How To Style Tall Boots 16 Ways
When I feel that first truly crisp fall breeze of the season, I know that my favorite season is settling in.
That means it’s time to spend Sundays rooting for the Giants, (and not being disappointed if they let me down) swap out my usual chai latte for a caramel apple butter chai (yes this is real and you can currently get one at The Hive) and break out the tall boots for the season.
Tall boots are not just for fall—in fact, as a New York/New Jersey gal you’ll probably find them in my outfit rotation at least once a week between now and March.
I know—buckle up northeastern gals, we’ve got a looong winter ahead of us. But at least we’ll look cute right?
From sleek black leather to soft suede, they offer versatility, warmth, and a touch of sophistication to everything from dresses and skirts to skinny jeans.
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In this post, I’m sharing some of my favorite ways to style tall boots that are both fashion-forward and easy to recreate for your everyday looks.
Whether you’re aiming for a bold, statement look or something a bit more classic and understated, these outfit ideas have you covered.
So, dust off your favorite pair of boots (or treat yourself to a new pair—there are shopping suggestions below) and let’s dive into these ideas for styling tall boots in the fall and winter months.
16 ways to style tall boots
Artsy Girl
A plaid oversized blazer paired with tall black boots and a pleated skirt brings a creative and effortlessly chic vibe. Add a beret for extra artsy-ness.
Basic Fall Girl
In need of a PSL or a real pumpkin? A cozy sweater and jeans combo with suede over-the-knee boots is a perfect casual look for the local farm.
Bold Mini Dress
Make a statement with a neon mini dress and sleek black boots for an eye-catching and confident look.
City Chic
A silky, flowy dress and tall boots create a polished look that’s perfect for a day out in the city.
Classic Mini Skirt
Pairing a black mini skirt with tall boots gives a timeless, preppy feel whether you’re headed to the office or running errands on the weekend.
Comfy and Cozy
Stay stylish and warm in an oversized sweater dress paired with fleece-lined tights and tall boots for the ultimate cozy fall look.
Cozy for Winter
Layer up in a houndstooth coat and turtleneck with your tall boots for a cold-weather-ready, fashion-forward outfit.
Denim Midi Skirt
You may not think of a denim midi skirt when you picture an outfit with tall boots, but pairing this one with boots that hit just above the calf makes the look work.
French Chic
Channel French girl vibes with a polka dot dress and over-the-knee boots for a sophisticated yet effortless feel.
Long Sleeve Dress
Tall tan boots paired with a jewel-toned sweater dress give this look a polished and autumn-appropriate feel.
Monochrome Style
Black and white doesn’t have to be boring—pairing these 60’s inspired tall white boots with a patterned mini skirt and leather blazer screams “fun!”
Over Skinny Jeans
Tuck your favorite skinny jeans into tall over-the-knee boots for a casual yet elevated street-style look.
Plaid Coat
A cute plaid shacket paired with tall black boots can be dressed down, or in this case dressed up if paired with a faux leather mini dress.
Puff Sleeve Dress
Add a bit of drama with a puff sleeve mini dress and tall boots for a fashion-forward ensemble (and match your bestie in the process!)
Statement Coat
Let a bold, printed coat take center stage while pairing it with tall boots for a cozy-chic winter look. In this case a leopard coat with a pink faux fur collar does the trick.
Sweater Dress
A cozy cream sweater dress styled with tall boots is the perfect go-to look for chilly fall days. The tan over-the-knee ankle boots bring some warmth to the look.
Materials for tall boots
Leather
It’s hard to go wrong with a great pair of leather (faux or real) tall boots because they’re durable, sleek and will last for many seasons.
Suede
When it comes to fall and early winter, suede adds an instant element of warmth to your outfits—just make sure not to wear them out in the rain or snow!
Rubber
If you are in need of a tall boot that can endure the elements, consider picking up a classic pair of rubber rain boots.
Styles of tall boots
Sleek: a pair of sleek tall boots is giving the opening scene of The Devil Wears Prada—you’re on the move and have places to go.
Slouchy: the tall slouchy boot may feel a little bit 2006 to you, but with the right styling these boots can add an instant laid-back vibe to any outfit.
Western: you don’t have to be headed to the rodeo to rock a pair of cowboy boots. In fact, any boot with a bit of Western flare can be great for any occasion.
What to pair tall boots with
Skinny jeans: There will always be discourse about whether skinny jeans are in or out, but for me they are definitely a constant in my wardrobe.
Styling tip: tall boots look best when worn over skinny jeans
Midi skirts: Just like at the start of a romcom, this pairing may not make sense together at first but over time you will grow fond of it.
Styling tip: I think it’s so chic when midi skirts are paired with tall boots that disappear under the hem of the skirt.
Sweater dresses: When in doubt, you can bet that I’m reaching for a comfy sweater that I don’t need to wear pants with. What a genius piece of clothing.
Styling tip: over-the-knee boots look super cute with mini sweater dresses because of how the proportions land
Socks to wear with tall boots
Your favorite ankle socks that you reach for during the summer months aren’t going to cut it under tall boots.
To prevent socks slipping down, these are some of my go-to suggestions for socks to pair with your tall boots in the colder months.
Colorful tall socks: I personally love when socks poke out of boots and no one does cute fall socks like Free People (which I can say as a former FP stylist!)
Extra cushy socks: Bombas sells these mid-calf socks that look like they’d be perfect with boots! I think I’ve influenced myself to buy these after reading the reviews.
And there you have it! Are you adding some new tall boots to your wardrobe this year? How will you be styling them? Tell me in the comments!
yours,
Austen
PS - If you’re more into ankle boots, don’t forget to check out this related post.