10 Midi Skirt and Dress Styles to Embrace

Midi skirts are trendy, but many of us avoid them due to fear of frumpiness. After all, we’re the vivacious, spirited, self-confident women who invented the mini. And yet, there’s something so appealing about being able to cross our legs or sit like a guy, and not have to think about tugging down hems when we stand up. I’m a pretty picky fashion editor who doesn’t endorse every trend, but this one gets an unexpected five stars. Here are 10 whys and ways we can all get on board. 

Andie MacDowell in a midi-dress length just above the swell of the calf; Rachael Ray in a straight midi just below the calves.

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1. There’s a midi for every body, leg shape and length

The term “midi” applies to any length from two inches below the knees to just above the ankles. The easiest lengths for most women are just above the swell of the calf (a couple of inches below the knees) or just below the calves (so that a few inches of ankle show). The most unflattering length is exactly at the widest part of your calf. A good tailor can tweak any midi to hit exactly where it’s best for you. Even an inch can make a difference between beautiful and blah, so go for it.

Diane Lane in a pencil midi just above calves; Lela Rochon in a pleated midi that's inches above her ankles.

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2. You can always use another new black skirt, right?

So, start with a style you usually wear in a longer length — a pencil, pleated, wrap or A-line skirt. The familiar silhouette will enhance the appeal, and it’s pretty risk-free. The worst that can happen is that you shorten it to your normal hemline — but I suspect you’ll be hooked.

Nicole Yvette Brown in a slim taupe knit midi; Jenny McCarthy in tailored black pencil midi.

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3. Slim cut midis work like squeeze-free skinny jeans or leggings

Narrow midis in pencil trumpets that fit and flare at the hem, and knit tube skirts provide an elongated tapered base. They keep the outline of your curves in plain sight but don’t reveal thigh or leg proportions (or squeeze) like skin-hugging leggings and jeans do. Trim midis work with any top — fitted or full. Feel free to add tucked-in T-shirts and silky blouses or untucked full-cut sweaters, jackets and tunics.

Designer Carolina Herrera in belted flared midi suit; Publicist Peggy Siegal dons a midi.

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4. Fuller-cut midis provide added flair (and flare!)

Fuller midis make an even bolder fashion statement than slim midis and come in A-line or pleated styles. Just keep skirt proportions and your body/leg proportions in sync. (See tip No. 1.) Show a few generous inches of leg at the ankles for balance and some body definition with a fitted top, V neckline or belted waist. For evening, just add a black jacket or white blouse to a generously cut skirt — and you’re done.

Spanish singer Luz Casal in a shirtdress; Regina Hall in an A-line midi wrap skirt.

Raymond Hall/GC Images/Getty Images; Dave Benett/Getty Images

5. Waist definition restores legginess

Worried that a long skirt will make you appear to be standing in a ditch? This comes up a lot with those of us 5 feet 4 inches and under, and also taller women with a long torso and shorter legs. The trick is to show the waist and draw attention to it or where your waist would be (sometimes this means cheating with a slightly higher or wider waistband). Look for midis with a belt, elastic cinched or tie-waist, then tuck in your top or add a nipped waist jacket. Any or all of these will create the illusion of a longer lower body.