How To Wear Ankle Boots Over 50 - A Well Styled Life® (2024)

It’s bootie season, and I couldn’t be happier. I find them one of the comfiest footwear options for cooler weather because they’re stable around your ankle which provides more support than a shoe. They also keep your feet warmer and dryer during nasty weather. There are plenty of flat and low heeled ankle boots with flexible soles, arch support, and available in varying widths so there’s no need to sacrifice comfort for style with ankle boots. Today, I’m updating this post from 2019, with some new ideas for how to wear ankle boots over 50.

With leggings

This year’s version of my above booties is available in Medium, Wide, Extra Wide, Super Slim, and Narrow widths. Yes, they’re an investment but mine has paid off year after year because they fit my wide foot and are incredibly comfortable.

Ankle boots with a higher shaft are great for tucking leggings into. It gives a long lean line when the boot and leggings closely match in tone or color. For extra staying power, you can tuck the bottom of the legging into a pair of short socks which helps to keeps them tucked in. This look is great styled with a longer sweater, jacket, or tunic which covers the top of the leggings and your backside.

Related-The Modern Way To Wear Leggings After 50

With Skinny Jeans

Tucking skinny jeans into ankle boots doesn’t work well because they come untucked the minute you sit or move around. Skinny jeans are also notorious for bunching against the top of ankle boots which makes your legs look shorter. Here are two solutions-

• roll up and leave 1/2″ of ankle between the boot and your pant. You can fold over twice to have a narrow cuff or one large fold. Be aware, the wider the cuff, the shorter your legs will look. If you cuff your jeans, wear a shorter top to help elongate the look of your legs.
• You can also simply hem your jeans which I prefer for my short self.

Skinny jeans look best with some ankle showing so cut-out or split-shaft booties like these are a great option.

Related –How to Shorten Your Jeans and Keep the Original Hem

With Straight Jeans or pants

Straight jeans look great worn over the top of the ankle boot. Be sure your jeans are long enough to cover several inches at the top of your ankle boot. This works best with ankle boots that have a close-fitting top.

With Bootcut Jeans

The perfect combination. Have your jeans reach the top of your arch or you can hem them longer than usual to cover a small heel which will help elongate the look of your leg.

ankle boots with width options

Related –How to Look Taller and Slimmer

The selection of booties this year is extensive so there are plenty of options to choose from at all price points.

Are you a fan of booties? How do you like to wear yours?

Thanks for reading and be sure to wear what makes you feel confident.