I Want to Look Classic and Expensive in 2025, so I’m Wearing My Jeans and Boots Like This, This, and This

If you want to dress in a way that looks and feels expensive, your options are wider than you might think. Sure, you can lean into polished staples like a crisp white button-down shirt tucked into a sleek black pencil skirt with knee-high boots, or slip into a black midi dress paired with pumps. But elevated style doesn’t always require a dressier formula. Sometimes the most luxurious looks start with the simplest foundations: jeans and boots.

While denim and boots are often labeled as “casual,” the real level of sophistication depends on how you style them. Yes, the fit, fabric, and wash or color of your jeans and boots matter, but the top, outerwear, and handbag you choose to pair with them also count.

To help you understand what it takes to create a jeans-and-boots outfit that looks trust-fund-level rich, I’ve pulled five of my favorite looks from the coolest fashion people I follow. With that said, keep scrolling to check them out and shop the essentials along the way.

Styling Notes: Every fashion insider knows that the secret to making a winter outfit look like you hired a stylist is relying on your coat to do all the work. Here, that’s exactly the case with the cape-style jacket Marilyn threw over straight-leg jeans and black ankle boots. Yes, the vintage-like denim wash and pointed-toe shoes are important details, but when your jacket is the outfit, everything else doesn’t matter as much.

Shop the look:

ZARA Shawl Collar Knit Cape

Madewell The Longline Straight Jeans

Staud Wally Ankle Boots

Banana Republic Vegan Leather Satchel Handbag

Styling Notes: While we all might have a list of trends to try this winter, simplicity remains the best choice. Pairing a heavyweight trench coat, especially if it’s in chocolate-brown suede, with slim-fitting jeans, kitten-heel boots, and a polo sweater (triple points if it’s in navy because nothing looks richer than navy and brown), will always keep you stylish without the fuss.

Shop the look:

ZARA 100% Suede Coat ZW Collection Limited Edition

Quince Mongolian Cashmere Polo Sweater

Khaite Farley High-Rise Straight-Leg Jeans

Flattered Xena Boots

Reformation Medium Silvana Bucket Bag

Styling Notes: For those suffering from blue and black denim fatigue, we have a remedy: corduroy jeans. These pants—often available in warm shades like tan, brown, and forest green—evoke a cozy feeling, perfect for the cold-weather season. They also add dimension, interest, and freshness to your wardrobe, so when you pair them with your trusted black wool coat, ankle boots, and gray sweater, those pieces feel new again.

Shop the look:

J.Crew Relaxed Crewneck Pullover

& Other Stories Voluminous Belted Wool Coat

ZARA ZW Collection Wide Leg Corduroy Pants

H&M Chunky Chelsea Boots

Sézane Gabin Bag

Styling Notes: The easiest way to fake an expensive-looking outfit is to wear a tonal ensemble, like black jeans, a black leather jacket, and black boots. Here, the short zippered topper, wide-leg pants, and pointed-toe shoes are all classic silhouettes, but what makes it feel current is the on-trend plaid shirt, which was tucked into the jeans and layered very cleanly under the jacket.

Shop the look:

Quince 100% Leather Cropped Zip-Front Jacket

Everlane Flannel Shirt

levi’s 318 Wide-Leg Jeans

Free People Easy Does It Vegan Boots

Styling Notes: This may be controversial, but I actually prefer wearing white jeans in fall and winter. Something about their unexpectedness makes them feel chicer. And there’s nothing more elegant than pairing them with a white sweater for a crisp look and contrasting them with black boots for an edgy moment. While you can choose a brown leather jacket as shown here, white jeans and black boots also look polished with a long black wool coat, white puffer jacket, or gray oversize blazer.

Shop the look:

Free People Sloane Faux Leather Jacket

Gap Cashsoft Crewneck Sweater

Everlane The Mid-Way Jeans

KHAITE Nevada Leather Ankle Boots

COS Belted Clutch Bag