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.
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.
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.
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.
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.
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.
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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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 :-)
Hi Roshanda, You could wear either. It’s just personal preference. The shorter ones are more fashion-forward/edgy and the tall ones more elegant.
I have ankle booties with gold bling. What kind of dress should I wear?
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
Hello! Great post!
Thanks, Deborah! Very inspiring.
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.