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Q. I got these great boots from my husband last year and I haven’t worn them because I don’t know what to wear them with. They are Stuart Weitzman tall boots that are very fitted and hit just below the knee, in a beautiful wine color. Help me because he thinks I don’t like them because I haven’t worn them!

A. First, count yourself lucky that your husband has such great taste and bought you such a stylish present. Second, pull those boots out of the closet - now! Not only is a wine colored tall boot incredibly chic this season, but it can be worn with so many looks you (hopefully) already own.

Don’t let the wine color throw you, treat this as a neutral - the same as you would brown or black. In fact, wine pairs well with virtually every other color: black, brown, navy, cream, camel, green… the list goes on. Now that you know the color matches everything, wear your tall boots with: skinny jeans or leggings tucked into the boots, boot cut jeans worn over the boots, skirts and dresses paired with tights and your boots. On top, everything from chunky knit sweaters to pretty, feminine blouses will work.

Once you finally wear them, we’re betting they’ll be your new favorite shoes - and remember to thank your husband!

Q. I am a college student in the perpetually rainy state of Missouri. I own Hunter rain boots, but as it tends to be hot and muggy when it rains here, I have no idea how to wear them. My go-to combination of a sweater over skinny jeans is much too warm, and I don’t really like wearing leggings. What do I pair with my boots to avoid being sweaty and wet, while still remaining chic on campus?

A. If skinny jeans or leggings tucked into your Hunter boots aren’t working for you, then sub in a cute skirt to pair with your usual sweater combo. A dress also looks great with rubber boots. Here are 2 looks for inspiration:

Q. Do you have any suggestions for boots that be worn in the rain that aren’t rain boots? I want boots that aren’t Uggs for fall/winter but I don’t want to ruin leather ones by wearing them when it’s wet and gross outside.

A. There are many chic rain boot options that aren’t Uggs and aren’t made of rubber. Aquatalia and La Canadienne are famous for their waterproof/weatherproof leather and suede boots that come in a variety of styles and heel heights. Stuart Weitzman also offers a few rain proof styles. And for lightly rainy days when you’re not stepping in deep puddles, a rugged boot like the ones from Frye should hold up well.

We found a ton of great options for you, check them out:

Q. I recently had knee surgery and am relegated to flats and lower wedges. Any good options for fall/winter? What about formal evenings?

A. Speaking strictly from a style perspective (and not a medical one), you have many chic flat shoe options this fall. Ballet flats continue their reign as the go-to flat shoe. Look for jeweled embellishments, studs and animal prints this season. Tall flat boots are also incredibly hot this season. Here are a few options for you:

Flat shoes for evening can be tricky. Look for rich fabrics like velvets and metallics as well as pretty embellishments like jewels, flowers and ruffles. Here are some options for you.

For more fall shoes, check out our fall shoe guide

Q. For some reason I stuggle with wearing patent leather shoes. I have a couple of pairs of shoes that are patent; one is navy and one is dark red. I don’t wear them because I question if it’s the right time of year. What season is it appropriate to wear patent or is it always ok to do so? Please set me straight.

A. Patent leather used to be strictly a spring and summer skin, but in recent years, it has not only been okay to wear in the fall and winter, it has actually been a trend (read this post from last year). For fall, we love patent leathers in black, red, navy and purple, but more important than the color is the style of your shoe. If the silhouette is fall-appropriate, then go for it. Below are some patent accessories that are new for fall for inspiration:

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