The Most Fashionable Shoe Choices To Pair With Your Dresses This Season

Shoes are a key element to any look. They can dial an outfit back to make it more casual or elevate the look for more formality. Plus, shoes are a great way to give off personality without ever saying a word. In fact, a 2012 study by The Journal of Research in Personality showed that participants were able to guess a good number of someone's personality traits by simply looking at their shoe choice. Knowing this alone should have you questioning your shoe choices with every outfit you put on.


The shoes you pair with a dress determine the entire look. Where once heels were the go-to shoe for dresses, this season, anything goes. Especially during winter, heels may not make for the most practical shoe as your feet may get too cold or worse — you may be more prone to slipping on ice. Plus, heels and your personality might just not like each other — and that is okay!

Luckily, there are plenty of options that will make for the ultimate pairing with your favorite dress. We have curated our top six picks for shoes to pair with your dresses this season.

Knee-high boots

Knee-high boots are the shoe trend of the season, especially when paired with dresses and skirts. The trend piggybacks off of the aesthetics that are also on fire this season, such as old money and academia. These types of boots have a sleek silhouette that dresses up any look, while remaining warm and more comfortable for the winter season.


A dress is a perfect way to show off the entire boot. We love knee-high boots with a plaid babydoll dress for a chic and classic outfit, as styled by fashion influencer Micah Dearman on Instagram.


Loafers are another shoe trend picking up steam due to the popular academia TikTok aesthetics. Coincidentally, the loafer is a great shoe to pair with your favorite winter dresses. With a longer dress, frilly ankle socks with your loafers often add a feminine touch to the look. For a shorter dress, wearing knee-high socks or tights add a retro vibe that will also help keep you warm.


Instagram fashion influencer Sarah Mantelin shows us how it is done by wearing loafers and tights with an oversized shirt dress. The loafers and tights balance out the shirt dress for a perfect mix of masculinity and femininity.

Grunge boots

Grunge boots are another fall and winter shoe trend that happen to pair very well with dresses. Like loafers, these boots play off the masculinity they bring to the traditionally feminine dress look. Combat boots are perhaps the most common edgy boots to wear with dresses.


MasterClass recommends wearing a sweater dress and tights with your combat boots for an equally chic and warm outfit. If you are looking to make a bold statement this winter, you can also pair a very feminine dress with your grunge boots.

Casual sneakers

Whether vintage Reeboks or chunky New Balance dad shoes, casual sneakers are great to pair with dresses. They are also much more comfortable and safe to wear during the winter months, as heels and snowy conditions don't tend to mix well.


Sneakers are not new to the dress scene but are most often seen worn with short sundresses. In winter, try wearing your favorite sneakers with a feminine fit and flare long sleeve, or a maxi dress and jacket like Instagram fashion influencer @superkombi.


Clogs are one of the hottest shoe trends of the year. This once-considered "ugly" shoe has made a resurgence with celebrities like Kendall Jenner and Rihanna hopping on the trend. Other Y2K trends have returned with vengeance and clogs are proving to be no exception.


The clog trend is versatile in more ways than one, as the shoe goes with almost any outfit and comes in a variety of styles, colors, and heel heights. They even pair well with your fall and winter dresses, such as knit maxi or an oversized sweatshirt dress as seen on fashion Instagram influencer Viviane Audi.

Cowboy boots

Yee-haw! The cowboy boot trend has infiltrated the market over the past several years. While there are some obvious ways to wear cowboy boots, such as with blue jeans or denim shorts, there are some unconventional ways to wear the shoes as well. One of these ways is with your winter dresses.


The boot will keep your legs warm while making a fashion statement. Instagram fashion star @mdfhima has cracked the western boot code, pairing a pair of suede cowboy boots with a dark green sweater dress.