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The Tall Boot Trends We Love (+ How To Wear Them and Our Picks)

I don’t want to say ankle boots are out (in fact, I would never say that) but I am feeling very giddy about the tall boot trend happening right now. This trend is surprisingly versatile because any style of tall boot goes. Flat boots, chunky heels, animal print, skinny heel — it doesn’t matter. It’s all about tall boots that are just under or above the knee and how to style them. And folks, I am LOVING how the fashion influencers are styling them. I’m talking boots with skirts, shorts, and dresses, oh my. It’s truly a trend that might have me swapping out my matching sweats for a real outfit which is saying a lot. But enough talk. Let’s observe the style IRL.

Over-The-Knee Boots

image via glamour

Okay, there is a lot to love or hate here depending on your style. I personally chose to love the power clashing, the oversized tarnished leather jacket, tiny purse with those killer snakeskin boots. This is the tall boot trend I can definitely see myself wearing. I love how the dress is long enough to layer over the boots, making this an effortless unexpected winter outfit.

image via who what wear

Again, the long dress or long coat draped over the boots is *chefs kiss*. There is something wonderfully androgynous about this look and it 100% nails the effortless vibe. I mean this outfit really requires three elements: 1. the long dress or coat, 2. the oversized bag, and 3. the tall boot. How easy is that?

image via paola mathé

This look reminds me of the time I wore over-the-knee high socks and a bright blue mini skirt to a Christmas party back in 2012. It was questionable so I am reluctant to get on board but I can’t deny how good Paola looks here. It’s not the outfit for me, but it’s undeniably chic. The plaid skirt sweater combo is giving me Gossip Girl in the best way (I am rewatching the original version right now–it’s still so good).

image via katie sturino

Another trick to styling the over-the-knee boot is pairing it with a cropped shirt and a long coat. It’s all about mixing the lengths of each article of clothing so the outfit feels dynamic and interesting. A long skirt, long coat, and tall boots might be hard to work with so it’s best to vary the lengths for a more put-together look.

Here are a couple more fun ideas:

And our boot picks:

1. Sam Edelman Boots | 2. Vince Camuto Boots | 3. Snakeskin Tall Boot | 4. Stretch Over-The-Knee Boot | 5. Tall Riding Boot | 6. Serra Second Boot | 7. Rowee Black Crocodile Boot | 8. Parisha Boot | 9. Janna Boot | 10. Amiga Western Boot | 11. Kelsi Dagger Boots | 12. Tanzee Bone Boot | 13. Saoirse Boot | 14. Tommi Boot | 15. Tonya Heeled Boot

Under The Knee Boots

Okay ladies, midi knit dresses paired with knee-high boots is happening. This look is perfect for LA “winter” and I love how well a body con dress pairs with tall boots. If you want to step it up a notch, pair a shorter body con dress with a trench coat and you’ll absolutely be turning heads.

image via vogue

The trench coat and tall boot combo is my second favorite look. Oh did we forget to talk about how the trench coat is back?? It’s true. I even have vintage Burberry trench coats favorited on my TRR account, patiently waiting to be purchased. But the real story here is that tall boots, a trench coat, and a pattern mini skirt is a KILLER outfit and one I am dying to try.

image via chanel mckinsie

This is another look that is bringing up outfits from my past. There was an entire summer in high school where I only wore cut-off denim shorts and ankle boots and so I am pumped to try it with tall boots this year. Shorts and boots are notoriously a fashion faux pas but I will always get behind a rule breaker that looks this good. Also is it worth mentioning that reptile is still very in?? I am very pleased by this.

image via vogue

I leave you with my favorite look. I’ll take a feminine prairie dress with knee-high cowboy boots any day. I actually have this image ingrained in my brain so I can recreate once I find a dress and belt combo that even comes close to this.

