BEHIND FRANCES MAY’S FLOOR-TO-CEILING GLASS WINDOWS, the nostalgic and the modern have formed a perfect union. The airy downtown loft exudes a vaguely antique charm, while metal racks lining the walls showcase independent creations, from Therese Rawsthorne’s asymmetrical silk “Snake Charmer” dress to Gitman’s 1982 vintage-stock plaid oxford shirts. But the collection of classic cuts and avant-garde designs isn’t appealing only to Portland trendsetters—their grandparents will be won over as well.

In fact, a grandparent is hand-picking half the merchandise. In 2008, co-owner Pamela Baker-Miller partnered with her grandmother Connie Codding to open the Southwest Portland boutique. “There is a certain timelessness to her choices,” says Baker-Miller. “She has a totally different concept of fashion that spans a lot of experiences and time.”

A graduate of the Pratt Institute, Baker-Miller brings her background in painting to her bold selection of rich colors, textures, and lines—all infused with a healthy dose of composition and practicality. “I like things that look different, but aren’t too ‘costumey,’” she says.

Eventually, Baker-Miller, who learned to sew from her great-grandmother, Frances May Williams, hopes to use the family eye for style to launch a house brand.