Dear Jeanne,
Are pencil skirts really a “must-have” for every woman? I’m pear-shaped and have yet to find one that actually flatters my figure.
Emily
DEADLINE: JUNE 27

Dear Emily,

Let’s get one thing straight: In my stylebook, there’s no such thing as a “must-have”. We’re all too sophisticated for those kinds of fashion dictates by now. And just because something’s on trend does NOT mean you’ve got to rush right out and subscribe to it. There are more than enough options out to keep every woman of every body type satiated. The old adage of “To thine own self be true!” must always take precedence. That being said, if you like the look of pencil skirts—and personally, I adore them—and are keen to try and find one that you find flattering, try a little harder. First of all, there are a variety of these “pencil skirts” around—many taper toward the knee. But there are also those that hang straight down. I find the ones that are tapered could tend to make you look a little bottom heavy, if that is indeed an issue. Try a skirt that isn’t tapered, but rather hangs straight down. That might alleviate the problem. There’s also the question of length. I find the most flattering length for most skirts to be right at the knee—either just above, if you happen to have nice knees, or just below, if you’d rather hide them. The newer mid-calf lengths that are coming back are a bit tougher to carry off, no question. However, they can, in some cases, elongate a body. But of course, the right look of a skirt largely depends on the right footwear. A little height will always prove flattering, even if it’s only a wedge. But I digress. We’re talking skirts here…not shoes.

Make sure the pencil skirt you choose isn’t too tight, and in a fabric that will hold its form. A stretch fabric may be too clingy. But most importantly, it’s the top you plan on teaming with your skirt that will help you disguise any figure flaws you feel you might have. If you feel you’re “pear-shaped”, you’ll want to draw attention to your top. Pair a print or colourful shirt, sweater or jacket with a dark pencil skirt. An off-the shoulder top could also be very flattering. You might also try a fabulous scarf, again to draw more attention to the top half of your body. If you feel comfortable tucking your top in, go with a slim belt to accentuate your waist and give you a curvy look. And a peplum waist jacket with your pencil skirt could give you an ultra-feminine curvy line. But a longer, looser top should do the trick to disguise your bigger bottom. And with the slim proportion of a pencil skirt down below, and a nice pair of sleek pumps or more delicate strappy sandals, you should get the trim look you crave. Again—back to shoes—I’d avoid anything clunky. That could really throw off the proportion.