The Perfect First Date Outfit

“Should I wear a suit?”

“Should I not wear a suit?”


Should I dress casual?”….. “Should I wear a tie?”


Sound like someone you know?


Relax, it’s not that complicated.  I know you want to make a good first impression,


So does she. 


Remember, you’re both in the same boat, if anything; she’s probably more stressed out than you are.


Whether you’re in your twenties, thirties, or sixties; I’m going to introduce the perfect first date outfit for you.


Although wearing a nice suit is usually just straight up sexy, it could come off as a bit boring or even intimidating as a first date outfit choice.


So even if you’re Michael Douglas in Wallstreet, skip the suit.


Now, by no means am I saying that you should keep it casual, because as much as you don’t want to overdo it;


You certainly shouldn’t down play it either.


The Perfect First Date Outfit:

NUMBER 1 RULE:  You’re wearing a sport coat.  Throwing on a jacket is absolutely necessary, trust me, she will dig it!

Your jacket / sport coat is the most important part of your outfit, so wearing the right one is key.


Make sure your jacket is not formal, ideally it should be a low thread count, woolen jacket or tweed and if you’re in a warmer climate; a nice cotton jacket will suffice.


Next:  Fold and tuck in a nice pocket square which compliments your outfit.


- Image Courtesy: Pinterest
The Perfect First Date Outfit


Shirt Options: 

  • Any casual button down shirt or Oxford shirt (I prefer a button down collar as well)
  • Long sleeve polo
  • Turtle neck or long neck.


If it’s cold:  Throw on a thin sweater over a nice oxford shirt and make sure your jacket fits nicely over your sweater.


Your Pants:

Your age will play a role in selecting which pants to wear;

Above 45:  Wear some nice jeans, just make sure they are not too light in color, a slight fade is okay, a tear is not.  If you’re not comfortable wearing jeans, it’s perfectly okay to wear chinos.


Between 30 – 45:  Chinos or jeans, either will fly.


Below 30:  Chinos.


Shoes:  Try to stick to an outfit which suits a nice brown leather belt and brown leather shoes.



Remember:  A Gentleman always irons his clothes, creases his pants and polishes his shoes.


You want her to appreciate what you’re wearing and you certainly want her to feel special knowing that you have put some thought into your outfit.


Oh, and just this once, save the elephant trunks for a future occasion 🙂


Walk the walk, talk the talk and rock the look!



Gurri Kahlon

Legend and Stick


A brand focused on a Selective Collection of Suits, Shirts and Fine things in life for the Sartorial man.


Credits: all images courtesy:  Pinterest

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