For the second part of Jenn's dilemma posed on my Facebook page, she asked what her boyfriend should wear to go to her mom's 60th birthday dinner at an upscale restaurant. Here are my suggestions, and remember, every piece is under $50!
Option 1: Let your guy shine a bit in his own right! Use a jewel tone button down shirt and ground it with black pants. Find a complementary tie to dress the look up a bit. A wrap-around watch adds a bit of interest to his accessories. If it's cold out, use a military style jacket for extra masculinity.
Option 2: An argyle sweater is always a great option. It can be layered with a white t-shirt for a more casual look, or a button down shirt to be dressier. Make the button down a contrasting pattern in a similar color palette for visual interest. Pair this with a great pair of gray slacks, and the same military jacket as in option 1 if necessary. Use a classic silver watch and a plain black belt as accessories.
Option 3: If the restaurant is more on the casual side, let your guy be comfortable in dark denim jeans. But dress up the look with a white button down and black blazer. An interesting scarf keeps the outfit from being boring. A great pair of black loafers is perfect for all of these options (and most outfits your guy will wear).