Fall Outfits with Boots

Man and woman having fun outdoor, wearing fall outfits with bootsFall isn’t the start of a calendar year, and yes, the falling leaves are technically dying. But something about the season sparks a sense of renewal. If you’re anything like the footwear-loving folks at Vionic, you view autumn as the best time to overhaul your wardrobe.

When curating seasonal ensembles, it can help to start with your shoes. And what shoes are at the heart of fall fashion? You guessed it: boots. Read on for tips, trends, and outfit ideas to wear with boots this fall. Then, learn how boots should fit!

14 Cute Fall Outfits with Boots

Can’t figure out what to wear with boots? The good news is that they go with a vast range of outfits and clothing styles, plus you can dress them up or down for just about any occasion or weather. You can even choose waterproof boots to keep you chic on rainy days!

But if you’re still feeling stuck or just need a little inspiration to get your wheels turning, you’ve come to the right place. Find our favorite fall outfits with boots below.

Combat-Inspired Boots and an Oversized Button-Down

First up is combat boots with an oversized button-down shirt, a modern take on early 90s fashion.¹ The edgy lace-up styles from Vionic have leather uppers with matching laces and interior zippers for easy on/off.

You can go full-on grunge with a plaid shirt or take a more contemporary route with a crisp white button-up shirt. We love this look with leggings, skinny jeans, or a mini skirt with tights. Ever asked yourself, “what are combat boots?” We have more info for you!

Ankle Booties and Cropped Pants

Everyone can use a good pair of ankle heeled booties for their fall wardrobe, but what to wear them with? Since this shoe style is meant to highlight your lowermost leg, go with a pair of cropped pants.

Jeans, chinos, or trousers will do. And before the frigid winter weather hits, you shouldn’t be too cold, even with a couple inches of ankle exposed. Finish this look with a simple long-sleeve shirt or a slouchy sweater tucked casually into the front of your pants. If you’re looking to get into the winter boot trends, this look is perfect. 


Lug Boots and Athleisure

One thing we appreciate about athleisure wear is that it can be paired with non-sporty staples, like sandals in the summer and lugs in the winter. A hybrid of heavy-heeled combat boots and sleek Chelsea boots, the lug boot features a chunky heel and wide elastic gore panels.

Whether you reach for yoga pants, running tights, a half-zip hoodie, or compression shorts and an oversize crewneck (if the weather permits), you can’t go wrong with this modish, laid-back look.

Chelseas and a Trench Coat

The Chelsea boot is a slim-fitting, ankle-high style with elastic side panels and a pull tab on the back. It comes in various colors and materials, including rubber, leather, and waterproof suede.

Whichever hue or finish you choose, you’ll be dressed to impress in Chelseas and a trench coat this fall. The combination is practical yet polished, versatile, and definitely weather-friendly.²

Miniskirt, Tights, and a Long Jacket

High heeled black boots

Short skirt? Long jacket. There’s not much more this 90s-inspired ensemble needs except a pair of tights and chunky heeled knee high boots. As for your top, you can lean into the era with a fitted turtleneck, a sheer button-down shirt over a camisole, a leather jacket, or a basic long-sleeve tee. Step into the season with confidence by exploring our collection of women’s tall boots.

Jumpsuit and Riding Booties

With a modest shaft height and a low heel, riding booties are versatile and sleek with a practical appeal. Vionic’s styles have weather-treated leather uppers and leak-proof zippers to ensure dry feet all season long. To keep things simple, opt for a full-length jumpsuit, the ultimate all-in-one ensemble.

Trousers, Blazer, and Leather Booties

Aiming for a professional vibe? Consider wearing high-waisted pressed trousers with a black blazer and leather booties. To complete this polished look, slip into a plain tucked-in tee or gauzy blouse, grab your favorite handbag, and you’re good to go.

Skinny Jeans and Sneaker Booties

If you’re on the hunt for a good streetwear look this fall, we recommend sneaker booties and skinny jeans. While some say skinny jeans are on their way out, there’s no denying the universally flattering fit.

Check out the women’s sneaker booties from Vionic. The sporty-chic shoes are available in zip-on and lace-up designs with suede, leather, or textiles uppers.

