How To Dress Like A Man — 2019 Update

John LeFevre
9 min readApr 22, 2019

Men’s fashion is in a state of crisis. It doesn’t matter where you look, from the recent Twitter debate over cargo shorts (they’re objectively awful) to the endless stream of bright-eyed graduates starting their careers, or the haggard, white-collar masses traipsing from airport lounge to departure gate in pleated slacks and tucked-in golf shirts.

But nowhere is this more obvious than in the world of young finance, a culture best illuminated by an increasing number of very popular “finance meme” accounts on Instagram — like Arbitrage Andy, Lit-quiditiy, and Finance God.

This dude owes me a beer for censoring his face

Look no further than the Manhattan finance bro and the ubiquitousness of his fashion crutch of choice — the midtown uniform: button-down Oxford shirt, chinos, sleds (Gucci loafers), and, most important, a fleece vest. I understand the appeal of the Patagucci for the finance bro set. It’s like a fraternity; they want to fit in. The fleece vest hides their gut and sweaty armpits. It’s comfortable, considerably cheaper than a decent suit, and is durable for those sloppy nights out. But none of that makes it okay.

Generally, the problem with men and fashion is that guys try too hard or not at all. As I see it, particularly in finance and in the business world, it’s a function of risk/reward. Guys need to be pragmatic, live in the safe zone, and keep it simple. In that context, here’s everything you need to know:

Business Casual

  • I’ve shopped everywhere — from Madison Avenue and Saville Row to Taipan Row — and this Mizzen & Main ($125) shirt is by far the best shirt I’ve ever owned. Having seen the brand online for a couple of years, I was skeptical until I recently bought one.
This is literally a picture of my favorite shirt
  • It’s versatile, machine washable, wrinkle-free, sweat-resistant (so no need to be afraid to take off your jacket), fits perfectly tucked or untucked, and is more comfortable than a Lululemon or James Perse tee. It’s stretchability also makes it slimming for most body…

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John LeFevre

Signed contracts with Goldman Sachs and Simon & Schuster, and paid lawyers more than I made. Author of STRAIGHT TO HELL (not about @gselevator or Goldman Sachs)