What's wrong with tucking the shirt in? I think it looks fine there.
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Untuck and unbutton shirt, uncuff jeans, sag them a bit. I've never liked the way JPs look on anybody, but I guess lots of other people do. I'd swap them out for pretty much anything with a better/more defined shape, including vans, common projects, desert boots if you must (gasp!), boots with a heel (from anywhere), pretty much anything. The cuff hits that low sneaker awkwardly, try it again in two years when those jeans are like 4-5 shades lighter. I like your glasses. Do more badness with dat hair.
First fit pic.
Roll your sleeves down just a little bit. I feel they look best when you roll them to just above your elbow, but it looks like you've rolled them a good three or four inches past that.
He'd be fine with that roll if he unbuttoned one more button and didn't try to tuck it in. Shirt cuff is also fighting with the cuffed jeans and pulled-up pants.
First fit pic.
Try going for a modern version of Buddy Holly.
With the Purcells:
And with different shoes:
Warning: Spoiler! (Click to show)
And yeah, Synthese, two things: first, I have always had a rough time figuring out hair; I'm hoping that I can just keep growing it out longer and then, from time to time, get a quick trim on the sides and a thinning-out up top. Second, I think you're right about the shoes. Not that I don't love my Purcells (I do), I just think that a black boot with a heel (and/or maybe Chelsea-style?) would be pretty sweet with the cuffed jeans.
(Also: the shirt-sleeves wound up running higher. Woops.)
Today is casual day at wurk and on these days I have started wearing jeans with untucked shirt because tucking in jeans looks weak 90% of the time. I get a fair amount of grief about it from co-workers as well as "yep keep doing that, looks better."
Yeah, it works sometimes, but (and go look in the MC casual thread) you either look like a dork or somebody's dad 9/10 times. I think it's okay if you're older but in this case, definitely untuck.
@thewho: looks infinitely better with the second shoes , but don't unbutton the bottom of the shirt like that and I kinda agree that the shirt sleeves are rolled up a bit too high - but fix those and it's a good look. As for hair, maybe just put some shit in it - synth, I also wouldn't mind knowing how you get yours to look like that lol.
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