Why I Keep Telling Regular Guys to Wear Bootcut Jeans
To be very clear: My personal menswear crystal ball doesn’t show the roomier jean trend swinging back towards anything slimmer than a straight-leg anytime soon. (Levi’s, after all, are only just getting started with their new, looser designs.) But that only strengthens my second opinion: That every man today should have a bootcut jean in their wardrobe, for those occasions that call for a little more personal flair.
That’s because a bootcut jean has all the relaxed ease of a wider jean—the generous leg opening gives you the same versatility with footwear choices, as a heeled boot, off-duty loafer, derby or sneaker will always work—but the slimmer silhouette above reads just that little more sophisticated, especially when paired with a blazer, knit, or leather jacket for a night out.
As someone who frequently helps regular guys dress better as part of my work, the goal of a bootcut pickup is not to encourage cowboy cosplay. It’s to bring some versatility into your denim rotation, so you’re not always reaching for the same relaxed or straight-leg pair, reliable as it may be. A bootcut gives you a new shape and some more interesting lines, and almost magically pairs just as well with cropped jackets like harringtons and truckers as with longer styles, like overcoats or trenches.
As for what I wear personally? I’ve become quite fond of vintage Levi’s 517s, both for their built-in fades and the joy of the hunt. But to remove some of that trial, error and time, the pairs below are my strongest off the rack options, ranging from true classics to some new brands that have already perfected the cut.
