The hardest part is over. You asked her (or him) out, she (or he) said yes. Keep the momentum going in a first-date look that exudes casual confidence. If you’ve got a laid-back style, the easiest way to take that look to date night is to elevate. More buttoned-up in your day-to-day? Keep your look polished with dressed-down options in tailored cuts (translation: DO NOT wear a suit).
Here’s how to dress for a casual date.
Do Dark Denim
A casual date calls for denim. If you told her casual, she will most likely be in jeans or a casual dress, so it’s important you stick to the dress code. Instead of your relaxed fit or light-wash weekend denim, opt for a dark-wash straight-leg jean. It’s universally flattering and will work with a variety of shirts—plus, the darker wash will lengthen your legs, making you appear taller. Be sure to add a leather belt to your jeans if your shirt will be tucked.
Dates Call for a Collar
A collared shirt is almost always a must for a first date. Unless the two of you are off on a serious sporting adventure, wear a button-up shirt or polo. For a cozy dinner, choose a button-up shirt in a classic print, like windowpane or gingham. Headed to an outdoor concert or a night of bowling? Wear a solid polo and amp up your style with some color.
Opt for Sharper Shoes
When in doubt, a dressier shoe is the best option. A chukka boot or a casual loafer will work with dark-wash denim or chinos (if you insist). A canvas sneaker is acceptable for a more laid-back date, but don’t pull out your old, tattered sneakers. A clean, like-new shoe shows you care and will complete your whole outfit.
Ditch the Accoutrements
Man jewelry should be minimal. Stick to a classic watch, unless you think you’ll be looking at it often. Simple is better on a first date. Her focus should be on you, not your necklace or class ring.
Finally, here are a few first date dos (though we know you’ve got this):
- Be prompt. Picking her up at 7? Be there at 7. If you’re meeting somewhere, get there 5 minutes early so she will see you when she arrives.
- Have questions ready. This shows you’re interested in getting to know her. Don’t ask them all at once. Let the conversation evolve.
- Put your cell phone away. Keep it out of sight to eliminate the temptation to check it. If you must have your cell phone out, set it face down on the table.
- Have a plan. Don’t pick her up and say “what should we do?” Choose your destination beforehand—then have a couple options ready for later in the evening if all is going well (like after-dinner drinks at a jazz bar or ice cream and a walk).
Above all, be yourself! Nothing is sharper than a man who is comfortable in his own skin.