Ignore the calf measurement of 14.5 inches because this boot fits my 13 inch calf perfectly when tightening the strap by one more hole. There is room to tighten the strap even further, so this boot will probably also fit a 12 inch calf. Extremely comfy, supportive, and tapered at the ankle. Fab Sleek Ruggedness.

This version of Stuart Weitzman’s “50/50” boot works well for narrow and slightly larger calves because of its stretchy back. I have a version of these that are four years old and they’re the most comfortable boots in my wardrobe. You might need to size down half a size.

As I write these boots are on sale for $297.49.

Aquatalia makes extremely well-made weatherproof footwear that will keep your feet dry all Winter long. The ‘Diane’ boot comes with a suede and leather combo upper, a little sassy mixed media in a casual style that’s not rugged, moto or equestrian. They have a back zipper closure and textured rubber outsole for sure footing. You might need to size up half a size because they run small. Also available in Espresso.

Sloshing through puddles becomes tons more fun with these stylish wellies. Hunters are the Rolls Royce of rain boots. They are comfortable, flattering, durable, fit like a dream, and have an adjustable calf buckle. The length is especially great for long-legged lasses. Available in eight delightful colours (the enamel has stolen my heart). Be sure to check out the many rave reviews on the Nordies website too.

Now this is a boot with loads of pizzazz! This camel leopard print pull-on boot has a soft stretch suede upper designed to hug your legs. The sleek silhouette and 2 1/2″ heel make this a good option for dressy occasions. The cushioned footbed and flexible sole will add to the comfort factor. They will be especially versatile if you are prepared to pattern mix your outfits. Flop proof with solid dresses and skirts.

This best part about this boot is that it slims at the ankle, making it ideal for midis and dressier occasions. It runs true to size and is available up to size 12, some sizes in narrow and wide widths. It’s stretchy pull on nature makes it work for both a narrow and wider calf. I did find it hard to pull on, but that will loosen up over time. The addition of an insole will soften the footbed.

Currently 20% off.

I own a very similar pair which are as comfortable as my bedroom slippers. Buttery soft leather, a solid flat heel and a stretchy weatherproof back make them a winning combination. A beautifully made boot that pulls up over the leg with ease. They cost a fortune and I nabbed mine at the Nordstrom Anniversary Sale. But the truth is that I could walk the streets of NYC flat for days on end with these on my feet. No blisters and no foot cramping. Priceless. Runs true to size.

The leather on these boots is perfect. A little distressed, deliciously cognac and very soft. I just LOVE the outside zipper and dainty buckle detailing. So unique. The sturdy sole is great for bad weather. These boots work best on a regular to tall -ish height gal with a 15 inch calf circumference. The shaft height is too high for petites so don’t even try. Runs big so size down half a size.

This flat boot offers support with it’s one and a half inch wedged heel. The leather is soft and buttery and the almond toe attractive and elongating. I found it very comfortable. It can be worn cuffed or as an over the knee style. Easy back zip access and available in black and taupe from sizes 4 to 12. It works well on a fairly narrow and a regular width calf.

This is a refined Frye boot style. It won’t work on narrow calves but it’s stellar on a regular sized calf. Easy to pull on, comfortable and super fab in all the colours except black (this style in black looked bland somehow). Bordeaux gets my vote with Cognac coming in as a close second.