What To Wear On A First Date

First dates can be tricky and so can first date attire. Sometimes you don’t know what to wear and since its an ice breaker, I’m going to share with you exactly what you should be wearing on a first date. There’s a good chance that you met your date using an online dating site or casual app. However, which way you met them isn’t really all that important today. What is important is that you’ve lined up the opportunity to meet them and you need to put that time to good you by being prepared. Here are a few suggestions on what you should wear on a first date. Full disclosure, I use the same approach on all my dates.


First Date Attire and Wardrobe Tips

Nice Shoes
Your shoes are one of the first things that get noticed on a date. Therefore, it’s extremely important that you spend time choosing the best shoes for the occasion. Now, please note that I’m not suggesting that you wear some awesome Ferragamo shoes if you’re taking your date to a local dive bar or a football game. You’ll look like a douchebag if you do that. Instead, plan accordingly and wear a clean suitable pair of shoes or sneakers. Just steer clear from the Chuck Taylor’s. They are out of style as much as many don’t think so.  Wearing nice shoes can make you a dating master.

Nice Watch
Women notice what’s on your wrist and hands. Be sure to put on a nice watch for your date. Wearing a nice watch doesn’t say that you’re completely full of yourself. Instead, it screams that you somewhat have your shit together and can afford to purchase a nice item. You don’t need to have a Rolex either. You can find a nice classy looking watch online for a low dollar amount, so don’t make up any excuses for not wearing one.

Nice Shirt
This isn’t super important if it’s a spur of the moment hook up that you met locally on the go. However, if you’re going on a planned date, you want to make sure that you are dressed nicely and that means wearing a nice shirt. Don’t show up to a dinner wearing a tee shirt. Unless you think you some WWE professional wrestler or a juice monkey, no one wants to see you wearing a tank top or undersized tee shirt. It screams douchebag at first sight. Play it cool muscle man and keep it classy.  This goes with the tips I talked about here that include hygiene.

Forget The Tie
Unless you’re going to a professional event, loose the tie. You’re not going on a business meeting. You don’t need to look like a stuffy ‘all about business’ guy. I have friends that are richer than most business men out there and they don’t EVER wear ties on dates. They dress normal and that’s what works really.

New Underwear
If by chance you play your cards right you might find yourself in a position to get laid. If this does happen you certainly don’t want to look like a slob wearing old undergarments. Do yourself a favor and buy some designer underwear to have on hand for any special date night.

Well, that about sums up my dress for success tips for anyone that’s preparing for a date. Be sure to at least adhere to a few of my first date attire tips, if not all of them. Lastly, go light on the cologne, but don’t forget to spray it once or twice.

Ricky Decastro


I moved to Miami from California in 2017 to start a new life and found the dating scene to be a disaster! As an avid writer, I decided to start Dating God to document my experiences. The Good. The Bad. And of course, the UGLY.