How to wear booties with skirts, dresses and pants – we show you 12 chic ways

by Sylvia

How to wear booties with skirts, dresses and pants! |

Booties are key for a well edited closet. More versatile than their knee high sisters, booties will take you through all four seasons.  As the temperature continues to drop, we take these booties beyond jeans and leggings pairings and venture into skirt and dress territory as well.

Yes, it is easy to rely on old faithful styling and not run the risk of creating a disproportionate look with the wrong dress-booties combination. However, we’ve got you covered with twelve looks covering pants, skirts, and dresses.  The key is to make sure they flatter your legs and lend a lean and chic look to your ensemble.

Booties with pants

Booties with pants, jeans, and trousers |

Booties with jeans or trousers are quite possibly the easiest style choice. However, there are some guidelines to follow so you don’t create a disproportionate and unflattering silhouette.

The key is to select booties that can carry a tune on their own and don’t mind being the star of the show (because they will definitely be on display).

Monochromatic looks (blue booties with blue jeans or black booties with black trousers) also create a longer and more flattering look. Select a slim or straight leg that hovers right above the top of the boot. Jeans (or even trousers depending on the occasion) can be styled with a cuff to add a more casual chic look.

Shop the above looks below.

Booties with skirts

,Booties with long and short skirts |

The general rule regarding skirts with booties is “the shorter the skirt the taller the boot”.  Of course, this rule can be broken depending on styling and body shape. Longer skirts can get away with shorter booties (such as with the longer Anna Sui skirt above).  You can also promote a more lean look by keeping the bottom monochromatic (like the black tights and black booties look above). Showing more of the ankle also allows you to get away with a shorter boot, as does a heel to elongate the leg (like the peep toe booties above paired with the showstopping Vivienne Westwood skirt).

Shop the above looks below:

Booties with dresses

How to wear booties with skirts |

Like skirts, pairing booties with dresses can sometimes be a tricky endeavor. The key here is to once again pay attention to getting your proportions right and promoting a long look that does not chop your body in half. An easy style tip is to go for a monochromatic look that creates a lean look.

Booties are short enough to not shorten your leg (especially when paired with a shorter dress and leggings). Also, wearing booties outside of the black color selection (like the gray or brown pair featured above) creates a more complementary look.

Shop the above looks below:

Ready to add more versatility to your closet with the four season boot? Shop some of our favorite selections below.

How have you been wearing your booties this season?


{ 8 comments… read them below or add one }

1 denton

My wife loooves booties.


2 Greetje

I find this particular styling extremely difficult. Which is why I copied Dan when I saw how good those brown booties halfway up your calf worked for her (and me). I haven’t found anything else yet to style with a skirt or dress. Really difficult.
The boots and booties you have shown are excellent but I am still hesitant. Not with the ones of For sure the most expensive ones from your selection…. trust me to pick them. But I have seen them cheaper and still good on Cla’s blog (Glam up your lifestyle).


3 Lisa

I am going to be very unpopular here, but I don’t like booties. I feel like my feet look like Frankenstein feet when I wear them, and also that it cuts off the line of the leg and makes me appear shorter. (And I’m tall! That’s not normally a concern of mine!) Some of these outfits are beautiful, but for my tastes, they’d look better with other shoes.


4 Terri

Booties are great, but I can’t stand the look of bare ankles with them. I don’t know why, but they look slutty to me that way. I DO wear them with black, colored, or decorated tights or socks.


5 Meryl

I love pixie boots and think they look very sexy with a skirt, I don’t like high heels so some cute pixie boots are my dress up shoe of choice. I recently went to a Miista sale and got white lacy booties, blue and brown booties with a swirly flock pattern and some black and pink knee boots. I’ve actually not worn the knee boots as they don’t work with trousers and with a skirt looks too…Erm..trashy! Booties all the way!


6 Linda

I just bought a pair of ECCO boots called Babette. they are the most comfortable boots I have ever purchased! I have bunions, narrow heels and use othotics. so to find a pair of boots that work for me is next to impossible. These are great.


7 Tammila Goodwin

I am petite and even though I am slim Booties don’t look that great on me. When I wear them with leggings my family laughs and says I look like an they are right. Cute boots just not for me.


8 lkla

Pretty much agree with most of the above. Booties don’t appeal to me as something to wear with dresses and skirts. And I don’t understand the trend of wearing them with trousers and jeans with several inches of bare ankle–isn’t that a little chilly in the fall and winter? That being said, some of the ankle boots (a better name) shown are great: I love the Kories, Sam Edelman, Summit White Mountain, and Toga Pulla.


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