Jeff Ruby's Steakhouse – Lexington

Jordan Cabernet Sauvignon 2017 (Alexander Valley) — $155

In a list where the markups are uniformly steep, Jordan at $155 is the least painful entry point into the serious Cab category. It's marked up about 2.4x retail, which is still aggressive, but Jordan consistently punches above its price bracket and holds its own next to bottles costing twice as much on this very list. Order this before you reflexively reach for the Caymus.

Caymus-Suisun Grand Durif

Most tables at Jeff Ruby's are locked in a Cab tunnel and never look up. The Grand Durif — a Petite Sirah-dominant blend from the Wagner family's Suisun Valley project — is darker, earthier, and more interesting than anything Caymus proper puts out. It's the kind of bottle that makes your steak taste like a better idea than it already was, and half the room has no idea it's on the list.

Silver Oak Cabernet Sauvignon 2016 (Alexander Valley)

Silver Oak is a fine wine, but at $235 against a $85 retail price, you're paying a 176% markup to drink something that every steakhouse in America already has on the list. The name recognition is doing a lot of heavy lifting here. Put that money toward the Jordan or stretch it toward something from the Italian reserve section instead.

Far Niente Chardonnay (Napa Valley) + Seafood Tower

Far Niente Chardonnay has the weight and richness to stand up to a full raw bar spread without steamrolling the delicate stuff. The wine's restrained oak and bright acidity play well against briny oysters and chilled shrimp, and it signals to the table that you know what you're doing without blowing the whole wine budget before the steaks arrive.