The Best Bermuda Shorts and Tall Boots Pairings to See You Through Fall (and Even Winter)

With fall’s impending arrival, you’ve probably set your sights on picking up all the seasonal basics. You know, jeans, sweaters, sweatshirts, etc. But there’s one summer staple you can rock straight through fall. We’re talking about Bermuda shorts. If you’re worried the bottom half of your legs will get chilly once temps dip, there’s an easy solution. Pairing Bermuda shorts and tall boots is the best way to stay warm and stylish over the coming months.

There are some tricks of the trade, though. First, you should look for Bermuda shorts that hit a little below your knees. It’s amazing how many different lengths are available.

Second, make sure you favor shorts with wide legs. Why? You need to make sure the top of your over-the-knee boots will (comfortably) fit underneath. So skip those tight denim versions because you don’t want to cut off circulation. FYI: Slipping the boots on over your shorts is not an option.

Last but certainly not least, make sure you pick boots you’ll really get a lot of mileage out of. That means selecting ones that will go with other things hanging in your closet.

See the slideshow above for the coolest Bermuda shorts and tall boots pairings for fall. You can even flaunt them well into winter.