My Favorite Boots To Wear With Dresses

One of my favorite things about fall is finally getting to wear boots with dresses again. Choosing the right boots to wear with dresses can completely change the feel of an outfit. Knee-high boots make a dress feel polished without being too dressy, suede creates a softer, more relaxed look, and ankle boots are perfect when I want something a little more casual.

Over the years, I’ve found myself reaching for the same boot styles again and again. Which pair I choose usually depends on the dress I’m wearing, the occasion, and whether I want the outfit to feel polished, relaxed, or somewhere in between.

In this guide, I’m sharing the boots I actually wear with dresses and skirts, how I decide between each style, and the pairs I’d recommend this season.

If You’re Choosing Just One Pair of Boots to Wear With Dresses

• Best everyday boot: Leather knee-high boots
• Best for casual outfits: Suede boots
• Best with shorter dresses: Knee-high boots
• Best with midi dresses: Ankle boots or suede boots with a slit dress
• Most versatile color: Cognac

These are the styles I rely on most and build outfits around year after year.

This post contains affiliate links, where I may receive a small commission from purchases made through those links (at no cost to you). 

 My Favorite Boots To Wear With Dresses

Suede Boots

Suede boots, especially slouchy suede styles, are the pair I reach for when I want a dress to feel a little more relaxed. They soften the whole outfit, while smooth leather boots tend to look a little dressier. They’re also incredibly warm, which makes them one of my favorite boot styles once the weather starts getting colder.

I especially love suede boots with midi and maxi dresses that have a slit. Showing a little bit of skin above the boot keeps the outfit from feeling too heavy. It’s one of my favorite combinations for lunch with friends or other daytime occasions when I want to look pulled together without feeling overdressed.

These are the pairs I’d buy today if I were adding suede boots to my wardrobe:

I have a post on how to care for your suede shoes if you’re looking for tips.

Leather Knee High Boots With Dresses

Knee-high leather boots are probably the style I reach for most with dresses. I don’t wear heels with dresses nearly as often as I used to. Most of what’s on my calendar isn’t very formal, and heels can sometimes make an outfit feel dressier than I want. Knee-high boots give me that same polished look, but they feel much more effortless for everyday.

I especially love them with shorter dresses. I like just a little bit of leg showing above the boot because it keeps the proportions balanced and feels a little more refined. It’s one of my favorite ways to wear shorter hemlines, and I think it works just as well for daytime as it does for dinner or a night out.

When I’m shopping for a pair, I look for a comfortable heel height, a shaft height that works well with dresses, and a timeless shape I know I’ll wear for years.

I’ve included a mix of investment pieces and more affordable options below:

 

Ivory Boots

I don’t reach for ivory boots nearly as often as my brown or black boots, but there are times when they’re exactly the right choice. I like them with dresses that already have a little ivory or cream in the print because they tie the whole outfit together without adding another color.

This dress is a great example. The ivory boots blend in beautifully with the print and keep the outfit feeling light. Cognac boots would have worked too, but I like how the ivory keeps the overall look softer. They’re also one of my favorite ways to transition into spring, especially with floral dresses.

 

Ankle Boots and Skirts

In addition to dresses, I apply the same idea to skirts. For shorter dresses and skirts, I usually choose knee-high boots. I like the extra coverage, and they keep the outfit feeling polished without being too dressy. When I want a more casual look, though, I reach for ankle boots. They feel easy to wear, and I like that they show just a little bit of ankle as you walk. They’re also one of the easiest boot styles to wear with jeans, which makes them a great investment.

When I’m shopping for ankle boots, I look for a comfortable block heel and a timeless shape that I can wear with dresses, skirts, and jeans. The more versatile they are, the more I’ll wear them.

I’m wearing the Downtown boots, and they’ve become one of my most-worn pairs because they’re so comfortable. Even with the pointed toe, I can wear them all day without any issues. They come in sizes 33–45, along with narrow, medium, and wide widths, which makes finding a good fit much easier. The plush foam padding is another reason I keep reaching for them. If you plan on wearing them with socks, I’d recommend going up half a size. I share more about the fit, sizing, and how they’ve held up over time in my full Margaux shoe review.

Riding Boots With Dresses

When I know I’ll be doing a lot of walking, riding boots are usually the pair I reach for. I prefer a low stacked heel because it still gives me a little height while keeping the boot comfortable enough to wear all day. I especially like riding boots with shirt dresses because they lean into that classic equestrian look.

In addition to wearing your riding boots with dresses, they also pair extremely well with slim jeans or leggings and a chunky turtleneck sweater. I’m wearing these comfortable riding boots from Sarah Flint. You can read more about the brand in my Sarah Flint Guide.

Black boots

Black boots are still one of the most versatile pairs in my closet, especially with black, gray, navy, burgundy, and other cooler colors. While cognac is my most-worn boot color overall, black creates a little more contrast and is usually the pair I reach for when an outfit has cooler tones.

FAQ On Wearing Boots With Dresses

What boots look best with dresses?

The best boots depend on the style of dress and the look you’re going for. Knee-high leather boots are my first choice because they feel polished without being too dressy. Suede boots create a softer, more relaxed look, while ankle boots work well when I want an outfit to feel a little more casual.

Can you wear boots with midi dresses?

Absolutely. I especially like ankle boots with midi dresses because showing a little bit of ankle helps keep the proportions balanced. Suede knee-high boots also work beautifully with midi dresses that have a slit.

What boots look best with short dresses?

I usually choose knee-high boots with shorter dresses. I like just a little bit of leg showing above the boot because it feels balanced and keeps the outfit polished without feeling overly dressy.

Can you wear flat boots with dresses?

Yes. Flat boots can look great with dresses. I personally gravitate toward boots with a low heel since I’m 5’2″. I like the little bit of height they add while still being comfortable enough to walk in all day. But flat boots absolutely work too.

What color boots go with floral dresses?

It depends on the colors in the print. Cognac is my most-worn boot color because it goes with almost everything. If I’m not sure which boots to wear with a floral dress, that’s usually the color I reach for first. If a dress has lighter tones, ivory boots can keep the outfit feeling cohesive. Black or dark brown boots are a great choice with cooler colors and darker prints.

Are knee-high boots still in style?

Yes. Knee-high boots are one of those classic styles that come back year after year. I especially love them with dresses because they feel timeless and work for everything from casual daytime outfits to dressier occasions.

If you’re building a classic fall wardrobe, this post on how to style boots walks through how to wear them with dresses, skirts, and everyday outfits. You may also enjoy my guide to transitioning your wardrobe from summer to fall, where I share more of the pieces I reach for this time of year. Still not sure which style boots are right for you? Read my guide on finding your personal style.

Pin this post to Pinterest so that you can refer to it later when you are looking for timeless outfit inspiration.