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

This photo of Imani Randolph was one of the first to convince me that tall boots are absolutely appropriate for summer or early fall. Think about the difference the shoes make versus a sandal or sneaker: By pairing boots with her tennis skirt and tee, she looks cool in the most early fall-appropriate way.

Tall Boots with a Long Dress

Here, Saks Potts paired a shimmery strapless “carpenter bag” dress 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 boot to look even cooler.

Tall Boots with Denim Shorts

My very well-dressed friend (and fellow Byrdie contributor), Jo Rosenthal, is so great with 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. Rosenthal paired hers with a tank, which is great for summer but remains relevant into the cooler months with the addition of a cardigan or blazer.

Tall Boots with White Loungewear

When I saw this photo of Naomi Elizée, I immediately wanted to copy it because after over a year of quarantine, most of us have accumulated at least some sort of lounge set, statement pajama shorts, or nightgown. What appears to be a gauzy shirt dress could easily be a cotton PJ set and cowboy boots. The idea here is to pair something gauzy and dainty with the statement footwear, and I love the contrast.

Trousers Tucked into Tall Boots

Here, Kathrine Maron styles her tall boots with baggy trousers tucked into the shafts. For one, I love these boots—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

Here Randolph is again, wearing those incredible buttery yellow Vince boots (these—sadly they’re sold out, but these are similar) with a mesh long skirt (hers is from Los Feliz Shop). Similarly to how Saks Potts styled their long dress, I love how the skirt covers the top of the boots. Even cooler, the skirt is mesh, so you can still see a hint of them. The way she styled 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 black boot with white jeans is the perfect contrast. Mary-Kate Olsen’s boots are obviously riding-style, which I don’t personally own, but I think you could get a similar look with any tall, black, slim-leg boots. Pair them with your white jeans, a belt, a white tank, a blazer, and some effortless but cool sunglasses for a very Olsen-esque result. 

Tall Boots with a Mini

Tyler McGillivary's outfits are exciting, original, and refreshing. I love how she mixes colors and patterns, as illustrated here. While both the boots and skirt/top combo are certainly statements, the short hem of the skirt allows for some breathing room with her leg. It’s a great way to style a boot and mini—the more the merrier.

Statement Tall Boots with Casual Wear

Elizée once more shows us a 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

Hi, it’s me, in a great pair of thigh-high boots (which I was obsessed with in high school and then about six 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 now, then swap for a sweater when it gets colder. It’s a really easy summer-to-fall pairing, trust me.