- Associated Press - Monday, November 7, 2011

There’s fall and spring, winter and summer - and there’s boot season. For many fashion fans, that’s the best time of year.

Time to break out the cowboy boots and jeans, riding boots and leggings and maybe your best black work trousers and those cute high-heel booties you bought last year.

They’re all easy, almost no-fail pairings. Finding the right skirt to go with boots, however, is more likely to trip you up, especially this particular season when it seems anything goes with hemlines.

Do long skirts get tall shafts or shorter ones? What’s the rule on miniskirts? And can functional weather-friendly boots meet a fashion-forward midiskirt somewhere on the middle of the calf?

“Boots can do it better than almost anything when it comes to pulling your look together, but it also can cut you up,” said celebrity stylist Cristina Ehrlich.

She added: “You have to put your outfit on. If your eye goes straight for the foot, then something isn’t right. You want a full ‘look.’ “

Since proportion matters, she suggested that every outfit get the mirror test because what works for one skirt might not for the next, even if they are similar styles.

It’s all about lines. You don’t really want the top of the boot to meet the hemline; it could be longer or shorter - and filled in, when needed, with opaque tights, said Jen Ford, fashion news director at Lucky magazine.

Miss Ehrlich, a style spokeswoman for Via Spiga, said the most foolproof boot choice is a to-the-knee shaft and a wedge heel, probably in black suede. But, she added, you would be surprised how easy it is to incorporate a dark purple, bottle green or gray suede into an existing wardrobe, even one rooted in black.

With a 2- or 3-inch heel, there’s really not an outfit you can’t wear with these boots. She would put them on in September and not take them off until April - and that’s traveling to different places and climates.

“With the wedge, you get comfort and gain a few inches. You can dress it up or dress it down,” Miss Ehrlich explained. “It’s chic and cool.”

She put Ashley Greene in a pair recently for a daytime event. The “Twilight” star wore them with a fitted legging and a cashmere-and-leather baseball-style sweater, Miss Ehrlich said. And that was in sunny Los Angeles.

“You can wear a boot in warmer climates,” she said. “I had been based in Los Angeles for many years and winter was still synonymous with boots.”

Miss Ford recommended a workhorse boot that is just a couple of inches shorter than the knee, more like mid-calf. With tights in the same color, you will still get the illusion of a longer leg, but there’s a chance to do some trendy color blocking here, and, she said, you also can capture the playfulness that can come with an ankle bootie, especially if you go for a lace-up style and at least a bit of a heel.

It works for pencil skirts, longer lengths and even some minis, Miss Ford said. It’s that to-the-knee skirt that will prove tricky with these boots, too. For that, there really is just the ankle boot.

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.”