One thing you learn as a working professional is that there's a more comfortable alternative to pretty much any situation—including nights out. This is something I realized when, as an intern, I attended the Prospect Park Summer Soirée dressed in a black dress and 4-inch heels that were pretty cool but also pretty hard to walk in. Jane Bishop was my boss, and as we already know, she's incredibly chic in the most natural of ways. The vibe that night was almost casual—looser dresses, flatter shoes, undone hair. Thanks to an “anything goes' atmosphere, it's not so much that I looked out of place, but by the end of the night, as I was making my way out of the park in the rain and mud, I realized that dressing down gives you more freedom to actually enjoy what you're doing. So, below, some suggestions to take you from August into fall.
Stone Cold Fox Farrah Dress : Something super short with a relaxed bell sleeve for your consideration. It fits loosely, which is all the better for eating, dancing around, or doing anything, really. Looks best worn with flats—slip on some sandals now and an ankle boot later.
Tibi Denni Loafers : Or, you could slip on these babies from Tibi—I can't sing their praises enough. I have a similar pair in white that I wear over and over again. They look really polished with whatever they're worn with but allow your ankles be 100-percent out there. Free the ankle.
Forever 21 Ribbed T-Shirt Dress : Yes, this is from Forever 21, and it's conveniently priced at less than most Seamless orders. And it's good—really good—as are most ”dthings from F21. I picked up a turtleneck version after seeing Diane Kruger in it—stretchy, simple, and works year round (and sadly no longer available). But anyway, onward and upward. Style this one right with weighty shoes—maybe a chunky flat or a sandal with a low, blocked heel. Maybe a mule. Your shoe collection is your oyster.
The Lair Leather Hendrix Belt : Another option is adding a belt that defines the waist. This one also looks good with high-rise trousers, jeans, and culottes. With two buckles, it's satisfyingly symmetrical. All of your other belts will look lopsided after welcoming this one into your life.
Vanessa Seward Adrienne Leather Shoulder Bag : Hands free, of course, because you have better things than a bag to hold....like a drink!
—Claire Knebl
Image of Amber Valletta via Getty.
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