Well done overall and I love the vest-and-jean combo in particular.The weather in NYC has been cold and wet for the last 36 hours or so, and is only supposed to clear later this afternoon - not weather conducive to getting elaborately dressed up, hence today's more casual attire.
Sports jacket - Chester Barrie via Austin Reed (both brands now consigned to the dustbin of sartorial history)
Shirt and suede vest - Brooks Brothers
Trousers - Levi's
Pocket square - Ede & Ravenscroft
Boots - Magnanni
Cap - Paul Stuart
Face mask - New & Lingwood
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I'm thinking you need (notice how easily I spend your money) a classic grey or brown herringbone sport coat. To be sure, you'll bring your own flair to it with the outfits you assemble around it, but I think it would be a nice addition to your incredible wardrobe. It would have been fantastic over today's rig.
Over the years, I've owned Austin Reed suits and an incredible Austin Reed trench, which, at the time, seemed to be on par with Burberry.