Bermuda Shorts and Boots Outfits for Fall |Best Knockoff Luxury Clothing

@amaka.hamelijnck and @_paulineleroy_ wearing Bermuda shorts with knee-high boots.

(Image credit: @_paulineleroy_; @amaka.hamelijnck)

published 7 November 2025

There’s a brief, glorious window every fall when it’s not quite cold enough for heavy layers but just crisp enough to pull out your favorite pair of boots. Enter the outfit combo fashion people are clinging to before winter fully sets in: Bermuda shorts with boots. It’s the unexpected pairing that bridges seasons perfectly—long enough to feel fall ready yet breezy enough for those lingering warm afternoons. Whether you’re running errands or heading to a coffee meeting, it’s a cool and stylish way to master transitional dressing.

Style insiders have been spotted wearing this combo everywhere from L.A. to Paris, proving it’s far more elevated than it sounds. The key is in the proportions: structured Bermuda shorts that hit just above the knee paired with sleek knee-high or chunky boots instantly create a leg-lengthening silhouette. Add a crisp button-down or a slouchy knit tucked in, and suddenly your outfit feels both effortless and intentional—exactly the kind of balance that defines great fall style.

For a more polished take, lean into monochromatic tones—think taupe leather shorts with matching suede boots or black Bermudas with glossy patent pairs. Finish it off with an oversize blazer or tailored coat draped over your shoulders, and you’ve got an editor-approved ensemble that looks straight off the street style circuit. The beauty of this pairing lies in its versatility—it can read minimalist, Western, or even preppy depending on the styling.

But here’s your friendly warning: The clock is ticking. Once temperatures drop for good, this fleeting combination will be swapped for wool trousers and full-length coats. So for the next three weeks, take advantage of the in-between weather and wear the look that’s defining this season’s most stylish transition—the Bermuda shorts and boots duo that’s too good to retire just yet.

See the outfit inspiration below and shop the key pieces along the way.