11 Men's First Date Outfit Red Flags

By Khoi Nguyen

11 Men's First Date Outfit Red Flags

Don't judge a book by its cover is what they all say.

It's age-old wisdom that's easier said than done. Because let's face it, everyone judges. Especially when it comes to appearances. But there's no substance to appearance. Aren't we supposed to place more value on the non-superficial attributes and qualities that make up who a person is on the inside? Yes, of course, but we don't always. Just look at the dating landscape in 2017, where we pick and choose our potential dates with a swipe of the finger, and it's all based on appearance.

And with appearances in mind, there are things that men just shouldn't wear on a first date. Many of these may seem like common sense, but according to my research, (I asked over 20 women) men are still making these style mistakes when it comes to dating.

Before getting into the list, I believe that there's some non-negotiable dressing/grooming etiquette when it comes to first dates. They are as follows:

  • Unless you're a rock star celebrity, DJ or entertainer of sorts, avoid anything distressed with holes and tears.

  • Clean and iron your clothes before the big date. Dirty and wrinkled clothing is not a good look, period, let alone a first date.

  • Groom yourself to avoid an unkempt appearance. Clean up with a fresh cut (a few days prior) and a clean shave. She'll notice and appreciate it.

  • Dress one level above the typical dress code for the date venue. It's always better to be overdressed than underdressed.

Now that we've covered the non-negotiables, let's dive into the list of 10 men's first date outfit red flags.


Ignoring the fact that they're ruining marriages across America, baggy cargo shorts are the epitome of bad style. They're unflattering and will make a teenager out of a man. Sure, they're practical, but do you really need all of those pockets on a date?


It goes without saying, but anything with crude, racist or sexist remarks across the front is in bad taste. Especially avoid an Ed Hardy style graphic tee with metallic, paint splashes and skulls. It's way too distracting. Your shirt shouldn't be the focus. And though some graphic tees can be tasteful, there are better options for a first date.


Don't show up to a first date in the clothes you wear to work, whether that's a suit, scrubs or construction gear. Show a little consideration for your date. Go home, take a shower and freshen up. And if you absolutely can't, make sure you let your date know in advance or at least prepare ahead of time, with some fresh body/face wipes.


Basically anything that can pass for gym clothes should be avoided. This includes hoodies, running shoes, sweatpants or sweatshirts of any kind. Put in a little effort into your presentation. Even if it's a more casual venue, athletic gear is simply inappropriate first date attire. If this is your aesthetic and you swear by it, then go with more of an athleisure look that's tailored and refined. Unless you are going hiking or doing yoga, save the athletic gear for the gym.


This includes, ties, bowties, vests, suits, shiny shoes. This isn't the opera, (unless your first date is at the opera) typically first dates lean casual. Dressing too formal can put you wildly out of place, plus you run the risk of outdoing your date which is always awkward, according to women.

11 Men's First Date Outfit Red Flags


If you're nowhere near a large body of water, flip flops shouldn't be seen in public. It's entirely too casual even if you're at the beach. There are better alternatives like espadrilles or boat shoes.


Ask any menswear enthusiast what the number one rule of men's style is and they will all tell you that FIT IS KING. Wearing oversized clothing on a date not only looks bad, but your date will notice. Avoid looking like a kid playing dress up and wear clothing that fits comfortably and well.


A first date is an opportunity to set that initial impression. And there's no better way to show your date that you are not only a man of style, but that you care about your appearance than to wear a well fitting blazer. It's a great way to instantly level up your look. Additionally you can add a simple pocket square to show her that you're a man of details. If you decide to go the blazer route, skip the tie. It's too closed off and you want to present yourself in an open manner.

It goes without saying, but never wear an untucked shirt under your blazer. It's sloppy. Are you trying to be casual or more dressed up? Pick one.

11 Men's First Outfit Red Flags


You're not starring in Magic Mike. Keep the shirt buttoned up. 1 or 2 buttons undone is fine, but anything more than that and you run the risk of causing all types of awkwardness with your date. And she'll probably be too polite to say anything about it. If it's too hot out, wear a lighter, more breathable shirt made of linen or summer-weight cotton.


This is a critical mistake many men make in general. For a first date especially, you do not want to be leaving a trail of your masculine scent everywhere you go. It will not only suffocate your date, but anyone else you come in contact with. Don't go soaking your clothes with your bottle, two sprays to the neck and one on the wrist will do the job.


No we're not talking Halloween. What I mean is dressing in an inauthentic way that's not representative of your personal style. One of the ladies I surveyed said, "when I went on a first date with my ex-boyfriend he like slicked his hair down and wore contacts and this really stupid plaid dress shirt, and that's so not him. He usually has messy hair and wears glasses and band t-shirts. After the first date, I went home & thought 'we're just gonna be friends'...I didn't start to like him until I saw I guess 'the real him'"

The takeaway? Be authentically your true self not only in the way that you present yourself, but also in the way that you dress.

Check out the video About THis below!

11 Men's First Date Outfit Red Flags

Khoi Nguyen is the Founding Editor of www.gentlemanwithin.com. He created Gentleman Within to help equip men with style to CRUSH IT in life. He believes that style is worth caring about, and that through style, men can become their best selves.

If you liked this article, visit his site and check out the free PDF download of 17 Ways To Be More Stylish in 2017 and Beyond It covers 17 interesting things that you can do to begin improving your style, today.