Stylish Boots to Pair With Different Dresses
Whether you are going for edgy and bold or sweet and breezy, boots and dresses can be mixed and matched with various patterns and textures for a multitude of styles. This all-season combination is a great choice for bringing your dresses into the cooler months.
Our favorite boots to pair with dresses include combat boots, lace-up boots, Chelsea boots, Frye boots and ankle boots. Read more to learn about which dresses each boot looks best with.
Almost any dress with combat boots
One of the most current high-fashion-and-streetwear-mimicking-menswear looks we love involves pairing women’s combat boots with a wide variety of dresses or skirts. Finding the perfect pair of lady’s combat boots is the key.
The Doc Marten is, of course, a timeless choice. Fashion houses like Prada, Louis Vuitton and Chanel have popularized the classic combat boot recently with added touches. Finding boutique boot options can be a real budget-friendly way to get the styles you want.
Once you’ve found a combat boot that works perfectly for you, pairing them with your favorite dress is simple. Combat boots are amazing with above-the-knee, mid-calf and maxi looks! Soft, flowy fabrics, clingy knits and more structured blends all look great with a pair of nicely fitting combat books.
Lace-up boots are a good alternative to combat boots, if you happen upon a special pair while shopping. They also pair well with a wide variety of hemlines.
To-the-knee or below with Chelsea boots
Our next favorite look involves pairing women’s Chelsea boots with a dress or skirt that’s worn to the knee or below. This look can be paired with or without tights and works well into colder months. Adding a short jacket creates a beautiful silhouette with this look. As a general rule of thumb, a boot + dress combo lends well to layering.
Find your favorite Chelsea boots in a shade of brown, tan or black and pair with a sweater dress or midi. We also love Chelsea boots with flowing hemlines that are layered with accessories, such as a nice hat or a bag.
Fabulous with Frye boots
Frye boots are another top boot choice. These rugged mid-calf boots are traditionally worn with jeans or leggings, but they can be a great addition to a dress.
Shop for a good pair of leather Frye boots that will last years to come. We love short sweater dresses and feminine options with a bit of volume, pleats and long sleeves.
Classic ankle boots
Ankle boots are a closet staple. They’re easy to shop for and come in a wide variety of materials, colors and heel heights. Different boot types pair nicely with skirts above-the-knee to midi lengths. Try an ankle boot with your seasonal favorites, including floral skirts or autumnal dresses.
Some styling pointers
Our recommendations for favorite boots and dresses can help extend your wardrobe through the seasons. To make great style choices, we recommend choosing capsule wardrobe separates that are versatile.
Delicate cotton or cotton-blend dresses that have volume will pair great with Chelsea boots and combat boots. Structured dresses to the knee are one of our favorites with Frye boots. Try a maxi length with a combat boot for a streetwear-inspired favorite. And don’t forget to pair your ankle boots with something short and simple.
Adding in some necklaces and trendy purses can elevate your look. Grab your favorite boots and put together a new stylish and comfortable look today!
Tess DiNapoli is an artist, freelance writer, and content strategist. She has a passion for yoga and often writes about health and wellness, but also enjoys covering the fashion industry and the world of fitness.
