It’s not surprising that a lot of women tend to think of jeans and casual pants when they’re considering what to pair with boots, but the reality is, wearing boots with dresses and skirts opens up a slew of new opportunities to use what’s already in your wardrobe, and in doing so, you may even expand your fashion comfort zone.

If you already wear boots with dresses, then you don’t need further convincing of why the look works, and you can skip straight to the tips below. But if the concept of pairing dresses and boots is a new one to you, then let me point out a few of the reasons that the combination works so well.

Wearing Boots with Dresses
Model Arizona Muse – Larry Busacca/Getty Images.

The Benefits of Wearing Boots with Dresses

First and foremost, you get to actually show off your boots. Yes, I know, the same can be said for tucking jeans or leggings into the boots, but let’s face it, skinny jeans aren’t very kind to a lot of us, and leggings… well, they have their place, but there are some occasions and events when the dressier fare is required.

Another great reason to pair boots with dresses and skirts is that — depending on the type of boots — it can be one of the most flattering combinations you’ll ever wear. This is especially true with taller boot styles, which help create a longer, leaner, and more cohesive look. Additionally, women who are self-conscious about their legs will find that mid-calf, knee-high, and over-the-knee boots allow them to wear skirts and dresses that they might not otherwise be comfortable in.

And finally, combining the right pair of boots from with your dress — creates a chic, polished, and confident look that’s actually quite addictive. In fact, I truly believe that if you give the combination a try, you’ll find yourself wondering how you ever got along without pairing the two.

Tips for Wearing Boots with Dresses

Okay, enough with the convincing, let’s get to the actual tips for how to wear boots with dresses: and, you’ll be happy to find that there really isn’t a lot to learn, but do know that experimentation is your friend.

There are so many different kinds of boots, dress styles, and body types that it would be impossible to offer suggestions that would work for everyone. And besides, there aren’t any hard and fast rules on this topic. However, I do have a few tips and suggestions for getting comfortable with the boot and dress combination, and advice on how to find that magical look that works for you.

1) Keeping it Simple

To simplify the process, start with a simple dress — like a sweater dress, a wrap dress, or even a long tunic — and pair it with a pair of simple, tall, flat boots. If you like tights or fancy stockings, feel free to add them into the mix for a bit of pizazz, but skip really trendy boot styles, or anything that’s too defined — i.e. don’t start with a halter dress and a pair of cowboy boots. The reason behind going so simple is that this look is going to work for just about everyone. It’s practically foolproof.

Wearing Boots with Dresses
Pictured: Theory ‘Jiya S Loryelle’ Dress

2) An Easy Balancing Act

The combination I described in step one is so simple and generally flattering that you could actually call it a day there. But if you’re looking for ways to up the ante, then the next thing to try is the half and half approach: half of a dressy outfit, paired with something more casual; half-frilly with something more utilitarian; or half-glamorous with something really simple. Still, no cowboy boots and sexy dresses, because both of those items fall under the “attention-getting” heading. You could, however, try a pretty cocktail dress with a pair of simple boots; or a pair of western boots with a plain but feminine dress.

Wearing Boots with Dresses
Pictured: McQ – Alexander McQueen Loop Stitch Cable Dress

Additional Things to Keep in Mind

Though I said above that experimentation is the key to making boots work with dresses, there are a few words of caution that I’d like to pass along.

The main bit of advice is that sometimes you don’t have to try so hard; a pretty pair of simple dress boots will work well with just about any skirt, suit, or dress you might normally wear to the office, so you don’t have to go all crazy and throw a pair of Doc Martens into the mix just to shake things up. Experimentation can be good and is definitely fun, but it’s also not always necessary.

And finally, I wanted to point out that you should try to find a pair of boots that work well with your body type — and, since most boots do look good on most body types, I’m mainly talking about ankle boots and booties here. They’re awesome, and anyone can wear them with jeans, pants, or maxi skirts. But there are a few caveats with ankle boots that you may want to be aware of if you’re trying to pair them with shorter dresses, and aren’t blessed with the height and legs of a supermodel. You can read more about these dilemmas in this article on what to wear with ankle boots.

Wearing Boots with Dresses
Pictured: Diane von Furstenberg ‘Bentley’ Dress. Wearing Boots with Dresses

My Top Picks for Boots to Wear with Dresses

  • Riding Boots: A pair of riding boots is guaranteed to go with a variety of different styles of dresses in your closet. I like Ralph Lauren riding boots because they have a timeless look that you’ll be able to wear for many years. Check out the Ralph Lauren Maryann Riding Boot on
  • Over-the-Knee Boots: Dolce Vita makes a great pair of comfortable over-the-knee boots. These boots also have a wedge heel that will elongate the leg.
  • Flat Boots: A classic pair of flat boots is another great option if you’re looking for a versatile boot that looks good with everything. Loeffler Randall makes a great pair of comfortable knee-high boots that also come in rich brown color.
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