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Few pairings rival the effortless polish of a dress and boots in colder months. It’s a winning sartorial match, one that is both quick and sophisticated, and makes you feel put together in a flash. From sweater dresses to printed dresses; ankle boots to over-the-knee boots, the combinations are endless.
For new and on-trend ways to wear, take notes from the fall-winter 2025 runways. Minimalists might consider a white shirtdress paired with second-skin glove boots, as seen at Givenchy while maximalists might opt for an embellished dress with croc-embossed boots, like those at Fendi.
Wherever your style may take you, the dress and boot formula is a reliable one that can go from office hours to weekend getaways—the ensembles below are proof. Just add a coat or leather jacket, jewelry, and maybe a belt, and top it off with a great bag.
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Red Dress + Burgundy Boots
A bold red dress finds its match in high-gloss OTK boots. Sticking to shades in a single color is an easy way to make a bright primary hue feel less daring.
Lace Dress + Glove Boot
Opposites attract! Louis Vuitton gives us proof in concept with a lace-trimmed dress and glove boots. The result? A look that’s equal parts romantic and edgy.
White Shirt Dress + Black Glove Boot
Nothing says timeless quite like a crisp, white shirtdress paired with sleek, black glove boots—an enduring look for effortless polish. For the true minimalist, opt for zero or little jewelry.
Drop Waist Dress + Brown OTK Boots
A pink drop-waist dress paired with brown satin boots strikes a refreshing balance of soft and strong.
Brown Sweater Dress + Coordinating Slouch Boot
Brown is the new black! The warm neutral has surprising dimension when worn head-to-toe. Channel Sportmax with a felt cap and an oversized fringe bag for a maximalist touch.
Checked Dress + Cowboy Boot
Plaid gets a feminine spin as a dress, complemented by a cowboy boot for a subtle nod to the West. Loop a belt around your waist for definition.
Mini Dress + Knee-High Loafer Boot
Elevate a itty-bitty mini with a pair of knee-high boots; it’s a versatile combination that works from a day brunch to a dinner party. For cooler temperatures, knot a sweater around your shoulder or slip into a cropped lady jacket.
Lace dress + Snake-Skin Boots
Boho isn’t going anywhere. Indulge in the trend by bringing this Zimmerman look to life with a flouncy lace mini and textured snakeskin-print boots.
Sweater Dress + Knee-High Boots
Grab your knit dresses—it’s sweater weather! Take pants out of the equation and opt for tall boots instead—add depth with a statement necklace and colorful suede clutch.
Floral Dress + Lace-Up Boot
Strike a harmonious chord by grounding fall florals with lace-up boots in this pretty meets punk look. A tried-and-true combo that resonates no matter the dress or shoe.
Drape Dress + Glove Boot
A palette cleanser. A draped dress in white, ivory, or ecru paired with tonal boots makes for a lesson in refrained elegance.
Pinstripe Dress + Riding Boots
Tailored pinstripes gain an equestrian touch when styled with black riding boots. Top off with a sweater tied around the neck and a compact top-handle bag.
New Neutrals: Wool Grey Dress + Snakeskin Boots
Fall’s unsung heroes are anything grey and snakeskin. Worn together, the effect is subtle yet striking.
Embellished Dress + Croc-Embossed Boots
Toughen up sparkle with croc-embossed boots—Fendi proved the mix works.
