The Ultimate Guide to Wearing Boots With Dresses


(Image credit: @cassdimicco@michellaccc)

In case you missed it, we've officially entered fall. With this period comes a whole new set of things to be excited about, especially for the fashion set. Autumn is the time when many people decide to get serious about rebooting their closets. For some, that looks like investing in a few trends, and others do a total closet clean-out. While the latter option is noble, the start of the new season can usher in added pressures to "ditch" everything old and bring in the new. There's nothing wrong with wanting to replace a few worn-down staples, but the idea that you should buy an entire new wardrobe every season is unsustainable for the planet and your wallet. It's crucial to find new ways to style items you already own in a way that adheres to the autumn aesthetic.

If you're unsure what pieces lend themselves to doing just that, let us give you one place to start: your dresses. As counterintuitive as it might seem that a dress worn at the height of the summer could transition into the fall, it's definitely possible. To prove that point, we scoured the internet to find outfits that show how to wear boots with dresses. After hours of research, we narrowed down the 10 best boots to pair with every type of dress. Plus, we shopped out the best boots on the market based on longevity, price point, quality, and editorial perspective. Consider this your master class in making last season's dresses feel relevant through styling.



As surprising as it might seem, Western boots are one style the fashion set regularly opts for when transitioning their favorite frocks into the fall. Ranging from knee-length to right above the ankle, the pointed shape of these boots elongates the legs when paired with a dress. The style also adds an intriguing visual juxtaposition between the softer aspects of a dress and the overall rugged feel of these boots. In order to reap the maximum styling benefits of this footwear, try pairing it with either your favorite slip or a sweaterdress. As long as the hemline doesn't cover the boots, they'll look good. 

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Knee-high boots styled with dresses are always a crowd-pleaser—as evidenced by all the looks above. In order to achieve a seamless transition of dresses into the new season, you'll want to be very intentional about the type of knee-high boots you buy. First, you want to opt for a pair that either matches what you already own or comes in a relevant trending color that can be styled with neutrals easily. Secondly, if you want the style to elongate your legs, opt for a version with a pointed toe over others. Lastly, you want to consider whether you want the boots or the dress to be the focal point of your outfit, as that will impact whether you go for a slightly-above-the-knee dress to show off the shoes or have them blend in seamlessly underneath a midi dress. 

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Chelsea boots work for casual and semi-formal outfits, making them the perfect footwear to pair with dresses in the fall. What's great about these boots? They're versatile. Not only can you shop them in various lengths, colors, and materials, but the styling possibilities are also endless. You can pair this boot style with everything from a floral number to a simple slip or relaxed sweaterdress. Just add a leather jacket or cardigan to your look to stay warm on cooler days.

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Don't think you can keep those short dresses out for the fall? Think again. Make dresses with shorter hemlines (e.g., minis, blazer-dresses, and even oversize shirts) feel appropriate for fall by pairing them with very tall boots that graze the thigh. Opting for this boot style will allow you to show a hint of skin between the top of the shoes and the dress's hemline without freezing this fall. Our only advice is to err on the minimal side when it comes to your overall look since these boots already walk on the side of maximalism. 

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Another boot style that can add that signature fall flair to your favorite dresses? Chunky lug-sole boots. In recent years, this footwear silhouette has been a fan favorite among the fashion set because it's comfortable and cool. When deciding what type of dress to wear with chunky lug soles, go for something that will up the contrast between the two items, such as a flowy baby-doll dress or a simple shirtdress. Finish off the look with edgy outerwear to make the dress only cool in the metaphoricall sense, not temperature wise.

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Ankle boots are one of the more straightforward boot styles to pair with a dress. Compared to other footwear, this style doesn't require as much thought when crafting an ensemble. You don't have to worry about the shaft of the boot being too high and looking odd next to the hemline, whether the edgier details will pair well with the frilly elements of the dress, or whether the shoes themselves are too casual. No matter what dress you're wearing, ankle boots will make the look feel pulled-together. However, if you don't know what type of ankle boots to buy, we recommend going for a pair that can be styled for casual and formal occasions to maximize the styling potential. 

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If you thought that moto boots could only be paired with denim shorts or leather trousers, think again. When it comes to making dresses feel more fall ready, there's no better footwear up for the job. The style is not only versatile, but its rugged aesthetic also acts as the perfect balance for delicate dresses. Just be sure to really lean into the rebellious spirit of these boots by pairing them with unexpected dresses—e.g., ones made from sheer lace or featuring billowing silhouettes.

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Take your dresses to new heights this fall by styling them with platform boots. Sure, one might argue that the allure of this style has to do with its recent surge in popularity, but that's far from the truth. For instance, the benefit of styling these boots with a minidress is that they will make your legs look extremely long in a good way. Pairing them with a maxi dress can ensure you don't have to take the item to the tailor in order to shorten the hemline. Ultimately, these boots act as the quickest way to accentuate the best parts of your figure, making them all the more appealing. 

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There's no better way to stomp your way into the fall than with a pair of trusted combat boots. But just because you'll likely be adding more rugged footwear into your daily mix doesn't mean you have to give up your frilly frocks just yet. In fact, in order to give your ensembles a little edge, we recommend pairing combat boots with a printed dress. It doesn't matter if it's a floral dress, a geometric-print mini, or an abstract midi so long as they're paired with lace-up combat boots this fall. 

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(Image credit: @andi_mun@luciacuesta_@monikh@pia_mbd)

You've made it to the end of this story, and hopefully, by now, you've got ample inspiration on how to transition your dresses into the fall by being intentional with your shoe pairings. But if you're still on the fence about which boots are the best, then you'll want to turn to the style that works without fail every time: riding boots. The preppy style is not only versatile enough to be paired with every type of dress, but it also adds an air of elegance to every ensemble. Lean into the timelessness of this style by coordinating the colors and keeping the accessories minimal so that the boots can be the focal point of the outfit. 

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Jasmine Fox-Suliaman

Jasmine Fox-Suliaman is a fashion editor living in New York City. What began as a hobby (blogging on Tumblr) transformed into a career dedicated to storytelling through various forms of digital media. She started her career at the print publication 303 Magazine, where she wrote stories, helped produce photo shoots, and planned Denver Fashion Week. After moving to Los Angeles, she worked as MyDomaine's social media editor until she was promoted to work across all of Clique's publications (MyDomaine, Byrdie, and Who What Wear) as the community manager. Over the past few years, Jasmine has worked on Who What Wear's editorial team, using her extensive background to champion rising BIPOC designers, weigh in on viral trends, and profile stars such as Janet Mock and Victoria Monét. She is especially interested in exploring how art, fashion, and pop culture intersect online and IRL.