With warmer weather approaching, you may be tempted to ditch the closed-toe shoes — but I’m going to stop you right there. Learning how to wear ankle boots for the season ahead will reveal that they’re actually the perfect spring shoes you never knew you needed. Hear me out!
I get it: After a long winter you’re probably itching to put your favourite ballet flats or loafers back in rotation. But during transitional, tough-to-dress-for weather, short boots are actually your best bet. Why? They boast all the style and coverage of knee-highs but without the bulk. And they go with pretty much anything — don’t listen to the naysayers who call them “outdated.” (They’re already making a huge comeback among fashion insiders, anyway.)
There are truly endless ways to style this versatile shoe style — and the best ideas are right ahead. Bookmark these outfits for inspiration the next time you can’t figure out how to wear ankle boots.
How to style ankle boots, at a glance
It's anything but twee.
For casual Friday
One of the few downsides of ankle boots is that they can sometimes cut your legs at an awkward spot. But any of those worries are completely erased with a pair of vintage-inspired cigarette jeans that sit comfortably just below the ankle, with your boot popping out from underneath. Styled with an easy T-shirt and a relaxed blazer, the look is perfect for a laid-back (but still professional) office ’fit, and can be easily taken into evenings and weekends, too, with subtle changes to your accessories. Sub in a collared shirt or blouse for every other day of the week.
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For a lunch date
Traditionally, shorts and boots are a bit of a style no-no. But in recent years, fashion ‘it’ girls have found their own clever way around that outmoded rule: styled with ankle boots and a matching blazer, pleated shorts give off a polished yet playful vibe. It’s an easy way to dial up the style stakes for a casual daytime meet-up of any kind, from power lunches to coffee dates. Opt for black or navy shorts for office days, paired with black or brown boots. For days and nights out, go more bold, with bright shades like red, or interesting patterns — think zebra or leopard print.
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For casual weekend days out
Elevate your Saturday afternoon outfit by pairing kitten-heel boots with a luxe handbag. While an athletic jacket and joggers could lean too casual, high-end accessories keep things feeling current and help an otherwise quite casual outfit feel like an elevated affair. Pop on a pair of hoops to finish the look, and you’ll be prepared for any impromptu run-ins on the street.
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For dinner with friends
With jeans, ankle boots feel wearable and relaxed. The pairing is a traditional fashion combo for good reason. But styled with a midi skirt, they give off a much more polished air. Go for a bold pattern — like tartan or polka dots — and reach for boots in a complementary colour. You don’t need to wear head-to-toe print to make an impact; one piece is plenty to get the point across, as long as the print or shade is bold enough.
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For happy hour
We don't know what it is about animal print, but leopard jacket can make even the chillest closet staples feel a bit more sultry. Go for dark-wash jeans, heeled ankle boots, and luxe black accessories for a more evening-coded look. A casual tank top below helps keep things breezy — and won’t cause you to overheat in a crowded bar or on a particularly balmy spring day.
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