Mordechai Rubinstein Styles Himself After a David Hockney Painting

Mordechai Rubinstein’s mother wanted him to be a rabbi; today, the street-style photographer and man about town wears his yarmulke beneath a rotating array of fedoras, beanies, and caps. He’s known for his colorful, mix-and-match get-ups — bold prints, jaunty hats, J.Press and Brooks Brothers shirts, and khakis. (His voice-mail message concludes, “If your pants are rolled up above the ankle, a reminder: it’s fall.”) Rubinstein took a circuitous route into fashion: After a short-lived stint at F.I.T. in the nineties, he started working retail at New Republic Clothiers, then moved on to do PR for Jack Spade. While there, he sold a line of dead-stock vintage ties from the fifties under the moniker Mister Mort, a name he’s since adopted on his blog MisterMort. The site chronicles his daily run-ins with offbeat dressers on the streets of New York, Paris, or London, like a more egalitarian Sartorialist (who, coincidentally, is also a fan). His street-style photos have appeared on AnOtherMag.com, Men.Style.com, AContinuousLean.com, and in Details and T Magazine’s blog, among others. He was named the associate market editor at Men’s Vogue in the summer of 2008. Since the magazine’s demise, he has become the marketing manager for Dockers, where he’s looking to shake up brand stereotypes and “disrupt the sea of beige,” as he puts it. We chatted with the trend-spotter about dress shoes, thrifting, and the sanctity of hats.

Who are your favorite designers?
Mark McNairy, Alber Elbaz.

What’s the first designer item you bought?
I bought these amazing wool crêpe DKNY pants from Century 21, and one night I fell asleep on the train at 4 a.m. When I woke up, I felt the air go through them — someone had sliced my pockets with a box cutter and taken my wallet. I was just devastated. I patched them up, but I never wore them again.

Where do you like to shop in New York?
I love secondhand stores, like Star Struck and Church Street Surplus. I like how the garments tell stories. The salespeople are all telling bullshit stories, too.

How would you describe your style?
The Duke of Windsor meets David Hockney. It’s super-tailored, but also fun and colorful and whimsical. I wear Brooks Brothers oxford shirts and khakis or 501s pretty much every single day.

How important are accessories?
I change my shoes five times a day, and I have way too many hats. I’ll wear the same clothes three days in a row, but I can’t wear the same hat twice in a row. Hats are the only things I don’t like to buy used.

What trends are you appreciating right now?
I like that men are getting dressed up more — less sneakers, more hard-bottom shoes.

What trends are you ready to see retired?
High-top boat shoes, suede boat shoes, designer boat shoes … all non-Sperry boat shoes.

What’s one item you’re saving up to buy?
I’m having an overcoat made.

What should every man have in his closet?
Cedar shoe trees, and maybe a fedora. I see too many guys without their heads covered — it’s freezing out.

What’s something you never leave the house without?
Common sense and my camera.

Mordechai Rubinstein Styles Himself After a David Hockney Painting