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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.
Cottage Sweater: Muskoka Dry Goods ($595) - made in canada Knit Slubbed Shirt: Circle of Gentlemen ($250) - made in turkey Laser Cut Belt: One X One ($98) - made in canada Leather & Suede Boots: J Shoes ($255) - made in thailand Lyocell and Cotton Jeans: Adriano Goldschmeid ($285) - made in usa
College-chic with striped sweater over a shirt and jeans with cuffs and shoes (important: not sneakers) to give you a casually polished look. Brownie points for well groomed hair on the head and face.