7 Casual Shoes That Play Exceptionally Well With 2020's Dress Trends

If it seems like all we do is talk about dresses, well, you'd be right. But can you even blame us for going on and on about them when each new dress trend is even chicer than the last? Whether it's the '90s-style slips or all those pretty puff-sleeved numbers, suddenly all we want to do is throw on a frock and call it a day. The only other consideration to make when putting together a dress outfit is which shoes to wear which, as the headline suggests, we're about to get into here.

Ahead, we're sharing all the casual and easy-to-wear shoes that will look really, really good with all of the cool dresses you're probably already wearing. From boots to sandals to flats, there's something for everyone. With me? Good, then simply continue on to discover these casual shoes with dresses, see how the fashion set it styling them, and, of course, peruse our favorite shopping picks for each. 

Retro Sneakers

Throwback kicks from brands like New Balance, Nike, and Reebok are the new "dad" sneakers. They're clunky, but not too heavy-duty, and look especially cool with tall socks and any of the pretty dresses currently trending.

Pairs well with: Floral dresses, puff-sleeve dresses

sneakers with dresses


dresses with chunky sneakers



Minimalist Mules

The '90s are calling. Super-sleek and pared-back mules, especially in neutrals like beige and black, are the versatile closet staple fashion girls wear with everything from dresses to jeans.

Pairs well with: Reworked shirt dresses, slip dresses

mules with shirt dresses


best casual shoes with slip dresses



Tall Boots

Fall is coming, whether we like it or not, and with it some new and improved boots. Classic knee-high's are here to stay and whether flat or heeled, they happen to look great with any number of dresses, but we're especially fond of wearing them with little mini dresses.

Pairs well with: Simple mini dresses

shoes with slip dresses


tall boots with mini dresses



Fishermen Feet

Fisherman-style shoes are the latest "ugly" shoe trend to emerge this year and fashion girls have been all over the style, especially The Row's Gaia sandals. Unlikely as they may be, they're definitely comfortable and a cool way to toughen up a feminine frock.

Pairs well with: Interesting LBDs, puff-sleeve dresses

shoes with summer dresses


shoes with black dresses




These modern-day flatforms remind me so much of the ones I used to wear back in the late '90s only a lot more wearable. Black sandals of any variety from slides to flip-flops are made all the chicer with a lifted sole.

Pairs well with: Wide-cut and billowy dresses

casual shoes for dresses


sandals with printed dresses




Another unlikely shoe style? Clogs. Thanks to new designer versions from Jacquemus and Loewe, they've never been cooler than they are now.

Pairs well with: Knit dresses, slip dresses

flats with knit dresses


flat shoes with dresses



Lace-Up Sandals

Last but not least are, in my opinion, the prettiest shoes of the bunch: lace-up sandals. While they can definitely be casual, they really do elevate whatever you wear them with, which makes them the perfect companion to outfit basics.

Pairs well with: Tank dresses, printed dresses

sandals with dresses