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.

RELATED: Jeggings are Trending, Again. Here’s How to Wear Them in 2020

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.

Shop similar styles: Nine West boots ($189); Naturalizer boots ($220); Good American jeans ($99); AG jeans ($188); Madewell blazer ($168; $118); Liverpool blazer ($119)

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.

Shop similar styles: Louise et Cie boots ($249; $150); Aerosoles boots ($250); Joe’s jeans ($168; $100); J Brand jeans ($228); Levi’s jacket ($128); Edwin jacket ($198; $139)

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.)

Shop similar styles: Sam Edelman boots ($200; $119); Steve Madden boots ($200; $120); ALO leggings ($78); Athleta leggings ($89)

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.

Shop similar styles: Sam Edelman boots ($200); Loeffler Randall boots ($695); Scotch & Soda skirt ($135); Mille skirt ($168)

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!

Shop similar styles: Vince Camuto boots ($230; $140); J.Crew boots ($328); ASOS Curve dress ($40; $28); Sister Jane dress ($281)

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.

Shop similar styles: Vince Camuto boots ($240; $120); Schutz boots ($238); Eloquii dress ($100); Staud dress ($245)

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.

Shop similar styles: Gentle Souls by Kenneth Cole boots ($170; $100); Franco Sarto boots ($199; $120); Madewell skirt ($88; $62); Sandro skirt ($280; $168)

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.

Shop similar styles: Frye boots ($170); FP Collection boots ($228); Halogen skirt ($79; $36); Lulus skirt ($54); Express sweater ($80; $40); Garnet Hill sweater ($169)

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.

Shop similar styles: ASOS boots ($64); Schutz boots ($238); Mango skirt ($60; $40); Blank NYC skirt ($98)

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.

Shop similar styles: Silent D boots ($158); Villa Rouge boots ($295); Madewell boots ($298); Alias Mae boots ($340)

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.

RELATED: How to Wear Ankle Boots in 2020 (Including 2 Styles to Retire)

PureWow may receive a portion of sales from products purchased from this article, which was created independently from PureWow's editorial and sales departments.