Early this fall, when it was priced at $355, I half-heartedly tried on this Gap leather jacket and quite enjoyed its dulled yet oily finish and its near-perfect fit. Ten weeks later, when it was marked down to less than $95, I snatched it up as my sole selection from the end-of-season fashion sales.
It’s since helped me look 95% cooler and tougher than I actually am, so God bless the good old Gap.

I know J. Crew earns all the internet ink for its constant collaborations with better-buzzed brands and its curatorial approach to merchandizing, but their actual in-house offerings rarely impress me. Over the last few seasons their sizing, fits, and pricing haven’t prompted me to pull the trigger on anything except two pairs of super short shorts and a single grey T-shirt with the word GUARD printed on it (though that T-shirt has become my current favorite, I will say.)
Whereas each season at the “boring” and bad-buzzed Gap I’m able to find at least two styles of pants that fit, perfectly unfussy, and read as completely era-less; and with their constantly re-designed and re-branded denim department there is usually a pair or two every few months that manages to get everything just right as well.
They still stock the mundane, middlebrow building blocks of Chandler Bing’s business-casual wardrobe (lax khakis and lime green button-ups), but when I sift through the middle-American snooze I find A.P.C.-like pop-over tops in rusty madras, tab-collared chambray shirts with stitch-striped cuffs, and trim trench coats in navy wool that Jakob Dylan would (and will) envy me for.
It’s never risky, The Gap – and aside from short shorts and jumpsuits, neither am I. So we’re a real good fit.