An age appropriate list for the younger gentlemen in the forum. I really admire the guys who can look classy all the time but can pack all their clothes into one bag and move with minimal fuss. 1. Authentic vintage jeans. Old 501's are classic, but otherwise, a pair of jeans that you've worn in yourself are fine. 2. Sneakers. Chuck Taylors are good, as are Stan Smiths. But I swear by Puma's. 3. A little cheating here, but a slim white cotton shirt, and a similar shirt in a very pale blue. Gucci makes very elegant shirts, but for a real treat, get them custom made by Luigi Borrelli. 4. A slim back suit. Bespoke is best. Emporio Armani is a good choice if you don't have a trust fund. 5. A charcoal grey suit. Again, bespoke is best. Otherwise, go with a good, conservative but stylish cut from Zegna or Canali. This suit is going to be used to get you a job, remember? 6. Plain front black lace ups. Cap toes are more traditional for business, its true, but I think that plain fronts look more elegant, and besides, you're in your twenties, not your fifties. Since you only have one pair or shoes, for play or work, you may as well splurge on Prada's. Still the coolest shoe despite all the hype. 7. Cheating again here, but 3 good ties, one in a matte silver with some pattern to wear with the black suit in the evening, and one subtle paisley to wear with the charcoal suit for the businessman with a flair look, and a pindot tie to wear for those sobering job interviews. My choices would be Zegna for the paisley, Gucci for the matte silver, and Charvet for the pindot 8. A casual jacket to wear around town. Leather is nice, but is a little limited. A mid-hip length charcoal wool coat from John Varvatos can be worn over your suits or with jeans. 9. A good watch. You're not 50, so you don't need a Cartier (you have your eye on your father's anyways.) You're not a member of the Triads, so skip the diamond encrusted Rolex. In fact, since you know quality and don't need to flaunt it, skip the Rolex altogether, along with obvious brands like Omega.. But since you do have a rich uncle, ask him for an understated style from IWC. 10. A navy blue cashmere crewneck, maybe from Malo. TSE is another good choice. This is so that your girlfriend, wife, random woman at the bar, has an excuse to nuzzle up against you. 11. Okay, I've gone over the limit, but for your own edification, I suggest that you treat yourself to a funky piece by a designer like Dirk Schonberger, Martin Margiela or maybe Paul Smith or Dirty Youth of UK. It'll spice up your wardrobe, and show that you've a couple of years left to be cool.