Parting gifts for guests: truffles in shot glasses and flash drives loaded with music from the evening. Photo Gallery »

Stationery, etc.
All printed items—invitations, menus, table-tent labels—are from Paper Source. “It’s faux woodgrain printed with an ink-jet printer,” Surratt says.

Vintage attire
Every guest wore at least one item of clothing or an accessory from the 1950s or ’60s. Surratt completed her ensemble with period costume jewelry and a retro updo; Hernandez’s vintage cuff links, tie clip, and black wingtip shoes gave his look Mad Men–esque appeal.

Libations
Christine Busby worked with Dean Schlabowske of Cellar Rat to pair wines with food. “The complexity and dryness of the sherry worked beautifully with the spiced nuts, and the Coteaux du Layon was awesome with the cheeses,” she says.

Sweets
Every item on the dessert table was labeled with a wine pairing suggestion. Berry-topped chocolate pots de crème went with Malvira Birbet; white chocolate fondue with Anselmi Prosecco; mini currant-almond tarts with Barbadillo Amontillado sherry.

Greenery
A stack of vintage suitcases strung with Christmas lights stood in for a tree; instead of flowers, Surratt gathered bits of nature from the couple’s Wisconsin cabin retreat. “Evergreen clippings, pheasant feathers, sprigs from everywhere—mixed with a little faux greenery,” she says.

Party favors
Vintage shot glasses with chocolate truffles inside and a bowlful of red flash drives loaded with old-school holiday tunes sat on a mirrored tray in front of a placard reading “Take me home with you.”