I sometimes dress like a 4-year-old boy (literally), but then I read a quote somewhere that it’s just as easy to wear a dress as it is to wear shorts and a T-shirt. And so much prettier! So, we thought we’d share a few favorite dresses, and the lovely Hadar agreed to model. Here are three looks…

Tomboy: This effortless linen dress looks good even when it’s wrinkled, making it perfect for bike rides and weekend getaways—or cheese shopping at Murray’s. We discovered it at Lou & Grey, a new line at Ann Taylor Loft with really lovely basics. (Sandals from Madewell.)

Feminine: This silk maxi looked like a watercolor painting as Hadar strolled down Bleecker Street. I loved how flowy and eye-catching it was—with two flirty slits—and it would be beautiful for a brunch with friends or dinner in a garden. (Sandals from Target.)

Sexy: All my friends swear by James Perse jersey dresses—you feel like you’re wearing a T-shirt, but you look a million times sexier. This black dress, with ruched sides and a slim fit, would be gorgeous for a date night. (Sandals by Splendid, also available in this fun color.)

Which dress would you choose? Which suits your personality best?

(Photos by Julia Robbs for Cup of Jo. Thanks for modeling, Hadar!)