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

Yusra Siddiqui
·3 min read

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.


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.

Converse Chuck Taylor® High Top Sneaker ($55)

Converse Run Star Hike High Top Platform Sneaker ($110)

Converse Leather Chuck Taylor All Star ($70)

Cowboy Boots

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.

Zara Animal Print Cowboy Heeled Ankle Boots ($50)

Jeffrey Campbell Dagget Western Boot ($260)

Isabel Marant Denvee Suede Knee Boots ($875)

Dad Sandal

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.

Teva Hurricane Drift Water Friendly Sandal ($40)

Arizona Love Trekky Chic Faux Pearl-Embellished Canvas Platform Sandals ($220)

Birkenstock Arizona Big Buckle Slide Sandal ($150)

Combat Boots

If you're looking to add a little edge to your look, this is the way to do it. I love the juxtaposition of a chunky stomper boot with a feminine dress.

Ganni Track Sole Combat Boots ($475)

Sam Edelman Lydell Mixed Media Combat Boot ($150)

Dr. Martens 'Jadon' Boot ($180)


I didn't think this one through till recently when I spotted chunky 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.

Steve Madden Malvern Loafer ($89.95)

Stuart Weitzman Mickee Flat Loafers ($450)

Zara Leather Loafers ($99.9)

Knee Highs

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.

Staud Benny Boots ($330)

Mango High Heel Boots ($80)

H&M Knee-High Leather Boots ($149)

Strappy Sandals

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.

Jeffrey Campbell Fluxx Sandals ($130)

& Other Stories Strappy Leather Heeled Sandal ($129)

By Far Edita Sandals ($123)

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This article originally appeared on Who What Wear

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