Sub out the gingham for a solid white shirt or maybe even a blue windowpane, and I think it's a great look. I'd fear the B&W ging + knit blue tie + navy and gray is a bit too much for me.
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Damn you razor thin guys for your preternatural ability to pull off the casual vest! I like everything about that, Julio, except the shoes. Are they black? I think this look cries out for a less contrasting sand, beeswax, or rich brown desert boot or casual leather shoe. You have an excellent casual summer look but the dark shoes let it down. You did say it was evening, so I understand why the dark shoes were chosen, but in that case the white pants should also substituted for something darker.
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@Kenneth: Yup, black shoes. I've never had luck with desert boots; they tend to look clunky on me, which doesn't help when I'm so thin. Hopefully I'll find a streamlined pair similar to this: http://bit.ly/OzfVMI
@Cody: I like the watch, too. It's a Michel Herbelin watch I acquired years ago, though I know nothing about that particular watchmaker.
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I actually really like the tie, Kenneth! I am, however, ambivalent about the pairing of black/white gingham with a navy sport coat. If the navy's super dark, maybe nobody will notice, but I feel like there would be better shirts for the job?
And I also think the casual vest is an underdone look, outside of steampunk costumes.
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@Julio - What are those chukkas? They look like Edward Green. I hear AE is coming out with a new line of chukkas, maybe they'll hit the spot! Alternatively, how about something like this? http://meermin.es/ficha_articulo.php?id=2200
I'm thinking about using Meermin's MTO program to get their chukkas on a sleeker last with that gorgeous rapello suede and a leather sole. Would be simply outstanding with a relatively casual suit.
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a couple of WIWTs:
shirt from gap, dockers D1 khakis (long i know, but i'm dealing with that for now), timex watch, cole haan shoes
calibrate gingham shirt (got a few compliments on that one, although someone from upper level management asked if it was made from a picnic blanket), jcrew chinos, cole haan loafers
shirt from the gap, jcrew chinos
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