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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. I am attending a fall wedding soon and am wondering how to look stylish and classy while maintaining warmth (I live in a very chilly climate.) What would you recommend wearing to such an event?

A. When it comes to fall and winter weddings, we women often have to suffer the cold weather in order to look stylish. Strapless dresses and strappy sandals are worn year round, regardless of the outside temperatures.

Since your wedding is likely inside, you really only need to worry about dressing warmly for the short walk from the car. You can either invest in a pricey evening coat that you’ll rarely wear, or you can stick with a classic wool coat in 3/4 or longer length. I’ve even seen chic New Yorkers somehow “work” a puffy coat and black tie dress for a dressy evening out. Or, you can try one of this season’s big trends: a (faux) fur jacket or chubby. Not only will it look great with your evening dress, but it will look fabulous with casual jeans and a sweater. Here are some favorites at every price range:

Q. I’m trying to think of a Halloween costume that is still a costume, yet chic and stylish. Any ideas?

A. If batgirl, the sexy secretary or naughty nurse aren’t your style, we’ve put together some stylish Halloween costume ideas using many of the items already in your closet. Have fun!


Beyonce’s Single Ladies - Go with a couple of friends and dress like Beyonce and her dancers in the “Single Ladies” video. Wear a swimsuit or leotard, stockings and heels; tease your hair into a half up/half down style and wear a gigantic oversized cocktail ring.


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1950s Housewife - Wear a ’50s style dress with an apron and classic pumps. Carry an oven mitt and pie or a feather duster. Bonus points for retro hair.


Marilyn Monroe or ’40s Pin Up Girl - If you’re blonde, go for the Marilyn Monroe look; brunettes can be a pin up girl. Wear a retro-styled halter dress and pumps, add retro curls to your hair, and follow these makeup tips courtesy of celebrity makeup artist Brett Freedman:

For bombshell makeup, start with a foundation that’s a shade lighter than you usually use (try Revlon’s Custom Creations foundation). This sets the stage for the crisp, retro look. Shade the crease of your eye with a soft beige-y taupe shadow. With a sponge-tipped applicator, apply a matte, bone colored shadow (or pale face powder) all over lids and add a silvery shimmer along the brow bone to highlight. The black liquid liner is very important. Run from tear duct to outer corner very close to the lash line. Extend liner up and out. Corner false lashes finish this alluring eye look. Fill out lips with a true blue-red lip liner and fill in with a deep red lipstick. Use very minimal blush in a soft pink. Ice the cake with Marilyn’s iconic mole aka your black liquid liner!


Prom Queen / Bridesmaid / Pageant Girl - Find a new use for that old prom dress or bridesmaid dress (the tackier the better!) with one of these costumes. Add a tiara and perhaps a date in a powder blue tux for Prom Queen; a tiara, a bouquet of flowers and a sash with your town or state on it for Pageant Girl (don’t forget your pageant wave!); for the always-a-Bridesmaid costume, carry a beat-up wedding bouquet and mess up your hair a bit so it looks like you knocked a few girls down to catch the bouquet.


Hippie - Put all those boho-chic clothes to good use and put together an outfit from the age of Aquarius (find pictures of the musical Hair for inspiration). Pull out the flared jeans, hippie tops and vests and frizz out your hair.


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Robert Palmer girl - Here’s a costume that’s Simply Irresistible: grab some girlfriends, a little black dress and a guitar, slick your hair back and wear pale foundation, smokey eyes and red lips.


Lady Gaga - If you’re adept with a makeup brush and willing to go pants-less, adopt one of GaGa’s many looks for your Halloween pleasure. Get the makeup how-to here.

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