Classy, Sexy, and Powerful – How to Wear a Suit Like a Boss

Man in Tailored Suit

If you don’t have a suit in your closet you are missing out on one of the greatest assets you could wear.  The suit is a true display of class, power, sexiness, and confidence and has been worn by men since the 19th century.  In the early 1900s suits were as common to wear as a tee shirt and jeans are today.  I’m not going to give you a history lesson on the evolution of the suit, you can read Wikipedia or jump over to GQ if you want to know more.  My goal today is to give you the quick and dirty on how a suit should be worn.  I’m going to break this up into sections so you can wear a suit like a boss!


Suit pants typically come with the suit jacket.  You can buy separates depending on the look you are going for, but if you are going to own one or two suits you should just buy them together.  Before you think about bringing a suit home from the store, try it on!  Seriously, why would you waste your time picking out a suit and then come home to realize that the pant legs are too long or the waist is too big?  When you are being fitted for the pants you should have enough room around the waist to put your fingers inside the band and that’s it.  If you can fit your fist in there, then the pants are too big and you need to either go down a size or have them taken in.  You want your butt to look lifted and firm and not saggy like you just took a dump in your pants.

The length of your pants is one of the most important aspects of wearing the suit and you should always try on the pants with the pair of dress shoes that you plan on wearing, or at least borrow a pair.  The bottom of the pant leg should rest just on top of the tongue of the shoe and be about an inch above the back of the heel.  If your pants are any longer or bunch at the bottom, you’re going to look like a clueless clown and people will make fun of you.

If you start to grow out of your pants the first thing you will notice is that you can see the inside of your pant pockets.  Don’t let this happen, either drop the weight or buy new pants that fit you.


You may not think that the shirt is a big deal, well it is.  This is the most versatile piece of your suit that will allow you to change the suits entire dynamic by picking the right color or style to go with the suit.  Yes, you can wear a white shirt with any color suit, but why not have some fun and move away from always wearing a white shirt?  Size is extremely important.  Have your neck and your arms measured.  Make sure that you are able to still stick a finger in your collar when your top button is fastened.  There is nothing more uncomfortable than a shirt where the neck is too tight. 

Your sleeve length is also key.  The sleeve cuff should come to the end of your wrist and should never cover any part of your hand.  You want to make sure that you have at least 1 to 2 inches of your sleeve longer than the sleeve of your suit jacket.  If it is too short, when you take off your jacket people will notice that you have super long monkey arms.

Tuck in your shirt and make sure that the shirt is long enough that it won’t come untucked if you lift up your arms.  It’s a pain in the ass to have to tuck in your shirt every time you go and reach for something.

Make sure that the shirt fits your chest and mid-section.  If your buttons start to undo themselves or look like they are pulling away from the shirt then it’s too tight.  You should be able to freely sit down and move around without having to deal with a button popping.


Your jacket really is what makes the suit a suit.  Make sure that the color of the jacket matches the color of the pants unless you are going for a two-toned suit like a tan jacket and black pants.  If you try to match a random pair of black pants with your black jacket you will find that the colors are off.  That’s why it’s always best to buy the pants that match the jacket.

Make sure that the jacket fits you so that you have room to move, you don’t want to be Chris Farley “fat guy in a little coat” and ruin the jacket.  The jacket should come down just past your side pockets.  Your jacket should fasten in the front without pulling.  If it is pulling on the button when you fasten it, the jacket is too small.  You should have enough room between the jacket and your body to place your fist.  Any less the jacket is too small, and any more it’s too big.


The great thing about a suit is that you can wear one with or without a tie, depending on the look you’re going for.  If you’re going to wear a tie make sure that it isn’t too short or too long.  The bottom of the tie should just touch the top of your belt.  If it is any longer you are going to draw attention to your crotch and if it’s too short you’ll look like a clown.  If you can’t get it to the top of your belt, you’ll be safe with it being about an inch or so shorter, but I really don’t recommend going any shorter than that. 

The color of the tie should always contrast the color of your shirt.  If you are ever unsure of what color goes with what shirt Google it.  I found this to be the best method for matching shirts and ties.


Remember that your socks should always be the same color as your pants.  So, if you wear a navy suit, wear navy blue socks.  Patterns on the socks with different colors are totally fine, just make sure that the majority of the sock matches the pants.  Now there is a caveat, depending on your style and the style of the suit, you may be able to wear different color socks and still successfully pull it off; however, as a general rule in a business setting or black-tie event, they should match the pants.


Here are some color options that will compliment your suit:

Navy Blue Suit:

  • Shirts – light blue, yellow, salmon (pinkish-orange), light pink, white
  • Shoes – brown or oxblood are perfect, use black only if you have no other choice
  • Belt – brown or black (belt should match your color of shoes)

Black Suit:

  • Shirts – light green, yellow, pink, red, gray, white
  • Shoes – black
  • Belt – black (belt should match your color of shoes)

Brown Suit:

  • Shirts – light or dark green, yellow, light or dark blue, salmon, white
  • Shoes – brown
  • Belt – brown (belt should match your color of shoes)

Gray Suit:

  • Shirts – light or dark blue, light or dark purple, pink, black, white
  • Shoes – brown, oxblood, or black
  • Belt – brown or black (belt should match your color of shoes)

Tan Suit:

  • Shirts – light or dark blue, purple, pink, white
  • Shoes – brown, oxblood, or black
  • Belt – brown or black (belt should match your color of shoes)

These are just a few recommended colors.  Keep in mind that you can also use pattern prints and the shirts don’t need to be a solid color. Also, don’t forget to accessorize. Carrying a man bag is a must! Good luck and have some fun with your suit options!

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