The chunky boot is a remnant of 2020, when it was one of the year's biggest fashion trends (via Who What Wear). Now, it remains a closet staple in 2021, and for good reason. "This shoe trend is surprisingly versatile, but if you want to get specific, the best types of dresses to choose are casual mini dresses, sweater and knit dresses, and relaxed-fitting midi dresses," Who What Wear explained.
To best pair dresses with chunky boots, you have a few options. You can shimmy into a minimalist dress that will allow the chunky boot to do the speaking, or you could try a shirtdress. The latter will create an attitude around your outfit that you won't get with a traditional dress. Chunky boots can also be so nonchalant that they pair perfectly with a dress that's topped with a sweater. This look can be cutesy or grunge — or simultaneously both!
Moreover, if you're chilly and don't want to wear a sweater, the perfect combination for you is chunky boots with a dress and a jacket (via Lulus). The right jacket can really elevate a dress, and with chunky boots, the outfit can become nothing short of chic. For example, Lulus recommended a plaid jacket over a little black dress or a tailored coat over a sweater dress.
Overall, mini dresses appear to be the biggest recommendation, per Who What Wear. This is likely because mini dresses show off your legs, which will counteract the chunky boot's ability to make your legs look shorter or stubbier. These two together keep your proportions in tact nicely, but at the end of the day, these boots are going to look good with any dress you've got.
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