12 Ways to Wear Dresses With Boots This Fall

As bittersweet as it may be to say goodbye to the summer season, there is already much to look forward to with the unofficial start of fall. Not only is another fashion month about to be underway, but it’s finally time for a refreshing change of pace in your wardrobe. There is so much more room to experiment with style as temperatures drop—hence why any fashion aficionado will tell you that fall is their season of choice. As we reincorporate layers, jackets, and boots into our everyday wear, things are about to become more visually interesting.

One of the simplest items to pair with a good pair of boots? An equally good dress. So before you put away all of your summer clothing, remember that we’re still in that in-between weather phase. Dresses can help ease the transition and act as a one-stop-shop for achieving a well-styled, early fall look. Whether you’re erring on the more casual side or going for an evening look, a reliable dress and boots combination will instantly make you feel your most stylish.

It’s barely even September and I’ve already worn my favorite pair of knee-high black riding boots with a black off-the-shoulder dress for a night out. There are so many types of dresses—including mini, midi, maxi, and beyond—that will be your go-to with boots for the upcoming months. Below, we've compiled 12 outfit ideas to wear dresses with boots this fall.

With A Slip Dress

Starting strong, fashion influencer Pernille Teisbaek shows us how to wear a black slip dress with a pair of Miu Miu motorcycle boots. What makes this look so good is the balance of the delicate nature of a silk slip dress with lace detailing in contrast with her intentionally worn-in moto boots. Sometimes opting for the non-obvious footwear choice makes for the best outfit (and probably the most comfortable).

With A Knit Mini Dress

Elsa Hosk styled her knit Michael Kors mini dress to perfection. She expertly paired the turtleneck dress with this season’s hottest trend: deep-brown suede accessories. From her pointed-toe boots and slouchy shoulder bag to her western-style belt buckle, Hosk nailed the fall dress and boots combo.

With A Printed Mini Dress

Animal print was seen all over the designer runways (like Prada, Alaïa, and Isabel Marant, to name a few) for fall 2024. So prepare to stun with a printed mini dress and boots outfit this season. Extra points if you can layer with a classic trench coat when it gets chilly. Add a boot with a block heel to take your outfit to the next level.

With A Blazer Dress

My favorite thing to wear as soon as the temperature drops, even just a little, is a tailored blazer. Plenty of brands make blazer dresses that look super chic with a waist-cinching belt, but my advice is to find any oversized blazer in your closet that can double as a dress. Style it with a crisp collared shirt underneath for an extra polished look. And with short hemlines like this one, thigh-high boots are the finishing touch to complete the outfit.

With A Shift Dress

One of the most classic wardrobe staples from the last 100 years (in part due to Coco Chanel) is the shift dress. Flattering on most, the loose mini silhouette is as classic as it is versatile. In this case, an all-black sleeveless version and patent leather over-the-knee boots will give you an effortless look. Bonus points if you add a classic quilted Chanel bag and a black hair bow (also a Chanel signature).

With A White Dress

At this point, we all agree that wearing white after Labor Day is not only acceptable but encouraged. And this square-neck maxi dress with an asymmetric hemline is exactly that. You can easily extend your white dress's wear from summer to fall via a few styling tricks. Jeanne Damas aced this theory by pairing her white dress with suede brown boots, a bag, and a leather trench coat.

With A Fringe Dress

With the rise of boho-chic thanks to Chloé’s fall/winter 2024 runway comes the return of fringe. Not only will fringe jackets be super popular this season but so will fringe dresses like the brown one above. With their inherently flowy nature, fringe dresses go so well with a heeled structured boot and a matching suede clutch.

With A Ruched Maxi Dress

An outfit that never fails me is a long-sleeve maxi dress with boots. Stylish yet comfortable, this gray version with ruched gathered detailing is the easiest thing to throw on without overthinking. You’ll still look put together without having to find separates to style together. Accessorize your maxi dress and boots outfit with a snakeskin envelope clutch and a silver cuff and you’re good to go.

With An A-line Midi Dress

There are few dresses as flattering as the A-line silhouette. Cinched at the waist and wider towards the bottom, this style accentuates your shape. Add a pair of white knee-high boots underneath for the ultimate lady-like look.

With A Gown

Boots and an evening gown may not be the first thing you associate together…but they should be. Any evening gown, especially this black halter-neck iteration, will bode well with a pair of heeled boots for your next black-tie occasion. As I mentioned earlier, sometimes it’s the non-traditional choice that makes for the best outfit. Prepare to ditch your pumps for boots this fall.

With A Scoop Back Dress

When you’re looking to reveal a bit more skin (without overdoing it), a scoop-back cocktail dress is the perfect option. You can wear a long-sleeve version with or without tights and a pair of knee-high block-heeled boots for any parties you’re invited to. A dress with a contrasting texture will also add a lot more fun!

With A Denim Mini Dress

When leaning into a more casual look, you can’t go wrong with a straightforward denim dress. Pair with camel-colored suede boots to bring out the dress’ subtle thread detailing. Add silver statement earrings and cat-eye sunglasses to top it all off.

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