No one cares what brand you wear, so buy whatever is comfortable and fits well and doesn’t stick out the top of your pants. The advantage to “tighty whiteys” or boxer briefs are that they don’t clump up inside your pants and show through. You should have white socks for your sneakers and black socks for your dress shoes. If you wish to purchase dress socks for your dress shoes, that’s entirely up to you, since no one will see them unless you are sitting down. You should always wear a white T-shirt under a white button-down; if you wear a printed shirt under it, we can tell.
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