Spotted in London: This Jean & Boot Combo Is the Key to Effortless Winter Dressing

Jeans and boots are practically my uniform, but if years of relying on this tried-and-true combination has taught me anything, it’s that not all pairings are created equal. Some stop at functional, whilst others feel distinctly elevated. Case in point? Olivia Dean’s latest look.

Stepping out in New York, the singer styled one of the chicest denim silhouettes I’ve spotted this season, opting for a slouchy, low-rise pair in a rich, dark blue wash. While mid-rise, cigarette-cut jeans have dominated winter wardrobes of late, Olivia’s relaxed alternative felt even cooler, with the kind of nonchalant ease that I could only hope to achieve.

Then came my favourite part. Rather than leaning into something overly casual—as would be tempting to do, given the relaxed denim choice—Olivia sharpened the look with a pair of pointed-toe boots in a dark chocolate mock-croc finish. Cut with a sleek stiletto heel, they brought drama and elegance to the laid-back denim, while also tapping into the deep, decadent colour palette fashion people are gravitating towards right now.

Completing her look, she slung Bottega Veneta's Maxi Veneta Bag (£6730) over her shoulders, its glossy leather mirroring the richness of her boots. A cosy bomber jacket and fuzzy earmuffs added warmth, rounding out what might just be one of the chicest winter outfits I’ve seen this season.

If you’re as inspired as I am, keep scrolling to shop the low-rise jeans and heeled boots I’m bookmarking now.

Shop Low-Rise Jeans and Heeled Boots:

COS

Facade Straight-Leg Jeans

These straight leg jeans have wrap-around seams for a sculptural effect.

Be quick! These won't stay in stock for long.

Reformation

Cary Low Rise Slouchy Wide Leg Jeans

Reformation's Cary low rise jeans are a fashion person's favourite.

Jimmy Choo

Frankie Ankle Boot 85

The mock croc finish lends these such an elevated edge.

Stradivarius

Low-Rise Jeans

These look more expensive than they actually are.

H&M

Heeled Leather Ankle Boots

Style these with low-rise jeans to get Olivia's look.

Arket

Cloud Loose Wide Jeans

Shop these whilst they're on sale.

Mango

Leather Pointed Ankle Boots

Pointed-toe boots will always be my go-to, whenever I want to dress up a winter look.

Free People

We the Free Tennessee Low-Rise Boyfriend Jeans

These also come in eight other shades.