When I got started working on my style, I was pretty confident that I was already way ahead of the curve. Now, when I look back, I just wish I had a time-machine that would allow me to slap my past self across the face. How very wrong I was.
Truly, when I think of the past, I simply hang my head in shame.
But then I look in the mirror and see the progress I’ve made since then, and instead of shame I feel a sense of pride.
When I think of where I came from and where I am now, I am 100% confident that any man can do what I did, no matter where they’re at now.
They only need a few rules to follow.
So what I’ve done is take the most important lessons that I’ve learned and put them into this manifesto.
These are the strategies and mindsets that have helped me go from oblivious wreck to a sharp looking guy. These are the guiding principles that all Style Restarters should follow.
Just imagine an empty wardrobe. What are you gonna fill it up with?
Rule #1: Start From Scratch
When you want to rebuild your wardrobe, you have to start from the beginning.
Now I’m not telling you to discard of all your clothes right away. I’m pretty sure society frowns upon naked men going clothes shopping. But, you should accept that eventually you are going to get rid of most (if not all) of your current clothes.
Sometimes it will be hard to say goodbye to your favorites, but it’s something that must be done to make progress.
Don’t worry though. You’ll get new favorites.
Systematically you will trade in your current wardrobe for a more suited, more refined and better orchestrated one.
Rule #2: Forget Everything You Think You Know
One of the hardest things I’ve ever had to accept was that my fashion knowledge was nonexistent.
In my researching stage, I would often read something that completely flipped my world upside down.
Something I had deemed inconsequential turned out to be of vital importance, while things that I considered to be crucial turned out not to matter much at all.
You need to accept that you may not know as much as you think. Otherwise you may feel like you can skip important lessons. You must think of yourself as a complete beginner, so you don’t gloss over anything that could help you see the light.
Simply assume you know nothing, so you’re open to learn everything.
Rule #3: Focus on the Basics
You Can’t Get More Basic Than a Plain White Tee
Now that you’ve forgotten all you know, what do you think you should be your first focus?
The basics, of course.
I can’t begin to tell you how much you will benefit from just knowing the basics alone. I always say it’s half the battle, but in truth it’s more like three quarters.
Too many men shoot themselves in the foot by getting the basics wrong. Don’t be one of them.
Rule #4: Build a Solid Wardrobe Foundation
Rebuilding your wardrobe starts with a solid foundation. You need to gather a collection of versatile items that will match well with almost anything.
Think basic items like white shirts, dark blue jeans, grey sweaters and black shoes.
Items like these will serve as training wheels while you’re learning to get the basics right, and offer support when you start adding more eye-catching pieces to your collection.
Rule #5: All Clothes MUST Fit
This is the golden rule. It’s what I consider to be most important. Getting this wrong will sabotage anything else you try.
It’s all about the fit, guys!
If there’s no other rule you’ll follow on this list, at least promise me you’ll follow this one.
Rule #6: Keep it Simple
You have to remember that you’re a man, and there’s no need to be extravagant. You don’t need a lot of bells and whistles to look great. You can just keep everything simple.
Leonardo DaVinci once said that simplicity is the ultimate sophistication.
This is very true for men’s fashion. Stop overcomplicating things.
Rule #7: Trim Your Wardrobe
You have to keep your wardrobe trim. There’s no benefit in having a bulging closet. It’s only impractical.
You won’t be filling your wardrobe up with lots and lots of clothes. You don’t need many to have a great arsenal of stylish outfits. You’d be amazed at how few you really need.
Also, you will periodically prune your wardrobe for items you no longer wear, no longer fit or look washed out. You will discard these items.
You will keep your closet decluttered.
Rule #8: Expand Your Options
You don’t want to be that guy that wears the same outfit day in and day out. You need a bit of variety.
Does this seem paradoxical to you with the previous rule?
Let me tell you that it’s entirely possible to trim your wardrobe and expand your options at the same time. Just make sure all your clothes work well together.
Layering will help you create more interesting outfits
Rule #9: Learn to Layer
Knowing how to layer clothes will give you ultimate use out of everything in your closet, and it will help you create more interesting outfits.
