Alessandra Rich built her namesake label in 2010 after working in interiors and designing her own wedding dress, with no formal fashion training. That outsider start still shows in the dresses, which borrow from vintage codes without behaving like museum pieces: florals, polka dots, bows and ruffles are pushed into high-impact evening shapes. Choose the silhouette first, then decide whether the print should whisper or arrive before you do.

The separates keep the same mischievous femininity but give it a little more room to move. Rich has described her imagined women as not so perfect that they become boring, and the tweed, silk and lace-trimmed pieces make that idea tangible without turning every outfit into costume. Let one detail lead, whether it is a collar, a bow or a flash of shine, and leave the rest of the styling direct.

Our honest take: Alessandra Rich is not interested in blending into the background, and that is the point. The pieces suit an intense social calendar, but they can also work for someone willing to wear a dramatic dress without waiting for a red carpet to justify it. If you take one thing away, make it this: keep the styling simple enough that the dress gets to be complicated.

To round out the look, see Altar'd State Dresses and Marlies Grace Bags and Dresses.