Dear Avery: How can I make my over-the-knee boots look less “Pretty Woman” and more class- or work-appropriate? And how do I avoid buying Uggs and find a practical yet fashionable boot?

The opportunity to wear boots is perhaps the best thing about the temperature dropping. Obviously, rain boots are a practical, comfortable and usually fashionable choice throughout the fall. They come in every color and pattern imaginable and as long as you don’t buy the $19.99 pair from Target, they should hold up for at least a few seasons.

Unfortunately, however, the rain boots trend took a very, very wrong turn somewhere along the line. Brands like Hunter now offer knee-high rain boots that lace up the front or have wedge heels. That is just unacceptable. I sincerely hope salespeople will flat-out refuse to sell anyone a pair of wedge-heeled lace-up rubber galoshes, especially at $175 a pop.

My personal choice for fall and winter boots is the Bean Boot by L.L. Bean. They are rubberized, lace up to mid-calf and now come in a shearling-lined style that is warm, comfortable and basically as stylish and functional as winter boots can be. Let’s face it, the regular suede Uggs are neither practical nor useful during Western New York winters. You’ll look like an idiot slipping and sliding in your sopping-wet, salt-stained Uggs in three feet of snow.  Stop being a diva and get some practical shoes.

As far as over-the-knee boots go, I take my hat off to you for even owning a pair. I love those boots as long as they’re done right. That means no skin-tight mini skirts or dresses, and no patent leather hooker boots decorated with zippers and safety pins. A slouchy suede boot with either a very low heel or a stacked platform heel is probably the best choice and they look great with leggings, very tight jeans or stockings underneath a loose-fitting dress or skirt.

If you’re somehow impervious to the recent batch of cold weather we’ve had and you’re looking to bare your legs, try adding a pair of thigh-high wool socks underneath the boots in a neutral tone. The extra layer will be warmer and will also help you seem as though you’re wearing more clothes, which can’t hurt. When done right, these boots can look awesome, but use your judgement: you don’t want to experience that awkward moment when someone mistakes you as a street walker.

Dear Avery: I’m afraid that the guy I like thinks my style is too prissy. What subtle pieces can I add to the outfits I wear that will make me look more badass and alternative? P.S. I don’t do studs, skulls or checker prints.

Since studs and skulls are two of my favorite things, that makes this question kind of hard. But there are easy ways to incorporate slightly more hardcore, less frilly pieces into your wardrobe. When shopping, a few key things to look for are black and white stripes, contrast and anything leather.

Black and white vertical stripes always make me think of Keith Richards or pirates, both of whom are probably a lot edgier than you. Black and white in general always looks stylish to me—something about the contrast lends a hardcore edge to your look, even if you’re just wearing black jeans and a white v-neck. Add in some vertical stripes (which, by the way, are always slimming) and you’ve upped your coolness factor. This could be as simple as a striped top, or you could get really edgy and layer your stripes—vertical over horizontal can look really cool, as long as you stick with black and white.

Another way to look B.A. is to add in a little bit of leather now and then. If you’re into leggings (which, come on, who isn’t?), H&M makes a black pair with leather patches from mid-thigh to a little past the knee. This subtle addition of leather is fashionable without being over-the-top and will help you feel slightly more hardcore without straying too far away from your style. Paired with a soft, cozy black sweater or a boxy gray sweatshirt, you’ll be comfortable to boot. Plus, the contrast between a soft, feminine sweater and tough leather will be cool and fashion-forward.

But don’t be afraid to wear some of your girly pieces, too. If you like pearls, try mixing them in with a few silver chains or something with rhinestones. If you often wear pastel colors, they’ll still look great with leather leggings and ballet flats. And sometimes, adding some edge to your ensemble can even be as simple as a cool band t-shirt with ripped jeans and an armload of jewelry. Adopting a more alternative look isn’t about completely changing your style. And besides, you shouldn’t change your personal style for a guy. Chances are, he’ll be so distracted by your winning personality, he’ll hardly notice what you’re wearing anyway.

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