I am delighted that tall boots have made a trendy comeback. I’ve been wearing both of my newer pairs of tall boots a lot, and I’m loving it. My tall black casual riding boots with pointy toes are worn over jeans, although I can also wear them under a dress with socks or pantyhose. The dressier tall ink blue boots that I bought in London last year are to wear with skirts and dresses. I do not wear those over jeans.

It’s extremely hard to find tall tailored boots to fit narrow calves with a calf circumference of between 12 and 13.5 inches. Calf circumferences of 14 to 15 inches are the easiest to fit because they’re the industry’s sweet spot.  Calf circumference of 15.5 to 16 inches are a little trickier to fit, but wider than 16 inches, and you’re back in easy terrain because tall boots are offered with extended calf measurements.

If fitting the calf area wasn’t hard enough, the length of the boots (shaft height) can also be tricky to fit. The industry’s sweet spot is for regular height and tall gals. As a shorter person — unless you’re barely petite, or have relatively long legs — tall tailored boots are generally too tall. 

Sites like Poppy Barley, Ariat and DuoBoots, will custom make tall boots to fit, which is one way to go. The success rate however, is mixed. If things work out, then you’re lucky. Over the years, I’ve seen clients order custom-made boots that fit well in the calf, but they’re still too high or short in the shaft, and comfort in the toe box is not guaranteed. 

At 5ft 6”, I don’t battle with shaft heights. But with a calf circumference of 13 inches, most tall boots are too wide at the calf. I am pedantic about fit, and intolerant with boots that gape at the calves (and ankles, for that matter.)  That said, I have go-to brands that generally do a better job of fitting a narrow calf.

  • Aquatalia
  • Stuart Weitzman
  • Cole Haan
  • Blondo
  • La Canadienne
  • Chanel
  • Prada
  • Donald Pliner
  • Peter Kaiser
  • Dr. Martens
  • Robert Clergerie 

Unfortunately, tall boots by these brands are pricey.

 You simply have to keep on trying tall boots until you find a pair that fits. Here’s a head start for those with narrow calves that are comfortable, look sharp, and fit well.

Visit the collection page to see the items alongside my descriptions.