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On the Fly

For Distinguished Gentlemen

  • On the Fly
    One Embarcadero Center, San Francisco, CA 94111 (Map)
    +1 415.765.0993

If you’ve ever wanted to be part of the Old Boy’s Club, or just look like it, take a trip to On the Fly in Embarcadero One at Front Street in the Financial District. This is the spot to find brandy snifters, khakis, fancy cufflinks made out of old footballs, Hush Puppies, and more.

Though On the Fly has sold good online for seven years, its brick-and-mortar store opened in San Francisco only a few years ago. The company recently moved its retail shop into a 4,500-square-foot-space directly above the original store, while the former space is now devoted to tailoring.

On the Fly carries anything that smacks of old money, Ivy League, or country club, from clothing and accessories, to grooming products and housewares. It’s a big store and there’s a lot of ground to cover.

The store offers a wide variety of dress and sport shirts, polos, knits, and T’s. Choices range from an Ike Behar solid twill French cuff dress shirts ($135) to a Thomas Dean lime flowered number ($71). A Derek Rose Basel T-shirt ($65) is luxurious to the touch.

To complete a casual look, On the Fly stocks Bills Khakis, including the original twill or lightweight cotton poplin (both $115-$120) and chamois cloth ($165-$170). For something more dressy, look to the store’s trouser selection from Corbin, such as the Super 120 gabardine or Worsted wool trousers with a flat front or reverse pleat (all $175), or the featherweave spun microfiber ($175).

When it’s time for work, check out On the Fly’s selection of suits, including ones from Peter Millar in solids or pinstripes in navy or charcoal (all $750).

For your feet, the store carries Michael Toschi golf shoes ($550), Martin Dingman Trevor penny loafers ($235) and Hush Puppies, such as the Revere boat shoe ($90). But there is also a permanent Wolverine pop-up store within On the Fly that carries the largest inventory of the company’s footwear outside of its Michigan home base, including Bradford wingtip oxfords ($243) and Darby boots ($169-$225).

A shoe-shine station is stocked with Saphir Pate de Luxe wax shoe polish ($16), Renovateur Nubuck/suede sprays, applicator brushes ($14) and chamois cloths ($8).

A favorite spot of mine in the store is the cufflinks section. Cufflinks add throwback class and a touch of whimsy without a lot of effort. There are choices for about every interest, including cufflinks made out of old Yankee Stadium seats ($170), typewriter keys and Scrabble pieces ($60), and a rainbow of silk knot choices ($12). San Francisco Giants’ fans can wear a piece of history by sporting cufflinks made of baseballs from the 2010 World Series.

Real or perceived, refinement is a key word here. For example, you can train yourself to recognize and identify the different fragrances present in wine with Make Scents of Wine 54 Aroma Master Kit Le Nez Du Vin ($399). You can study grapes on the DeLong wine grape varietal table ($25). Or, you can just drink a fine wine from a Ravenscroft vintner's choice decanter ($85).

The store is male-centric, but if you’re a woman who likes the juxtaposition of the female form versus masculine tailoring, this is a great resource. For example, I was digging on the Bills Khakis limited edition retro plaid Parker shorts ($57). There’s a tailor downstairs, so it’s easy to alter the fit.
If On the Fly fits your vibe, you should know that a couple of blocks away on Sacramento at Sansome is an extension of the store, Wingtip, a 21st Century interpretation of a men's club. The club features a bar, game room, and a study with workstations. Wingtip is open to men and women, and the members’ monthly dues are fully redeemable at the store or online. That is, if you have the thousands of dollars to spend on the store and a serious shopping habit.