Here are a few more styling ideas if you are interested:

And of course our picks:

1. Louise Et Cie Tiley Boot | 2. Riva Tall Block Heel Boot | 3. Target Ansley Boot | 4. Larina Waterproof Boot | 5. Snakeskin Tall Boot | 6. Taysha Tall Boots | 7. Suede Slouchy Boots | 8. Tall Brown Boot Memory Foam Sole | 9. Franco Sarto Boot | 10. Matisse Western Boots | 11. Heeled Scrunch Boot | 12. Lug Sole Boots | 13. Francie Boot | 14. Chunky Wide Calf Boot | 15. Itinerary Tall Boot | 16. Square Toe Heeled Boot | 17. Fin Tall Western Boot | 18. Dorica Boot

What’s your favorite look? Are you rocking tall boots or sticking with trusty ankle boots this year? Tell me everything. xx

Opener Image Credit: Photo by Veronica Crawford | From: Six Fall Sweaters I’m Loving (+ How To Wear Them)

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Ash W
2 years ago

Anyone else out there feeling a little bit…Alexis? 🙂

2 years ago
Reply to  Ash W


2 years ago

Thank goodness tall boots are back – I never really stopped wearing them when ankle boots took over a few years ago, because oftentimes I want the extra warmth of the taller boot plus socks! I do still wear them over jeans or leggings in addition to with dresses and skirts, though, and I guess I’m old enough to not care now if that’s out of style (hello 30s! Ha.). I have the Madewell leather boots from the knee high roundup and adore them – comfy and a great heel height that’s easy to walk in, but also easy to dress up or down and a little sexy. Catch them when madewell has a sale and the price is much more reasonable too – I think I got at least 30% off when I bought them!

2 years ago
Reply to  Jessie

I never stopped wearing them either, for the exact same reason- they keep me so much warmer! Both pairs that I have recently broke (the sole was coming off), and I’ve had to stick to ankle boots for the past 2 weeks…my ankles and legs have been very cold! Might have something to do with the fact that it’s been hovering between -10 and 20 degrees that whole time, but I can’t wait for my new tall boots to arrive!

🥰 Rusty
2 years ago

Nice to see more diverse images! 👍

2 years ago

Real question, no snark : How do these boots fit into the closets we saw yesterday?

2 years ago
Reply to  Mouseface

I use pool noodles in my boots to help hold them up. Much cheaper than the actual boot inserts you can buy. I get mine at the $ store.

2 years ago
Reply to  Mouseface

I ended up getting an under the bed box from The Container Store:
I use tissue or boot forms inside the boots to preserve their shape. I really wanted them to live in my closet, but this was such a more realistic solution.

2 years ago
Reply to  Mouseface

Two liter bottles top down

2 years ago

I live in a snowy mountain town so these looks are 100% not relevant to me but I LOVE the oxblood cowboy boot with the prairie dress!!

Joyce Garrity
2 years ago

not going for over the knee, like the look but will date fast. .. thinking of the planet. I don’t toss boots, so pulled out my knee highs and will put most shorter boots in the attic

2 years ago

I still have my Stuart Weissman 50/50 over the knee boots. I wore them so much, and they are so comfortable, but they’ve stayed in storage for awhile. I do love the over the knee boots with a mini look, but I’m not much of a mini skirt person, so I’ll pair them with something else. Admittedly, I’ve been loving my Nisolo Carmen Chelsea boots lately. Comfortable, practical, and great looking.

2 years ago

Oh I wish so much that you had included one of Emily’s personal looks tall boots looks (that I personally coveted and may, or may not have purchased almost all of the pieces for myself…). She wore a practical and super cute look for those of us who live in seasonal/wintery places and have to dress for “real weather”, (but still want to look cute!). Emily wore her blue Alex Mill Britt jacket over a chambray shirt, black pants (I wear fleece lined leggings), and Loeffler Randall boots (I swapped the boots for a more affordable and waterproof pair of Sorels). It is one of my favorite Emily looks. I love fashion, and I appreciate it even more when there are options for “real life” looks too! I hope you will find and post this picture (again) for inspiration! Tall boots here in Portland, Maine are a necessity, but I still want to look cute even in weather

2 years ago
Reply to  Stacia

Oh! I just saw the post with Emily’s Loeffler Randall tall boot look: Fall Fashion: The One Essential Piece We All Need.

2 years ago