Best Bet: Forever 21 Striped Pom-Pom Beanie

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For the soon-to-come dreary winter days, take a cue from our street-style shots (see: model Vasila Pavlova) and try a fun pom-pom beanie. This brightly hued striped version is a playful upgrade from the standard slouchy knit in drab shades of gray and black, but will still keep you happily warm. Just because snow days don't exist now that you're a grown-up doesn't mean you can't dress as if you're ready to hop on a sled.

Forever 21 striped knit pom-pom beanie, $8.80.