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What to Wear with Leggings

Leggings are everywhere you look—bus stops, museums, restaurants—women of all ages are wearing leggings tucked into boots and topped with winter coats. And no wonder, who doesn’t love a pair of black stretchy, comfy leggings? So easy to slide into winter boots, and then swap with a pair of flats once you’re indoors. Leggings feel like you’re wearing pyjamas. But what to wear with them? How do you dress them up for work or dinner out? Especially if you’re older or rounder?

Here are some ideas from my sketchbook.

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# 1: Go Long

You’ll need a top that’s long enough in the back to cover your derrière, and long enough in front to cover the crotch area. (You know why.) Not a dress—that rarely looks good because the proportions are off. Your best bet is a tunic top. Tunics are designed to be worn with leggings: not too short, not too long. Perfect to wear to work or an informal dinner.

 # 2: Find the right shape and length

Chunky, boxy knitted sweaters may look great on tall, thin models, but they make the rest of us look dumpy and fat. To make matters worse, most sweaters are cut straight on the sides, resulting in a figure-hugging look, which has a tendency to highlight any defects or extra curves.

The trick is to find a shape that works well with your figure. You need something with clear visual lines and some semblance of structure. A tunic top that skims the parts of your figure that you want to show and minimizes the rest. Unless you are Robin Hood wanting to show off a set of powerful thighs, you will want a tunic that ends somewhere between the crotch and mid thigh. As with a mini skirt, the taller and thinner your legs are, the higher the hem line can go and still be flattering. When in doubt, look for an A-line shape that fits at the shoulders and swings down and out from there.

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#3 Keep it chic

The best winter outfits allow you to show some skin, without sacrificing body warmth. Tunics with a transparent layer—lace, gauzy chiffon, silk—work really well. They will keep you warm and still looking chic, delicate and feminine. They offer a little more modesty without making you look like a tent. They hide many a surface flaw (scars, blotchy skin, a few extra pounds) without anyone being the wiser.

Transparency adds an air of mystery, and makes you look more like a woman and less like a schoolgirl.

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#4: Find the right fabric

Patterns are more forgiving than solid colors. Particularly random patterns, rather than rigid ones (checks, plaids, stripes) which tend to distort and amplify any extra curves.

Don’t go near any shiny fabrics. Shine works best as an accent than an all-over effect, so keep it for your shoes, bag, jewelry, hair accessories.

Darker colors —navy, espresso, forest green—are kinder than lighter colors, but all black will drain your face of color and make you look like a widow. If you must wear black, add some bright color with your winter hat, scarf, gloves, bag.

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