A Guide to Styling Boots With Dresses

From laid-back and breezy to sophisticated and dressy, the combination of boots with a dress is endlessly versatile and always stylish. While fashion rules are meant to be broken, some basic styling tips can go a long way in helping you put together the perfect ensemble for any occasion. 

Let’s take a look at five of the most popular women’s boot styles and how to select a dress that really pops with them.

1. Chelsea Boots

Every women’s footwear collection should include at least one pair of Chelsea boots. While they’re certainly having a moment in recent times, Chelsea boots are an iconic, timeless style that works with a wide variety of outfits. If you don’t have any Chelsea boots (or if they’re just not your thing), your favorite flat ankle booties will probably work fine as a substitution.

Pair your Chelsea boots with a midi or mini skirt for a cool look with a ‘90s vibe that really works well as a summer wardrobe staple. On cooler days, Chelsea boots work great with a sweater dress. Try cinching the waistline with a statement belt that matches the boots for a bold, put-together look. 

Chelsea boots can also complement avant-garde styles, so try wearing them with an asymmetrical dress or a dress with prominent patterns or colors. Oversized, minimalist dresses work wonderfully with Chelsea boots too, as the boots provide some flavor without being distracting. On the other hand, they can also add just the right amount of chunk to a sleek, slim-fitting dress.

2. High Heel Boots

High heel boots are a fantastic choice if you can’t decide if you want to wear heels or boots! They can run the gamut from edgy to prim and proper, depending on the style of boots and the attire you pair them with. They can also add a few extra inches to your height. 

High heel boots—especially knee and thigh-high styles— make an excellent pair with sheet dresses and vintage dresses with bold colors, patterns, and buttons, as well as high-fashion designer dresses. They’re also a great choice to go with oversized sweater dresses to add a bit of glamour to the look, or wear them with a mini skirt for a fun and flirty aesthetic.

3. Western/Equestrian Boots

Western and equestrian boots can both add some big flavor to an outfit. They work especially well with summer and springtime clothes—think flowy dresses with lots of ruffles. Floral patterns are great for a country aesthetic, or go for a boho-chic dress with a wide flat-brimmed hat for a cool look that’s still put-together.

Because western and equestrian boots are typically statement pieces, it’s usually best to let them do the talking (and the walking!). If you’re going to wear them, go all-in and let them be the star of the show. A simple white dress with some showy cowgirl boots is a fun look that requires very little effort.

4. Moto/Combat Boots

Moto boots and combat boots (and Docs!) can often be worn interchangeably. After all, both have edgy, chunky designs that will have you feeling like a queen while you stomp around town! These styles pair perfectly with basically anything black, so don’t be afraid to let your inner goth out. A black dress, black tights, and black moto boots is a tough-yet-feminine look that always works. Some silver or gold accessories can add that finishing touch if you want to spice it up.

Besides black, moto and combat boots work great with big, vibrant colors like yellow, red, or green. If you’re looking to add a little bit of a punky vibe to your wardrobe, consider a plaid or faux leather mini skirt, or even some big cat patterns. Tights are optional, but you can’t go wrong with black tights to match black boots.

5. Ankle Boots

Ankle boots are easily the most versatile style of boots to wear with a dress, so if you can only choose one style, that’s your best bet. A pair of neutral-toned ankle boots—especially black or brown—will pair with most dresses. 

Pairing them with a dress that ends around the mid-thigh area is a classic look, with or without tights depending on your mood (and the weather!). If you prefer a longer dress, choose something with a hem that ends just above the boot—no touching! Maxi dresses don’t usually work with ankle boots, although a maxi dress with a slit up the side can be a fashionable exception.

Confidence Is Key

Hopefully these tips will help you dress for success, but try not to get too obsessed about it! As long as you feel comfortable and confident, that’s all that matters. Dresses and boots are almost always a match made in heaven, and there’s nothing wrong with a ‘rolled out of bed and put this on’ kind of vibe! As long as you’re happy with how you look, lace up and pat yourself on the back for a job well done.