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What Shoes Look Best with Ankle Pants?

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what shoes look best with ankle pants by wardrobe oxygen

I had a reader reach out to me asking about what shoes look best with ankle pants. While she has ankle-length jeans in her wardrobe, she has never owned ankle pants before and was wondering which shoes work best with them. With a focus on work fashion, she desired ideas of what shoes to wear with ankle pants to the office, especially when the weather is colder.

I'm hoping you can help. I bought a pair of ankle pants on a whim. The problem? I don't usually wear ankle pants, I have ankle jeans I wear with sandals and my low-top Converse sneakers, but I don't know what kind of shoes look best with ankle pants. And how do you style ankle pants in the winter? Can you help?

Pant silhouettes change, but the ankle pant is here to stay, especially as an option for business casual workplaces. Ankle pants can be wide-leg, they can be as slim as skinny jeans, or have a more straight cut. Below my advice should work with most style of ankle pants, with a focus on what to wear to work.

What Shoes Look Best with Ankle Pants?

a collage of three photos of Kate Middleton wearing ankle pants with black pumps
Kate Middleton wearing black pumps with a range of styles of ankle pants.

Pumps

A classic pump with a traditional vamp (not too high, not too much “toe cleavage“) and pointed or almond toe is a great choice with ankle. The lower vamp provides more exposed skin, to give space between pant hem and shoe, offering balance. A heel also offers a lengthening effect, which can make ankle pants look more proportional.

However, you don't want too high of a heel or it can look like a costume. From a subtle heel to about 2.5″ inches is best. Slim, kitten heel, or block are all great options.

Flats

Not all flats are created equal; when it comes to styling ankle pants you want a flat that has a lower vamp and plenty of structure. The first shoes I thought of were my Ally NYC flats, made of leather and have an elongated pointed toe and firm sole.

Even with an elongated vamp, flats can still feel a bit… flat and can shorten your appearance. You may wish to consider either a print or a shoe low contrast to your skintone.

Shoes Low Contrast To Your Skintone

When you choose a shoe that is low contrast to your skintone, you elongate the leg line, and your shoes don't compete with your ankle pants. This is also a great tip when styling skirts and dresses that are below the knee.

Low contrast means a color that is close to your skintone (beige, tan, brown, etc.) or a color that isn't a shade of brown but still blends nicely. Blush pink, copper, mauve, cream… these will provide the same leg-lengthening effect while giving you more options.

Printed Shoes

They say leopard is a neutral, and I find that to be especially true when styling ankle pants. A leopard-print flat or low pump works with pretty much any skintone to give a cohesive look for the workplace and beyond.

Other prints can work too, but you want the print to not steal the spotlight. A print that is either more subtle or close to your skintone will provide the best effect.

How to Style Ankle Pants for Winter

collage of three photos of Tracee Ellis Ross wearing ankle pants with boots
Tracee Ellis Ross styling ankle pants with boots.

Ankle boots can feel as though they are just for warmer months, but some styles look downright chic with cold-weather footwear.

High Shaft Ankle Boots

If you're looking for a way to stay warm while wearing ankle pants, a high-shaft ankle boot can be just the ticket. The key is to find a boot that is tall enough that it slips under the hem of your ankle pants.

With wider leg ankle pants, you can carry off a variety of styles of ankle boots. The boot can be flat, it can be heeled, and it can have most any style of toebox. You can elongate the frame with a boot the same color as your pants, or add interest with a contrast color.

With slimmer leg ankle pants, you want to keep the boot slim. Look for elongated, almond, or pointed toes. The boot will look best with at least a hint of a heel.

Knee-Length Boots

Consider tucking your ankle pants into knee-high boots to get more wears through the colder months. While previous seasons only saw knee-high boots with skinny pants, right now it's totally acceptable to have your pants blouse out over the top of the boot shaft.

Pop Socks with Loafers or Brogues

Take a cue from the boys; with recent trends for slimmer and shorter suit pants, men have gotten creative with their hosiery. Choose a menswear-inspired shoe like oxfords/brogues or loafers in whatever color you desire, and then get a fitted dress sock that is a cool pattern to tie your whole look together (or be the statement with neutrals).

As with all other styles of shoes recommended for ankle pants, keep the shoe trim. Think a man's dress shoe more than a pair of Doc Martens. Sleek and tailored will provide the best effect and ensure your “pop socks” will get the attention!

This post was originally published in 2014 but updated for current trends.

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20 Comments

  1. I’m the one who originally posed the question. I’m going to ignore the nasty comments from the miserable troll.

    Just this Saturday I had that exact pair of leopard print shoes in my hands. I’ve been wavering on whether or not I should go back for them, but after taking a look at the rest of my fall/winter wardrobe, I think I will. They are fun but not too crazy. I like the other ideas, like a tucked in shirt with open cardigan as well. Thank you!

