Like peanut butter and jelly, a dress styled with a pair of sneakers is a classic, fail-safe combination. Fashion girls have been cementing the look as a street style staple since the mid-aughts. While the fashion It crowd hardly invented the trend of eschewing heels for sneakers (my middle school self lived and died by the ole pop-punk princess uniform: an A&F skater dress and a pair of beat-up Converse high tops), they did catapult the styling combo to mainstream success.
The allure is understandable. An off-the-shoulder billowy dress finished off with a set of skater shoes, a cocktail minidress styled with a pair of bulky Triple S sneakers—the seemingly discordant dressed-up/dressed-down ensemble achieves the ideal laid-back look. It’s stylish yet gives off an air of having put in minimal effort.
Naturally, the sneaker-and-dress look flourishes best in the summer. Now that it’s June, we’re on the prowl for the most affordable summer dresses on the market—the better the price, the more options we can stock our wardrobes with. And as a little treat, we’ve also whipped up a selection of our recommended sneaker pairings. Scroll down to shop 16 summer-ready dresses, all under $45.