How to Succeed in Hipness Without Really Trying

All puns aside, it’s not difficult to put together a stylish outfit if you have some simple pieces that fit correctly. In my opinion, there are five items every guy should have in his wardrobe. They are:

1.     Light blue button-up shirt.

2.     Levis 505, 511, or 513 jeans.

3.     Low-top sneakers that are in acceptable condition.

4.     A jacket that isn’t a hoody.

5.     A watch.

You’ll notice I didn’t put a suit on the list. That’s because I don’t believe that every guy 18+ needs to own a suit, to be honest. I certainly don’t own one, because I don’t work in an office and rarely go anywhere formal enough to actually require it. That being said, suits are awesome.

You’ll also notice the list lacking a necktie or bowtie. Although I wear them all the time (because I’m a damn dirty “hipster”), not every dude out there dresses like he’s going to Princeton (I do not attend Princeton).

So anyways, back to what is on the list.

*Note: The pictures I've included are from the internet as examples of some good choices (i.m.o.), and while I can't say they're all that cheap, I can assure you that these are pretty popular brands at thrift stores.

Light Blue Button-Up Shirt

Everyone looks good in blue; it’s a universally flattering color. It’s the most popular favorite color in the world, apparently, and it goes with pretty much everything. I actually can’t think of a pair of pants that wouldn’t go with a blue oxford, they are just that versatile. They’re also incredibly popular, so you should be able to go into any thrift store in the world and find one in your size for less than 10 bucks. Just make sure you don’t get anything too fancy if you’re going to wear it casually. If it’s long enough that it would make sense to tuck in, look for another one, or know that you should probably take that sucker into a tailor’s to get shortened.

Levis 505, 511, or 513 Jeans

505: Straight fit

511: Skinny fit

513: Slim fit

These are 513s.

I personally prefer Levis skinny fit jeans the best, especially the pairs that are made with some stretch (breaking my synthetic material rule). But all three of these are super comfortable, pretty damn stylish, and will last you more than a couple of years if you treat them right. Plus, they’re usually not more than about $50 new, not a bad price for a pair of jeans that’ll last three or more years. Or, if you’re not too picky about what fit and color you want, it’s almost impossible not to find a pair of Levis at a thrift or second-hand store. They’re classics.

Low-Top Sneakers That Are in Acceptable Condition

Converse All Stars freaking rock.

Cheap, easy to wear, and pretty much infinite in styles and colors. If you’re going for a classic style, there’s Converse, Keds, Vans (not the slip-ons, those are dorky), etc. For skate shoes (which I personally think are awesome) there are Adidas, Supras (their high-tops are legendary, but their low-tops ain’t bad), DC, and pretty much any shoe brand that has a skate team. I know Vans are also skate shoes, but you can’t say they’re not classic. Any of the brands I listed can be found used and cheap, so find a pair you think kick ass, and prepare to wear them all the time (hint: looking for second-hand footwear? eBay.).

I say "acceptable condition" because sneakers don't have to be kept in perfect condition to look good. You can beat them up, just make sure they're not falling apart. Getting a pair of good quality sneakers from a thrift store are a good investment – they'll cost as much as $15.00 and will last at least a year or so (more, if you treat them well).

Or, if you want a super unique pair of sneakers, and you have some extra bucks to spend, get a pair of Solerebels. It’s a great company based in Ethiopia that pays its workers 3x the average salary, provides them with healthcare, and sends their kids to school. But it’s not a charity, just a company run by people who care about their workers.

A Jacket That Isn’t A Hoody

Found on ebay.

It’s ok if you wear that super comfortable UCLA hoody to the grocery store, but if you’re trying to impress a lady (or gentleman), wear a jacket. This can be anything that’s comfortable and looks good: a denim jacket, a leather bomber, a thick cardigan, a blazer, anything. Just try getting it in a color that’s neutral (black, grey, dark blue, brown) so you can wear it with virtually anything in your closet.

A Watch

I don’t care if you get one that costs $4,000 or $4.00, just get a watch. Not a digital one either, but a classic timepiece (that doesn’t clash with your belt/shoes). For some reason, wearing a nice-looking watch makes women more attracted to you, and men take you more seriously. I think it’s because they make you look more mature, but who knows. Just trust me on this one.

Theoretically, you could get all five of these for as low as 50 bucks. And for five wardrobe staples that you’ll wear the hell out of for years, that’s a price worth paying.