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At the tail-end of 2025, menswear feels like the climax of WWE’s Royal Rumble: trends are piling up in the ring, and it’s hard to know where to look first. Our suggestion, at least when it comes to shoes? Ignore the bickering and stick with Chelsea boots.
<br/>
<br/>
What makes the Beatle-approved slip-ons so blessedly trend-proof? Simple: Good design is good design, and few shoes do so much with so little. There’s a reason everyone from Mick Jagger to Marc Jacobs swears by Chelsea boots, and their unmatched versatility goes a long way in explaining their appeal. There’s no shame in cheating on ‘em occasionally with a lug-sole derby or a barely-there loafer, but if you’re in the midst of overhauling your winter style, we'd keep a pair of Chelsea boots front and center on your shoe rack.
<br/>
<br/>
To prove it, we rounded up 15 of our favorites on the market, from $150 riffs you can wear with abandon all season to the $1,500 riffs you can wear with abandon all your life. Finding the perfect pair can be hard, but pulling them on couldn’t be easier.
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These Boots Are Made for Rockin’
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