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.
