So how do you pull off a necktie without looking like a stuffy businessman? Easy. The key to wearing a tie is to keep it in proportion to your frame. “You don’t want to wear a men’s tie and look like you’re playing dress up,” says Rygorsky. So instead of raiding your BF’s closet, try the little boy’s department. “Ties in boys’ sizes are the perfect length to wear with a cute oxford, and thankfully a lot of them come pre-tied.”