Mark Zuckerberg is having quite a month. The Father of Facebook just turned 28, bought out Instagram for $1 billion and is now facing the most lucrative point in his career: Going IPO on Friday. We’d offer him a congratulatory “poke” but sadly, that option’s no longer available. For those of you who aren’t familiar with the IPO acronym, it stands for Initial Public Offering– meaning that the company will finally be open to stock holders where the likes of Wall Street—-and even you!—- can purchase a part of the social media company.

But with the estimated $100 billion that’s supposedly coming his way, we’re wondering whether the Harvard dropout will invest in a new wardrobe. Will he finally change out of his usual uniform consisting of dowdy college hoodies, sweat-drenched Adidas shower flip flops, and tattered baggy jeans, into something more uh, dapper? Better yet, the question posed is this: Can all the money in the world transform someone from HTML geek to sartorial chic? Fashionistas can only hope!

To give him an extra boost, we’ve enlisted the help of several fashion experts from designers like Carlos Campos, Alan Eckstein from Timo Weiland and Simon Kneen of Banana Republic, to editors from GQ and Esquire, to buyers and the likes to see what kind of advice they’d shed onto Silicon Valley’s hottest star. And regardless of whether he takes our suggestions or not (note to Marky Mark: you really, really should!), happy IPO Day! We’d definitely like to send you a congratulatory poke soon—- this time, live and in-person.