High vs. Low: A Classic Black Wrap Dress

High Low Black Wrap Dress

High, $380; Low, $85

The beauty of our High vs. Low posts is that there isn’t always a clear winner or a winner at all. Last week, we featured a backless loafer, in a modern leopard print. In that case, it’s a trend, one worth wearing, but I don’t want you spending a lot of money on. Today is a little different.

A classic black wrap dress is one of those rare items that will never, ever go out of style. When I was 22 years old, I purchased my very first Diane Von Furstenberg, a vintage black wrap dress from the late 70s. It was the first item of clothing I ever bought that made me feel like a real grown woman. I wore it all the time, including my engagement party, on my honeymoon and for many years after. Of course, since having two babies and discovering a love of wine and cheese, it doesn’t fit anymore. I was a waif back then, but I’ll never get rid of it. Instead, it’s in storage for my girls. I imagine it will be so special to see them wearing it as they head out to have the kind of magical night you only get in your youth, knowing that I had an equally amazing time wearing it when I was their age.

From the moment I put on that dress, I was hooked. It felt congruent to my personality and aesthetic. The style is chic and comfortable, feminine but never trying too hard, definitely fun, yet also reserved. Every season I add a few more to my wardrobe, happily paying full price, and downright gleeful when I find one on sale. Oddly enough, I’ve never replaced that very first timeless and classic black dress. In my real-life, I wear these dresses all the time and have a deep affection for Diane Von Furstenberg the woman, so splurging on her dresses is a treat, but also cost efficient because I get so much wear out of them. My two big splurges are always: great fitting jeans and a DVF wrap dress.

So if you think you would get a lot of use out of it, and it fits in your budget, it’s a worthy splurge. Keep in mind, size wise, this classic dress, in general, runs small. I usually wear a size ten in DVF but wear a size 6 in Ann Taylor and most Nordstrom brands. Keep that in mind when ordering.

If, however, a wrap is not at the top of your priorities list, or maybe you’ll only occasionally wear to dinner or a work event, this faux wrap by Ann Klein made me do a double-take. It’s pretty darn similar, and wait for it, $85.00. So it’s a bit of a no-brainer. If you pick it up now, with the holiday not too far away, you’ll get your money out of it before the start of the New Year.

How should you style a wrap dress? In most cases, the simpler, the better. A classic pump, in black, natural-to-you or a bold print is always a winner. The cut and drape of the dress almost require a heel, so ignore some of the new modern styling of it showing them with loafers or (gulp) sneakers. Don’t do that; you will look ridiculous. If the neckline is too low for your liking, or just not appropriate for the occasion, a slim cami underneath, also in black, will fix it. You’re more likely to run into this issue with DVF’s version. For a night out, pick up some double-sided tape to help the neckline stay in place.

Regarding accessories, scale is important. Do not, under any circumstances, carry your casual shoulder bag or a satchel. It will be too big and bulky. You want something sleek and modern, like an envelope clutch with a shoulder strap or chain.  (I like this one for under $60.) Skip the necklace and instead, have some fun with a dangly earring, if you’d like, or an oversized stud.

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Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

  1. Thank you, again, for providing various options on a classic! Some of us have grown an affinity for wine and cheese, too. 🙂

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