1. A leather jacket.
You need one, and for no other reason than you just do. It’s also one of the few things I’d recommend investing in. Because the more you wear it, the more you’ll break it in and the softer it’ll get.
However if you choose not to invest in a leather jacket, you can usually buy a used one that’s already worn-in at a second-hand shop. I found one for $40 at Buffalo Exchange.
2. Something overall-y.
I suggest going for an overall that’s different from your average denim one — one that you couldn’t easily buy at American Apparel. For example, this vintage Jean Paul Gaultier overall-style shirt that I found at a vintage store in London. It has the Degas ballerina print on it. That is all.
It also helps if you have friends with money, because then they’ll lend you stuff like this gingham Versace overall dress (also vintage):
3. Bright pants.
Think: bright skiwear from the 80s. Something silky-looking — it could even be polyester. What Giuliana Rancic would call a “statement piece.”
4. A raincoat.
It’s just nice to not have to hold an umbrella and it’s even nicer when you’re doing it in Christian Dior. Now, hold up. Before you get all I-can’t-afford-this crazy on me, I found this at Beacon’s Closet for $45. There is hope, you just have to be willing to look.
5. A silk Japanese jacket.
Because…why not? eBay is a fantastic place to start looking for one.
6. A gingham something.
I think I can confidently say I own one of the most coveted pairs of gingham pants. They’re from Chloe Sevigny for Opening Ceremony’s first collection and Chloe said they were her favorite piece:
Just make sure not to cheap out on this one because there’s nothing as obvious as cheap gingham fabric (as every dude knows). Again: second-hand shops are your friend. And if you happen to actually like your paychecks, try something like this Prada masterpiece from their fall 2013 collection:
7. A good flannel shirt.
The world is overrun with flannel shirts so you must navigate this piece carefully. You could collect a truckload of boring flannels OR you could invest in a single nice one like I did.
8. A nice collared shirt.
You may not take yourself seriously now, but someone at some point will. And when that time comes you’ll wish you had taken heed of my advice and bought a collared shirt for yourself. It should be optimal for layering and also try looking at the collar before you buy it; personally, I think a round collar is prettiest.
9. Something with fringe.
Like chokers (re: classy ones vs. dog collars), fringe can either be very good or very bad. As a precaution: don’t overdo it on the fringe and don’t go overboard with the Western look. Other than that, I have no additional words of advice except to just follow your taste. I found this buddy at a thrift shop in Paris called Pretty Box.
10. An unconventional plaid.
And by this I mean a plaid dress or plaid pants — anything but the basic plaid flannel. Perhaps it comes in orange on a wool oversized blouse, like so:
11. Ripped jeans.
And the paths to the perfect ripped jeans are threefold:
- DIY – or do it yourself by taking a razor and scissors to them. There are a plethora of Youtube tutorials on this.
- DID – or do it doggy. Give them to your dog, for a naturally distressed look.
- Purchase them – or buy them pre- and professionally-ripped. Ripped jeans come in a range of styles and prices. These were expensive, but worth it (I told myself) because they’re handmade.
12. A dope-ass long dress.
Balls, galas — they do exist. Not that we’d ever be invited to one, but it’s always good to be prepared. I found this pretty number at Scout in Los Angeles.
13. A varsity jacket.
It looks good if you juxtapose one with a nice dress. The contrast is dreamy. You can get yourself a free varsity jacket too — all you have to do is work at Opening Ceremony for a year.
14. Black dress(es).
I hate when people tout the importance of the “perfect little black dress” because no such thing exists. Which is why you always need a couple black dresses in your closet at any given time. Also, velvet. You can’t go wrong with velvet.
15. A fair amount of sneakers.
I live by this awesome motto that goes: heels are never worth it — you should try it sometime. It leaves you with a ton of extra money to spend on things like sneakers, which, as it happens, don’t give you scoliosis and are fortunately in right now. Just make me one promise: never — and I mean never — buy a pair of sneaker wedges. Aside for that: Nikes are cool, as are the Adidas Stan Smith shoes. And if you have the money and want to make me jealous: go for the new Chanel or Dior sneakers from their spring/summer 2014 collections.
16. A cool tee.
Something to make your guy friends jealous. Like this David Lynch for Supreme t-shirt that I found on eBay.
Sophomore makes cool t-shirts too!
17. A good jumpsuit.
If it wasn’t so hard to take a piss in them, I would never take off these jumpsuits.
They’re made by Layla Racy, an up-and-coming designer you need to know about if you want to stay at all relevant. And, with the diaphanous feel of a silk muumuu, the comfort level is dangerously high.
18. An oversized sweater to lay and die in.
This could be purloined straight from your dad’s closet — which, by the way, I recommend revisiting (dads usually don’t know how good they have it). But if you’re going to go out, you may as well do it in style, in which case you’ll want to get your hands on something like this:
19. A suede oversized button-down.
I got this one at Beacon’s Closet for under $25 and, I’m not kidding, I wear it practically every day. It looks good thrown over any outfit and the suede adds a nice bit of extra texture. 
