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 I want to try them with a dress. Since I’m 46, I wonder 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’s how I have worn them.


black sweater dress ankle boots

Ankle Booties + A Dress Makes it Edgy: Dresses are naturally proper and ladylike. Pair your dress with ankle booties to tone things down and add a modern edge.

booties with a dress




rust sweater dress with wide belt


Which booties are best with which style of dress? It’s a preference, but sleek ankle boots generally look best with dressier/elegant gowns, while chunkier, heavier booties pair well with more casual/natural dresses. Here are a few more style tips to help you look your best.



Sweater Dress - Red and Black

1. Balance Top and Bottom

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


black dress with Dresses with Booties - Work Dress

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 simple, then an ankle bootie with some stunning hardware or additional interesting detail ( like a lace-up bootie) will 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.


Dresses with Booties - Sweater Dress

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 bootie give off a more casual, laid-back look.



How to Wear a Sweater Dress | Red sweaterdress with slouchy black suede booties

2. Wide Cuff Booties Slim

If your calves are vast 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. There are a lot of scrunchy boots that fall into this category.


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.

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7 thoughts on “How to Wear Ankle Boots With A Dress

  1. Hi, This is exactly what I needed for an event tonight. I have a red/black knee-length sweater dress and wondered if I should wear ankle-length or knee-length boots. I’m 51 :-)

    1. Hi Cynthia, It depends on the bling. For example, a gold buckle at the ankle can be quite classic, and you would wear a traditional outfit, maybe a jacket, with cropped pants and a shirt. Gold studs on a pair of booties are edgier, and you may wear a leather moto jacket with your outfit. So it’s not all bling suits one look! I hope that helps! Cheers, Deborah

  2. I have just started to wear my shoe boots with dresses, I worried it didn’t look right at first, but I have had some good compliments.

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