Pearce Cleaveland

There’s an elevator at the Pendry hotel on Fifth that runs from the underground Oxford Social Club, with its $1500 Saturday night bottle service, up to the ground-floor Lionfish restaurant, home to Eater “Top-50 Young Guns” Chef Jose Ruiz, and then up again to the rooftop pool, with its…well, what? “A lot of people were like, ‘It’s just the pool at the Pendry,’ and it’s not just that,” says our hostess Beth. “We have a happy hour up here that’s not just for our hotel guests; we’re local-driven. We want everyone to feel welcome to come up here. And the chef from Lionfish does the menu.”

The pool at the Pendry, with happy hour revelers in background

Tonight — a media night in May — that means bite-sized portions of four appetizers, including oysters in a very clever Mignonette (Chardonnay, shallots, and vinegar, left to sit until the vinegar is tangy but not sour). It also means journalist-sized portions of booze, a steady parade of plastic tumblers pinkly bearing the rooftop bar’s Hot in Jalisco: blanco tequila, grenadine, grapefruit, and lime, with a habanero infusion to keep the palate awake and interested as the night wears on.

The Wife and I settle into a white canvas cabana to watch the world go by and discuss who wears what best. Eventually, the world stops in for a chat, in the form of Pearce Cleaveland, a Marketing Scientist for Clique Hospitality. (Clique has partnered with Pendry to operate the spots accessed by this particular elevator.)

Cleaveland has just finished a ten-year stint in Las Vegas, a place that, however lawless its reputation, still enforces certain standards. “There is a suit and tie for meetings in the day,” he reports, “and a suit and tie for dinner, and a suit and tie for the night club” — a code oddly reminiscent of his days growing up in Atlanta, when “there was a suit for church, and a different church outfit for after.”

The formality worked for him. “My great-grandfather was in the clothing business, and I’ve inherited a lot of stuff that’s now completely trendy — the very skinny Mao-collared smoking jacket, the single-button tuxedo jacket, the three-button suit with the huge, wide lapels that is starting to come back.” Not that he wears them much any more. “I have a closet full of suits, but a nice thing about San Diego is that you see a weird breadth of people: a person in a three-piece suit with an ascot, and they’re with a person in board shorts and flip flops, and that’s just normal. I adapted easily. I change the cedar in my suit bags regularly, and I let them sit. I know they’re there if I need them.”

And the loss of exterior standards has not occasioned a surrender to the forces of California Whatever: Cleaveland’s ensemble is casual but still carefully curated. The short, soft collar on his shirt says he won’t be wearing a tie this evening, while the popped collar on the jean jacket marks it as an intentional throwback, as do the brassy pins (a spaceman and the words “We’re doomed,” intended to evoke C-3PO). The stretchy trousers with their riding-pant flares are by Random, a skate company that also makes pants. “They’re versatile,” Cleaveland notes. “Sometimes, I wear them to the beach.” But with the right shoes, they’re proper enough for the pool at the Pendry.