The wrap dress is a perfect uniform for fall, the most middle-aged season of the year

One woman’s style journey in her 40s took her back to an old classic
By Elizabeth Bastos  Published on 10/03/2018 at 12:29 PM EDT
Jakob Owens/Unsplash

In the year of Our Lady of “Feel Like A Woman” Wrap Dresses, 1974, Diane von Furstenberg was only 27 when she made the first wrap dress, but it’s like she knew what I would need at 45.

DVF knew.

Her long-standing, aspirational style advice is to “…stay true to yourself.” Great! Piece of cake! For those gifted in style maybe “stay true to yourself” is easy and powerful, but for me in middle age it’s been a koan, a puzzle of cardigans.

What is true to myself? Is it a button-down? Capris? Birkies? What is, like, my relationship with clothes? Fashion psychology is now a thing.

I wanted to find out. I started keeping a clothes journal. In middle-age in a spiral notebook I was revealing the style of “my true self” by recording what I felt good wearing, and doing a little sketch of it, too (as a kid I used to love drawing clothes and making my paper dolls 18th-century royal ambassador-like sashes). Here’s what I have discovered. One would think that by one’s middle 40s one would 1) know what one likes to wear and 2) wear it. But this is not the case for me.

How can I possibly be this old and not know how to clothe this body-ody-ody? By middle age my grandmother had a distinct style, “a style uniform” as fashionable minimalists call it now. Hers was pumps, A-line skirt, patterned button down. My grandfather had suit, spectacles, wallet and watch. They went to the grave so ensembled.

By 50, my own mother mind-melded with Eileen Fisher knits in the lovely colors of ripening stone fruit. Yet here I was, fussing, a grown woman going, Wha? and Whycome? in the Urban Outfitters, musing on Do I dare to wear a jumpsuit recommended by The Cut? ( I daren’t.) What you wear makes a difference in how you feel. The research is in and I felt bad in a jumpsuit, okay?

Fran Lebowitz, she of a profoundly beautiful style uniform of well-tailored menswear, has said that, “People’s innermost thoughts are never as revealing as their jackets.”

In the second half of life I simply wanted my (choice of) jacket to reveal that I am warm, creative, approachable, forgiving, and trending positive—like, I listen to a lot of Oprah’s SuperSoul conversations and Tara Brach podcasts.

I wanted to feel good in my clothes. So I said to hell with separates.

In fall, the most middle-aged season, while in middle age, I am Team Say Yes to the Deep V-Neck Knee-Length Wrap Dress, Tied Casually at the Waist with a Belt of the Same Fabric. Feel like a woman seems archaic. However, in a wrap dress I do feel the creative energy of the universe. Better than I did in pants, anyway.

I’m in pants detox.

Being all one piece of fabric, the knee length wrap dress foregoes all the decisions and higher math of separates, there is no fear of VPL (visible panty line to the uninitiated), which allows me to think less about what I am going to wear and more about who I am.

It’s forgiving-flattering. In the knee-length wrap dress, I’m obviously not going to solve all the problems of the world, but I finally look like I know what to wear, and that’s one problem solved. And now that I have fewer decisions to make about my look, I can apply myself less distractedly to the larger fashion plate of the world, to the things that really matter.

Like… what shoes to wear with this perfect dress.

Wrap up this fall

If you’d like to embrace your middle age—or any age—we’ve rounded up the best fall frocks we could find. Scroll through the dresses below for a variety of colors, sizes and styles.

Didi Leopard Print Wrap Dress

Start your wrap collection with this fierce dress by the master herself, Diane von Furstenberg. This classic style has powerful leopard print and will quickly become your favorite statement piece.

Purchase at Saks Fifth Avenue for $373.

Daytime Dapper Wrap Dress

This vibrant wrap dress combines bold colors and a fun print with a traditional cut. It’s perfect for work or grabbing brunch with your friends.

Purchase at Modcloth for $85.

City Chic Plus Polka Dot Wrap Dress

Put a polka dot on it! Polka dots are timeless; this wrap dress is not only fun but comfortable as well.

Purchase at Lord & Taylor for $119.

Maternity Plaid Midi Wrap Dress

Channel your inner ’90s goddess in this plaid print wrap dress. A pair of Docs and a couple of small barrettes will complete your homage to the era of Nirvana and Daria.

Purchase at Gap for $70.

Soft & Sexy Plush Wrap Dress

What better way to welcome the cooler months than a soft, fuzzy wrap dress? Available in both navy and grey, this dress pairs perfectly with some knit tights and boots, keeping you stylish and warm all winter long!

Purchase at American Eagle for $28.

Printed Wrap Dress

Hop on the prairie dress train with this down home wrap dress. Add some strappy sandals or cowboy boots to finish off the look in any weather!

Purchase at Lucky Brand for $139.

Coral Navy Full Length Wrapped Maxi Dress

Brightly colored, you sure to stand out in this maxi wrap dress. With a flared hem, you’ll have lots of room for movement, so why not take this dress dancing?

Purchase on ModLi for $69.

Belted Faux Wrap Dress

Not quite ready for a full on wrap dress? Try this faux wrap dress from plus size maven Ashley Stewart. Snag it in black with a bright red accents and take it for a night on the town!

Purchase at Ashley Stewart for $38.

Satin Velvet Wrap Dress

This sweet dress takes the wrap style in a fancier direction. Dress this up or down.

Purchase on Frank & Oak for $129.

Belted Wrap Dress

This sleek black, belted number will empower you to take on the board room—or a night on the town.

Purchase on Vince for $375.

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