Put This On launched their second Kickstarter project last week (Season One is here) and to celebrate all the men they've helped dress like grownups, we reached out to Jesse with an idea. What if he could work some of his compassionate yet firm magic on some of the men who work at Kickstarter who may or may not be in need of a little coaxing? Luckily, Jesse was up to the challenge and the guys were up for donning their best plaid and posing for the camera with, frankly, a surprising level of enthusiasm.
Here are the photos we sent to Jesse, with his responses below. Read carefully, dress accordingly, and don't forget to check out the project. It ends in two days!
I have to say that I'm pretty impressed with this group of volunteers. My standards are pretty modest for "bunch of developers at a tech startup," but I think that on the whole these guys look pretty good. It's definitely a group of looks that could work in high school or college as well as at this age, and it's possible that they'll start to wear by the time these guys are in their mid-30s, but I think it's a good-looking group of dudes.
Let's start with AARON. First of all, I like that his pose seems to suggest that he's willing to fight me if it comes to it. Sometimes when you're well-dressed, a little of that "bring it on!" attitude can really help. (And by "bring it on!" attitude, I mean the attitude demonstrated by the sassy cheerleaders in the hit film "Bring It On." By the way, how great was Ian Roberts in that movie?)
Aaron's wearing a pretty basic outfit, but I think in a basic outfit like this, details can make a big difference. I'd say he should consider swapping the zip-up hooded sweatshirt for a crew-neck pull-over version (if he really needs a sweatshirt - it's still warm in New York, right?). I'd also trade in those pre-distressed jeans. The distressing adds to a very boot-cut-y look. A straight cut in dark denim could help here. He also might consider more richness and contrast in the colors of his shirt, since he has very light skin and dark hair.
COOPER's shirt is one of my favorite pieces in the whole set. It's a great color combination for summer-fading-into-fall, and it's not preppy in that annoying way. The colors also really work for him. He should watch the pre-distressed jeans, and remember to at least approximately match his belt to his shoes. He might have considered white sneakers for summer, but he looks downtown-y enough to pull off black.
I like ANDREW and ZACK's looks. Andrew's got a very simple look for what I presume was hot weather. I think you always look good in a white t-shirt that fits well, and sometimes shorts are simply a necessity. These look simple and clean, which is what you should look for. The only problem here is that all this simplicity calls attention to Andrew's eyebrow piercing, which is very, well... Lolapalooza. I think if Andrew added a distinctive accessory, he'd improve the look. Also, he should watch the summer neckbeard action.
I think Zack looks great. I love the well-faded jeans (that appear to be faded the old-fashioned way - through wear). His t-shirt looks like it's seen better days, and I'd consider tucking it in if I was wearing a second shirt on top. Man bracelets are very trendy right now, but they're a nice way to add a little spice to a simple look, and Zack is far from over-the-top with his.
JARED's look feels a little more sophisticated than some of the others, perhaps because he's wearing a dress shirt. He looks like someone who's casual but could be taken seriously. Two things he could change: a v-neck undershirt won't show at the collar (that's a big no-no for me), and if he gets those jeans hemmed, he'll have a much cleaner line through his legs, which I think will do him a world of good. The puddling emphasises his thinness in a bad way - a cleaner line will help his thinness be a positive. He also might consider a higher rise in his jeans if he's going to tuck his shirt in, as that'll help keep the shirt from poofing at the waist.
MIKE's look strikes me as very LA - I think it's that pastel polo shirt. Boat shoes are somewhere on the line between trendy too far gone, but I think Mike wears them well here. He'd benefit from a distinctive belt. Maybe a rope-y one or something New England-y with nautical hardware to pick up the boat theme. I think the soft colors work well for him - he has much less contrast in his coloration than some of the other guys, with light sandy brown rather than dark brown hair.
Here's the thing with SAM - when you're big, it's important to dress cleanly and sharply. It's not fair, but when you're big, it's easy to see slovenliness, even where you might not on a skinny guy. Sam should pull up his pants a little and get them hemmed so they don't pool at the ankle. And probably get a slightly slimmer cut in the future. Baggy makes him look heavier than he is - and he isn't super overweight or anything. In that spirit, I'd also ditch those ratty skateboard shoes and commit to either a mid-forearm neat shirt roll, or buttoned cuffs. The shirt is generally a step in the right direction. The colors work great for him, and a rich pallette on top, in solids or dense, simple patterns like this will look great on someone like Sam. I'd also even out the beard, and keep the stick. The stick is awesome.