Can You Wear Boots With a Dressy Dress?

Rachel Bilson looks fabulous in booties and a dressy white dress.

Photo: Jason Merritt/Getty Images Entertainment/Getty Images

When the seasons transition from hot and sticky to blustery and cool, you may think it's time to retire your frilly frocks to the back of the closet. Resist the urge! A fancy dress looks fabulous with boots, whether you're going for a look that's perfect for cocktails and a night out or a casual weekend. Keep that dress out of storage and throw on some tights. It's time to bring some frill to the fall.

Equestrian Riding Boots

When the weather outside is frightful, cozy boots are just what doctor ordered. However, flat, knee-high boots don't exactly go with a suit. To make the warm boots you're dying to wear appropriate for the office, pair them with a dress. A gauzy silk or ruffled dress keeps things at least business casual, and is just contrast enough against more rugged shoes. For a shorter dress, add tights to keep things modest.

Posh Booties

With their closed toes, high heels and full coverage, booties are just right for a more dressed-up look that's still sensible. Wear high-heeled booties with a dressy dress for a special event or a more formal office. The high heels and sleek style make them very cool, but the closed toes keep you a bit warmer than a peep-toe or even a standard pump.

High-Heeled and Knee-High

Like flat boots, high-heeled, knee-high boots add a rugged touch to a fancy dress. To keep things from looking too bold, the dress should very nearly reach the top of the boots. This look is perfect for the weekend, the office or a party. For an even more high-fashion look, try thigh-high boots with a minidress -- but save this style for the club or more daring venues. This is definitely not a just-running-to-the-store outfit.

Winter Boots

Whether your winter boots are fur-lined, lace-up or wedges, this Eskimo-esque style can work with a dressy dress, but is definitely more of a challenge. A dress with Hunter wellies? No. But suede, fur-lined, high-heeled boots with opaque patterned tights and a dress can work. The dressier the dress, the dressier the shoes need to be.

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