Tonight will be epic and you want to look your best. Just to make sure, you’re taking an extra hour to get ready. You’ve gotten ready for nights out in the past but now you’re a part of the Well Dressed Academy and around here we do things differently.


Most of the items are self explanatory, otherwise I added very specific and helpful explanations. Side note, one of the items on the check list is to have your phone fully charged …..plug it in now.


Before getting dressed

Most of these items are basic. To save on time and avoid forgetting a step, have everything laid out prior (moisturizer, deodorant, fragrance, etc). I lay my watch out with these items to avoid forgetting it. 

  • Quick shower: restarts the body odor countdown clock.
  • Floss, brush and mouthwash. Fresh breath is a must at all times.
  • Moisturize: face, hands and any other exposed body parts. Just trust me on this one fellas.
  • Deodorant, use antiperspirant if you sweat a lot.
  • Groom: Shave or trim.
  • Fresh balls powder, you’ll thank me the day you realize how important this is.


Getting Dressed

Now you’re so fresh and clean-clean, it’s time to get well dressed. Ideally you know what you’re wearing beforehand. All items should be ironed/steamed.

Wear your best underwear (Free of holes and discoloration).

Underwear should not show.

 Your undershirt is underwear, if you’re wearing a collared shirt without a tie, wear a V-neck undershirt.


Dont't be this guy.

If this is a problem….

…get sweat guard undershirts.

Sweaty pits are style killers. Get sweat guard undershirts or SweatBlock wipes. Worst case, cover up with a sports coat. Sweating in your sports coat isn’t recommended due to the staining but at least you’ll be able to high five with confidence. Just remember what your jacket is covering up…so keep it on.

Pop your collar.


Cowardly Collar

Cowardly Collar

If you’re wearing a sports coat don’t allow your shirt collar to get pressed under the jacket.

Belts should match the fabric and color of your shoes.

Line Up



Lined Up

Lined Up

Line up your shirt placket, belt and trousers fly. Being lined up makes you look centered visually.

If you’re wearing a jacket (highly recommended) wear a pocket square. Ensure that the square is always visible.

Suit jacket buttons rules:

  • Two button jackets: only the top button should be buttoned
  • Three button jacket: middle button or Top and middle. Never all three and never top only.

Jackets buttoned incorrectly restricts movement and negatively alters your silhouette.

Give your shoes a quick wipe down with a lint free cloth.

Lint brush: Run a lint roller over your sports coat and trousers.

Night carry:

  • Cash (singles) for tipping
  • Condoms (you never know).
  • Nice Pen (in today’s digital age having a pen is classy).
  • Business cards.
  • Breath freshener (mint preferably to avoid chewing), when you pop a mint offer the person or people around you.
  • Floss stick

Style tip: Wear an accessory that will subtly attract attention i.e. Elaborate pocket square fold, boutonniere (lapel flower or pin), stylish hat, bow tie, cool cufflinks etc.  Why? These accessories act as conversational pieces.

Fully charge your phone before leaving the house. Also free up some space for taking photos or video.

Social tip: Have a few photos in your phone that adds visual to an interesting story.

Give yourself one quick look in the mirror.

The night is yours!


While you’re out.

The night has begun and you’re having a blast. There are a couple things you want to keep an eye on to remain styling.

  • If you’re wearing an overcoat, make sure you collar is popped and your pocket square is showing once you remove your coat.
  • Unbutton your jacket when you sit and button when you stand. Keeping your jacket buttoned when you sit can damage the jacket. Practice this at home to pull it off smoothly.
  • Breath, keep it fresh, excuse yourself after a meal to floss.

And there you have it. A well dressed man pays attention to the small details, soon this will be second nature. Make tonight a night to remember.


 Dress Well Gentlemen!