High-Waisted Jeans and Block-Heel Boots

We’re all about block-heel boots in the fall, with their sturdy soles and vaguely vintage appeal. The styles from Vionic boast exceptionally soft leather uppers and interior zippers for effortless on/off.

Can you wear jeans with heels? You bet! We recommend high-waisted styles, whether you prefer wide-leg, skinny, boyfriend, mom jeans, or boot-cut. If you’re wearing fitted jeans, opt for a slightly looser top, such as a slouchy sweater. And with relaxed fits, balance the look with a slim-cut shirt.

Shirt Dress and Ankle Boots

Want to wear fall dresses with boots? Consider a shirt dress. It’s feminine and flirty but also fashion-forward. And like actual shirts, there are tons of styles to choose from, including t-shirt dresses, button-downs, poplin, wrap, utility, and denim shirt dresses.

Since this dress style is typically on the shorter side, you may want to wear tights or nylons to keep warm. As for your shoes, your best bet is a pair of simple ankle boots. If you’re wanting more tips on how to wear ankle boots fashionably, you’ve come to the right place.

Leggings, Booties, and an Oversized Sweater

Woman in fall boots leaning against an old truck

One of our favorite fall-back ensembles for the season is leggings, booties, and an oversized sweater. This casual getup is effortless, undeniably cozy, and flattering on all figures.

Go with a long, loose-fitting top, whether it’s a thigh-length cardigan, a crewneck sweatshirt, or a slouchy knit sweater. Almost any boot will do, but we love low-heel styles like Chelseas and sneaker booties.

Pencil Skirt and Sock Boots

When you’re heading to the office, a networking event, or a board meeting and want to wear boots, we highly recommend sock boots. Vionic’s styles feature a sweater-like knit fabric around the ankle and weather-treated suede over the forefoot, toe, and heel.

What about the rest of your outfit? We adore the look of pencil skirts, which work well with blouses, fitted button-ups, mock-necks, and bodysuits. Throw on a formal-leaning raincoat or trench, and you’re all set.

Hidden-Heel Wedges and Fitted Black Jeans

If you want to elevate your look without looking overdressed, you should definitely consider a pair of hidden-heel wedges. The designs we carry at Vionic are reminiscent of high-top sneakers but with a 2-inch heel lift, entirely concealed within the soles. Slip into a pair of fitted black jeans, put on a simple t-shirt or mock-neck, and throw on a sportcoat to complete the look.

Heeled Hiker Booties and a Midi Dress

When it comes to fall footwear, we’re big fans of heeled hiker booties. These glamping-inspired shoes flaunt a chunky lug sole and a thick block heel with about 3 inches of height.

While they might seem hard to style at first glance, you’d be surprised how versatile heeled hiking shoes are. Go with a midi dress or midi skirt in a laid-back material such as cotton, flannel, linen.³ A knitted sweater dress is a great choice too. For outerwear, consider a leather jacket, a cropped denim coat, or a suede moto jacket.

Comfortable Cold-Weather Boots from Vionic

Inspired by these fall outfit ideas? You can probably throw together at least a few autumn ensembles with pieces you already own. But if you’re in the market for a fresh pair of fall boots, take a look at the fashion-forward styles from Vionic.

We carry timeless designs and on-trend styles, many of which have weather-treated (if not waterproof) uppers and durable rubber outsoles that will stand up to the outdoor elements. From chunky lugs and Chelseas to low-heel booties and sneakerized boots, we have it all.

What’s more, all Vionic shoes are designed with podiatrist-engineered arch support. They’re also built for stability, proper alignment, and all-day comfort.

Shop our women’s boot collections today!


External Sources:

  1. Anna Laplaca. “16 New Boot Outfits I’m Adding to My Fall Outfit Checklist”. Who What Wear. Nov 8, 2021. https://www.whowhatwear.com/new-fall-boot-outfits
  2. Kathi Burns. “How to Wear Boots”. Wiki How. Feb 25, 2021. https://www.wikihow.com/Wear-Boots
  3. Rickie De Sole. “Outfits to Fall For? Shop 6 Ensembles Perfect to Wear Right Now”. Vogue. Oct 23, 2021. https://www.vogue.com/article/fall-outfits-ideas-to-shop-now

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