How To Wear Ankle Boots In The Winter When You’re Over 40

It’s winter and you may already be sick of snow, ice, slush, and all the other sartorial issues of the season, but you can definitely still have fun with fashion during the depths of winter while being sensible. There’s no denying that sometimes we need to wear snow boots simply because they are practical (and it is indeed possible to find a stylish pair of snow-proof and water-proof boots as you’ll see in this article). But getting a new and fashionable pair of ankle boots can boost your wardrobe and your mood if you have the winter style doldrums. Ankle boots work almost all year round depending on your climate, and with nearly everything in your closet. Here’s how to wear ankle boots with almost anything you own.

How To Wear Ankle Boots Over 40

Ankle Boots with jeans fountainof30

Casual: How To Wear Ankle Boots With Jeans

Ankle boots work well with nearly all types of denim, from traditional straight leg jeans to trendier silhouettes like flares, wide legs, ankle crops, or even skinny jeans or boyfriend jeans. We tend to prefer rounded toes with skinnies and other more narrow denim cuts and almond toes with wider legs or flares, but you should definitely play around with the different silhouettes and see how they work for you.


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Sam Edelman’s “Petty” ankle boots are becoming a modern classic, and we like them with virtually any type of jeans. These Frye and Co. zip booties are equally easy to pair with jeans and we especially love the cherry colorway with blue denim. Want to make more of a statement? Try something in an animal print like these (nearly) flat boots by Dolce Vita. If you live in a snowy or icy place, these Sorel Joan of Arc wedges can be a good solution that is both practical and stylish.

Ankle Boots With Leggings fountainof30

Casual/Athleisure: How To Wear Ankle Boots With Leggings

Ankle boots can dress up basic leggings, especially when paired with a longer top or sweater. That said, we don’t recommend that you wear leggings or workout tights with ankle boots in the majority of cases. Generally if you look like you are headed to or coming from the gym, you should be wearing sneakers instead of ankle boots. We tend to like sleeker low-heeled ankle boots or flat ankle boots such as these from Gentle Souls by Kenneth Cole, as well as lace-up ankle boots like these by Aquatalia.

Ankle Boots for Dresses And Skirts fountainof30


Dressed Up: How To Wear Ankle Boots With Dresses And Skirts

Ankle boots can be incredibly flattering and a great option with dresses and skirts in the winter. Wear ankle boots in the same color as your tights for a long, lean line. This works especially well with black and it’s probably the easiest color when it comes to matching your shoes and tights. These boots by Aqua at Bloomingdale’s look just about perfect.

Alternatively, go for studs, zippers, and other unique details that would otherwise be covered up when you are wearing pants. For a splurge, we love these Valentinos (which would also be amazing with denim); these Zadig & Voltaire studded boots have excellent lines and there are little bit western, a little bit heavy metal which might make them more versatile than you think.

Ankle Boots With Jumpsuits fountainof30

Dressed: Up: How To Wear Ankle Boots With Jumpsuits

Jumpsuits are quickly becoming a modern classic, and ankle boots or booties are often the ideal pairing. We’re fans of combining slightly pointy high heeled ankle boots with jumpsuits (especially versions with wider legs) or something that makes a major statement like these gold heeled ankle boots by Ferragamo, these round heels by Kenzo, or these by Sophia Webster. Actually we just love bold block heels like these with everything.

How To Wear Ankle Boots With Trousers fountainof30

Work It: How To Wear Ankle Boots With Trousers

Ankle boots are the ideal winter footwear with trousers for work or anytime you are wearing a dressier pair of pants. We’re fans of simple black ankle boots like these by Loeffler Randall with trousers or suiting-style pants of course, but something unexpected like these snakeskin Vince Camuto ankle boots can be an excellent way to put an unexpected twist on a pair of basic neutral pants.

Keep in mind that a slightly taller ankle boot can work better with these types of pants if you don’t want to flash any ankle in a more formal work environment, or in general.

A great pair of boots can be a worthwhile investment since you can likely wear them for much of the year with a lot of different pieces and settings. We suggest that almost everyone can benefit from having one basic pair of ankle boots in black leather or suede or the neutral that works best for you (gray, taupe, cognac, and chocolate brown can all be good options) as well as a fun pair in an animal print or with interesting embellishments like studs or a creative heel treatment.

What is your favorite pair of ankle boots and how do you wear them?

Shop all the ankle boots featured above:

– Jacqueline Zenn

Pictured at the top, styled by Net-a-porter: Gianvito Rossi Margaux 60 leather ankle boots, $995  |  Chloé Susanna shearling-lined studded suede ankle boots, $1,380  |  Gianvito Rossi 70 leather Chelsea boots, $1,245

You may like to read more of Jacqueline’s styling posts for women over 40 like 2019 Fashion Trends: The Year In Review and How To Wear Puff Sleeves When You’re Over 40.

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