Photo Credit: Jewish Press

If you live in a cold climate, boots are a necessity for winter. I get so many comments from non-religious friends asking how I stay warm during the winter in skirts and dresses, but, as many of you know, a pair of thick tights and boots paired with a dress/skirt can keep you warm and comfortable – especially if you choose fleece-lined tights or warm leggings to go with your boots.

Knee high flat boots


My go-to boots for every day are classic suede flat boots. It can be hard to find boots that don’t go over the knee these days, but they can be found with a little extra hunting. If you cover your knees, over-the-knee boots are not the ideal style to wear with a dress or skirt because the proportions are usually a bit off. However, I have seen people pull it off successfully and, as you know, I’m not a believer in black-and-white fashion rules. If you choose to go for the OTK route, stick to boots that are more fitted for a streamlined look.

Ankle boots

Ankle boots can look amazing with skirts/dresses and there are so many fun options on the market! If you choose flat booties, I’d suggest sticking to ones that are a shorter length to elongate your legs as much as possible. Booties that come up too high can look awkward with dresses or skirts that are a more modest length.

For heeled ankle boots, I still wouldn’t suggest that they come up too high but there is more leeway, as the heels will do some of the elongating for you. Chunky heeled boots are on trend and much more wearable and comfortable than stiletto heels, but if you’re ok with a stiletto-heeled boots, props to you!

Snow boot

For snowy and rainy winter days, it’s nice to have a waterproof option. If you don’t want to spend money on a pair of snow boots, rain boots with thick socks will do the trick in a more affordable way. If you specifically want snow boots, Sperry, Sorel, and LL. Bean have options worth considering. I tend to favor rain or snow booties (my favorites are the Kate Spade rain bootie) because they are more comfortable to walk in and aren’t as heavy/clunky as knee high boots.

If you have narrow or wider calves, don’t worry; there are options for you!

DSW has a nice range of wide calf boots on its website. Other stores that have options for wide calf boots include Zappos, Nordstrom, and Eloquii.

For narrower calves, Ted and Muffy have a range of boots that you can customize to your calf measurements (whether your calves are narrow or wide) although keep in mind that they can be on the pricier side. Otherwise you can search Zappos and Nordstrom for narrow calf boots as well.


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Shira Rosenbluth, LCSW, is a licensed clinical social worker in New York City. She has a passion for helping people feel their best in their body at any size and specializes in the treatment of disordered eating, eating disorders, and body-image dissatisfaction using a weight-neutral approach. She’s also the author of, a popular body positive style blog. You can find her on Instagram @theshirarose. Find more about her therapy practice at