My freshman year of college I bought a pair of tall Frye riding boots that quickly became the star of my fall and winter wardrobe for the next six years. I wore them so often that I had to have them resoled twice. But when I pulled them out of the back of my closet recently during a major wardrobe overhaul, I found myself wondering if I could still pull them off without looking dated. So, to Pinterest I headed to find all the knee-high boot outfits a gal could dream of that are also fresh, modern and 2020-level chic. Below, ten gorgeous ensembles that are easy and fashion forward, all featuring our favorite fall knee-high style—plus two combos to avoid at all costs.
10 Knee-High Boot Outfits That Won’t Look Like You’re Stuck in 2016 (Plus 2 to Skip)
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1. wear Riding Boots With: Jeans And An Oversize Blazer
Lean into the preppy nature of this equestrian style by tucking in some high-waist skinny jeans and layering a structured blazer on top. Be sure to choose a jacket that hits at or below your hips, not above; a cropped cut will throw off your proportions in an unflattering way.
2. wear Snakeskin Boots With: Denim On Denim
There are certainly ways to make this exotic print work with other printed pieces, but we prefer letting it stand out against a backdrop of dark-wash denim. Pro tip: Try buttoning up a denim jacket to wear as a top in place of a chambray shirt, like Coterie member Babba Canales.
3. wear Black Boots With: Matching Leggings
Create the illusion of miles-long legs by slipping black leggings into a pair of tall black boots. As for your top, feel free to play around with brightly-hued sweatshirts, puff-sleeve blouses, longline blazers or whatever current trend your heart desires. (Although, similar to the note above, try to avoid cropped styles as they’ll end up making your torso looking weirdly short.)
4. wear Block Heels With: Long Prairie Skirts
The utilitarian shape of a chunkier heel helps to offset the sweetness of voluminous ruffles or dainty floral prints. Opt for something that hits just above, at or just below the knee, like Jessie Loeffler Randall’s pink-frilled skirt, rather than mid-calf or maxi lengths, to avoid losing your shape altogether in all that fabric.
5. wear Pointy-toe Heels With: Short Prairie Dresses
The prairie trend—puff sleeves, ruffles and an abundance of volume—may have started back in 2018, but it’s shown no signs of slowing down as we head into 2021. If you prefer shorter silhouettes over long flowing frocks, we love the look of playing with opposites and pairing some sharp structured boots with your minidress. Thanks for the inspo, Coterie member Coco Bassey!
6. wear Looser Styles With: A Long, Fitted Sweater Dress
We’re not talking about slouchy boots, but the ones that fit slightly wider than your calf and are stiff enough to hold their own shape rather than conform to your leg. Pair these with a cozy knit dress that ends at the top of your boots, but not above.
7. wear Flat Boots With: A Mini Skirt
One of the best fashion tips we've learned over the years is: The shorter your hemline, the lower your heel. So, as you might expect, the shortest hem of all warrants no heel at all, no matter what style of shoes you prefer. As for tall boots, we love combining a preppier mini with some tougher black boots or, on the flip side, a casual denim skirt with posh riding boots.
8. wear Slouchy Heeled Boots With: A Midi Skirt And Sweater
Amplify the cozy nature of bunchy boots with a flowy skirt and oversize knit layered on top. To avoid being overwhelmed by the combo, stick to lighter hues and delicate prints like mini florals or polka dots.
9. wear Any Style With: A Pencil Skirt
Knee-high boots and pencil skirts are a classic dup we just can’t get enough of. And while we like this combo best with heeled boots and a straight-fitting skirt (as opposed to one with a ton of stretch that hangs on every curve), you can make it work for just about any style boot from equestrian to snakeskin to clingy suede.
10. Wear Any Style With: Monochrome Separates
When in doubt, pick one color or color family and stick to it. Any of the above outfits will look brilliantly chic done up in shades of a single hue. Feel free to play with textures and fabrics too, to add extra depth to your look.
Don’t Wear Them With: Baggy Or Loose Pants
No matter what style tall boots you own, never wear them with trousers that don’t tuck neatly or create puckering or billowing at your thighs. You’ll end up looking like a 15th century swashbuckling pirate. Opt for slim-fit bottoms, like skinny jeans or leggings, to create a more streamlined silhouette.
Don’t Wear Them With: Shorts And Tights
It may have worked for the cast of Gossip Girl back in 2010, but at this point the combination looks dated and juvenile—two things we try to avoid outside of Halloween dressing. If you really love the look, try a minidress instead to bring things back into the 2020s.