What to Wear With Tall Boots

How to Wear Women's Taller Boot Styles

Model Arizona Muse attends the 2012 CFDA Fashion Awards at Alice Tully Hall on June 4, 2012 in New York City.
Larry Busacca/Getty Images Entertainment/Getty Images

Casual or dressy, flat or heeled, a pair of tall boots is one of the most versatile footwear items you can have in your wardrobe — but you still need to know what to wear with them.

By tall boots, I'm mostly referring to those that are about knee high, but many of the following tips will apply to styles that fall between a few inches below your knees to a few inches above your knees (also known as over-the-knee, OTK, or thigh-high boots).

It's also worth noting that, while many different boot styles will work with the outfits I've listed below, simple, classic styles are, by far, the most flexible style. Those western-flavored Frye's may rock with those skinny jeans you just picked up, but a simple black knee-high boot will work with those jeans, as well as just about everything else in your closet.

Here are a few of my favorite things to wear with simple, taller boot styles.

Long Skirts

A maxi skirt, or any skirt that is long enough to cover the top of your boots is one of the most flattering items you can pair with tall boots. While many women tend to think only of fuller skirts as a match for knee-high boots, narrow skirts can look fabulous with tall boots as well.

For this combination, you can go with just about any heel height or shape, but for women who can't wear heels (or just need an occasional break from them), flat boots are a really great choice here because you can have a completely dressy outfit while still wearing flats.

Short Skirts

One of my favorite ways to wear tall boots is to pair them with shorter skirts, ranging from minis to knee-length styles.

For added warmth, and because my legs are a crazy shade of pale, I prefer to use fun tights; stockings with a bit of sheen; or opaque hose in this combination. But if you've got the legs for it and aren't afraid of getting cold, there's no reason you can't go the bare leg route.

Skinny Jeans

One of the only things that makes me feel bad about the fact that skinny jeans look so horrible on me is that they're really the only type of jeans that are good for tucking into tall boots. But if you love cigarette jeans, you're in the enviable position of being able to tuck them into everything from dressy heeled boots to casual flat styles.

Naturally, the same holds true for leggings or any jeans or pants that you don't have to bunch or fold to tuck into the tops of your boots.


Gauchos, or wide cropped pants, aren't always in fashion, but when they are the absolute best footwear for below the knee styles is a pair of tall boots.

But, you'll definitely want to avoid wearing this style of pants with boots that are too casual or trendy. Skip the fluff and heavy hardware, and opt instead for a simple-heeled dress boot, or a flat boot that has a bit of polish to it, lest the whole outfit becomes too sloppy.


It's nearly automatic to think of pairing boots with skirts, but for some reason, many women don't think to wear them with dresses. They should though, because the look is dynamite.

I'm not talking about frilly, puffy, party dresses, nor am I referring to formal wear — although I have seen the latter combination rocked a couple of times. The dresses I'm talking about are your standard, everyday sort of dresses: wrap dresses, sweater dresses, shifts, minis, a-lines, and empire dresses.

Again, this look is best with simple, classic tall boots, and is not meant for overly-casual or super-trendy boot styles.

Outfits to Avoid With Tall Boots

  • Baggy or pleated jeans and pants: Not that they're flattering anyway, but tucking these styles into tall boots creates the dreaded "ballooning" effect that could destroy the self-esteem of nearly any woman. If you're blessed with a long, lean body, feel free to tuck in those loose cargo pants to your heart's content, otherwise, steer clear of this combination. And, while you're at it, leave any wide-legged pants — even those with flat fronts — on the outside of your tall boots.
  • Shorts: I know, we've all seen celebrities doing it, but wearing shorts with tall boots should really just be considered as one of the many perks of being a star. For the rest of us though, this look usually isn't a good one.

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