Here’s where we enter the Goldilocks Zone. A button-down shirt is the safe, responsible choice—like ordering a salad when you secretly want fries. But which button-down?
An Oxford cloth button-down (OCBD) is the holy grail. Its collar rolls like a gentle wave, and it says, “I might own a boat, or I might just have good taste in thrift stores.” Avoid anything with a spread collar so wide it looks like a bat signal.
10 Stylish Essentials to Wear Under a Sport Coat for Men
Now, the popover shirt—a button-down with only three buttons and a half-placket. It’s the shirt equivalent of a mullet haircut: work-hard, play-hard. Wear it unbuttoned at the top for a breezy, “I just solved a crossword puzzle” vibe.
The Undershirt Trap
Should you wear an undershirt? Yes, but only if the person you’re dating will never see it. Wear a V-neck that hides deeper than a spy’s identity. If your undershirt peeks out, you look like an accountant who eats glue.
Pro tip: white undershirts are for funerals and prison. Okay, not really, but a gray or nude undershirt disappears under white dress shirts like a ninja in a snowstorm. Don’t let your undershirt scream louder than your personality.
