I've spent all of my twenties traveling back and forth, for life, not for pleasure, and one of my Samsonites eventually bit the dust, zipper broke. That thing probably pulled about 15 or 20 cross-Pacific hauls. So yes, good luggage. I'm sure most have a decent bag for carry-on use, here on styleforum. I had a prada messenger in waxed canvas and leather that looked like a cleaner-lined Filson bag, that did me quite well for traveling. A nice watch, almost necessary. People are gonna see what you're wearing on your wrist - and if you see a young person wearing a nice watch, frankly, you are bound to take them a little more seriously than the guy with the shiny Fossil or Armani watch. I know this was supposed to be non-clothing stuff, but a lot of dudes have added clothing, so I will add my two cents too: -you need at least one suit, black at the very least, no matter your occupation. You'll probably go to a couple funerals in your twenties and you don't want to look like a dag. Add in a nice slim black tie. -good black shoes. -a black overcoat if you can afford it. -a really cool black leather jacket -a good peacoat -a nice pair of white sneakers that you feel most comfortable in. I have like 10 pairs, actually. -a perfect pair of jeans that exude comfort and your own personal style. 5 pairs if you're lucky and can amass that many pairs of perfect jeans. I have like 20 pairs of jeans but since the raw indigo ones are always in a state of flux, color and fit-wise, I only ever have 1 or 2 pairs of 'perfect' jeans. -a decent bag for business use I agree that a camera is essential. You're not getting any younger, so taking photos while you still look halfway decent and cool is a good thing. Even the miniscule point and shoot digital cameras take good enough pictures for this purpose, so you're not out much there. I have always had those kinds of cameras and then picked up a Nikon DSLR kit for $300 when ebay was having the 35% cashback. I don't mind having it, of course, but do wish I had a cheap small point and shoot I could pocket for going out, so i might look at getting one. One should spend the money and buy good SPF lotion. Daily sunblock will help you look better as you age. I use Kiehl's SPF 25, I think it is, and it functions as a moisturizer well enough, too. It's not particularly expensive IMO but I know some may not spend as much on this kind of stuff. I think everything is disposable really, including clothes, and should be treated as such, but this stuff is all good for living your 20's out comfortably and memorably.