Q: “When suiting up, should I match the color of my socks to my suit pants or shoes?” – Ken J. 

A: As you can see from the picture above, we’re not all too serious about matching your socks to either your pants or your shoes. If we really had to choose, we’d say match your socks to your pants, to avoid what Glenn O’Brien calls the “Bootee Effect” (looking like you’re wearing bootees by matching the color of your socks too closely to your shoes). Or put another way, you’d much rather have your legs look long rather than your shoes look tall. Does the color of your pants have to match your socks exactly? Of course not, just close, like we did in the pants/sock combo seen here.

But if you asked us for the real answer, we say, to hell with matching your socks with either. Instead, use your socks as a chance to flash some color.  Match it to your shirt, tie, pocket square, boutonniere and maintain the tone of the outfit like we recommend in our article on Stepping Up Your Sock Game. We interpret “tone” rather liberally. Sometimes that means wearing a contrast color. Pick up a pair of colorful, unconventional socks from a company like ZoraabHappy Socks or Sock it To Me and infuse a healthy dose of lighthearted personality to an otherwise serious outfit.

Just don’t take this concept over the top by pairing your white gym socks with your suited getup. Yes, it’s unconventional. Yes, it doesn’t match your loafers or your suit pants. And yes, it will look like a day past laundry day.

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