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Jack Dorsey's 23 Most Sizzling Fashion Moments

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

Posted on September 23, 2013, at 1:21 p.m. ET

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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