This Outdated Boot Style Was on My "Do Not Buy" List—21 Pairs That Converted Me

As a fashion editor, I'm always on the cusp of new shoe trends. What's new and what's next is often what I turn to in lieu of looking back at boots and flats of time past. What was once the peak of fashion in 2015 might be considered cringey in 2025, so when a pair of chunky Chelsea boots landed on my doorstep to test and try out, I'll admit I had my reservations at first.

I'd seen dozens of glowing reviews on TikTok about Steve Madden's Jones Boots, and given their chic, elevated design, I decided to throw caution to the wind and wear the controversial style. No joke, it only took about 10 minutes of walking in SoHo before I got stopped by a gaggle of women in line for coffee to ask where I got them. When I was walking into one of my favorite designer stores to window-shop, a sales associate also told me she was obsessed with them. Clearly, the tides are turning on chunky Chelsea boots.

I usually prefer slim, ultra-seek kitten-heeled boots, so I was pleasantly surprised by my platform stompers from Steve Madden. Over the last few days, I've reached for them again and again, each time opting to wear the luxe-looking, zippered style with my favorite chunky cashmere sweater and straight-leg jeans. Although they're sitting at just $130, they look four or five times the price. If you know, you know.

Below, shop the chunky Chelsea boots I've gotten tons of compliments on and see some of the best Chelsea boots you can buy now.

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