One way to avoid looking costumey is to mix in other elements to throw off a look that is otherwise pretty consistent.
For example, I love these new Cole Haan penny loafers. When you wear them with a white oxford button-down, trim dark-rinse jeans, and a conservative tie, however, it starts to look like you’re dressing for a cotillion.
Throw an edgy jersey motorcycle jacket on and your prepster look gets some edge. Clashing style genres can coordinate well when done right.
Give it a try –
shoes – Cole Haan
tie – Bows ‘N Ties c/o
shirt – j.crew similar
jeans – Uniqlo
jacket – H&M similar