Jack Dorsey’s 23 Most Sizzling Fashion Moments

Now that Twitter is going public, its creator can expand his famously stylish wardrobe even more.

1. The time he wore his clear sunglasses with a crisp white button-down and alighted from a matching car.

Getty / Kevork Djansezian

2. That time he opted for “cowboy billionaire casual” in a red fitted tee and boots, and carried a leather jacket like it was a cool murse.

Getty / Kevork Djansezian

3. And then when he put the leather jacket back on because it looked cool.

Getty / Kevork Djansezian

4. The time he wore a Prada suit to the TIME 100 Awards and the logo was so attracted to him that it kept self-replicating.

Getty / Jamie McCarthy

5. The time even Barack Obama was transfixed by the crispness of his lapels.

Getty / Brendan Smialowski

6. The time he had a NOSE RING and Adrian Grenier hair:

7. The time his collar formed a mathematically profound right angle.

Bloomberg / Getty Images

8. The time he accessorized with a keenly on-trend banana:

9. When Anna Wintour deemed him chic enough to use as a leaning pole.

Getty / Andrew H. Walker

10. The time his shirt perfectly matched his eyes:

Getty / Mike Morse

11. The time Nicolas Sarkozy was like, “Nice blazer, man.”

12. That time a stranger accosted him merely to ask where he got that lovely periwinkle blue oxford.

Getty / Bill Pugliano

13. And he was like, “LOL, like you could pull this off.”

Getty / Bill Pugliano

14. That time he held up a hammer that was more stylish than Justin Bieber:

Getty / Jemal Countess

15. The time he was given an award for Best Carefully Windswept Hair:

Getty / Steve Jennings

16. That time he was like, “dude, do you even see this windbreaker?”

Getty / Kevork Djansezian

17. “Do you even SEE this fitted tee?”

Getty / Kevork Djansezian

18. “Yeah, I handcoded this smashing khaki suit.”

Getty / Brian Harkin

19. The time this guy asked him how he got his jeans so precisely stonewashed and he chuckled inwardly.

Getty / Bill Pugliano

20. The time he needed three pairs of sunglasses to fully manifest his awesomeness.

21. The time he out-fashioned everyone at TechCrunch Disrupt because come on.

Getty / C Flanigan

22. The time he made a straw fedora look sort of OK.

23. In high school when he looked like this:

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