The Best Tall Boots to Transition from Summer to Fall

A tall boot achieves everything I want from a shoe: To complete, or even anchor, an outfit. I’ve been itching to wear tall boots ever since I tucked them away in the back of my closet for the summer. But, seeing people absolutely knocking my metaphorical socks off on Instagram by pairing their boots with tennis skirts, shorts, mesh, slip dresses, and even gauzy summer sets, I've now realized tall boots are absolutely late-summer appropriate, and possibly the best transitional outfit item to really hype yourself up for fall.

The best thing about tall boots is they're both sturdy and forever cool if you get the right pair. Ready to upgrade your style, but not sure where to start? Ahead, see 10 of my favorite looks, featuring specific boot picks, so we can all enjoy them together for early fall and beyond.

Tall Boots with a Tennis Skirt

With the right outfit, tall boots are absolutely appropriate for summer or early fall. Think about the difference the shoes make versus a sandal or sneaker: By pairing your boots with a tennis skirt and tee, you'll look cool in the most early fall-appropriate way.

Tall Boots with a Long Dress

If you're looking for maximum drama, try pairing your favorite long dresses with tall boots. I love when the hem of a dress or skirt passes the top of the boot’s shaft—it looks intentionally put-together. Instead of pairing your long summer dress with sandals, try a pair of boots to look even cooler.

Tall Boots with Denim Shorts

My very well-dressed friend (and fellow Byrdie contributor), Jo Rosenthal, has mastered this silhouette. A pair of long shorts with tall boots—with about six inches to a foot of space in between—creates an effortless finish. Going with a tank on top is great when the weather is warmest but remains relevant into cooler months with the addition of a cardigan or blazer.

Tall Boots with White Loungewear

Over the past couple of years, most of us have accumulated at least some sort of lounge set, statement pajama shorts, or nightgown. Whether you have a gauzy shirt dress or a cotton PJ set, you'll find it pairs beautifully with cowboy boots. The idea here is to pair something dainty with the statement footwear, and I love the resulting contrast.

Trousers Tucked into Tall Boots

For an effortlessly cool look, try styling your tall boots with baggy trousers tucked into the shafts. I love a pair of boots like these—they’re not wide at the leg, so they create a Captain Hook silhouette in the best way. To cap it off, the laces add a utilitarian twist. 

Tall Boots and a Mesh Skirt

Pair some incredible, buttery leather boots with a mesh long skirt for a look that makes a statement. Similarly to the long dress silhouette from earlier, I love how the skirt covers the top of the boots. A mesh skirt style is especially fun, as you can still see a hint of them. This is a really fun way to ring in fall, for day or night.

Tall Boots with White Jeans

This is just how I'll be styling white jeans for the foreseeable future. A tall, sleek pair of black boots with white jeans is the perfect contrast that's Mary-Kate Olsen-approved. Even if you don't own riding boots, I think you could get a similar look with any tall, black, slim-leg style. Pair them with your white jeans, a belt, a white tank, a blazer, and some effortlessly cool sunglasses for a very chic, Olsen-esque result. 

Tall Boots with a Mini

Mixing colors and patterns, when done well, is always a great way to make your outfit exciting, original, and refreshing. While both the boots and skirt/top combos here are certainly statements, the short hem allows for some breathing room on the leg. It’s a great way to style boots and a mini—the more the merrier.

Statement Tall Boots with Casual Wear

Some statement footwear is a great way to style something you probably own—athletic shorts and a tee—really, really well. Pairing the look with tall boots rather than the typical sneakers makes this outfit easy but so smart.

Thigh-High Tall Boots and Long Dress Shorts

I got a great pair of thigh-high boots I was truly obsessed with in high school, then got them back out several years ago when they trended yet again. If you kept yours like I did, try pairing them with loose-fitting dress shorts (or even cut an old pair of trousers to make them knee-length) and a tee on warmer days, then swap for a sweater when it gets colder. It’s a really easy transitional pairing—trust me.