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Thomas Dean - Long Sleeve Spread Collar Small Popling Print Shirt: Not only does it have a geometric pattern that pops against the deep navy ground, it has a really cool contrast plaid trim under the collar and cuffs.

Bugatchi - Regular Fit Gingham Sport Shirt: It looks great with dark denim, and the contrast interior trim on the collar and cuff create a polished finish.

Zachary Prell - Mead Standard Fit Plaid Sport Shirt: It can be worn for a sophisticated look with dark grey wool pants or with dark wash jeans for a more casual look – we are always fans of shirts with versatility.

Zachary Prell - Estevez Standard Fit Plaid Sport Shirt: Olive is a terrific accent color, and pairs with dark purple effortlessly in this plaid shirt.

Hugo Boss - Shaded Check Sport Shirt: Since we often opt for dark wash jeans for a casual evening out, we know the importance of good shirt options to go with them. With the importance of plaid this season (and really, most seasons), this is just what you need.

John Varvatos Star USA - Moda Charcoal Glen Plaid Wool Blazer: The fit is trim and contemporary, perfect for a stylish night out.

Zachary Prell - Grenier Sport Shirt: If you’re looking for something a little more casual, but still stylish for a night out, this dark plaid sport shirt is the way to go.

Theory - Slyvain Solid Dress Shirt: When you wear this under a sweater, be sure to keep the foldover collar nice and stiff – you don’t want the collar to have a wide spread over the neckline of the sweater.

Peter Millar - Thai Jacquard 1/2-Zip Sweater: The black and grey jacquard pattern in this cotton sweater provides a dash of character.

Vince - Single Pocket Shirt: It’s really sophisticated in design and works wonders under a basic navy blazer or charcoal cardigan.