The fresh winter breeze marks the stylish return of ankle boots with heels — a timeless favourite that keeps evolving each year. Their beauty lies in their versatility: sleek enough for office days, elegant with long dresses, chic with skirts, and effortlessly paired with tailored pants.

With just the right lift for added height and stability, these boots are your go-to for both fashion and function — and yes, they’ll keep your ankles toasty, too.

Explore this season’s ankle boot trend and discover how to style them for every winter occasion. 

Ankle Boots with Heels: What are the trends of the season?

This autumn/winter, we're embracing the timeless appeal of classic black ankle boots with heels — but with a subtle twist. Think gold accents, textured finishes, and refined details that elevate the look without overpowering it. These boots are versatile enough to take you from desk to dinner, but the key is smart styling. Match them well with your outfits so you can get more wear without needing every pair on the shelf.

Ankle Boots with Pointed Toe Block Heel

This type of boot is classified as retro boots that are still timeless and will make you stand out from the crowd. With its plain design, you can almost pair it with everything! A must-have staple in your winter wardrobe. This is enough for this Winter season. 

Styling idea:

If you want a sleek and dressy vibe, pair it with a midi skirt and fitted turtleneck. For an off-duty option, wear them with denim jeans and a chunky jersey/jumper for a polished finish.

It also looks great with a knit sweater dress and longline coat, or try them with straight-leg jeans and a chunky jersey for a warm, casual look.

For something super versatile, the pointed toe block heel boots are easy to throw on with a knit sweater dress and longline coat, or try them with straight-leg jeans and a chunky jersey for a warm, casual look.

Shop the boots here: Mister Leather Ankle Boot BLACK, Mister Leather Ankle Boot TAN

Ankle Boots with Rounded Low Wedge Heel

If all-day comfort is a priority, these rounded toe ankle boots with a low wedge heel are a must-have. The subtle lift offers just enough height without sacrificing stability—perfect for everyday errands or casual office wear.

For a relaxed, laid-back look, pair them with dressy pants tucked into the boots and a lightweight knit or jersey top. Or go classic with rolled-hem denim to show off the ruched leather detail.

Want something more elevated? These boots also complement midi dresses beautifully, with the ruched design adding a touch of texture and chic edge to your outfit.

Shop the boots here: Blanch Natural Comfort Leather Ankle Boot BLACK, Blanch Natural Comfort Leather Ankle Boot TAN

Ankle Boots with Rounded Low Block Heel 

If you’re after smart, stylish comfort, ankle boots with a rounded toe and low block heel are a solid choice. The sturdy sole and easy fit make them perfect for long days—whether you’re working, running errands, or heading out casually.

For a polished office look, pair them with straight-leg jeans or tailored trousers and a tucked-in blouse. On weekends, go for cuffed denim and a cozy oversized sweater. Want something more feminine? A belted shirt dress (think denim, corduroy, or plaid) adds structure and works well with the sturdy sole of the boots. Layer with a trench or longline coat for added warmth and sharpness. 

Shop the boots here: Ring Leather Ankle Boot BLACK