A Gentleman’s Guide to Stylish First Date Dressing…


  1. Who are you? –  Please, please, please do not go on a first date and project a false image!  Sure, I make my client’s into an extraordinary version of who they are at the core.  To create a false image never does anyone a whole lot of good and more often than not, reeks havoc on your confidence – it is rather uncomfortable to be something you are not.  When I work with clients, we start by determining who they are and what they want.  Then – and only then – do we start to work on what to wear!
  2. Carnival Fun – A great date, as long as neither of you gets sick on rides.  It would be a good idea to check first!  A polo pique` shirt and a pair of cargo shorts will carry you through this date.  Make sure you have a clean white t-shirt on underneath the polo, which will give a finished look to your outfit and showcase your attention to details.  Go for a nice pair of leather sandals or slip-ons – they will look great with this laid back look.
  3. Dinner & a Movie – This is a fun date – lot’s of fun with little pressure.  It also gives you an opportunity to show some personality in your style of dress.  Jeans or khakis work well, though I do recommend steering clear of the plaid shirt & t-shirt combination – everyone she dates will be wearing that.  Mix it up, have fun.  Throw on a t-shirt and jeans with a linen jacket and you will definitely set yourself apart from the masses. 
  4. Reservations –    First, do yourself a favor and make the reservation- she will notice.  Unless required, lose the tie.  Wear on of this year’s summer suits paired with a dress shirt that showcases a great pair of cuff links.  Finish it off with a something different – perhaps a pocket square.  Think about a money clip instead of a wallet – again, something different.  Attending to the details makes a huge impression, one that will set you apart from anyone else she dates.
  5. Happy Hour Rendezvous – Since you will probably be meeting after work, think about your outfit in the morning instead of panicking at 5 o’clock.  If dressed for business during the day, the easy route would be to lose the tie and loosen your collar.  If you want to project a more laid back look, be sure to pack a pair of jeans to change into that evening.  If in a business casual atmosphere, a nice pair of pants and dress shirt will work well and carry you successfully through the date.
  6. Tee time for Two – Another great summer date, if you both enjoy a round of golf- four hours of getting to know each other and the bonus is that you get a look at how she competitive she is.  Dressing for this date is an easy one – A nice pair of shorts and a short-sleeve pique` polo paired with that essential white shirt should carry you through the day – you can’t go wrong.
  7. Last, BUT not Least… – The most important thing you can wear on a first date is a set of manners – chivalry is not dead and is much appreciated.  Open all doors, treat all service people with respect and listen to her when she speaks – be a polished version of who you are at the core.  If its not meant o be, no amount of chivalry or dress will get you to the second date.  However, if its something special, these tips will ensure that you present yourself in a manner that will keep her coming back for more!
Questions??  I am always available for a complimentary consultation – Call me and I will be sure to steer you in the correct direction!


Valarie Stock


Reid Park LLC

Direct. (215)622.4422




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