Chances are you follow the so-called rule that blue socks are for jeans, tan socks are for khakis, and charcoal and black are reserved for your dark suits. Our advice? Live a little. Working in a stripe or a bit of argyle can easily bring a small but healthy dose of fun to your look. Here’s how to work bold socks into your wardrobe this fall.

The General Rule: The goal here is not to match, but to coordinate. Pick a pair that will offer up some contrast with color and pattern – simple stripes, argyle, or paisley in hues that complement the rest of your ensemble are a good place to start.

How to Pull Off the Casual Look: This is easiest to execute when the rest of your look is basic. Begin with jeans or chinos, add a Henley or light sweater, then finish with the socks and a pair of chukka boots. Give your pants a few rolls so about two inches of sock shows when you stand.

How to Pull Off the Suited Look: Attending a wedding? Trying to amp up date night? Pair your suit with a button-front in a check or stripe and choose a different pattern for your socks – think polka dots or a simple colorblock. Finish with oxfords or loafers. The show is on when you sit.

When to Avoid Them: For serious business meetings or somber occasions like funerals, stick to your tried-and-true neutrals. There’s a time and place to be fun and playful. This isn’t it.

Amp up your sock game this fall. Shop our Men’s Fall Shoes & Bold Socks: Wear Them Together Boutique, which opened Thursday, September 11, at 11AM ET.

By Chrissy Makkas, Staff Writer

How do you work bold socks into your look? Tweet us at @ruelala to share.

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