How To Wear A Midi Dress Over 40

I’m not typically a fan of wishy-washy trends. I like a dress that knows what it truly is and isn’t afraid to express it. A mini, for example, knows it’s short and sassy, while a maxi is long and breezy. But a midi? It can’t seem to make up its mind.

Fortunately, I decided to give it a try. Again. After all, it had been a good 20 years or so since I’d last explored this in-between style. And here’s my take.

While nothing will ever beat the flattery of a classic knee length skirt (the exact spot on the knee depends on your body and your Fashion Fit Formula), a midi can be a close second. Here’s why:

1. It covers more leg. And that’s a good thing, if your legs aren’t your favorite or you want the modesty of more coverage.
2. It’s comfortable. A midi offers more coverage and ease of movement.
3. It’s stylish and flattering. When chosen properly, of course.

If, like me, it had been a while since you’d tried on a midi, here 5 strategies for pulling off this trendy-yet-classic style in a flattering way over 40.

All of these dresses can be found right here in this catalog.

(For reference, I’m 5’2 1/2″, which is pretty short. 🙂

How to wear a midi dress over 40! (It can be done!) Which of these styles is your favorite?

Try A Fitted Style

The length and the volume of a midi dress together can be hard to pull off, so trying a more fitted and streamlined style can make all the difference. This Roxane dress from Antonio Melani is fitted throughout, and ruched where it counts, for maximum flattery.

Belt It

A midi dress is hardest to pull off when it’s flowy and oversized. Instead, try a style with a self belt, or belt it yourself, so avoid the drowning-in-fabric effect.

Show A Little Skin

I said a little. I see you, you saucy thing, trying to take this advice too far. 🙂 Exposing strategic parts of your body, whether it’s your neckline or arms or lower legs, can keep a flowy style dress from swallowing you up.

Consider a Slit

Refer back to the previous tip, where I suggested showing a little skin. A slit is a way to show a little leg, strategically, without overexposure. It’s usually found in dresses made of silky, drapey (and not crisp fabrics), another point in their favor. Drapey fabrics lay a bit closer to the body, creating a more flattering line.

Try Something Out Of The Box

I did not want to try this dress on. Seriously. It looked so over the top. But it was hanging there, in my size and color, practically begging me to take it for a spin, and I’m so glad I did. It’s not my favorite of the bunch, but it does fit, and it reminded me that, unlike hair, clothes aren’t a commitment. If you don’t like something, you can just change your outfit.

Trying a new silhouette can teach you so much about your body and your style, and it keeps things interesting.

What do you think of these strategies for buying a flattering midi dress? And which of these is your fave? Let me know in the comments!