10 Things NOT To Wear On A First Date

There are certain things that you 100% must not wear on your first date. If you do, you’ll end up going home alone. Let’s be honest, there’s a good chance you’ll be going home alone anyway especially if you’re not a smooth talker. However, if you want to put the nail in the coffin on that note, then wear any of the following things I’m about to share with you below.

Full disclosure: I wouldn’t be caught dead wearing any of the things mentioned below on a date. Not even a casual hookup. Perhaps to a trip to the mall with my high school buddies but that’s about it. There’s just no reason for you to do so. Not unless you want to get your ass kicked or look like a complete idiot.


Things I’d Never Wear On A First Date

This list is pretty condensed. I had quite a long list of items that I wouldn’t wear during any date night let alone a first date with someone I met online. These are the most important things to avoid.

Unicorn Tee Shirt


The classic unicorn rainbow tee shirt was amazing, right? It’s a funny conversation piece, right? WRONG. You walk into a first date wearing this tee shirt and you will not be taken seriously. There are some serious hardcore casual daters out there who will walk away the second they see a loser wearing this shirt. It’s something that the unemployed guy living in the basement would wear. Don’t give off that impression.

Anything Trump


Nothing against President Trump. In fact, some of his beliefs aren’t all that bad if you ask me. But there’s a line that you don’t want to cross during a date night and that’s politics. I’ve seen girls straight up flip off a guy wearing a Trump teeshirt and other attire with political messages. Look kemosabe do you want to bury your junk in some special V or are you looking to have a political debate? My point exactly! Take it off. The exception to this rule is if you’re both so much to one side that you met at a rally and french kissed each other wishing it was the candidate who you were kissing instead.

A Bow Tie


Steve Erkel wore a bow tie as did my college professor who was single living with his 15-year-old cat. Neither of them gets laid, ever. You’re not Leonardo DiCaprio in The Great Gatsby so don’t try and play it off as such. Bow ties are pretty dorky unless you’ve got a need for wearing one or it’s part of some required formal attire.



Unless you’re a surfer living in Hawaii or Malibu, CA then your best to leave the flip-flops and sandals at home. There’s really nothing that women find sexy about sandals. Want to really drive them away? Put some socks on and sport those sandals of yours. You’ll surely end up home giving yourself a happy tugging. Opt for some trendy sneakers or classic shoes – not sandals.

Puppies In Space Tee Shirt


I know, we’ve all got a healthy obsession with puppy videos and Instagram stories, but that doesn’t give you the right to sport them on your shirt. There are plenty of tees out there that have puppies floating around in space with tacos, pizza, rainbows, lasers, you name it. The same goes for those cat tees as well. You look lonely AF in those, just stop!

Those tee shirts are for people that hate getting laid. They’re for people that can’t stand one night stands and it’s because they never have them. Do yourself a solid and forget about wearing these tees dawning the infamous puppy in space.

Sports Fan Gear


I’ve tried this and I’m a fan of many sports teams. However, it’s an awful idea to wear sports apparel on a first date. There is one exception to the rule and that’s if you both met on some team fanatic forum or website. No other exceptions seriously! Showing up in your team of choice Starter jacket screams that this is all you have to offer e.g. not much.

WWE and UFC Attire


Juice monkey, lunatic, douchebag attire isn’t any way to impress women. No one gives a shit about your WWE, WWF, or your UFC tee shirt. Great, you can afford to buy clothes that promote kicking the crap out of someone. I’m sure she’s going to find that really comforting. It doesn’t scream that you’re potentially a psycho that’ll body slam the waiter if he fucks up the drinks. Nope, not at all…

Salmon Colored Pants


Unless you’re in a fraternity, you’re not going to want to bust these pants out during your first date. It’s a bold AF move for sure and one that I’d recommend not taking. Salmon colored pants are pink pants, that’s the truth to the matter. Don’t try and spin it any other way, really.



This is a huge no-no! You better not show up in Crocs or your date will end up leaving soon as she arrives. Crocs are for kids and parents put them on their feet for the sheer convenience. Grown men showing up to a first date wearing smelly fugly crocs is a dangerous move that I’d suggest not taking.



You don’t wear all these of course but you carry them on you and if visible then you’re an idiot. Never let someone see that you’re wearing any weapons at all. I’m talking about nunchucks, guns, tasers, knives, swords, and lasers or whatever the hell you drum up. These weapons will make a girl think one thing – you’re going to do something psychotic with them. You don’t look tough or cool carrying these weapons.

Well, those are the top 10 things I suggest never wearing to a first date or a date in general for that matter. Sure, if it’s someone you’ve been dating for a while then that’s a different story. They get how fucked up you are and your attire won’t change that. However, if this is a first encounter that you plan on making happen in the bedroom, then stick to the basics bro.

If you’re stupid enough to sniff around the USA Sex Forum and actually pay some girl to go out with you, then well, I guess it doesn’t matter what you wear as long as you’re paying. That said, you’re still a loser for paying. Whatever you do, wear a rubber (it’s part of the bootycall kit) or you’ll be sorry.

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.