I Get Away With Wearing the Same Dress Over and Over Again—10 Looks I Copy

I had a friend over the other day for quick weekend catch-up. Before we headed out to explore the city, I opened my closet to grab a light jacket, and she immediately gasped. I may or may not have an obsession with buying new dresses, so my closet was spilling out with probably well over 50 styles. My love for dresses is so strong because they make it so easy to get dressed.

Although my dress collection seems endless, you'd be surprised by how often I wear my favorite styles. I have an obsessive personality, and when I like something, I love it. It's all in the accessories and styling. Throwing a light sweater over your shoulders or swapping in bold accessories can make all the difference. Below, you'll find 10 looks that will inspire the endless styling opportunities you have in your own dress collection.

Summer Hat + Printed Maxi Dress

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(Image credit: @gracejoshua13)

A very easy way to make your summer dress collection feel brand-new involves investing in a quality straw hat. Not only is it practical and will shield you from the sun, but it's also very chic.

Get the look:

Cardigan + Knit Maxi

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(Image credit: @aimeesong)

Layering is another fabulous way to make a dress feel fresh. Nothing looks more effortless than throwing a light sweater over your shoulders before you head out for the day. It will certainly come in handy when the AC hits.

Get the look:

Basket Bag + Headband + White Dress

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(Image credit: @emmanuellek_)

The princesscore aesthetic is trending, so if you want the look, try following this simple formula. A white flowy dress paired with a headband and basket bag will never steer you wrong.

Get the look:

Button-Down Shirt + Bandeau Dress

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(Image credit: @linhniller)

Behold, my personal favorite way to style a dress. Throwing a white button-down shirt over my favorite styles has never steered me wrong.

Get the look:

Trench Coat + Printed Maxi

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(Image credit: @anna__laplaca)

It's never too hot for a trench coat. Okay, that's actually not true, but I still manage to find an excuse to wear one. It's giving London girl.

Get the look:

Bolero + Minidress

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(Image credit: @littleblackboots)

When you don't want to have bare arms but still love your collection of minidresses, a bolero comes in handy. It's possibly one of the most convenient trends for keeping you warm on particularly breezy days while still allowing you to show some skin.

Get the look:

Punchy Accessories + Black Dress

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(Image credit: @_sierramayhew)

Who says wearing a black dress has to be boring? Style it up with trendy accessories that make a statement, and you could be wearing the same dress for years.

Get the look:

Blazer + Sunnies + Minidress

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(Image credit: @nitsanraiter)

There is really something to be said about the power that a black blazer holds. Give off CEO energy when you style your dress with this timeless wardrobe staple.

Get the look:

Short-Sleeve Shirt + Activewear Dress

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(Image credit: @champagnemani)

Activewear dresses have become much more than something to sweat in. A cult favorite of fashion people, it'll go wherever life takes you—even if it's a night out.

Get the look:

Belt + Minidress

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(Image credit: @chasemarieee)

Adding a belt is always a good idea. Your dresses gain a second life when you pair them with this accessory.

Get the look:

This post was published at an earlier date and has since been updated.

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Associate Editor

Sierra Mayhew was always destined to work in fashion, but she didn't know it at first. Growing up with no choice but to wear a rotation of school uniforms and activewear, her love for fashion really blossomed when she moved away for college and was able to finally define her very own personal style. Shortly thereafter, she interned at Elle magazine and instantly knew that editorial was for her. After graduating from the University of Notre Dame, she worked for ShopBazaar, contributing regularly to Bazaar.com, and finally made her way to Who What Wear, where she is an associate editor. When she’s not working, you can catch her always trying to catch a flight, trying the latest fitness craze in New York City, or exploring luxury vintage boutiques.