Marc Fisher LTD Yentia Chelsea Boot This Marc Fisher LTD Yentia Chelsea Boot ($210) is a modern take on a classic silhouette. It'll look great with skinny jeans tucked in.

Kate Winslet's skinny jeans styled with toffee-toned Chelsea boots and an oversized blazer looked effortless and elegant all at once when she wore them for a New York outing. A great, well-fitting ...

Here are 24 boots and jeans that look great together. ... These Chelsea boots are endlessly chic and utterly timeless, you can keep them as a staple in your fall wardrobe for years to come.

Gwyneth Paltrow went for a walk with husband Brad Falchuk in cropped wide-leg jeans for summer. She styled the look with a casual striped top, a lightweight jacket, and practical Chelsea boots.

Buy now: Dr. Martens Graeme II Chelsea boot, $150, drmartens.com Tim Latterner is a writer and editor living in New York. His work has been featured in Architectural Digest, Vice, GQ, London's ...

A pair of broken-in, slim-cut jeans is another. Thanks to designers like Simon Miller, you don't even have to break them in yourself. Also on the list: A pair of tobacco suede Chelsea boots.

There's no need to be afraid of tall boots (and the thought of looking like "Pretty Woman"). There are a few simple tricks to keep in mind so you'll feel confident. Boots: Steve Madden Larah boots ...