If You're Unsure About Wearing Dresses With Boots, I'm Here to Convince You
With brisk, cold temperatures on the forecast for the foreseeable future, I've been trying to think of more cozy outfit combinations that don't only involve comfy jeans, chunky sweaters, or the same winter coat that I've basically been living in for the past four months (the cold weather fashion fatigue is starting to get very real, folks!). While layers might be the name of the game this season, that doesn't necessarily mean you have to sacrifice your own personal style to embrace them — or set aside your favorite dresses, for that matter. Transitioning all of your go-to summer and fall dresses into chic winter styles can be as simple as matching them with a great pair of boots and some tights — turning even the flimsiest dress into a darling winter look that packs ample warmth and style.
My guiding style principle when it comes to wearing dresses with boots is to mind the proportions. Ideally, any combination of the two would elongate, support, or enhance your figure, rather than appear forced or constricted. To help you nail the dress-and-boot combo this winter, I went ahead and shopped out a handful of frocks that you can easily throw on over your favorite boots. Whether you're opting to wear a long dress with ankle boots, a short dress with knee-high boots, or even a midi dress with Chelsea boots, the styling opportunities are truly endless. Scroll on to shop our picks for the best dresses to wear with boots this season!
— Additional reporting by Shelcy Joseph
Best Midi Dress to Wear With Boots: The Drop Karl Long Sleeve Smocked Midi Dress
Slip into a style that's as unique and elegant as you are with this The Drop Karl Long Sleeve Smocked Midi Dress ($32, originally $70). The colorful piece features a flattering square neck design, a relaxed silhouette, and long puff sleeves that feel as effortless as they look. Style it with heeled boots for an elevated yet relaxed winter style.
Best Dress to Wear With Chelsea Boots: Steve Madden Crissy Long Sleeve Dress
Frankly, you can pair this Steve Madden Crissy Long Sleeve Dress ($47, originally $79) with really any style of boot that you'd like, though I personally think it would go beautifully with a Chelsea or combat boot. With the frock's body-hugging silhouette, a chunky ankle or mid-calf boot will complete the look with an added structure that's sure to flatter your body in all the best ways.
Best Dress to Wear With Cowboy Boots: Wrangler Retro Western Denim Snap Dress
Few combos feel more classic than a pair of cowboy boots styled with a timeless denim dress — especially if they're as chic as this Wrangler Retro Western Denim Snap Dress ($46, originally $50). Unlike traditional styles, this piece comes with an open-collar design and wrap-tie accent that complete the look with a universally flattering fit.
Best Sweater Dress to Wear With Boots: Edikted Jazlyn Long Sleeve Rib Sweater Dress
This Edikted Jazlyn Long Sleeve Rib Sweater Dress ($90) will charm everyone at the next brunch party or office gathering. We love the frock's fitted rib fabric, plunging neckline, and functional midi length which helps to provide ample coverage and warmth, while still feeling totally breathable, too.
Best Dress to Wear With Knee-High Boots: Topshop Printed Ruffle Wrap Long Sleeve Minidress
This playful Topshop Printed Ruffle Wrap Long Sleeve Minidress ($93) features a deep V-neckline design that dials up the allure (and sass) of what's otherwise a classic cropped dress. We love the style's fit-and-flare silhouette. Dress up the patterned frock with a pair of a knee-high boots for an ensemble that can easily take you from day to night.
Best Amazon Dress: DB MOON Casual Long-Sleeve Dress
If you want a professional-looking dress that is also stylish, this DB MOON Casual Long-Sleeve Dress ($38, originally $46) is easy to dress up with heels, boots, or even a comfortable pair of sneakers. Plus, the style's airy material makes it the perfect piece to wear all day and with total ease.
Best Long-Sleeve Dress to Wear With Boots: Farm Rio Jungle Pattern Crewneck Dress
We love a printed dress, which is probably why this Farm Rio Jungle Pattern Crewneck Dress ($150, originally $200) immediately caught our attention. It has a relaxed yet put-together appeal that makes it a winner in our books. And with the frock's multicolored design, you can pretty much pair it with any boot in your wardrobe and be on your merry way!
Best Maxi Dress to Wear With Boots: H&M Square-Neck Jersey Dress
This H&M Square-Neck Jersey Dress ($30) carries a certain regal elegance, thanks to the style's vibrant yellow coloring, square neckline design, and breezy leg slit that's sure to accentuate your go-to pair of knee-high boots in all the best ways. Did we mention it also comes in a variety of other designs, too?
Best Ribbed Dress: Loewe Gray Anagram Embroidered Cotton-Jersey Midi Dress
This Loewe Gray Anagram Embroidered Cotton-Jersey Midi Dress ($890) offers a loungewear-inspired twist on the traditional tank dress, and we love its cozy yet understated color. Complete your outfit with a pair of ankle boots for a shoe that'll elevate your look in the most subtle way.
Best Shirtdress to Wear With Boots: Zara Belted Shirtdress
From brunch to the office, post-work cocktails, and beyond, this Zara Belted Shirtdress ($80) is a style you'll be reaching for time and time again. The understated piece boasts a totally timeless appeal that makes it easy to dress up or down. I'd personally style this with a pair of heeled ankle boots for the most elevated daytime ensemble.
Best Winter Dress to Wear With Boots: Superdown Sanja Sweater Dress
A cropped sweater style like this Superdown Sanja Sweater Dress ($78) might not be the most obvious outfit choice for winter, but that doesn't mean that it shouldn't be. Crafted from a thick, knit material, the style provides ample warmth through even the chilliest winter temperatures. Pair it with your go-to, knee-high boots for a fresh take on a wardrobe staple.
Best Off-the-Shoulder Dress: Dyanmite Long-Sleeve Asymmetrical Sweater Dress
This Dyanmite Long-Sleeve Asymmetrical Sweater Dress ($75) features thigh-high side slits and an off-the-shoulder neckline with a ribbed panel for a sleek, asymmetrical ensemble. It works as both a daytime and nighttime look — simply pair it with ankle boots during the day and throw on your favorite pair of over-the-knee boots come evening.