It's officially boot season, and even though our boot collection has expanded quite a bit in the last few years—hello, cowboy boots, kitten-heel boots, and awkward calf-length boots, to mention a few—there's a pair that will always be one step in front the rest. We're talking about our Chelsea boots. Whether classic black leather, patent, suede, pointed-toe, or heeled, we will never tire of all the variations of these staple shoes. Maybe it’s because they always add an effortless vibe to all our fall and winter outfits, maybe it’s because we’ve never stumbled upon a pair that isn’t comfortable, or maybe it’s because we haven’t found a style yet that we don’t like. Whichever the reason, all we need to know is that they’re great boots and will be a solid option no matter where the fashion tides take us.
If you’ve wanted to wear yours more but haven’t found the outfit inspiration you needed, then look no further than the 10 Chelsea boot outfits below. We’ve curated a selection from some of your favorite Instagram style stars, who’ve worn theirs with biker shorts, puffer jackets (trust us, it looks and sounds amazing), and everyone’s favorite animal print. In other words, there’s enough inspiration ahead for the rest of winter—and even those transitional weeks after.
Next up, find all the best ankle boots for a bit more variety.