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.

expensive looking jeans outfits

Photo:

@meccajw

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

expensive-looking jeans outfits for winter:

Photo:

@anoukyve

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. 

SHOP THE LOOK:

This is the perfect blazer to go with jeans. Pop it onto any outfit for an ’80s-style silhouette.

When looking for tops to create the double-denim look, search for rigid denim that could be worn like a jacket. The starchy texture makes double-denim looks appear more premium.

Even Kate Middleton wears jeans from & Other Stories.

Simple black kitten heels (slingbacks, sandals or boots) will work beautifully.

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

expensive-looking jeans outfits for winter:

Photo:

@kristincabat

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. 

A great pair of high-street jeans.

A great bodysuit is a wardrobe staple all year round.

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.”

SHOP THE LOOK:

It’s time to start thinking about knitwear. The best way to ease yourself into it is by wearing fine knits like this.

I tried these jeans on, and I was seriously impressed.

This style of ballet flats is proving popular this season. The Boden pair are one of the best in terms of proportion. 

4. Bright Shirt With Deep-Indigo Denim and Mules

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

SHOP THE LOOK:

For those looking to tap into the Barbiecore trend, look no further.

You’ve probably seen this denim shade all over e-com lately. It’s the middle ground between a mid-blue wash and black. The white stitching lends an intentional androgynous touch to the slim shape, as it’s the stitching most associated with menswear.

Classic yet statement shoes that will elevate most jeans looks. They look so premium despite their sensible price point.

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

expensive-looking jeans outfits for winter:

Photo:

@chrissyford

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.

SHOP THE LOOK:

& Other Stories basics are a cut above the rest. You may spend a little more, but they’ll last.

A straight leg is my favourite denim silhouette. I’ve tried these on, and the fit is reminiscent of my vintage Levi 501s, with the bonus of a little stretch.

Slightly chunkier than the infamous Horsebit loafers but not quite as chunky as Prada’s—a happy medium.

The black trench is an uncommon yet chic outwear choice.