    1. Sara, I’m only one inch taller than you and I waver between a size 12-14. Don’t get too caught up on the sizing labels – as you know, the label can vary based on the manufacturer and cut of the pants. Just be sure that the pants fit you well in the waist and rise, and don’t make you look distorted (not too tight, not too loose). I was skeptical about ankle pants when they first appeared on the scene a few years ago. I was also leery about me wearing a colored pant … I’m middle aged (in my mid 40’s) and thought I might look insane wearing a pair of purple pants. Then I saw a lady much older than I, at the mall one day, wearing a pair of green ankle pants and she looked so stylish! So, I got brave, and over time my entire pants wardrobe has moved from a classic trouser to all ankle pants! I work in a fairly casual environment, so I can wear them every day. I love them with a 2-3 in heel or a pointy toe flat. In warmer months, they look good with the right kind of classy / strappy sandal too! I have them in just about every color imaginable and I always look great! (I’m humble too). Just be sure to get the right proportions with your tops. You know the standards … front tucking looks great, a cute cami with a cardigan is awesome (not too long or too short), or a top that’s somewhat fitted and isn’t made to tuck (like a button down shirt or a top that has a tie back). As with any outfit, just be sure to have good balance in proportions for your body and you’ll look smashing! I’m frugal, so what I do is try on ankle pants in the stores, note what brand/size I need, and then I shop online (ebay) to find the same pants at a lower price. Pinterest has great images on all sorts of ideas for how to wear ankle pants (and leopard print shoes too!!!).

  2. I wear ankle pants alllll the time, and I’m always wearing them with flats and the very occasional wedge. I might be kind of biased, but I always think I look pretty smashing in them 🙂

  3. Great advice as usual, Allie. I do like the look of those trousers (pants) as I love forest green. I think ankle pants that actually end on the ankle (not some distance between the ankle and the calf) can be flattering on everyone. Luckily I’m medium height so what looks really short on a model turns into a true ankle-pant on me.

  4. I’m 5’5″ and a size 12, so not so far off from our size 14 gal.
    A lot depends on your shape. If you have an apple shaped figure -round middle, skinny legs those ankle pants look differently than if, like me you are channeling Serena Williams – curvy though the hips and thigh.

    I like ankle length pants because I have nice ankles, but I don’t get them unless they’re cut for curvy figures. I’d go with the pointy toe flats or loafers, and a bare or nude ankle. I’d go with either a high hip or a mid-thigh top because I want the viewer to focus on my great ankles, not my tennis player thighs. If I had good cleavage I’d show that off, sigh….

    The important thing to me is that no matter what your size you can look good in tapered pants if they fit properly and you put them together well.

    1. I am 5’6″ and a size 12, so I close to that too. All summer I have worn slim ankle pants with a chunky midsize heel and everyone compliments me on how “cute” I look. Now, have “cute” can I look 54, who knows. So, I hope our 14 gal goes out and gets some slim ankle pants and walks around all sassy and confident!

  5. This is just another example of poor advice. An honest person would have said – Lady, if you are 5’4” and size 14, stay well away from ankle length pants. They will make you look even shorter, fatter and stumpier. Especially if you go for a hip length top. Check returns policy and hope for the best, if not, donate to a local AmDram – no real life situations should suffer the sigh.

    1. WTF, Sophie. There are plenty of people 5’4″ AND UNDER of any size who look great in ankle pants. It all depends on how they fit. How is your comment more helpful than what you falsely call “poor advice?”

      1. Language, my dear.
        At this heigh and weight the lady is no Audrey Hepburn, and probably not a young lass either, otherwise she wouldn’t shop at Lands End. I am helpfully suggesting that she should make a conscious effort not to look ridiculous.

          1. Which bit? Asking to mind the language, or being frank? When one asks for advice one should be prepared to hear the truth, no? I believe in constructive criticism. If the lady wants to wear ankle length pants and look good, she should make sure her physique allows her to do that. At that height and size, she would better off in straight leg pants that would cover her heels. One should not just blindly follow some silly trend.

          2. Sophie, this is a warning. I have no issue with you questioning the content of my posts, but I do have issue with you starting arguments in my comment area. I don’t like to ban people but I will if you make this an unpleasant place.

            As for your issue on my advice, everyone deserves to have fun with fashion, and everyone has the right to wear what they want. If you don’t like that,you’re at the wrong blog. There’s a ton of blogs out there and one that would likely agree with your narrow-minded views 100%.

          3. Allie, with all due respect – I’ve merely expressed an opinion, albeit different from that of yours and your faithful devotees. Surely that’s allowed? We none of us are perfect, and sometimes criticism is helpful. And yes, if you call trying to look presentable being narrow-minded, so be it. However, name calling smacks of poor neighbourhood playground.

        1. What does her age have to do with anything? We will all be middle aged someday, if we aren’t already. Yes, Sophie, even you will age.
          Given the choice between looking ridiculous and being mean-spirited and nasty, I’ll take looking ridiculous.

    2. From the original request, she wasn’t asking for advice about her choice in pants. She stated that she had purchased the pants and then asked what to wear with them, specifically looking for shoe suggestions. I think Sophie’s comment therefore falls into the “assvice” category: unwelcome and unsolicited advice. Hopefully the questioner recognizes it as such.

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