13 Cool, Creative Ways to Style a Dress

In theory, a dress is the perfect item of clothing: You just throw it on with a cool pair of shoes and you’re good to go, right? But, if you’re looking to level up your outfits (or, if you’ve worn the same dress in the same way many times and are tired of it), there are some fun and surprising ways to wear a dress. Depending on the types of dresses you have in your wardrobe, they can serve as amazing layering pieces, particularly in the transitional spring and fall months. You can also pair some surprising accessories from your wardrobe to make even the most basic dresses in your closet feel new and exciting again.

If you’re still feeling stumped, here are a ton of ways to style your favorite dresses.

With a Colorful Jacket

There’s nothing that can elevate a look or make it more interesting than a cool coat—especially when the weather’s transitional and you might only need it for outdoors. This tweed dress is already colorful, but the addition of a faux-fur coat brings in dimensionality (not to mention a ton of whimsy).

As a Top Layer

You might not automatically look at a dress and assume it’ll work on top of your other clothes, but that’s exactly what makes it so fun. Because this black option is semi-sheer, it doesn’t obscure the layers underneath, acting almost as a cardigan or jacket.

With Wintry Clothes

A short, summery dress doesn’t have to be limited to the warmer months: When you pair it with tights, a coat, and even a beanie, the dress feels more “grounded.” By itself, the dress might look formal, but the hat and sneakers bring in a casual vibe.

With Contrast

If you’ve got a simple dress you’re dying to wear, but it’s missing a little “je ne sais quoi,” pair it with a contrasting belt (bonus points if you can get your bag to match). Both the dress and the accessories will be the focal point of your maximalist look.

In Place of a Suit

If you still want to look polished in the warm weather but don’t fancy a full suit (who wants to feel hot and clammy?) a suit dress can serve as a chic replacement. Here, the socks with heels and casual updo prevent the outfit from looking overly business-like.

As a Shirt

This is some black-belt-level layering: matching shorts and pants on bottom, partially unbuttoned, with a long dress on top worn as a crop top. If you want to try a similar look, keep the pieces all in the same color family so it looks cohesive.

Over Pants

In order to keep the look from feeling too dated, keep each piece sleek and polished. This looks like slim black trousers underneath a color-blocked dress, so it all feels like part of a coherent look. (If you want to channel a Y2K vibe, swap out the trousers with flare jeans.)

With Colorful Accessories


A simple linen dress is a must-have in your wardrobe—especially one like this that has buttons going down the front, which can give you a fun slit or v-neck when you unbutton strategically. Elevate it with accessories in a surprising color (i.e., yellow bag and sunglasses).

As a Layering Piece (Even in Summer)

If you have two complementary pieces, try pairing them together. This looks like a yellow shirt-dress underneath a black patterned overall dress. Both pieces are light, so it won’t feel too heavy even when it’s warm outside.

With Strategic Sheers

A simple knit dress is perfect to throw on and go when it’s summertime, but it can also be challenging to give it a little something extra. Undergarments (or even a bathing suit) in a contrasting color, which show ever so slightly underneath the dress, make for a surprising layer.

With Heavier Accessories

Don’t put your buckled combat boots away just yet! Obviously this would be a look for springtime instead of the oppressive summer heat (your feet might get…very sweaty, very quickly) but there’s no cooler contrast than a light and airy dress paired with “tough” accessories.

In Place of a Caftan

I’d argue that a loose and flowy dress is the perfect pick for a dinner date or a casual outing with friends, so long as the layers are light. This is a full head-to-toe tonal look, with matching sunglasses and bag, but you can also go with more neutral accessories.

As a Capital-M Moment

We probably all have them in our closet: the big, gorgeous summer dress that we’re dying to wear, but might feel like “too much” for a casual event. I say: Don’t be scared, and throw it on even if you’re not sure! Elevated accessories add polish, but you’ll still look summery-casual.