Dear Stylegirlfriend (is that your official title or do you prefer Megan?!?)
I’m a reasonably young guy (halfway to eighteen) and I was wondering: I want to dress nice but not look like I’m trying too hard. I don’t want to look like I’m going to a fashion show, but I’d like to slowly get away from the “worn hoodie and beat up running shoes” look. For example, would suede boots or a cotton military jacket work? Thanks for your time and I hope you have a good one! PS. You are totally hilarious!
- Cody (Sent from my iPod)
Reasonably young? Reasonably young at seventeen years old? Cody! Do you know how old I am? No sorry, I meant: do you know how old I felt until you called yourself “reasonably young” at 17? Not very Cody. Not very. But now? More so.
That said, I will answer your question through my resigned laughter and bitter tears. But only because you think I am funny, and I am nothing if not a total glutton for compliments about my wit.
I don’t want you to look like you’re going to a fashion show either, so we’re on the same page there. Beyond that, it sounds like you’re on the right sartorial track. You clearly know a thing or two about style already, with your suede boots and military-style jacket scenario (yes to both, by the way). That’s a huge advantage in terms of upping your wardrobe game. Some guys realize they could dress better but don’t even know where to start.
I would suggest phasing in clothes made in higher-end materials and a slim cut. You’ve got to give up the hoodies eventually (there’s not many jobs where they’re encouraged in the dress code), so start experimenting with more interesting textures and clothes that fit closer to the body now.
Make these wardrobe updates in a way that feels gradual, rather than abrupt (which will be easier on your bank account anyway). You don’t want to all of a sudden go from faded bootcut jeans to a three-piece suit. You can, however, go from faded bootcut jeans to a dark, straight-leg jean without causing too much whiplash for the friends who see you every day. From there, the jump from jeans to cords or khakis doesn’t feel so scary. Later, graduating from the khakis to a pair of wool trousers (or that suit) will be even easier.
This move works across your whole wardrobe – maybe next you’ll swap out your dirty old sneakers for a pair that’s fresh and clean (and clearly not meant for the gym, track, or court). The hoodie for a v-neck sweater. Do this with all your clothes, and you’ll slowly amass a closet full of great-looking, quality clothes, without anyone accusing you of going all Zoolander on them.
And for the record: my official title is actually “Your Highness Style Girlfriend Emeritus,” but you can call me Megan ‘cuz we’re cool like that.