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.

  • J

    I’ve found a similar approach to work for me. Rather than slowly stepping my whole outfit up, I full-stepped my outfit one piece at a time. I started with pants – baggy light jeans were replaced with fitted darker jeans. They received comments, but only once or twice. Later, I bought a leather jacket to replace my sweatshirts. At first, I only wore it when going out or to events, but started lowering the standard for what I considered to be fancy enough for the jacket until it became everyday wear, and nobody says anything about it now (it went from being “fancy” to being “just how I dress”). Finally, the big one: replaced graphic t shirts with solid v-neck tees and solid henleys for wintertime. Fit is key on these – 99% of tees and henleys don’t fit me. They’re either baggy in the body or tight in the chest/shoulders and short in the torso. Whenever I do find some, I buy them. By the time you change your t-shirts, nobody will even notice, because your whole outfit will just fall together nicely. Any comments you get will be “wow you look good” rather than “hey you changed your t-shirts”.

    If you noticed shoes were missing from my list – I got lucky with my pre-stylish-transition shoe choice, and they turned out to be suitable to my new style as well

  • John M.

    The real trick is “How do you dress sharper and not freak out your bosses into thinking that you are looking for another job”….or do you want them to feel that?

  • themodestman

    Great article, and something we definitely have to deal with. I don’t know why it’s somewhat embarrassing when you show up dressed better than your friend(s) and they sort of poke you about it.

    You just have to remember that people only make fun of others to feel better about themselves. And you will probably notice that they step their style up a little next time you go out. It’s better to be over-dressed than under-dressed.

    Thanks for the tips, Robert!


  • zd

    good article and tips for slow transitioning. I think this is the biggest thing holding back a lot of people, including myself. But now, I haven’t worn a shirt without a collar outside of my house in MONTHS, where before wearing a buttoned shirt is considered “dressing up”. I live in NW Ohio college town so the standard is… well, non-existent. M

    My transition was also somewhat slow but I think it helped that it happened gradually over summer vacation where I wasn’t seeing as many people as often. Currently, I’m at the stage of button ups, fitted dark jeans, vneck sweaters, henleys, muted colors, casual sports coat at times, and no one has “made fun”, and most girls around me have complimented me. Definitely a confidence booster.

  • Juan Carrillo

    Great article!!!! The transition phase is where many guys get confused on but you have seemed to ease us into it, and for that, I SAY THANK YOU.

  • Matthew Berg

    This also solves the problem of “I don’t have anything nice enough to wear out shopping for nice clothes.” :)

  • Eugene

    Thanks again, I wish I had a big brother like you when I was growing up. I thank you for what you are doing support you 100%. Whith your information online & e books I am catching up on my confidence & style. There has been a transition in myself & outer appearance. My peers no longer see me as the quiet guy but as a very positive & confidence person.

  • Nathan Spiwak

    Great article! I love the hints to improve your style without changing everything overnight. It also helps because you don’t have to buy a whole new wardrobe in one shopping spree, you can buy better items over time and slowly improve your image. Thanks for the tips!

  • Eugene

    This transition is helpful. I got lucky with my exprience. I transitioned abruptly at my workplace. And it happend when the client visited the office. Timing was perfect, i made a good impression. Managers gave me 2 thumbs up which lead to a promotion. As per friends it caused a bit of jealosy at first. As time progress they realized I was the same home boy. I became an influence on them & they are starting to dress sharper.

    In summary, I found that dressing sharper will result into somthing positive. Your friends are your friends regardless what. Great article to transition gradually, good to know next time

  • Robert van Tongeren

    That’s the beauty. Even when you transition smoothly, girls will at some point notice and applaud your effort.

  • Robert van Tongeren

    I understand it’s a little scary to out-dress you boss, especially when he is prone to wearing casual clothes. So just upgrade your own casual look, and gauge his reaction every time you level up.

    If he does react negatively, you may try reassuring him that you’re only trying to represent the company better.

  • Robert van Tongeren

    Thanks for sharing that. You’re a perfect example of how to skip levels with the upgrading technique.

  • Robert van Tongeren

    Haha, 2 birds, 1 stone!

  • Robert van Tongeren

    You’re very welcome :)

  • Robert van Tongeren

    Yeah, it’s the circle of insecurities. They feel bad, because they think you make them look bad, so they try to make you look bad. Then, you feel bad, and slump back into your old look.

    Time to end the circle, guys.

  • Robert van Tongeren

    Good job on upping your style game in one go.
    The upgrading technique is mostly for guys who find it a bit scary to change so drastically, but if you can pull off a swift transition, then I’m all for it.

