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Long gone are the days when styling a dress follows the same formula. Don’t get us wrong—we love to rock our minis and maxis with a trusty pair of heels, but there comes a time when you feel the need to switch it up in the wardrobe department. For so long, it was flowy gowns with sneakers (chunky ones, preferably) that dominated. Now, the go-to pairing is with boots. The problem? Figuring out which outfit combination actually works.
We’ve narrowed down 10 of our favorite approaches to the dress-and-boot conundrum that will be in your rotation for years to come.
Slip Dresses and Combat Boots
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The ‘90s are stronger than ever, and the return of slip dresses has seeped into our wardrobes. From our experience, the lingerie-esque piece is best worn juxtaposing its soft and feminine feel with a grungy lace-up boot. It not only adds a much-needed edge to a delicate silhouette but it may or may not have you feeling like you’re in an Olivia Rodrigo music video.
Denim Dresses and Buckle Boots
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It seems the shoe of choice this year has been none other than the motorcycle boot. Sure, the emerging style works with other leather pieces or baggy silhouettes, but why not level up with a denim dress? The row of buckles on the side adds a hardcore feel to an overall casual outfit. Best of all, this low-maintenance outfit seamlessly goes from day to night.
Maxi Dresses and Chelsea Boots
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In case you missed it, Copenhagen is the rising fashion hub we’re taking all sartorial inspiration from these days. The city’s kitschy way of styling has introduced fun ways to wear our dresses, and that’s with a chunky Chelsea boot. Take it from the locals themselves by opting for a colorful gown that gives a less serious but still very fashion-forward attitude. As for the boot, you can go for a neutral or add a pop of color with a vibrant sole. Either way, your feet will thank you.
Sheer Dresses and Leather Boots
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Sheer dresses are one of the best trends to come out this year. The skin-baring, cheeky look works especially well for those late nights out, but it doesn’t have to solely be worn with heels. This is where the wrong shoe theory comes into play: add a level of casualness with a pair of leather boots, letting your shoe of choice shine through the mesh fabric.
Cutouts and Thigh-Highs Galore
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For those who enjoy the sheer trend, cutout dresses are likely a staple in their wardrobe. However, if stilettos or strappy sandals no longer seem to do the trick, thigh-high boots can offer a luxurious touch. This is especially true if the dress has a high slit, which only adds to the already dramatic ensemble.
Shirt Dresses and Knee-High Boots
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Make a crisp shirt dress feel even more chic in the office by playing around with proportions. If you’re working in a plain itty bitty button-down, throw on a pair of knee-hitting leather boots.
You can either go for a tiny heel or a thick platform—both of which will give a bit of lift on the legs and elevate your look.
Baby Doll Dresses and Cowboy Boots
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Emma Chamberlain was on to something when she styled her yellow baby doll dress with red cowboy boots—and it still lives on our outfit mood board. A babydoll dress, both mini or midi versions, can add a playful and dainty vibe to the western silhouette.
Neutral Hues and Snakeskin Boots
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If you’re finding your color palette of the day to be on the more muted side of the spectrum, then spruce up your dress with a pair of embossed boots. We’re mostly fond of a snakeskin print, and whether you choose bright neons or toned-down neutrals, it’ll give a much-needed texture and vibrance to your look. Thankfully, with the advancement of technology, there are plenty of ethical choices to choose from..
Play With Colors
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Pairing colors together may seem like a decision destined to clash, but don’t be afraid to add even more color to an already bold dress. An ankle boot provides a comfortable and stylish option for exaggerating those vibrant hues without going overboard. Experiment with different prints and make a statement with this perennial staple.
Mini Dresses and Slouchy Boots
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If you’re into experimental fashion, a slouchy boot might just be the perfect addition to your outfit. To pull off this look, consider pairing it with a micro mini dress—whether that’s a T-shirt dress or a full-on LBD—to avoid being swallowed up by the bold silhouette. And the best part? Depending on the length of your dress, your boots can even double as pants, making it both stylish and comfortable.
