Warm and Chic in Winter Boots

In the cold months of winter, Jessie Randall, president and creative director of the high-end Loeffler Randall shoe line, essentially lives in boots. The New York City-based designer has about 15 pairs in regular rotation once winter arrives. "I like to be comfortable, and boots are the best thing to keep my legs warm," she says.

She sticks to pieces that will blend seamlessly with what she is wearing. With fitted jeans or pants, Ms. Randall favors slim-cut boots that come close to the knee and have a mini wedge heel. On colder days, she'll pull on slim-cut boots that end above her knees. "It's fun and sexy but also functional," she says, noting that with such high boots, she prefers a practical flat heel. For added warmth, she'll sometimes pick a boot lined in shearling or wool felt.

For the tall-boot look, the jeans or pants should be snug so the wearer has a clean, elongating line. Ms. Randall favors boots that aren't designed to look skintight, saying: "Everybody's leg is different, so sometimes the boot doesn't look like it's molding to the leg very well." Instead, she advises looking for a boot that has a straight shaft in a narrow cut. (If you happen to buy a boot that feels a little snug, Ms. Randall notes, a cobbler can add elastic near the top to help it fit better.)

Ankle boots, which Ms. Randall calls "a huge trend," can give a fresh look to a skirt or dress. "They're a little bit more masculine and they give your outfit some edge," she says. Ms. Randall favors ankle boots with a midsize heel, enough to give her "a little lift, which can make you look slimmer" without making it hard for the designer, who has three young sons, to push a stroller around.

When wearing trendy long skirts or midcalf lengths, Ms. Randall typically opts for boots that are tall enough to end above the hemline. "If you wear it with a boot that leaves just two inches of leg showing, it can make you look stunted," Mr. Randall notes. With short skirts, she says, "anything goes."

Ms. Randall avoids "big, clunky rain boots in those really bright colors that you wouldn't normally be wearing." Her rain boots are dark-colored and made of matte rubber. In snowy weather, Ms. Randall pulls on boots that have a thick "motorcycle boot sole" that gives her some traction. If you have a boot without a thick sole that you intend to wear in bad weather, Ms. Randall advises going to a cobbler to have a rubber sole put on the bottom. Many boots are made with leather soles, Ms. Randall says, and leather absorbs water.

If adding a rubber sole to your boot, she suggests wearing the shoes in the house "until it starts to break them in a bit" before having the new sole added. "Rubber doesn't stretch the way leather does, so it's great to get the boot to mold to the shape of your foot first," she says.

"The nicer the boot you buy, the more perishable it will be," Ms. Randall says, so she tends to wear rain boots when it's snowy out, changing when she gets to the office. If she does get her less-rugged boots soaked, she removes them as soon as she's home or at the office and gently stuffs each one with crushed newspaper or paper towels to absorb the moisture. (Avoid tissue paper or any paper product "that can dissolve and stick to your boot," she says.) Ms. Randall never uses a hair dryer to speed up the process, because extreme heat could dry out the leather.

If they are suede, she'll then take a brush designed for the material and smooth out the imperfections. With other kinds of leather, if there are marks or stains, she'll take it to a leather cleaning specialist to "make things look brand new again."

To best protect her winter boots, Ms. Randall makes sure to apply a very thin coat of Lexol, a leather conditioner, on them at least twice a season.

"All leather will naturally get dry and brittle over time," she says. "Conditioning your boots will help them look newer and fresher."