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


(Image credit: @sylviemus_)

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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, such as chunky Chelsea boots and classic 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.


(Image credit: @nlmarilyn)

WHO: Marilyn

WEAR: Skirt Suit + Collared Shirt + Chunky Chelsea Boots

Chunky Chelsea boots are the fall 2022 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 so current.


(Image credit: @smythsisters)

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.


(Image credit: @sophiabrenn)

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.


(Image credit: @sylviemus_)

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.


(Image credit: @fitzpatrickerin)

WHO: Erin Fitzpatrick 

WEAR: Patchwork Cardigan + Jeans + Lace-Up Flat Boots

This perfect-for-fall cardigan added some pizzazz to an otherwise simple jeans-and-tee outfit. Lace-up flat boots are practical and chic—especially at this reasonable price. 


(Image credit: @javiera)

WHO: Javi

WEAR: Crop Top + Boot-Cut 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 boot-cut jeans (another fall 2020 trend) and eye-catching printed ankle boots, which add interest to an otherwise neutral look.


(Image credit: @emmanuellek_)

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.


(Image credit: @annelauremais)

WHO: Anne-Laure Mais

WEAR: Trench Coat + Minidress + Knee-High Boots

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


(Image credit: @sofiamcoelho)

WHO: Sofia Coelho

WEAR: 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.


(Image credit: @venswifestyle)

WHO: Renia Jaz

WEAR: 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.


(Image credit: @shhtephs)

WHO: Stephanie Arant

WEAR: 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 them with square-toe boots for an edgy spin.


(Image credit: @fundachristopherson)

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.


(Image credit: @camillecharriere)

WHO: Camille Charrière

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 miniskirt) and finish with trendy cowboy boots.


(Image credit: @racheleveritt_)

WHO: Rachel Everitt

WEAR: Puff-Sleeve Shirt + Pinafore Dress + 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.


(Image credit: @champagnemani)

WHO: Imani Randolph

WEAR: Off-the-Shoulder Top + A-Line Skirt + Knee-High Boots

Imani's outfit is a lesson in mastering proportions. Copy this outfit and try a short skirt with tall boots and you're as good as golden. 

Next: A Viral TikTok Just Confirmed Everyone in France Is Wearing This One Sweater

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

Senior Editor

Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.