  • Robert van Tongeren

    You’re welcome! Buying a whole new wardrobe in one shopping spree is a bad idea for many reasons. I wouldn’t suggest it even if you had the money.

  • Scott S.

    Awesome post. Funny thing is that I was sitting at one of my favorite haunts, Healeo here in Seattle, one day talking with a man who did this same thing, upgrading his wardrobe and look over time. He did it as an experiment to see how it would affect him, people’s perceptions of him, and, eventually, his income stream. It worked for him. This go slow approach can also be considered a slow seduction, and after all in America at least, sex sells. This is the approach I’m going to take, as soon as I stop holding my wardrobe hostage because if my slight excess in my middle section.

  • Nidhi Sharma

    Brilliant. Thank you so much. This will make it easier to explain to clients.

  • Robert van Tongeren

    You’re welcome, Nidhi :)

  • Robert van Tongeren

    Thanks Scott. That man you talked about is a good role-model. He has seen the benefits of style first-hand.

    You shouldn’t hold your wardrobe hostage though, especially if the excess is only slight. You have no idea how long it could take to shed those last few pounds. Don’t wait for a future that could be months away. Take action on improving your style now.

    You can always have your clothes taken in once you achieve the body you want, but you want to look good in the meantime as well.

  • Adil

    Robert van Tongeren you have written a very great post.

    Great thing with this post is that it caters the people who are still out of the fashion circle. Though you touched on all the points. I just want to add one point for those who remained scared to dress sharper.

    I want to tell them that If they if they are confident enough to adopt the new sharper dresser in the level as Robert van Tongeren suggested, so at the end they will become the source of inspiration for the people around him and as the person will look unique with new looks, people will have great expectations from him both performance related and others; because people will feel that he is the person who don’t bothered to adopt change. But Intially they need lot of confidence for that.

    Thank Robert van Tongeren, I will look around your blog to find some more interesting posts.

  • will

    What a tremendous list. All I ever expect is some basics like underwear and socks from my wife, but i think i will print the items on this list i would live to get and slip it under my wifes pillow. I think those dress shirt stays are great. You’re right they look dorky when getting dressed standing in my underwear and socks, but to keep my shirt tails from creeping up would be great.

  • Dbakeca Italia

    nice tips

  • menstyle

    Thanks for the feedback Dbakecca!

  • Jonas N

    Very good article! I’m currently in the process of leveling up my wardrobe as well. As a 28y old HR professional I really felt it was time to catch up. It’s not like I dressed badly before but I didn’t put much time into composing my outfits. But a few weeks before Christmas i grew tired of still having cloth not suited for my age. I basically donated 80 percent of my wardrobe due to bad fit and clothes for the younger man. Spent soon of evenings reading real men real style and watching youtube videos. Then I went out and used my my knew knowledge to by myself a more interchangeable wardrobe at the Christmas sale. And guess what? So far it’s a huge success! I still feel like I’m missing something but can’t put my finger on what, though I’m not ready to take it all the way yet I’m starting to get there. Haven’t worn a Tshirt outside since a week before Christmas and it feels good. I’m really changing my way if thinking when it comes to confidence in the way I dress.

    Right now I’m between level 3 and 4 and starting so implement ties into my outfits. Working in a workplace that’s extremely casual some people have reacted to me wearing ties since its basically a border between casual and business for us. There’s no negative comments and everyone is very supportive.

    Thanks for an amazing article and website!

  • menstyle

    Wow! Congrats for the tasking the big step to change! Glad to hear that everyone around is supportive of what you are doing now style-wise.

  • BritGal

    I am not a man, so perhaps I don’t fully understand the rules of how men interact, but I always wonder why it’s so terribly important to be accepted and liked by everybody? Even as a young teenager, I didn’t really care how I was perceived by others. My personal style emerged at the age of 15 or 16, and consisted of tailored 1950s dresses, full-legged trousers as worn by Marlene Dietrich in the 1930s, cashmere jumpers, cardigans, and classic heels. Not exactly a popular look in the 1990s — especially for teenagers. I still dress that way, but I have now added dressy hats and gloves to many daytime outfits. It’s still not a popular look, but I couldn’t care less about current fashions, and blissfully ignore the proclaimed must-haves of this or the next season.
    Gentlemen, as a lady, allow me to tell you that a well-dressed man will stand out favourably. Well-dressed means that clothes fit the occasion and the man. Tailoring is very, very important. I prefer a man who is overdressed rather than under-dressed, because one cannot be overdressed in my book. Again, and I cannot emphasise this enough, a tailor is your friend.

  • menstyle

    Very well-said! Thanks for your input, BritGal!