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The most refined and sophisticated ankle boots that can pair with skirt suits (pencil skirt, please) have sculpted ankles, which most women will find flattering, Miss Erlich said. Those booties also do the bohemian look justice, so you can wear them with a maxi skirt, too.

There’s some room for over-the-knee boots with long or short skirts if you’re using a very careful eye about the proportion, but there’s almost no reason to try. Shoe designer Stuart Weitzman said over-the-knee boots already “had their run” a few seasons ago.

The buzz now, he said, is about the boots that bring fashion and function.

He said he likes the way faux fur and other luxe trim now adorn weather-friendly boots. It means, he said, that women don’t have to change their footwear when they get into the office or to a restaurant if it is snowing or raining. “We’ve turned weather boots into a fashion-looking item. … Those are great with your workday dress or skirt. They’re a little bit chunkier but they don’t have to be ‘rain boots,’ ” Mr. Weitzman said. “We’ve taken lessons from Uggs and Hunter and grabbed on to that by making them cool fashion looks that you can wear with anything.”

If shaft and shape matter to your hemline, heel doesn’t seem to be as big a deal. Unlike a strappy sandal where there’s usually not much to marvel at other than the heel, the boot itself is more the conversation piece, Miss Ehrlich observed.

“There’s something really flattering about boots with heels,” agreed Lucky’s Miss Ford, “but it’s really that there’s something very elegant and ladylike and flattering about boots in general. It doesn’t mean flats are out.”