Shoes to wear with ankle length pants

Last Updated on 2022-08-08 by azeez Lydia

Shoes to wear with ankle length pants

When it comes to fall fashion, nothing is more universally flattering than ankle-length pants. They’re the perfect mix of casual and chic, and can be dressed up or down depending on how you style them.

But what shoes go best with ankle-length pants? We’ve got your answer!

  1. Ankle boots – Ankle length is perfect for boots because it means that you can show off just a little bit of ankle without going full-on boot cut. Choose a boot that has an extra thick sole and great tread so they’ll be comfortable whether you’re walking on concrete or dirt.
  2. Heels – You may think that heels are out of the question when it comes to ankle length pants, but if you choose a pair of heels with a platform sole and straps that wrap around your ankles, they’ll stay securely on while also giving your legs some added height (which will help balance out the fact that your ankles are covered).
  3. Flip flops – If you’re going for a casual look with your ankle-length pants, then flip flops are definitely the way to go! Just make sure they have enough traction

Shoes to wear with ankle length pants

#1- Moccasins and Loafers

best shoes for ankle length skinny pants

Moccasins and loafers are super trendy and can be very stylish, however, they often work better in theory than they do in reality.  Every time I pick up a pair of driving loafers at the store I covet them.  Yet, once I try them on, they look just don’t look good.  In order for these types of shoes look right and not too masculine I think a little ankle showing helps.

Take how I styled these Tod’s metallic driving loafers with a pair of blush Boden skinny ankle pants.  It’s an updated preppy look that works well with this J. Crew chambray shirt, navy bag from MICHAEL Michael Kors and coral studs from MARC by Marc Jacobs.

#2- Ballerina Flats

Shoes for Ankle Length Skinny Pants

Ballerina flats are a pretty obvious choice to wear with skinny ankle pants.  Don’t pack these shoes away once the weather cools off.  Use them with more autumnal looks to create a chic transitional outfit like I did here using this pair of red flats from Cole Haan with these navy ankle pants from J. Crew and sweater and shirt combo top from French Connection.  To finish the look, I used this cognac Dooney Bourke satchel, geometric hoops from Max & Chloe and Bauble Bar bangle.

#3- Oxfords

shoes for ankle length skinny pants

Oxfords are fantastic with skinny ankle pants for the same reason that moccasins and loafers are, they look more feminine when a little ankle shows.  Plus, oxfords can easily take these  shorter pants well into the fall.  In this look, I styled these Franco Sarto oxfords with a pair of Theory ankle pants.  For a cool weather look, I added this Alice + Olivia sweater and finished the outfit with a burgundy bag from Rebecca Minkoff, leather wrap bracelet from Le Mer and drop earrings from Stella & Dot.

#4- Heels

shoes for ankle length skinny pants

Don’t discount heels when wearing your skinny ankle length pants.  Any heel height will work.  The benefit of wearing heels with these types of pants is they lengthen your legs.  Not only does this help balance out the shortening effect that cropped pants can have, but elongating the legs can make your hips and thighs look narrower.

In this outfit, I used these suede platform pumps from Calvin Klein with ankle pants from Reiss.  For a dressier look, I added this red blouse from Zara, gold and black clutch BCBG and layered necklace from Ann Taylor.

#5 Ankle Boots

shoes for skinny ankle length pants

To really get the most out of your skinny ankle pants try wearing them with boots.  The best boot styles are booties and styles like chelsea boots because, unless you ankle cropped pants are super skinny around the ankles, it will be tough to wear them with boots that require you to tuck  in the legs of your pants.  Instead, boots that fit under the pants will work best.

In this outfit, I styled these skinny, ankle length cargos with Lucky Brand chelsea boots and, for a weekend look, layered this coral top from LOFT under this easy camel cardigan from Theory and accessorized it with this leaf necklace from Modcloth and handbag from Frye.


Throughout the rest of the summer, don’t forget about your wedges and sandals as great shoes to wear with you skinny ankle pants.  As the summer winds down, and cooler weather comes around, look to these additional styles to create some fantastic outfits.

By popular demand here is a video which you have requested on what shoes to wear with ankle length trousers.

Basically, trousers which are not full length and where the hem finishes either slightly above, on or below the ankle are referred to as cropped trousers, ankle grazers, on the ankle, ankle or 7 eighths trousers (by M&S). The whole purpose of these cropped trousers is to show-off your lovely ankles.

Personally, I tell my clients to avoid ankle boots or shoes which cover up and add bulk around your ankles which defeats the purpose of wearing these shorter length trousers!

I love wearing cropped trousers in the winter too and I buy 100 denier knee-high pop socks or fine gauge woollen knee-high socks from a lovely brand called Falke. In the summer, I don’t wear tights but I make sure I rotate my shoes and I try not to wear the same pair two days running as sweat can make the leather insole smell.

Flat shoe options with cropped trousers are wide and varying. Consider ballet pumps, trainers (not too bulky), brogues, moccasins, flat slingbacks (as in the photo above), slip on shoes, strappy sandals, peep toes shoes etc. Basically, any flat shoe which doesn’t cover your ankles works really well.

If you prefer a heel, how about a kitten heel? a low to mid-heel looks good, especially if the shoe has a pointy toe as it also gives the illusion of elongating your legs. I find a kitten heel, a low stiletto or wedge works well and not a chunky block heel.

As a corporate stylist and personal stylist in Surrey and London, I often get asked to talk to women individually and in groups and this is one of the most popular questions I get asked: ‘What shoes to wear with ankle grazers’ and the ‘Best shoes to wear with ankle grazer trousers’ etc. so I hope this video answers all your questions.

The most important thing is to keep your ankles exposed with the right shoes. Enjoy the video below.

Best wishes

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