Black Boots May Be Classic But These 5 Outfit Ideas Will Make Them Feel Fresh

November 15, 2025 / Swedan Margen /

Much like a great white T-shirt and a cosy winter coat, a pair of black boots are, in my opinion, a non-negotiable in any hardworking wardrobe. Practical, polished and incredibly versatile, no matter which style of black boot you opt for, whether a buckled biker boot or classic heeled iteration, I can practically guarantee you’ll find yourself reaching for them time and again—especially now the weather has turned colder.

Yet while I’m all for an item that delivers on cost-per-wear, coming up with ways to style and re-style our favourite items is no mean feat. So, to avoid a self-diagnosed case of outfit fatigue, I thought I’d do some research and see how chic, stylish women are styling their black boots, so I can recreate their outfits using my own wardrobe. Here are five looks I’ll be wearing this winter and well into 2026…

5 Black Boot Outfits to Copy This Winter and Well Into 2026:

1. Gilet + Jeans + Hiking Boots

Style Notes: Let’s start with a great way to style black boots for everyday. Here Jess keeps things cosy, layering a fuzzy gilet and jumper with blue jeans and black lace-up hiking boots. The combination is effortless, easy to wear and perfect for busy days as the weather turns colder.

Shop the Look:

AGOLDE

90’s Pinch Waist Long Frayed High-Rise Straight-Leg Jeans

Grenson

Nanette Hiker Boots

2. Roll Neck + Jeans + Sock Boots

@sylviemus_ Black Boot Outfits wearing a black jacket, roll neck, jeans and heeled boots

Style Notes: While Slyvie’s black boot outfit relies on similar wardrobe staples to Jess’ — in its essence it’s also a jacket, jumper, jeans and boots — she puts a quintessential French girl spin on the look. Opting for a tailored jacket, roll-neck sweater and slim jeans, her look feels chic and elegant, while heeled black boots complete the polished feel.

Shop the Look:

Róhe

Mandarin Double-faced Wool Jacket

M&S

Pure Merino Wool Roll Neck Jumper

& Other Stories

Stretch-Leather Ankle Boots

3. Leather Jacket + Slip Skirt + Western Boots

@thealiceedit Black Boot Outfits wearing a leather jacket, cream lace slip skirt and black western cowboy boots

Style Notes: One of my favourite things about black boots is that they can instantly make any outfit feel autumn-winter approved, as Alice’s look here shows. Proving summer’s lace trim slip skirt trend can be worn into the colder months too, her leather jacket and matching boot combo gives the piece a tougher feel while also ensuring she won’t be left shivering on chilly days.

Shop the Look:

Nour Hammour

Ariste Leather Jacket

COS

Cashmere Crew-Neck Jumper

Mint Velvet

Cream Lace Satin Slip Skirt

Massimo Dutti

Leather Cowboy Boots

4. Black Blazer + Leggings + Riding Boots

@femmeblk Black Boot Outfits wearing black blazer, jumper, leggings and knee-high riding boots

Style Notes: Black boots and an all black outfit may seem an obvious choice, but trust me, this is a look that will always be incredibly chic. Take inspiration from Lydia and play with the textures and proportions of your look to add interest — think an oversized knit, figure-hugging leggings and a structured blazer paired with coordinating black accessories.