20 Things I Wished I Never Wore On A 1st Date

#11 Is A Life Savior!

20 Things I Wished I Never Wore On A 1st Date

A 1st Date Has To Be Planned From What You Say To What you Wear (Seriously)!

Let’s start off with a bold statement:  is it me or does a 1st date feels as scary as a heart attack at times (at least for me)?

Read More: Throwback Worstdays : 5 Fashion Trends That Needed To Die! 

Like everything in life, a 1st date is a try and fail process. One day you’re the worst ever and the next day you become the 1st date master.

For Some It Takes 2 And For Others It Takes Life.

Throughout my early days as a life’s student, I ‘ve been in countless of dates. I did it on purpose!

speed dating, 1st date, montreal love, montreal date, montreal dating, dating, boyfriend. what to wear in a date

Cc; Via Giphy

I went through the most harsh humiliations. The no-call no-shows & the clumsiest moments you could think of. Looking back, I can now say that serendipity is a real thing!

I’ve learned all the do’s and don’ts of the dating life. Now I’m in the right position to help you (and get your dating game on point)!  

Today we will go over the 20 things I wished I never wore on a 1st date (and trust me you shouldn’t too).

#1 An All White Outfit

This one doesn’t apply to every man, just to the clumsy ones. You go to the movies, a good restaurant or anything that involves you eating something and you know what can happen.

Indeed, A clumsy man just can’t help it! A drip of spaghetti sauce or some Pepsi you couldn’t swallow properly and your “wow” effect is gone.

Tip: If you still want to pull it off, avoid going to places where you can destroy the outfit.

#2 Pants That Are WAYYYY Too Tight

Comfort is everything and if you can’t sit down or get up on command, drop the issue!


Cc: via India Forums-

#3 Wearing Sunglasses Inside Or At Night

Wearing sunglasses inside or at night may feels like the cool thing to do but it backfires very rapidly.

Indeed, authenticity is everything on a 1st date. If that’s not your personality, don’t try to go overboard to impress a woman because it actually makes you look very unconfident or pretentious.

Tip: if you feel like doing it anyway, make sure you grab yourself a nice pair of vintage frames to make it look official!

#4 Ripped Jeans Too Ripped!

Once again, it goes back to comfort and making a good impression. Ripped jeans are fly don’t get me wrong but sometimes one false move can change it all if you understand what I mean (smiley emoji in full effect)

#5 Sandals

No fetishism involved but your feet tells a lot about you (and sometimes too much too).

If deep inside you know your pedicure game is not on point, don’t risk it.

#6 The “Do You Even Lift” Starter Pack

I give a pad on the shoulder to anybody taking their health seriously enough to get busy at the gym.

Perhaps, keep the “Gym Rat” attire at the gym, I’ve learned that the hard way…

#7 The “I Get Money” Starter Pack

When I was building my personal style, a voice in my head told me that wearing high end garments was a statement for success and taste (young and dumb they say).

Before any rapper ever said “Everything Designer“, I was living the “Everything Designer” life!

Being a walking publicity stunt for a Holt Renfrew is NEVER the way to go fellas.

Tip: if your charisma is not enough to seduce your date, she’s not the one!

1st date, dirty kicks, dirty sneakers, shoecare products

Cc: via Giphy

#8 Dirty Kicks

Believe it or not but women pay attention to every little detail and your kicks are the first thing they look at.

When you live in a “Life Happens” world, the best thing to do is to be war ready with your “Save The Sneakers” kit whenever you go out on a 1st date!

Tip: Moneysworth & Best has been a life savior for my sneakers and my love life!

too much accessories, don`t wear too much jewels, jewels

Cc: via Cool Men Style

#9 Too Much Accessories Is Like Not Enough Accessories

First impressions are the last. We want to look good and express our personality through our outfit.

As simplistic as it sounds, you will eventually learn the ultimate power of simplicity. Forget about a thousand bracelets and chains or  the gold watch to match the gold ring.

Tip: positive vibes and a good dinner should be enough.

#10 Grillz On A 1st Date

On this one it’s all about wins and losses. It either makes you look like the flyest guy on earth to your future better half or the most ridiculous.

Tip: never underestimate the “you never know” factor

#11 Wearing Your Best Smile Is A Must But Don’t Abuse It

This one goes without saying! Your smile is your secret weapon but also your worst enemy if you don’t know how to use it properly

Tip: if you feel like smiling every 2 seconds is the thing the do, send me a DM because we need to talk it out at this point!

#12 Dress According To The Temperature

When you come from a place like Montreal, you understand pretty quickly that temperature is a factor you can’t overlook.

Be ahead of the curve and make sure to dress accordingly because mama nature works in mysterious ways sometimes.

first date fails, 1st date, dating, love date, montreal dates, montreal dating, montreal love coach

Cc: via TheTrendSpotter-

#13 Avoid Risky Colours

At Montrealgotstyle, we always encourage our readers to take risks with their style. Thinking “Outside Of The Box” is a must in life but not always for your style.

Tip: if canary yellow is not your forte, well… canary yellow is not your forte!

#14 Never Pick The Wrong Graphic Tee

Graphic tees are life basically! They often express what we deeply feel or references we want to share with the world.

Unless you took months before taking a woman on a 1st date, for the most part you’re starting to get to know her.

As your new dating coach I would strongly suggest you to avoid graphic tees that send mix messages. My infamous “Your Room Or Mine?” didn’t make the cut as you can guess (the f**ck was I thinking!)

Tip: neutrality can never go wrong.

#15 A “Deep V” T-shirt

Why they even exist anyway!


#16  Sandals (With Socks)

If you read #5 and thought you could find a loop hole with this, you got it all wrong. In fact, adding socks to sandals is worst than worst (common fellas?!) .

Tip: if you have your feet game on lock, here are sandals you can buy!

#18 Don’t Forget #7

For real!

#19 Don’t Wear Anything You Had From An Ex Girlfriend

Clothes have a limitless power. This shirt you had from your ex is the old you, if you really hope to turn the page it starts with what you wear!

Tip: Just DON’T do it.

#20 Confidence Is The Best Outfit

Shyness and a lack of confidence can kill whatever you wear. You could follow all our previous suggestions but if you can’t hold a conversation and be in the moment; you’re doomed form the start.

Ps: thank us later!

What Do You Think?

Of course there are a thousands of other things to avoid on a 1st date and we would like to know what we have missed in our list. What else would you add to the list and why?

Let us know in the comment section now!


Access our deals, exclusive content and live interviews. Subscribe now!

Be the first to comment