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 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.
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.
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
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.
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.