First Date 101: What To Wear?

first date what to wear

Every time you step outside in Thailand you will see a bunch of sad ass farang running around in their fisherman’s pants, flip-flops, and stupid fucking “Same Same But Different” t-shirts. Don’t be like these guys, or as I like to call them, the NPC (No Pussy Crew).

These dipshits not only look ridiculous, but they lower the value of all of us in the eyes of Thai women.  Do yourself a favor and have some pride in your appearance.  If you look good, you feel good, you play good.  This directly carries over to your confidence with women.

Now that I got that expletive laced tirade off of my chest, I’ll tell you what you should wear on a first date, or any date, for that matter.

A suit and tie is going to be overkill, not to mention you may die from heat stroke if you wear it in Thailand.  So your go to date outfit should be a bit more casual.  A good pair of dark denim or chinos, a well fitting dress shirt, and a good pair of dress shoes.

Let’s break these pieces down into detail a bit more.

1. Dark Denim/Chinos:

A pair of dark Levis is a great choice for most men, and it won’t break the bank.  Personally, I like A.P.C. or some other brand of raw denim, but they can run you a couple of hundred bucks.  A pair of Levis will do just fine.  Just make sure you get something in a dark wash, no light blue dad pants.  Raw selvedge being the best.raw-denim-wintips

If you want to go with something a bit more lightweight, get yourself some Chinos.  Navy is a great color that will go with damn near anything.  Stay away from the khaki chinos, they scream “office drone”, especially when paired with a white or blue shirt.  Charcoal grey or blue are also good colors to go with.

Check out this very old dude, and very young dude, both looking good in a more casual first date option.


2. Dress Shirt:

Fit is king when it comes to clothes, and a well tailored dress shirt will make you look years younger and much more fit.  Your best bet is to head down to a reputable tailor and have one custom made, or get your measurements from them and get an off the rack shirt that fits well, and have it tailored.  Check out this post by Primer Magazine on how your shirt should fit.

Be sure to get a slim fit shirt, even if you are not so slim yourself.  Slim fit isn’t just for skinny guys.  It just means that there is less extra material around your arms and torso.  Modern fit is a better description.  Open up those top two buttons as well. Show off a little chest, girls love it.

As far as colors and patterns go, you can never go wrong with a plain white dress shirt.  Gingham is my personal favorite though.  A small to medium check gingham print in blue will look good on anyone.  Both Masculine Style and Effortless Gent have posts to help you pin down which color looks best for your skin tone.  This makes a world of difference in how your shirt will look on you.

first date shirt color

3. Shoes:

Last but not least, is your shoes.  I would opt for something in brown leather.  Stay away from black leather, it is much too formal.  A nice pair of brown wingtips, brogues or desert boots can go with anything from a full on suit, down to some jeans and a v neck.  I personally wear a pair of beeswax Clarks Desert Boots.  If you have to go more casual, a pair of canvas Chuck Taylor’s are never a bad choice.  Black, white, navy, all work well.


Putting It All Together:

Now that you have your basics put together, you can put it all together with a little simple mix and match.  If you want to go less formal, throw on a good fitting v-neck t-shirt.  More formal?  Throw on a navy blazer over your dress shirt.  In the middle?  Throw a navy blazer over your white v-neck.  Nearly all of these items are interchangeable.


Here are a few looks to get you started.  David Beckham has great style, and you can see him here rockin a more formal style on the left (nix the beanie) and a more casual look with the white sneakers on the right.  Just changing up your shoes can have a dramatic effect on how your outfit looks.

Ryan Reynolds below has a solid date outfit picked out.  Very easy to pull off.  The dude on the right in the white shirt and chinos looks good, though I would change those shoes.



As you can see, these are all pretty easy and basic looks.  Stuff any normal guy, I.E. not David Beckham model lookalikes, can pull off.  It’s just a matter of getting some solid, well fitting basics.  Once you have a pair of dark denim, chinos, few dress shirts, couple pairs of shoes, etc. you can mix and match your way to dozens of different date outfits.

Check out this post about how to create 20 different outfits with just 8 articles of clothing. 

There is a lot of information and links to digest in this post, but I suggest you take your time and go over them.  Upping your style is a very quick change that can make a dramatic difference in your attractiveness to the opposite sex.  A small investment of a few hundred dollars can lead you to getting way better looking girls than you did in the past.

If you have any style questions drop them in the comments below and I’ll do my best to answer them.

Happy hunting!

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