How to Wear a Cocktail Dress With Thigh-High Boots

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Thigh-high boots can be intimidating to wear. But there are ways to overcome the fear of looking like Julia Roberts in ‘Pretty Woman’. In fact, we recently wrote a style guide on how to wear over-the-knee boots.

As long as you follow the 5 simple guidelines featured in the article, then you don’t have to cringe at the thought of wearing thigh-high boots ever again. But let’s talk about something else. What about wearing thigh-high boots to say, a cocktail party or a high-profile event? Can you? Would you?

Today, we’re going to show how, courtesy of some famous personalities. True, a lot will depend on the kind of event you’re off to. If it’s the Oscars, then be ready to ditch the boots for a pair of high-heeled sandals and a long gown.

But if it’s a movie premiere, a launch, a more low-key award ceremony, a fashion shindig, or a company party, then go right ahead and pair your cocktail dress with those standout boots. Just remember to take note of the following:

1. Pick the Right Boots

The first rule of thumb is to make sure you pick the right pair of boots. Stay away from patent or high shine.

Next is to pick boots that are elegant, sleek, and sophisticated. Avoid bulky boots with extreme platforms or heels. Go with a silhouette that will easily complement your cocktail dress.

Highland Suede Over-the-Knee Boots, $439.99 – $798.00 at Amazon

Stuart Weitzman Highland Suede Over-the-Knee Boots

Lastly, make sure you wear boots that are classic and neutral in color. Avoid boots with too many patterns or too much decoration.  Black suede is always the safest and the easiest to pull off.

You may also wear boots made of matte black fabric materials like neoprene — just like Charley Webb’s pair below.

Charley Webb wears thigh-high boots with a black dressCharley Webb wears thigh-high boots with a black dress at 2013 Inside Soap Awards at the Ministry of Sounds in London on October 21, 2013

2. Pick the Right Cocktail Dress

Once you’ve acquired your boots, the next thing that you should do is to pick the right cocktail dress to match. Never use a dress that is too revealing or too sexy. Over-the-knee boots, no matter how simple they look, are oozing with sex appeal, so downplay them by going for a more conservative-looking frock.

Dresses with sleeves work best. If you’re going to use a dress that is glittered, sequined, or patterned, make sure your boots are classic and understated. Also, be sure to pick a frock that isn’t too short nor too long.

Maintain a 3-inch gap between the hem of your dress and the top of your boots. If you want to push it, maybe 5 inches max.

Lilly Pulizer Kariano Wool Crocheted Dress, $228 / French Connection Sequined Panel Dress, $298 / Milly Butterfly Sleeve Dress, $350

Cocktail dresses with sleeves work best

Here’s Petra Nemcova sporting a champagne-hued beaded long-sleeved number with her thigh-high boots. The conservative sleeves kept the boots from looking too sexy, while her glittery dress provided a wonderful contrast to the matte texture of her shoes.

Petra Nemcova wears a cocktail dress with thigh-high bootsPetra Nemcova wears a cocktail dress with thigh-high boots at the Atelier Pronovias 2014 Bridal Show in St. James Church in New York on November 12, 2013

3. Keep Your Accessories to a Minimum

Generally speaking, over-the-knee boots are statement accessories. That means you have to keep your add-ons to a minimum — especially if you’re going to pair your boots with say, a patterned or beaded dress.

Petra Nemcova (above) and Jamie Chung rocked their boots with barely-there extras. Petra went with a neutral clutch and very delicate strands of bracelets, while Jamie completely opted out of accessories save for a black hard case clutch and matching red lipstick.

Jamie Chung in a brocade red-and-black sheath dress by ParkerJamie Chung in a brocade red-and-black sheath dress by Parker attends the Victoria Secret Fashion Show in New York on November 13, 2013

Jimmy Choo Tamba Over-the-Knee Boots, $1,895

Indulgent stretch leather elevates a timeless over-the-knee boot with a smooth, svelte silhouette

Credit: Jeff Grossman / Jeff Grossman / Lia Toby / WENN