CITYist

Although they are quite possibly our favorite accessory to daydream about, hats are our least favorite to actually wear. Worries over which end of the chapeau spectrum we might end up on -prim and proper on foreign royalty or sloppy and unsightly on lazy frat boys- have inhibited us from donning more than a knit beanie in winter. However, sometimes an item comes along that makes you do a 180 on a trend, has you ready to throw insecurities to the wind and adopt a “I-hope-they-stare” attitude. For us, it was a handful of items that convinced us to change our hat-phobic ways. Scroll through for the caps that we’ll be wearing with reckless abandon for the rest of the summer.

Moody and Farrell Rabbit Felt with Silk Band Hat; $561, luisaviroma.com

Modcloth Banjo Band Hat; $17.99, modcloth.com

Trina Turk Black Cloche Hat; $142, trinaturk.com

Topshop Mini Roller Hat; $50, topshop.com

J.Crew Summer Straw Hat; 34.50, jcrew.com