Riding boots are the #1 boot trend of fall 2026, and the Sam Edelman Penny is the pair the trend is actually about. Real leather, whiskey brown — and brown is outselling black this season, so skip the black pair. $144 down from $200. Two honest caveats: the zipper is the weak point in over 100 reviews, and the calf runs generous, which is either the best or worst news depending on your legs.
Why riding boots, and why now
On August 6, E! News called it: riding boots are "set to win first place in the race for fall's biggest shoe trend." That is not one outlet guessing. Marie Claire, Who What Wear and Coveteur all landed on the same silhouette within the same week, and the runways got there first — Dries Van Noten, Gabriela Hearst and Acne Studios all showed rugged riding boots in warm browns.
The cultural version has a name: horse girl fall. Kendall Jenner has been wearing equestrian-chic all summer, the Princess Diana countryside look is back on Pinterest, and TikTok's #HorseBoy tag turned the aesthetic into a full trend cycle. Your adolescent horse-girl era is, briefly, the most fashionable thing you can wear.
What makes it more than a costume is that a riding boot is genuinely useful. Flat or low heel, knee-high shaft, no platform, nothing to twist an ankle on. It is the rare trend boot you can wear to work.
Buy the brown, not the black
Every source naming this trend names the same colours: chocolate, tan, cognac, burgundy. Net-A-Porter reported this month that brown and burgundy are outselling classic black — a reversal of the usual pattern, and a useful signal if you are choosing between colourways.
The Sam Edelman Penny in whiskey is the shade the trend is describing. It is real leather, a 16.75-inch shaft, a low stacked heel, and a small gold logo button at the top of the outer shaft. That button is the only decoration on the boot, which is exactly right — a riding boot that tries hard stops looking like a riding boot.
Black is the cheapest colourway at the moment, which is tempting and wrong. Black reads as a generic tall boot; whiskey reads as the trend.
The two things reviewers actually complain about
Across 2,857 reviews the praise is consistent: classic, well-made, comfortable, beautiful colour. But two complaints repeat often enough to matter, and nobody writing about this trend mentions either.
First, the zipper. It comes up in roughly 113 reviews — some report it sticking or not closing all the way up the shaft. It is the weakest part of an otherwise well-built boot, and worth knowing before you buy rather than after.
Second, the calf. Fit is the single most-discussed attribute, with 948 mentions, and the feedback splits: many find it generous, some find it narrow. In practice that means if you have ever fought a tall boot over your calf, this is worth trying — and if you have narrow calves, size carefully or expect some slouch. Sam Edelman also makes the Penny in a dedicated wide-calf version, which is the better starting point if calf fit is usually your problem.
So is it worth $144?
Yes, with the caveats above. It is real leather at a price where most trend boots are synthetic, from a brand with a long track record in exactly this silhouette, currently 28% off. The Penny has been in Sam Edelman's line for years, which is the opposite of a trend-chasing product — the trend simply came back around to it.
The alternative worth naming: Amazon has $50–60 riding boots in synthetic leather that photograph nearly as well. If you want the look for one season, those work. If you want a boot that survives several falls, the leather is the difference, and leather is what the extra $90 buys.
