16 New Boot Outfits I'm Adding to My Fall Outfit Checklist

·6 min read

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Maybe it's because I'm a November baby, but once the weather starts to turn crisper, I pull out all the stops to curate my ultimate fall wardrobe. In my humble opinion, this time of year brings out the very best in fashion, and let's face it: Boots are at the heart of it all. From roughly September through March, I wear boots more than any other shoes.

Since I'm already in full fall-outfit-planning mode, I have my eye on a few boot trends I want to try out, like chunky Chelsea boots and class knee-high boots. As for how to wear them? As you gleaned from the title, I compiled a roundup of 16 new fall boot outfits I fully plan on trying. For a little outfit inspiration and some of my favorite boots on the market, just keep reading.

WHO: Marilyn

WEAR: Skirt Suit + Collared Shirt + Chunky Chelsea Boots

Chunky Chelsea boots are the fall 2021 boot trend everyone has agreed on, and Marilyn's styling idea here is further convincing me. Her skirt suit leans classic and polished while the boots help to toughen up the look and make it feel oh so current.

Shop similar boots:

Mango Leather Track Sole Ankle Boots ($150)

WHO: Marianne Smyth

WEAR: Shacket + Straight-Leg Jeans + Chunky Boots

Now for the fall outfit formula you can always rely on: jeans, a cozy shacket, and ankle boots—made all the cooler with Marianne's chunky-soled pair.

Shop similar boots:

Loeffler Randall Bridget Chelsea Combat Boots ($395)

WHO: Sophia Brenn

WEAR: Trench Coat + Shoulder Bag + Trousers + Combat Boots

Fact: Throwing a trench coat on top of just about anything makes it automatically appear more put-together, and this is a prime example of that. Paired with combat boots and a cool bag, the look is as easy to re-create as it is practical and weather-friendly.

Shop similar boots:

Rag & Bone Shiloh Combat Boot ($525)

WHO: Sylvie Mus

WEAR: Oversize Button-Down Shirt + Knee-High Boots + Shoulder Bag

Will I ever be over '90s style? I don't think so. Sylvie's take on '90s-inspired minimalism is commendable, and I plan on trying to re-create my own version of this with throwback elements like a shoulder bag and knee-high boots.

Shop similar boots:

Vagabond Shoemakers Hedda Knee High Boots ($240)

WHO: Javi

WEAR: Crop Top + Bootcut Jeans + Printed Ankle Boots

Name a more classic pairing than jeans and ankle boots—I'll wait. Javi's take on the timeless duo feels fresh thanks to upgraded classics like bootcut jeans (another fall 2020 trend) and eye-catching printed ankle boots, which add interest to an otherwise neutral look.

Shop similar boots:

Good American 110mm Icon Booties ($249)

WHO: Emmanuelle Koffi

WEAR: Trench Coat + Knee-High Boots + Cardigan

In case you weren't convinced of the power a trench coat has to make an outfit, let this be my final argument. Emmanuelle threw hers on over a cute cardigan and paired it with knee-high boots. It's Parisian-chic.

Shop similar boots:

Who What Wear Cate Knee High Boots ($159)

WHO: Anne Laure-Mais

WEAR: Trench Coat + Mini Dress + Knee-High Boots

Throw on a long jacket over a mini dress or mini skirt and knee-high boots for an overall sleek effect, and if you want to freshen up the ensemble, grab a '90s-inspired baguette bag.

Shop similar boots:

Sarto by Franco Sarto Fera Over the Knee Boots ($170)

WHO: Najma Ahmed

WEAR: Leather Blazer + T-Shirt + Jeans + Platform Boots

Why wear a classic blazer when you can make it leather? An oversize blazer looks all the cooler in sleek leather but just as easy to throw on with jeans and a tee. It's also the outfit trend cool girls are leaning way into this fall.

Shop similar boots:

Dr. Martens Jadon 8 Eye Boots ($200)

WHO: Sofia Coelho

WHAT: Knit Vest + Collared Shirt + Trousers + Ankle Boots

I've already expressed my love for knit vests, but one more time couldn't hurt, right? This look hits the mark because it emulates that prep-school vibe that's trending right now, and the heeled ankle boots give it a polished feel.

Shop the boots:

Lola Cruz Pointed Toe Bootie in Camel ($242)

WHO: Renia Jaz

WHAT: Utility Jumpsuit + Riding Boots + Structured Bag

When you just can't be bothered to come up with anything complicated to wear, try this easy-but-cool jumpsuit outfit by tucking the pant legs into a pair of tall boots.

Shop similar boots:

H&M Leather Boots ($139)

WHO: Martina McFarlane

WHAT: Printed Minidress + Mini Bag + Croc-Effect Boots

Print clashing is not for the faint of heart, but done right, it's impressive. One way to test it out is by wearing textured boots as one print and a patterned dress as the other. Mock-croc boots work well for this.

Shop similar boots:

Schutz Maryana Flare Croc-Embossed Leather Boots ($238)

WHO: Stephanie Arant

WHAT: Cropped Blazer + High-Waisted Jeans + Square-Toe Boots

Traditional blazers are cool and all, but cropped blazers are hitting the spotlight this fall, and we couldn't be more obsessed with this styling of them. Try high-waisted jeans to meet the blazer hem and pair with square-toe boots for an edgy spin.

Shop similar boots:

Calvin Klein Cassia Square Toe Boots ($150)

WHO: Funda Christophersen

WEAR: Skinny Jeans + Knee-High Boots + Blazer + Oversize Sweater

All out of ideas with your skinny jeans? Take a cue from Funda's look here and tuck yours into knee-high boots for a fashion-forward spin. Tie a sweater over your shoulders to give your look even more style.

Shop similar boots:

Aeyde Laura Tall Boots ($675)

WHO: Camille Charriere

WEAR: Long Sleeve Tee + Shorts + Western Boots

Try this transitional look before the weather truly feels cold. Pair a long sleeve with simple shorts (or a mini skirt) and finish with trendy cowboy boots.

Shop the boots:

Zara Leather Cowboy Boots ($199)

WHO: Noni Cyngor

WEAR: Cropped Sweater + Cargo Pants + Lace-Up Boots

Ground relaxed cargo pants with sturdy boots, like combat or lace-up boots, and finish it with a cropped sweater for a look that's casual and comfortable.

Shop the boots:

Sam Edelman Garret Bootie ($180)

WHO: Rachel Everitt

WEAR: Puff-Sleeve Shirt + Pinafore + Chunky Knee-High Boots

The prep-school vibes continue. Layer a collared shirt underneath a pinafore dress (any sleeveless dress will do) and wear with chunky rubber boots. The Ganni pair below is a personal favorite.

Shop similar boots:

Ganni Country Boot in Black ($285)

Up next: Buy These 8 Fall Trends and Everyone Will Think You Got a Whole New Wardrobe

This story was published at an earlier date and has since been updated.

This article originally appeared on Who What Wear

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