Shop the Chocolate Brown Midi Dresses We’d Actually Wear

My sister in law visited last month, took one look at me in the chocolate brown midi I’d bought for a wedding shower, and said “that’s such a sad color for a dress.” Sad. Not unflattering, not wrong for my skin tone, sad. I have not stopped thinking about it. I don’t think she’s right, but I also can’t fully argue her down, because I’ve owned three of these dresses and one of them does genuinely look like it’s in mourning.

Here’s the thing about chocolate brown that nobody tells you until you’ve bought the wrong one. It is not just a safer black.

Black hides you. Brown, the good kind, the one that’s closer to a coffee bean than a paper bag, makes you look like you thought about it, like you have a whole personality that includes an opinion on Ina Garten. The bad kind makes you look like you’re headed to a HR meeting you didn’t want. I’ve had both hanging in my closet at the same time, which tells you everything about how thin that line actually is.

The impulse one, bought at 11pm during a sale email I should not have opened, sat on the hanger for four months. It was fine. It just never felt like a decision, it felt like something that happened to me. The one that actually earned a spot in rotation was the boring, sensible one I tried on in a dressing room, hated for exactly ninety seconds, then wore to two dinners and a work thing and got complimented at all three. That’s the whole scam of sensible shopping nobody warns you about. It works and it’s annoying that it works.

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Now, the length. This is where I have to be honest with you. Midi is a friend sitting down and an enemy the second you’re upright and moving through the world. Sitting in it, you look put together. Walking to the train, climbing stairs, getting into a low car, it becomes a hostage situation with your own ankles.

I’ve done the little shuffle step at a curb more times than I’d like to admit, and I’ve watched other women do the exact same shuffle and immediately made eye contact with them like we’re in a support group.

Shoes decide the whole thing, no negotiation. A flat sandal with this length makes you look like you’re avoiding a decision. A boot, especially with an ankle showing, saves it completely, gives the whole outfit a reason to exist. A heel is the gamble pick here, it looks incredible on someone with the confidence to not care about the shuffle step, and slightly costume-y on the rest of us mortals who are just trying to get to brunch. I own the heel version of this dress. I have worn it twice. I regret nothing and also I sort of see what she meant.