Is this a look?

My initial reaction is that the guy was probably required to wear a tie and was simply fulfilling an obligation.  This look sounds too dressed up and too casual, all at once.  If I were a style cop I'd give him a ticket for swerving recklessly between lanes.

i think the looks falls into the east coast ivy league, wasp area. Ive seen lots of similar photos in the last Brooks Brothers catalog actually. A nice cashmere polo style sweater over a shirt and tie would look perfectly acceptable to me, but I could be wrong. I think the look is best pulled off in a slightly more casual sense, perhaps a pair of heavy flannel trousers, shirt, tie, nice cahsmere polo sweater, and a corduroy sportcoat, maybe some suede chukka boots. Kind of college professor-ish, but not entirely without style.

Sounds preppy to me, or maybe he was trying something new, like those NYC guys who did a subversive Dilbert look for a while (slim, short sleever "dress" shirt with a skinny tie, skinny jeans, etc...) Either way, sounds like a look to avoid.

I try and avoid wearing one collared article of clothing over another. Lapels don't count towards this limitation.

Was the top button buttoned and the tie hitched right up to his neck? or was the top button unbuttoned and the tie knot a little lower? I wear ties with casual outfits every so often, mostly because I don't have too many chances to wear them with suits. But I never tighten them around my neck. They're always hanging a little below the unfastened top button (or two).

In my opinion it sounds good except for the tie. Casual with a touch of elegance but I don't believe it's something for a man under 40.