How to Style Slouchy Boots So You’re on the Right Side of Trendy

Blame it on the boho trend, or perhaps a few too many rewatches of Pirates of the Caribbean, but how to style slouchy boots has been on my mind. Having spotted this boot trend not just on runways like Isabel Marant and Louis Vuitton, but also on my walk to the local coffee shop, it’s been interesting to see the style transcend from high-end styling to something that can actually be wearable IRL.

What sets this style apart from other trends like cowboy boots or square-toe booties is the fact that there are a range of options currently on the market. You can buy ones with just-a-slight-slouch to full-on bucket boots, which means you can adapt the way you approach things depending on your tolerance for funkiness.

In general, my take has been to keep the styling relatively simple, leaning on capsule wardrobe essentials like a fall blazer, knit sweater, or simple knee-length skirt and letting the boots do the talking (or walking, really).

Ahead, you’ll find five fall outfit ideas for how to style slouchy boots that I’ll be trying out. I’ll also give my hard-won styling tips to help you look on the right side of trendy. Rest assured, there’s nothing pirate-y about these looks.

Long Fall Skirt + Suede Boots