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Q. I would love to invest in a pair of Frye Harness boots but I can’t decide between the shorter 8R or the knee-high 12R style. I’m only 4’11 so I’m concerned that I might look silly if I paired the 8R with a loose dress or skirt.

A. We are huge fans of the classic Frye Harness boot with its motorcycle styling and rugged good looks. Not only are they great looking, but they are built to last for years and only look better with age. We love them with jeans, leggings and yes, dresses and skirts.

Since you are 4’11, you are right to be concerned with the height (shaft) of the boot and how it works with your proportions. Depending how long your legs are, the 12R with its 12” height should hit below your knee, making it our top choice to wear with your dresses and skirts. If, however, the 12” boot hits higher than 1” below your knee, your better choice would be the shorter 8R boot.

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left: Frye Harness 12R, $222 at zappos.com

right: Frye Harness 8R, $192 at zappos.com

Q. I have two questions in one: I just got this cute but basic dress from Target in Charcoal. I am not great at accessorizing but would love to know what your suggestions might be. Also, could I wear knee high boots and tights with it? I’m short (5’3”) and curvy (size 12-14) and I have finally found a great pair of leather knee high boots that fit my thick calves but I’m afraid they make me look even shorter. Can short, curvy gals wear knee high boots without looking stumpy?

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A. Your dress was a great score for less than $20! It’s a simple, timeless and flattering silhouette that you’ll likely get a lot of use from. A necklace would be the perfect accessory to brighten up the monochromatic look. Look for one that doesn’t hang too low or it will compete with the button details at the waist. A fun patterned or textured tight can also add interest to your dress.

For shoes, opt for a nice leg lengthening pump or yes, your knee high boots. Petite curvy women can absolutely wear the knee boot trend. For the most flattering look, follow these leg lengthening tips:

  1. Opt for a boot with a 3” or higher heel that isn’t too chunky. Flat boots can be a tough silhouette for petite women to wear.
  2. Look for a shaft (the height of the boot) that hits an inch or more below your knee. A shaft that is too high and close to your knee can visually shorten the look of your legs. You may have to try on several different boots to find the most flattering shaft height for you, but try a 14” or 15” height to start.
  3. Wear your boots with a similar color tight, legging or jean for a monochromatic look. Black boots worn with black tights creates one long line, rather than “chopping” your leg in half with a different color.

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:

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