Shoe trends may shift from retro-inspired suede sneakers one moment to pointed-toe slingbacks the next, but knowing how to wear Chelsea boots stylishly has stood the test of time (and TikTok-fueled fads) as a hallmark of a true fashion pro. That's because those in-the-know understand that it's a classic for a reason: The best Chelsea boots have a way of complementing any outfit or aesthetic, they can be worn in any season, and they're one of the few shoes that can blend comfort with polished sophistication.
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