How To Dress Sharp Without Shocking Your Friends

casual dressed men

This is a guest post by my friend Robert van Tongeren over at Restart Your Style – if you enjoy it make sure to visit his informative website!

You want to dress sharper.

You decided this months ago, but when you look in the mirror, you still see the same guy looking back. You’re still in the same T-shirts, jeans and worn-out sneakers.

Nothing has changed.

You’re willing to try dressier clothes, but your environment is holding you back. Your friends and colleagues think dressing up means wearing a collared shirt, and anything dressier is reserved for job interviews, weddings and funerals.

Ultra-casual is the norm.

You’re afraid changing your look will backfire, and people will mock and scorn you. They will roll their eyes behind your back, call you a try-hard and treat you like you no longer belong.

So you’re stuck – afraid to dress outside of people’s expectations.

Afraid to change anything.

Afraid to stand out.

But what if you could change their expectations?

You’re Paralyzed by The Status Quo

The world has an unofficial dress code that everyone abides by. This dress-code is the status quo, and disrupting it is dangerous.

You have 2 types of guys in this environment.

  • The complacent — guys who enjoy putting zero effort into their appearance, and who want to keep everything the way it is. They like the status quo.
  • The discontented — guys who do give a damn about looking sharp, and who want the advantages that come with great style. They want the status quo to change.

You’re probably not the only discontented among your peers, but none of you wants to be the first to improve.

You don’t want to look like you’re trying to outshine anyone. You don’t want to rattle any cages.

You Can Change The Status Quo Without Rattling Cages

When most guys try to dress better, they shift drastically. They go from Comic Book Guy to James Bond.

That’s not just breaking the status quo. That’s ripping it to pieces and having it for breakfast.

Everyone around you will be shocked by the transformation. The complacent will resist, and the other discontented will need time to feel comfortable following your lead. You’ll be on your own.

You’ll need a lot of confidence and courage not to succumb to their pressure and slump back to complacent standards. So be honest with yourself — do you feel up to it?

If not, don’t worry. You don’t have to go from Comic Book Guy to James Bond overnight…

james bond comic guy

There are a few levels of style between these guys.

You Just Take It One Level at a Time

Imagine a big warehouse, many levels high. At the bottom level are ultra-casual clothes – graphic tees, ripped jeans, sneakers, etc. Every level upward the clothes get a little bit more polished, until at the top level, they have suits and tuxes.

You don’t have to go from the bottom level straight to the top. With the Upgrading Technique, you can work your way up, one level at a time.

Do the following…

  1. Consider the clothes you currently wear.
  2. Come up with alternatives that are one level higher.
  3. Write them down.

Boom, there’s your shopping list.

What follows are some ways you can upgrade various items:


  1. Graphic tees
  2. Solid tees
  3. Polo shirts
  4. Casual shirts
  5. Dress shirts

2nd layer Top

  1. Hoodie
  2. Sweater
  3. Zip-up cardigan
  4. Button cardigan
  5. Blazer or sports jacket


  1. Washed, distressed, baggy jeans
  2. Washed straight-leg jeans
  3. Dark-blue, straight-leg jeans
  4. Navy chinos
  5. Camel chinos
  6. Wool slacks


  1. Sneakers
  2. Clean, white/black sneakers
  3. Desert boots
  4. Loafers
  5. Brogues

(Note: These are examples. Feel free to skip, change or add levels as you see fit. )

You don’t want to upgrade all at once. Begin with transitional outfits. People will be less resistant to accepting the new items as part of your wardrobe.

Let me show you what I mean…

Say this is your first-level outfit:

    • A hoodie
    • A graphic tee
    • Washed jeans

And you want to upgrade to this outfit:

    • A zip-up cardigan
    • A solid tee
    • Dark-blue jeans

Then some transitional outfits are:

    • A hoodie, solid tee and washed jeans
    • A zip-up cardigan, graphic tee and washed jeans
    • A hoodie, a solid tee and dark-blue jeans

Once your environment is used to seeing you wear these new clothes, you transition into fully-upgraded outfits. Then, you start again.

Just keep upgrading until you are where you want to be.

Because you transition smoothly, the complacent will hardly raise an eyebrow. Your discontented peers will feel more comfortable transitioning with you. Your improved way of dressing will become the new normal.

You will have broken the status quo.

So Level Up  Your Style

Who cares if you’re the only one with the common sense to present yourself well?

It’s an advantage.

When everyone around you is a careless slob, you can stand out more easily. You only need a sharp casual look to positively affect your life. You don’t have to go all the way to the top level, as long as you go up.

Let the complacent keep their bottom-level clothes. You – and the beautiful woman in your passenger seat – will leave them in your rear-view mirror as you cruise your way to success.

The other discontented will love you for paving the way.

They want to come unstuck too.

They want to dress sharp.

They want the status quo to break.

They’re just waiting for someone to break it.

They’re waiting for you.

Go break it.