What To Wear Ankle Boots With


When it comes to skinny jeans, ankle boots are a pretty safe bet. The boot will do the same thing as a hemline and break up the dark pant leg. Being that ankle boots are typically more casual than pumps or sandals, they’re also a great way to keep your look interesting without going overboard on your look. If you’re not sure how high or low-rise your pants should be, pay attention to where the trouser cuff meets the shoe in this picture (and bear in mind that this is still super casual).

If you want something slightly different than standard skinny jeans, try flare jeans with some ankle booties instead! You can go for anything from light wash denim flares like these from Levi’s or even darker blue ones if that’s what you prefer—the key here is just getting some flare into your outfit in some way shape or form!

If you have boyfriend jeans but don’t want them looking sloppy by pairing them with heels (or whatever other footwear), try adding another layer of interest with an over-the-knee leather bootie like these from ASOS ! They’ll help elongate your legs while keeping things casual at the same time!


With shorts, the best way to wear ankle boots is with two-piece short sets. This will allow you to show off your ankles and show off your legs in a stylish way.

This can be done in a variety of ways. The main ones include:

  • wearing ankle boots with shorts that are longer than pants but shorter than skirts (think capris).
  • pairing ankle boots with mini skirts or even midi skirts if you want to go for something bolder and more fashion forward.

Skirts and Dresses

  • Skirts and dresses
  • Skirt or dress length
  • Style of skirt or dress (A-line, pencil, etc.)
  • Dress or skirt color and pattern
  • Dress fabric (silk, wool, cotton)

Leather Leggings or Tights

You can wear any type of ankle boot with leather leggings or tights. But you’ll want to keep the colors the same, and make sure that your shirt covers up most of the leg. For example, if you’re wearing black leather ankle boots, try pairing them with black leather leggings or dark denim tights. It’s also important to wear a long shirt so that it covers up your ankles when you sit down. It’s best not to wear a sweater over this look since it will make it look too casual and relaxed for work attire; instead try wearing a cardigan or blazer instead for an updated look on your favorite fall outfit! If you want to add even more style into this classic combination then try adding some color! This is where pastels come into play—they’ll compliment lighter colored leathers very well while still keeping things professional-looking at work during the day or out at night later on in the evening (but please don’t forget: don’t overdo it).


Culottes can be tough to pull off because they can look frumpy, but the trick to wearing culottes is to pick a pair that are properly fitted and are the right length (you don’t want them too short or too long). Culottes that are too long can make you look short and stumpy, so if you have any doubts about them being long enough, stick with something else.

Cropped Pants

If you like ankle boots, then you’re probably wondering what types of pants go well with them. Well, the answer is pretty simple: cropped pants! Ankle boots look great with cropped pants because they can be dressed up or down depending on what style of boot and how long your pant leg is.

The length of your pants is important when wearing ankle boots. If your jeans are too long for the height of your heel, it will look awkward and unflattering. High-waisted shorts tend to work best for this style combination as well as mid-rise styles that hit at about mid-thigh level or just below (depending on personal preference).

If you love bright colors, then try pairing a pair of burgundy suede heeled ankle boots from Steve Madden with dark washed denim capris from Express! The bold red color will make any outfit pop while still being subtle enough not to overpower everything else in the outfit!

Wide-Leg Pants

If you’re wearing wide-leg pants and want to add a pop of color, choose an ankle boot that matches. The same goes if you want to keep things simple and wear black or brown boots with your wide-leg pants. If you’d rather go for something bolder, try a pair of contrasting colored ankle boots and let them shine against the dark material of your pants!

Another trick is wearing heels—this way, you can pull off the look even if they aren’t super tall.

The best way to wear ankle boots is by wearing them with your favorite jeans, but you can also wear them with skirts and dresses, shorts, leather leggings and wide-leg pants.

It’s a great idea to wear ankle boots with your favorite jeans, but you can also incorporate them into your wardrobe by trying out other legwear options. Here are some ideas for how to wear ankle boots with different bottoms:

  • Wear them with skirts and dresses. Ankle booties look particularly good when paired with A-line skirts that have a high waist or a tulip skirt shape.
  • Wear them with shorts. Ankle boots will look amazing when worn on top of denim shorts, especially if they’re distressed or ripped. Just make sure that you don’t get too much exposure at the ankles if you’re going to be outdoors in cold weather!
  • Wear them with leather leggings and wide-leg pants (cropped). If your legs are super muscular, this might not work for everyone because it makes everything look bigger than it really is (but it’s very flattering). You can also try wearing ankle boots under wide-legged jeans or culottes—this will have the same effect as above but not quite so drastic since there isn’t any skin showing outside of the pant leg openings!

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