Blog: Crossroads Style

December 31, 2024 Styling Tall Boots This Season

Fall and winter call for tall boots! If you have a pair you’re ready to wear for work or play, we have some styling ideas to help you plan your next look. Check out 6 ways we love to wear them.

1. Paired with Tights

We consider this the easiest was to show off tall boots! Add a pair of tights for warmth and style. You can even choose a bright hue or textured knit for more visual interest.

woman in checked blazer, black skirt and suede tall boots

2. Coupled with Leggings

Elevate your favorite leggings with this classic riding look. A turtleneck and tweed blazer complete the outfit, all while keeping you warm and comfortable.

woman in leggings with tweed blazer and brown tall boots

3. Matched with a Mini

Make sure those boots are the main feature by pairing them with a mini skirt or dress. The flannel mini dress shown here hits all the right notes.

woman in cream-colored pair with plaid flannel dress

4. Pulled Over Jeans

You know your skinny jeans are just calling for a boots meetup. Add in a puffer jacket to complete this favored winter look.

woman in heeled alligator pair with jeans and puffer jacket

5. With a Long Dress

We like to add a long ribbed knit dress for a simple and effortless look, and we really love the monochrome pairing here. Plus, how cute is that belt bag??

woman with long black dress and black tall boots

6. Make Them Preppy

Pair them with a turtleneck sweater and wool plaid skirt for the ultimate preppy winter look. A pair in suede would be perfect.

woman with turtleneck sweater, plaid mini and tall brown suede boots

If you have pre-loved tall boots you’re looking to sell, visit one of our stores for a buyer assessment.

You can also see all the styles, trends, and labels we’re looking for this season with our seasonal selling guide. Or follow us on Instagram for more style inspiration.

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