7 Shoe Styles That Always Make My Dresses Feel 10 Times Cooler

I'm going to be honest here and admit that I've actually never worn heels with dresses. I'll include the mule or block heel in there once in a while but I think there are other styles that not only are more comfortable but simply make your dress look ten times as cool and elevated. If you're used to wanting to throw a pair of stilettos or pumps on with your dresses and want to change it up but don'tknow where to start, I'm here to help. It's my job to, after all. 

Below, I've listed 7 shoe styles that I always count on for pairing with any kind of dress from flowy maxis to silk slips. Whether you tone your dress down to the more casual side with a pair of converse or have knee-high boots that’ll complement your ensemble, your outfit will still feel complete even if you aren’t wearing heels. See for yourself below.



(Image credit: @fashionwithjazz)

You can never go wrong with a pair of classic chucks—I wore them in middle school and you'll still catch me wearing them today. They pair well with longer lengthed dresses that hit at the ankle.

Cowboy Boots


(Image credit: @thatgirlyusra)

Even if you're wearing cowboy boots underneath a long dress, just the sharp pointed toe already adds a cool-girl element to your fit. I personally love the taller versions, but the shorter ones are growing on me slowly. 

Dad Sandal


(Image credit: @itsmekellieb)

Back when vacations were a thing, dad sandals were all I wore with dresses. I haven't found a shoe that beats the comfort level on these.

Biker Boots



(Image credit: @LOULOUDESAISON)

I didn't think this one through till recently when I spotted classic loafers all over the fashion scene and thought I'd give it a try with dresses. SInce they're usually paired with more structured pieces, I think they add a contrast to the flow of a dress.

Knee Highs


(Image credit: @SYLVIEMUS_)

Slouchy knee-high boots look effortless yet elevated in the best way possible. It could be a bare leg moment with a mini dress or a subtle peek under a maxi dress looks just as good too. 

Strappy Sandals


(Image credit: @mariaalia)

If you still want a dressed-up element with a heel, I'd recommend a strappy sandal over a stiletto or a pump. They're comfier than they look, and they're clearly very loved by fashion girls everywhere.

Associate Fashion Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.