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beckettrobb: Tweed heaven.  With wool necktie and holiday-appropriate pocket square.  Suit, shirt, tie, and pocket square all by Beckett & Robb Bespoke.

Double breasted suit with a great checkered tie and a fun pocket square. Yes. CalgarysBestDress...

Canary yellow tie, patterned pocket square, brooch and tie bar

The difficulty with mixing dressy and casual elements is finding items in each category that work well together. In this case, a gingham check shirt with a tie in an earthy tone helps bridge the gap between the dressy look of a dress shirt, tie, and sport coat, and the casual look of a drawstring hoodie. This is very well done.

dreamboat! for all I know this man could be really old and I'd probably still be into it... you just can't deny the awesomeness of this outfit.

I like this look for a guy, but not so much the glasses. Remove the big bar at the top, and then they would be normal.:)

Plaid---Not so much my style, but this is definitely my son's preference. This just might be his wardrobe.