At the ripe old age of 26, I figure there are a few areas in which I’ve mastered the art of delayed gratification: I can resist snacking on whatever’s in my fridge while I’m cooking dinner (having learned from experience that this usually means I won’t eat the latter), I can turn off the TV at 1 a.m. when I’m just one episode short of finishing a series (even if it means I spend the whole next day thinking about The Night Of), and I can make my bed in the morning knowing that I’ll really, really appreciate it when I come home.
One exception to these baby steps toward maturity is shopping: If I buy a new dress, jacket, or pair of shoes, I pretty much have to wear them the next day. I can’t help it. Why spend money on something if you’re not immediately compelled to put it on your body, right?
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Of course, this means I’ve missed out on sample-sale deals for winter coats in June and swimsuits in December, but I’ve made my peace with it. Right now, though, it’s a tricky time: the arrival of fall fashion means that leather jackets and turtleneck sweaters are beckoning to be taken home, but AccuWeather is telling me to expect temps in the 80s for the foreseeable future.
One of the few pieces I feel OK about shopping is transitional dresses that can easily be worn from summer to fall: pinafore styles that will work with a T-shirt now and a thermal later, lightweight shifts with sleeves that won’t suffocate on the subway, and airy midi dresses that will stay in heavy rotation year round. In a solid color or a print that doesn’t instantly connote any particular season, they’re a low-risk way to get in on fall shopping without having to wait around.
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Ahead, shop 17 transitional dresses—one for every day from now till fall.
