The #1 Boot Trend of Fall 2020 (and the Coolest Ways to Wear It)

It’s officially boots season, and even though our boot collection has expanded quite a bit in the last few years—hello, knee-high boots, rubber boots, and awkward calf-length boots, to mention a few—there’s one pair that’s a step above the rest. We’re talking about Chelsea boots, specifically chunky Chelsea boots. Maybe it’s because they add an effortless vibe to all our fall and winter outfits, maybe it’s because they’re supremely comfortable, easy to put on, and practical, or maybe it’s because we haven’t found a style yet that we don’t like. Whichever the reason, they’re the dominating shoe trend this season, and we’re so here for it.

If you’ve been eyeing the trend 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 everything from relaxed jeans and big blazers to knit dresses. In other words, there’s enough inspiration ahead for the rest of winter—and even those transitional weeks after.

Marry Chelsea boots to another cool fall trend we’re into, leather Bermuda shorts.

The chunky boots add a cool edge to basic knitted dresses this fall and the outfit combination couldn’t be any easier.

Skip your basic booties when you wear jeans and a cool top and go for Chelsea boots instead to give the look a forward spin.

The heavy stompers create a cool contrast with pretty printed dresses.

Live in a warmer climate? Recreate this cool ensemble when you wear a big blazer over a bodysuit, though a mini dress would work just as well.

Although boots might not be your first thought when wearing a polished skirt set, Chelsea boots ensure the look is current.

Another big fall trend the boots pair flawlessly with? Sweater vests. Wear one with a mini skirt and collared shirt for the ultimate fall 2020 vibe.

Long column skirts also happen to look good with the chunky-soled boots.

If skinny jeans and pants are part of your style lexicon, try tucking them into a pair of mid-calf boots like so.

Lastly, wear them with your loungewear looks. Even if you’re running out for a quick coffee, the boots are a more stylish option than sneakers or slides.

Next up, find all the best dress outfits fashion people will be wearing this fall.