How to Wear a High-waisted Pencil Skirt
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How to Wear a High-waisted Pencil Skirt

The high-waisted pencil skirt has become a new wardrobe staple. The reason these skirts have gone beyond a passing trend is that they work so well for most body types.*  They add curves to slender/boyish figures and accentuate the waist for curvier women, for a classic hourglass shape

*The exception to this rule is what has become referred to as the “apple-shaped” body type.   If your waist is your biggest part, unfortunately you and the pencil skirt are simply not made for each other.

So how do you integrate this look into your wardrobe? Below are some tips to help you get the look right.

DO:  pick a fabric that’s seasonally appropriate. For winter pick a heavyweight knit or wool-blend material, so you’ll stay warm and look hot. In the summertime go for a lighter knit or synthetic-blend fabric that doesn't wrinkle easily.

DO:  make the look vintage. Call to mind the femme fatales  of 1940’s cinema by adding another vintage element: round toed pumps, back-seamed stockings or ruby red lipstick. But . . .

DON’T:   go so far as to make the look costumey. The idea is to integrate a vintage look into your modern wardrobe, so if you’re thinking of wearing Betty Paige bangs, bright red lips, back-seamed stockings, rounded peep-toe pumps, and  a vintage brooche — you’re probably going a bit overboard.

DON’T:  make the look boring. I’ve seen tons of women pairing plain black skirts with plain white button down shirts.  And while some would consider this look classic, or a “safe” way to give this look a try —you’ll look like a cocktail waitress at a country club.

DO:  pick a jacket or coat that works with the skirt. A pencil skirt accents the waist, so the jacket should do the same.  Pick a coat that hits at mid-thigh that either ties or is belted at the waist. An overly voluminous coat will swallow up your curvy look.

DON’T:  wear a pencil skirt that falls too far below your knees. This is a one-way ticket to Frumpville. Not only will you look shorter, you’ll look thicker too — and a lot like Sophia on The Golden Girls.

DON’T:  wear a pencil skirt that is TOO high-waisted. The perfect pencilskirt should sit right around your natural waist; it should definitely NOT serve as a push-up bra. Don't laugh, I've ACTUALLY SEEN women wearing pencil skirts this way.

DO:  make the look colorful. Pair the skirt with a brightly hued, cap-sleeved sweater; try a pair of pumps in a color other than black; or add bold, colorful accessories.  If you’re still not comfortable with this look yet (yes, it can feel strange going from low-rise jeans to high-waist skirts), it’s probably best to wait a season or two before you try to incorporate it into your wardrobe. The most important thing with any style or outfit is that you look and feel confident. It has been said that you should wear the look, the look shouldn’t wear you. Unless you own the look, you’re bound to appear as awkward as you feel.

©KatieK, December 2008

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Comments (7)

I love the advice. I tend to be unsure if things actually match or if it looks it's good to know what to try.

Ranked #8 in Clothing & Apparel

No fear!

very nice!

Great article, Katie! I love the look of a pencil skirt when pulled off well.

Nice work!

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I totally agree about the "waitress at a country club" bit. Everyone seems to think that's the only way to dress up a pencil skirt.