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I’ve been seeing lots of men pairing colorful socks with dress shoes. What’s up with that?

I’ve been seeing lots of men pairing colorful socks with dress shoes. What’s up with that?

There’s nothing wrong with the old black, blue and brown dress socks growing old in your top drawer. But especially this time of year -- when simple style resolutions go a long way and when the rest of your wardrobe is so full of muted tones -- a flash of color around the ankles can make you stand out … in a good way. As long as you still feel like your dress reflects your personality, the days when yellow socks under a pinstripe suit would get you laughed out of the conference room are gone.

Don’t Be Too Colorful
There are the dark red socks that pick up a pattern in your tie, and then there are the blindingly orange ones that call a bit too much attention to your feet. Wearing nice socks means crossing your legs at a meeting or on a date to offer a flourish -- not a distraction. Take a gamble with green or purple before anything neon.

Match Your Socks Wisely

Like any accessory, socks should match your outfit. Here are a few guidelines:

  • Horizontal stripes are good -- just not with pinstripe suits or corduroys.
  • Patterns are dangerous. Wear them with khakis or basic solid-colored trousers.
  • No white socks with a white shirt, or blue with blue.
  • Brown pants go with brown socks. Just make them very different shades.
  • Brown shoes go with gray socks -- every single time. Just try and find a pair of socks with a burst of color amidst all the darkness.
  • Black shoes make the animals on your socks look less silly.
  • Those socks with the diamond shapes? The ones with the simple dominant color but flashy hues up top? Those are argyle. They are your friend and go with almost everything -- especially suits.

You Get What You Pay For
While companies like Happy Socks offer colorful, surprising options for $10 to $13 a pair, they can also rip easily after repeated wear. Find something slightly thicker from J.Press (up to $40 a pair) or the department store -- look for words other than “cotton” and “nylon” on the label -- and they’ll last you a decade ... or at least until you next resolve to renew that sock drawer.

About the Expert

Jake Ward is a Chicago-based freelance stylist and fashion blogger. Professionally, he matches many things for celebrities who shall remain nameless. He owns more than 75 pairs of socks.