaggerating a little (hopefully none of you are going out of your way to match your underwear), but some of those questions are valid, and you may find yourself asking them once in a while.

(Side note, I despise the idea of “matching” your socks to anything, and you’ll see what I mean by the end of this article.)

So, if you’re a fan of these Back to Basics articles, you might find this one pretty useful.

Looking for the full-sized version? (right click, Open in New Tab)

So here’s a quick summary:

  • Athletic socks (white and black no-show socks, first sock column) for athletic shoes / casual sneakers only
  • “Dress socks” (everything from the second sock column, on) for every shoe other than athletic shoes
  • No thin / fine dress socks for athletic shoes
  • No white / black athletic socks for dress shoes
  • color tip: Be bold! Don’t worry about matching pants to socks
  • color tip: Pair socks with colors in your outfit, be a little experimental
  • fabric tip: Cotton and cotton blend striped and patterned socks for casual sneakers, casual or dressier leather shoes
  • fabric tip: Thicker cotton and wool varieties for casual leather shoes
  • fabric tip: Fine wool blend and cashmere dress socks for leather dress shoes

See what I did there? There’s absolutely no matching involved between socks and shoes. It’s about pairing socks with colors complementary to the rest of your outfit.

The “Match your pants to your socks” Rule

“But, B, isn’t there a rule that says you should always match (ugh) your socks to your pants? Black pants, black socks? Navy pants, navy socks? Brown pants, brown socks?”

This rule exists 1.) to give the simple-minded, “no gray area” type of guy guidelines to follow, and 2.) because visually, it elongates the leg (a good thing), whereas when you’re matching socks to shoes, it doesn’t do that.

This isn’t a bad rule to follow. In many cases, it’s sufficient.

However, you read the Effortless Gent. You’re not a simple-minded guy, and you know that the gray area most guys avoid is where you can have lots of fun, and where your personal style is developed and defined.

I say forget about this rule. I never deliberately match my socks to my pants. Instead, pick awesome socks with colors that are complementary to whatever you’re wearing. Most of the time, guys don’t have a chance to be too loud or daring with their clothing, but socks are one place where you can have a little fun.

How do I pair my socks with my clothes?

If you’re unsure how to pair your colors together, you may have to think back to art class in elementary school, when the teacher taught you about color relationships. Those same rules still apply.

To keep it simple, you want your colors to be complementary. Which colors are complementary? Bust out your color wheel and choose two colors opposite each other. If that’s too rigid a rule, you basically want the colors to feel good together.

Here’s how to figure out what feels good together. Check out this site, which lists all the basic types of color pairings.

Don’t be afraid of color

I’m a big proponent of color. Most guys don’t wear enough. Most guys stick to blue jeans, black up top, black shoes. Holy effing boring!

I’m encouraging you to explore color as you develop and define your personal style. Color is super important and keeps things interesting. As a refresher, check out the Back to Basics article about color that looks best for your skin type.

Looking for color pairing inspiration? Look through this site’s archives, browse other men’s style sites, check out the menswear stream on Tumblr.

Hopefully this Back to Basics article and my pep talk about going above and beyond your basic black sock convinces you to experiment more in the new year.

Let’s talk more about it

Hope that helps!

Leave a comment below, or we can continue this conversation over on our Facebook group.



socks: Hanes, Corgi, Happy Socks, J.Crew // shoes: Nike, Keds, Sperry, Tod’s, Clarks, LL Bean, Alden // credit: photo, photo

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