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

Welcome to #WhoWhatWearing, a series in which we highlight you, our stylish community of readers. Each of the following looks came straight from a photo you tagged us in on Instagram. Want to be featured next time? You guessed it: Use #WhoWhatWearing on the outfit posts you want us to see. 

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 emerging fall 2020 boot trend I absolutely want to try, 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.

WHO: Sonia Dhillon

WEAR: Puff-Sleeve Knit + Trousers + Chunky Boots

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

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 look is a prime example of that. Paired with combat boots and a cool bag, this look is one that's as easy to re-create as it is practical and weather friendly.

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.

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.

WHO: Solène OJ

WEAR: Leather Trench Coat + Knee-High Boots + Pearl Jewelry

In case you weren't convinced of the power a trench coat has to make an outfit, let this be my final argument. Solène cinched hers at the waist to create the look of a jacket dress and paired it with knee-high boots. It's all quite chic.

WHO: Chloe Hayward

WEAR: Trench Coat + Bodysuit + Wide-Leg Jeans + Square-Toe Boots

Throw on a long jacket over jeans and ankle boots for an overall sleek effect, and if you want to freshen up the ensemble, consider swapping in a pair of square-toe boots.

WHO: Mabinty

WEAR: Leather Blazer + Minidress + Knee-High Boots + Aviator Sunglasses

Why wear a classic blazer when you can make it leather? An oversize blazer looks all the cooler in sleek leather and worn with a minidress. It's also the outfit trend cool girls are leaning way into this fall.

WHO: Lindley Edwards

WHAT: Knit Vest + Collared Shirt + Pleated Miniskirt + Combat 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 combat boots give it a cool edge.

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.

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.

WHO: Charlotte

WHAT: Cropped Blazer + High-Waisted Jeans + Platform 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 platform boots for an edgy spin.

WHO: Anna Krauze

WEAR: Joggers + Knee-High Boots + Oversize Sweater

All out of ideas with your sweats? Get creative like Anna did 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.

WHO: Lola Faith

WEAR: Oversize Blazer + Tank + Bike Shorts + Combat Boots

Try this transitional look before the weather truly feels cold. Pair a big blazer with bike shorts (or a jumpsuit if you're feeling it) and finish with trusted black ankle boots.

WHO: Kelsey-Marie

WEAR: Tiered Dress + Sculptural Earrings + Lace-Up Boots

Ground an airy wide-cut dress with sturdy boots, like combat or lace-up boots, and finish it with bold earrings for a look that's interesting and surprisingly comfortable.

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.

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