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
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
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
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
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
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
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
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
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
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
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.

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.
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