5 Expensive-Looking Winter Outfits That Work Perfectly With Jeans

Although denim is characteristically relaxed, it’s often the foundation for creative expression and has birthed some of the most iconic looks, from Princess Diana to Cindy Crawford in the ’90s.

I was a little too familiar with denim in the Noughties, wearing kick flares with body-con T-shirts at every given opportunity and lacquering on sticky lip gloss before Y2K became the modish phenomena it is now. I’ve explored other aesthetics over the years, but when I reached my 30s, my appreciation of denim came full circle. By now, we’re all probably well versed in the importance of basic items like jeans and vest tops, but it can be challenging to figure out where to start with the elevation of denim outfits, particularly if you’re after something a bit more statement making. Really, it’s the simplest equation, as the casual characteristic of denim will pair with almost any top-half style—whether it’s a voluminous blouse, a tailored shirt or even denim.

As the seasons progress, denim shades are gradually getting deeper and complementing the flamboyant colourways of autumn/winter 2023. Also, since the reintroduction of milky-hued denim in 2018, white and ecru jeans dominate summer-to-autumn styling. Paired with cashmere in grey, navy and tan colourways, it’s an undefeatable match—whether it’s worn as a top or over your shoulders.

Then, there’s the importance of accessorising. That’s where you can be as minimalist or maximalist as your heart desires. Subtle additions, no matter how small, can change the tone of an outfit. Add an embroidered blouse with heeled slip-ons for a Parisian lilt, or adorn yourself with brightly coloured accessories to veer towards modern dopamine dressing. If you’re lacking inspiration or simply want to reinvigorate the denim in your wardrobe, continue reading to see the five expensive-looking jeans looks that have caught my eye. They’re guaranteed to inspire.

5 Expensive-Looking Jeans Outfits

1. Double Denim With Heels

Style Notes: It might not be everyone’s cup of cocoa, but double denim is a look that flits in and out of style for good reason. It’s classic. The combination of two classics will always suffice. 

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2. A Bodysuit With A Blazer, Wide-Leg Jeans and Boots

Style Notes: I love Kristin's simple yet polished look. Wide-leg jeans and sleek heeled boots elevate this simple look, and that dark denim with lighter tones on the top half just look so chic when paired together. 

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3. A Cashmere Knit With White Denim and Ballet Flats

Style Notes: Three classics are better than one. A fine-knit cashmere jumper will see you through most seasons, as will light-wash denim. Lizzy also wears the extended top-line ballet flats that are a current trend. If you’re not wearing your cashmere the typical way, revert to the familiar style hack of 2019 and throw it over your shoulders to imitate said "grandpa chic.”

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4. Bright Shirt With Deep-Indigo Denim and Pumps

Style Notes: Although I mostly wear neutral clothes, there’s something that draws me to this look. The dreamy Roger Vivier pumps paired with almost-black denim, electric pink and raffia create a technicolour look that has a classic, effortless and modern essence.

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5. Straight-Leg Jeans With a White Top and Classic Trench

Style Notes: Chrissy demonstrates a typical British day outfit when you’re untrusting of the forecast and have to dress for all seasons. Each component can be built upon or folded and packed away in the event the sun rears its head. To add the knit over the shoulders feature, add the jumper from look three.

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Next Up: Navy Always Looks Expensive—8 Colours to Wear it With This Autumn