How to Wear Ankle Boots With A Dress

Dear Deborah,

I love ankle boots and own a few pairs. I usually wear my booties with jeans or leggings but would like to try them with a dress. Since I’m 46, I’m wondering if this is an age-appropriate look, and if so, how do I wear them?  Thanks, Sheila

Hi Sheila,

Ankle boots can be worn at any age, and yes, you can wear them with dresses! Here are a few guidelines to help you look your best.

Which booties are best with which style of dress? It’s really a personal preference, but generally, fine, sleek ankle boots look best with dressier/elegant dresses, while chunkier, heavier booties pair well with more casual/natural dresses.

Ankle Booties + A Dress Makes it Edgy.

Dresses are naturally proper and ladylike. To tone things down and add a modern edge, pair your dress with ankle booties.

1. Balance Top and Bottom

This perky, fine knit red sweater dress with a beautiful pattern remains the center of attention when you keep the booties simple and elegant.

2. Pointy Toe Booties Are Sexy

If your dress is busy and has a lot of detail or pattern, go for a plainer ankle bootie that doesn’t have a lot of embellishment or detail. On the other hand, if your dress is plain, then an ankle bootie with some stunning hardware or other interesting detail ( like a lace-up bootie) will really make your outfit pop.

Booties with Pointy toes and slender heels are more feminine and sexier than booties with rounded toes and thick, chunky heels. These black booties, above, ooze sophistication and authority.

3. Nude Booties Elongate the Legs

Dark booties worn with a dress can look fabulous, but they can also shorten your leg line, so if that is a concern, try a pair of nude-colored booties in the shade close to your skin tone, or go with a dark bootie and matching dark opaque hose to create a long, lean line.

4. Cowboy Booties Make the Look Casual

Western-style booties are trendy and can be worn with a dress. Chunky knits or florals with this type of bootie give off a more casual, laid-back look.

5. Wide Cuff Booties Slim Legs

If your calves are wide and you want to wear booties with a dress, try an ankle bootie with a wider cuff. The wider cuff tricks the eye into making your leg look smaller in comparison. There are a lot of scrunchy boots that fall into this category.

Yes, you can wear a midi with ankle booties, but keep your leg line looking long. Short ankle booties that don’t go past your anklebone are most flattering.

Still unsure about wearing ankle booties with a dress? 

Then try a bootie/shoe. These half bootie/half shoes are a great solution when you are just getting used to wearing booties with shoes or when it’s just too hot out to wear a full bootie that completely covers the foot.