Ask Allie: What Shoes Look Best with Ankle Pants?

I'm hoping you can help. I bought these pants from Lands' End on a whim. I chose the evergreen color thinking they'd be fun for fall. The problem? I'm just now jumping on the slim and ankle length bandwagon, so I have NO clue what to wear with these. I'm especially stuck on the shoes. If it helps, I'm 5'4″ and a size 14. What would you suggest? Thanks!

A colorful ankle-length pant is a great addition to the wardrobe, bringing a fresh new look to closet staples. Problem is, the length and fit may be drastically different from the rest of your pants, making shoes confusing. A cropped pant, especially on those of us who aren’t tall and slim can shorten our figure, so a shoe that elongates the leg is your best bet. Below I offer four different types of shoes that work well with cropped pants like the Lands’ End Portico Ankle Pants.

Wardrobe Oxygen Ask Allie: What Shoes Look Best with Ankle Pants?

As seen on the model in Lands’ End, 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 such pants. However, with a classic/preppy feel as these pants offer, you don’t want the heel too high. Here I feature the MICHAEL Michael Kors ‘Flex’ mid-heel pump (1) which has been a favorite of mine for years because of its wearable heel height yet leg-lengthening pointed toe. The sole is flexible and rubbery, giving good traction when walking on slick sidewalks or over slippery fallen leaves and I find I can wear them all day with comfort. This height and style of shoe is a great way to make these pants work for the office. Pair with a blouse and jewel neck cardigan, or a blazer and shell for corporate-friendly looks.

Another way to lengthen the leg is with a “nude to you” shoe. Since I purchased a pair of nude leather pumps this summer, they have become the hardest working and most worn shoes in my closet. Here I feature the Cole Haan ‘Air Juliana’ (2) which comes in a variety of neutral shades and the wood heel keeps it from looking too dressy with the ankle pants. A shoe like this is chic all year long, this season, and seasons to come. A nude shoe can quickly dress up a pair of pants like these; pair with a crisp white blouse and sparkly necklace for happy hour, or silk camisole and pendant for cocktails.

I think one of the best ways to wear a colorful pant is with a colorful shoe. Sticking with the pump with a longer toe, I adore the Nine West ‘Ike’ (3) in dark pink suede. Dark pink with dark green isn’t too preppy looking, and a wonderful combination to highlight neutrals, basic black, denim, and chambray. Pink isn’t the only hue that works with evergreen pants, I’d also love these merlot leather pumps and these steel blue suede ones. A colorful (or print, as I mention below, an animal print is gorgeous with dark green!) shoe is great for business casual and the weekends; pair with a striped tee and cardigan or leather jacket, a simple merino v-neck or turtleneck, or a denim shirt so the colors and shapes can shine.

Finally, know that you don’t have to wear a heel with shorter pants to look balanced. An almond or pointed toe and low vamp can give that effect without the height. For this look I paired the Lands’ End ankle pants with a leopard flat from Dr. Scholl’s (3). The green beautifully complements the animal print, and adds interest to closet basics from a denim shirt to a black turtleneck sweater. You can switch out the leopard for any other print or color; these same flats come in a cute black and white polka dot, I adore the scallop detail on these magenta flats, and the rich elderberry Saffiano leather of these flats would look great with so many fall trends this season. As with the colorful shoe, a pointed or almond toe flat looks business casual chic with a blouse or sweater and weekend cool with a simple knit top and cardigan.

As for clothing silhouettes, it’s better to have items hit at the hip or higher so not to stunt your shape. A tucked-in blouse will lengthen the leg; consider tucking in a top under a cardigan so you still have the coverage without segmenting your body too much. As for what kinds of tops, most anything goes from crisp button fronts to ruffled silky blouses to Breton tees and cashmere twinsets. Once you start playing around in your closet you’ll find these pants can be quite versatile!

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  1. Sara
    September 24, 2014 / 7:35 pm

    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!

    • September 25, 2014 / 6:11 am

      My pleasure, Sara. And I apologize for the troll, glad you’re ignoring her. I think the pants are adorable and such a great price too! <3

    • Shannon MacLean
      May 7, 2017 / 10:35 am

      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. September 22, 2014 / 8:35 pm

    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. September 22, 2014 / 2:58 pm

    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. Ginger
    September 22, 2014 / 2:18 pm

    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.

    • Tina Molnar Comstock
      September 12, 2017 / 2:16 pm

      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. Sophie
    September 22, 2014 / 11:36 am

    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.

    • Anamarie
      September 22, 2014 / 11:45 am

      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?”

      • Sophie
        September 22, 2014 / 12:28 pm

        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.

        • Grace McNamee Decker
          September 22, 2014 / 12:45 pm

          Sophie, your tone is really obnoxious.

          • Sophie
            September 22, 2014 / 1:34 pm

            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.

          • September 22, 2014 / 1:44 pm

            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%.

          • Sophie
            September 22, 2014 / 2:20 pm

            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.

        • Aimee
          September 22, 2014 / 1:33 pm

          Please stop trolling on this site. You are just mean, plain and simple. That’s really all I have to say about it.

        • Rosie
          September 23, 2014 / 9:05 am

          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.

    • September 22, 2014 / 2:59 pm

      Sophie – there’s the door; use it!

    • Jenny
      September 23, 2014 / 10:34 am

      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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