How to Wear Ankle Boots

Ankle boots, motorcycle boots, flat boots, high-heel boots, over-the-knee boots...so many choices! Boots can be tricky to wear, especially ankle boots, so I put together this list of boot styles and what types of outfits look best with each. Enjoy!

Gwyneth Paltrow in sleek booties.

The Ankle Boot. This is the most confusing boot of all. The latest trend is to wear this style bootie with dresses and skirts. If that's your plan, you want a sleek, low bootie or a peep-toe bootie. Anything too high on the ankle cuts off your leg and makes you look stumpy. Also, I think they look great with tights for a leg-lengthening look. If you can wear a pump, then you can wear a low bootie! If you want ankle boots to wear with pants or jeans, you can go with the sleek bootie or a higher ankle style.

Some examples that are best for dresses/skirts:

Christian Louboutin Lady Derby Peep Toe Ankle Bootie

Christian Louboutin Lady Derby Peep Toe Ankle Bootie

Aquatalia by Marvin K. - Izzy - Wine Suede Ankle Boot

Banana Republic Samira Sleek Bootie

Best for Pants/Jeans: For pants or jeans, you can go with a higher, true ankle boot. There is no rule against wearing this higher boot with skirts or dresses and if you have great legs, go for it! However, for many people, a higher bootie makes you look stubby. The Banana Republic boot at left is a good hybrid. It can be worn either way.





Here are some choices for casual boots to be worn with pants:

Franco Sarto Lustre in Multiple Colors

Bandolino Quinlee Ankle Boot

Some tips:
1. Go for a classic style. While the studs, ruffles and zippers are fun, if you want a pair that will last you several seasons, you should go with a classic look, nothing too trendy.
2. Check the length. If you're wearing ankle boots with a skirt or dress, make sure the skirt/dress isn't too long, it will just look frumpy. You don't have to go with a mini skirt, but an above-the-knee style is best. Or, if you want to go longer choose a slim, pencil skirt rather than a long, flowy skirt.
3. Try them with ankle-length pants. Step out the box and wear a pair with ankle-length pants or jeans. The key is that the pants have to be tapered and narrow at the bottom--no crazy wide legs. Or, try a pair of skinny jeans rolled up above the ankle to show off the boot. Go wild!