I never really understood being fashionable. Fashion is such a subjective thing. Sure, there’s the timelessness of a well-tailored suit and a black dress, but for the most part it seems to me like it comes down to a popularity contest. Where the winner is a designer, and he or she gets to tell all the losers (the rest of us) what we should wear.  I mean how else can you explain drop-crotch pants?

That being said, I have gained an appreciation for fashion. Like the crazy conceptual stuff. This happened at the Alexander McQueen fashion exhibit at MoMa (pretentiously titled Savage Beauty). The key is to look at the clothing as pieces of art, not actual clothing anyone would wear. But appreciating fashion for the art it is doesn’t help with figuring out what shirt to buy. Hell, I’d argue that my wizard t-shirt with “Team Dragon” written across the back is just as artistic. OK maybe not just as, but it’s certainly a piece of art.

So when I decided it was time for me to step up my fashion game, insomuch as start having as close to a game as I can muster, I was at a huge disadvantage. If you don’t even get fashion, how in the hell are you supposed to be able to become fashionable?

Thankfully the fashion world decided to throw guys like myself a bone. It decided to partner with sites and create an online shopping experience where they present select fashionable clothing. All you need to do is buy stuff from the site, and bingo bango you’re immediately fashionable! This was a revelation for me. I jumped in and never looked back. JackThreads, Haute Look, MyHabit, Gilt — I got on all of that. JackThreads has become a staple of mine since they have the amazing bonus of discounting most of the items, so you’re not like paying $60 for a shirt, you can get it for a much more reasonable $30. The beauty of these sites is that most of them are geared for the regular guy. So it’s not like you’re ending up buying the aforementioned drop-crotch pants (though I guess you could if you wanted), because most of the clothing on there is the kind of stuff that you’d expect to see on a dude who you consider “sharply dressed.”

The pinnacle of this experience is with Trunk Club. The way that site works is that you’re paired with a stylist, and that stylist sends you a box (they call it a trunk, but it’s a box) with not only fashionable, but completely coordinated, outfits. Holy wow. That’s basically like the cool kid going “Hey, I’m gonna help you out here. Put this, this, and this on. You’re welcome.” Granted, the clothes tend towards the pricey, so you’re still having to deal with some sticker shock. But if you’re in dire need of an outfit, especially one that’s on the fancy side, it’s a good resource to have. And you only pay for what you keep, so you can send the entire thing back and the only cost is the slight inconvenience of going by FedEx to drop of the prepaid return shipment.

Knowing this, you could even game the system by just getting the stylist to send you a box of outfits, then sourcing the type of stuff you’re sent at a cheaper site. I mean I personally guilt myself into buying at least a pair of socks so I’m not completely wasting their time, but in theory you have a personal stylist (I’m not sure how many times you can send a whole trunk back before the company wisens up, so be careful with that).

Really there are only two pitfalls to carousing online sites for a new wardrobe. Technically three if you want to count the risk that you start spending money you don’t have, but I consider fiscal responsibility is a pitfall of life in general. Anyway, one is that while the sites are, for the most part, geared towards the average well-dressed gent, they do have some things that are more “cutting-edge fashion,” like these weird translucent rubber oxfords I peeped on Haute Look:

 

Even I know not to buy these.

So while the sites simplify finding clothing that’s fashionable, you still have to be careful and focus on items that toe the line of normal. Stuff like button-down shirts and henleys and whatnot.

The other pitfall is that since you’re essentially picking pre-made outfits, there’s always the risk that you run into another dude who had the same brilliant idea as you, and as a result is wearing the same outfit. I mitigate this risk by mixing and matching across sites. So while we may have the same pants, our shirts are different. This is a bold maneuver, since I’m opening myself up for mismatching, but the trick with that is to basically buy what the models are wearing, just source it across sites. So, take this snazzy shirt that’s again a Haute Look find for instance:

 

 

I can buy that shirt, then pop over to JackThreads and get some khakis. Or mix it up with khaki-colored jeans. I’m not sure where I’d source the pouty lips, but that’s probably something I’d have to talk to my plastic surgeon about. Also, I’d have to find a plastic surgeon. The point is, you have a roadmap to work within, and you’re less likely to make a fashion faux pas than if you go all cavalier into a store, close your eyes, and grab a bunch of stuff.

So if you’re looking to make a change in your wardrobe, hit the sites, find the threads, and be merry. Just don’t buy that shirt I just showed you. ‘Cause I’m kinda diggin’ it and I’d hate for us to see each other while wearing the same thing.