What to wear: Gitman Vintage chambray shirt, Buy It Now at Unionmade, $245; Champ cologne, Buy It Now at Need Supply, $34; Selvedge dad jeans, Buy It Now at Gap, $98; Yuketen shoes, Buy It Now at End Clothing, $561

You got her digits, you've been talking, and you're finally taking her out. Besides worrying where you're going to go and say, your biggest dilemma is what you're going to wear. You definitely want to put your best look forward, but without looking like a try-hard.

Start with a spritz on a subtle cologne, and break out the patterned shirt you've been waiting to wear. Then put on the newest dad jeans that are perfectly faded, and the crepe-soled shoes that everyone always gives you compliments on. You'll be killing it, and your confidence will shine through.