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10 Midi Skirt and Dress Styles to Embrace

Go with the flow with longer-length skirts and dresses

spinner image Regina Hall, Carolina Herrera and Michelle Yeoh
From left: Regina Hall, Carolina Herrera and Michelle Yeoh sport midi skirts. 
Dave Benett/Getty Images; Raymond Hall/GC Images/Getty Images; Gilbert Carrasquillo/GC Images/Getty Images

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. 

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spinner image Andie MacDowell and Rachel Ray
Andie MacDowell in a midi-dress length just above the swell of the calf; Rachael Ray in a straight midi just below the calves.
Dimitrios Kambouris/Getty Images; Jim Spellman/Getty Images

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.

spinner image Diane Lane and Lela Rochon
Diane Lane in a pencil midi just above calves; Lela Rochon in a pleated midi that's inches above her ankles.
Gary Gershoff/Getty Images; Paul Archuleta/Getty Images

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.

spinner image Nicole Yvette Brown and Jenny McCarthy
Nicole Yvette Brown in a slim taupe knit midi; Jenny McCarthy in tailored black pencil midi.
Leon Bennett/Getty Images for Essence; Amy Sussman/Getty Images

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.

spinner image Carolina Herrara and Peggy Siegel
Designer Carolina Herrera in belted flared midi suit; Publicist Peggy Siegal dons a midi.
Raymond Hall/GC Images/Getty Images; Dave Benett/Getty Images

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.

spinner image Luz Casal and Regina Hall
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.

spinner image Inka Friedrich and Melora Hardin
German actress Inka Friedrich in a leather midi; Melora Hardin in a pleated A-line midi.
Tristar Media/Getty Images; Tommaso Boddi/WireImage/Getty Images

6. Midis provide a safe playground to expand your personal style

A longer-length skirt makes everything you own look new. Whether you choose a midi skirt in a solid neutral, a pop of color or a playful print, your same blouses, booties, wedge sandals and ballet flats get reinvented by a simple shift in proportions.

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spinner image Lorraine Bracco ,Wendy Williams
Lorraine Bracco in a lacy midi skirt; Wendy Williams in a belted, pleated, full midi skirt.
Jamie McCarthy/Getty Images; Andrew Lipovsky/NBC/Getty Images

7. Midis manage show-off and camouflage opportunities

Have fabulous shoulders but like the idea of comfort and coverage? A midi skirt or dress lets you breathe, eat and move at work, events and parties — without being conscious of what’s going on with your belly, booty and thighs, and while spotlighting your assets at the neckline.

spinner image Angela Griffin and Deborah Hutton
British actress Angela Griffin and Australian editor and spokesmodel Deborah Hutton are both wearing midi dresses with a slit.
Samir Hussein/WireImage/Getty Images; Don Arnold/WireImage/Getty Images

8. Select a midi with a slit for an extra flash of leg

If you want a little more sass, look for a long midi with a knee-high slit (any higher, and it becomes tacky on real folks). A wrap-style dress and a shirtdress that unbuttons as needed are two good options, but some basic flowing midis offer a slit, too. A peep-toe pump or wedge adds inches to the exposed, leg but sneakers or mules are always a cool option for extra dash.

spinner image Kacey Ainsworth and Michelle Yeoh
British actress Kacey Ainsworth in a pleated ankle midi; Michelle Yeoh in a black midi skirt.
Jeff Spicer/Getty Images; Gilbert Carrasquillo/GC Images/Getty Images

9. Ankle-length midis are edgy — but watch the hemline

This longest midi works best in slim knife pleats for unrestricted movement and controlled volume. Tailor it to anklebone length if it hits the floor, or top of your shoes for proportion control. It looks contemporary when paired with booties or flats, not pumps.

spinner image Martha Stewart and Taraji P. Henson
Martha Stewart in a white knife-pleated midi; Taraji P. Henson in a full midi.
MediaPunch/Bauer-Griffin/GC Images; Dimitrios Kambouris/Getty Images for RH

10. A midi has all-weather, all-season, 24/7 versatility 

You can’t lose. Right now you can wear any midi with tights and boots or booties to get through chilly days. Add a leather jacket to toughen its feminine quality, and a silky, ruffled blouse or sparkly top to glam it up for special nights. Come warm weather, swap your footwear for sandals and enjoy the bonus of breezy bare-leg coverage.

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