How to Make your Millennial Booties Work in 2025 & 2026

There are a lot of so-called fashion experts making a lot of money off telling you to get rid of your millennial booties and buy their modern alternatives for 2025 and 2026. While I agree these booties are not looking modern or trendy a decade after they were at the height of popularity, that doesn't mean they can't be worn and look stylish.

I don't believe in throwing away perfectly good fashion; if you still own these booties it's because you find them comfortable and in good condition. Let's make your millennial booties work in 2025 and 2026 and not cramp your grown-ass woman style.

If you're not sure what I mean by millennial booties, here is a picture of me in some. These were very short ankle boots called booties. They had such a low shaft they usually exposed the ankle bone. They were usually made of suede and usually a taupe or tan color, had a side zipper, and often a cut-out on the side to have them show even more ankle. With an almond toe and low heel that usually was wood (or covered with a wood veneer), this ankle bootie was the perfect partner for skinny jeans, jeggings, and boyfriend jeans like I'm wearing in the photo above.

What really makes these millennial booties feel dated is the low-cut top and zipper. Otherwise, these are relatively inoffensive boots. Not the height of fashion, but not grossly inappropriate or bold enough a statement to even catch the eye of many. The key to making the millennial bootie work a decade layer is covering up the details.

Right now, a full-length jean and pant is very stylish. We're talking a hem that just barely grazes the ground and has a “break” or folds to lay on the top of the foot. This is the length you want to modernize your millennial booties.

Due to the almond-shaped toebox, this bootie is a bit more delicate of a shoe than a lot of boots on the market right now. Pairing it with a wide-leg or flare-leg jean will make it look even more delicate and small. Choosing a bootcut or baby bootcut jean will offer just enough flare to cover most of the boot, give it a bit of a Western feel which is very on trend right now, without overpowering it.

shop the look: earrings | scarf | sweater (XXS-3X) | corduroy jeans (24-35 & petite/tall) | bag

Another way to modernize the millennial bootie is to lean into a monochromatic look. Pair your taupe and tan suede ankle booties with cream, tan, taupe, and ivory pants. If your booties are a cool toned color (more gray than camel), go with ivory, taupe, and cool beige. If they are a warmer tan color, you have more options.

Using a waterproofing spray on your suede ankle booties will not only protect them from the elements, but may darken the color of the suede. This can also help to make them feel more contemporary and be a more versatile color.

shop the look: glasses | earrings | sweater (XXS-XXL) | bag | bootcut jeans (23-33 & petite/tall)

Pair these suede ankle booties with sturdy fabrics. Corduroy, denim, and velveteen are casual fabrics that make sense with the shoe's design. These are casual boots, do not try to make them work with suiting or dressier fabrics.

When it comes to hosiery, have it be low-contrast to the shoe and pant, and have it a casual fabric. Wool, cotton, and texture make sense and will bulk up the ankle area, giving the appearance of a higher boot shaft. However, your socks should only be showing if you're crossing your legs; you should be styling these millennial ankle booties with full-length jeans and casual pants.

shop the look: shirt (00-24 & petite/tall) | earrings | jeans (24-34 & 3 lengths) | belt (XXS-XXL) | bag | wool socks

If you are still rocking your millennial booties, they better be comfy and in stellar condition. Use a suede brush to keep them clean, take them to the cobbler to be reheeled and resoled. If these booties are not in good condition and/or not comfortable, it does make sense to replace them.

My suggestion to get long wear out of your next purchase is a black leather ankle boot with a higher shaft that slips under the hemline of your pants. The heel and the sole should all be black, no contrast stitching. Hardware should be minimal, and if there is an elastic gusset and/or zipper, it too should be black. The toebox, unlike the millennial bootie, should be slightly elongated; it can then be pointed, almond, squared, whatever appeals to you. Keeping it elongated, not snub, will make the ankle boot look more stylized so even if the trend heads back to snub toes, the boot looks purposeful.

I hope this helps! You do not need to get rid of a single item in your closet if it still fits well and is in good condition. Just switching up the styling can give it new life and may give your look the update it deserves!