Layering lets you really play around with the clothes you have, so you should learn how to do it properly.
Rule #10: Forget the Trends, Develop Your Style First
A lot of men think they have to be on top of all the latest trends to become more stylish. However, when you’re starting out it’s vastly more important to develop your own sense of style first.
Once you figure out what image you want to portray with your clothes, you can start adding the trends that work with that image.
Read more about the difference between being stylish and being trendy here.
Rule #11: Look Effortless, Not Botherless
A man shouldn’t look like he has spent hours meticulously orchestrating his outfit in front of a mirror. It’s a lot more effective when you look like you just grabbed some clothes out of your closet and put them on.
This doesn’t mean you want to look like you didn’t bother. Your clothes must still look good on you and they must work together in a way that’s pleasing to the eye..
You still want to look like you know what you’re doing.
Expand your comfort zone
Rule #12: Try New Things
When you’re developing your sense of style, you want to be open to new types of clothing. You should try things you never would have thought to wear before.
You’d be amazed how good you could look in items that you previously thought “weren’t you.”
In this article by Jay from KinoWear, he tells you to try on anything and everything in a store. “This one exercise of trying on anything and everything will teach you more about style than reading a thousand style articles.” He says. It’s good advice.
Rule #13: Learn to Love Colors
Most men don’t seem to like wearing colors that much. A lot of us stick to a basic color scheme of black, white, grey and blue. You should start expanding your color horizon.
You have to figure out which colors work for you, and the best way to do this is to try them out. (See previous rule)
Colors can really make an outfit pop, so you shouldn’t shy away from them.
Start With 1 Color at a Time
Rule #14: Wear Colors Sparingly
While you should learn to love colors, you shouldn’t wear too many of them at the beginning of your style journey. You’ll be in danger of incompatible colors, since you probably don’t know how to match them yet.
Stick to just wearing one color at a time for now, and keep the rest neutral. Once you’re further educated you can start trying to combine them.
Rule #15: Laugh of the Jabs
When you start improving your style, I can almost guarantee you will receive a few jabs from your friends.
The secret to dealing with this is to not care and laugh it off. Just crack a joke about it yourself. That way you’ll be in on the joke, instead of the butt of it.
Eventually your friends will get used to the new you, and the jokes will cease.
Rule #16: Be Open to Feedback
There may also be people in your life that will genuinely try to help you, so be open to their advice. Consider the person it’s coming from and what they have to say.
Usually you can tell when a criticism is genuine, or when someone is just trying to cut you down a few inches.
People who provide sincere counsel will usually be people that dress fairly well themselves.
You should also listen to the women in your life, as they are usually happy to give their honest feedback.
Rule #17: Be Honest With Yourself
You don’t want to look like someone that you’re not. You’ll feel incongruent when you’re sporting a look that just doesn’t fit with the type of person you are.
If you’re an introverted person, it’ll seem weird if you’re wearing very loud outfits.
If you’re a very laidback type of guy, you may not want to walk around in formal suits all the time.
Just try to look like a better dressed version of yourself.
Style reinvention takes time. There’s no rush.
Rule #18: Accept That it Will Take a While
Your sense of style is like Rome. It won’t be built in a day. It will take a while for you to fully grasp all the little intricacies that make an outfit great.
This is something learned over the span of month, if not years.
Hopefully Restart Your Style will help you get there faster though.
Rule #19: Accept That You Will Make Mistakes
We all make mistakes. None of us are immune to this. I still make mistakes to this day.
Look at celebrities who often have personal stylists or designers creating clothes just for them to wear. They are judged under a microscope. They make mistakes, but it’s because they try new things. Sometimes it works, sometimes it doesn’t.
This shouldn’t keep you from trying out new clothes. The road to success is paved with mistakes. You just need to realize when you’ve made one, accept it and move on.
Rule #20: Know That You’ll Get There Eventually
If you keep working on it, eventually you will have trained your eye for style. You’ll start to notice details in your own and other people’s outfits. You’ll know when something works and when it doesn’t. Selecting a great outfit from your closet will be as easy as riding a bike.
Take comfort in the knowledge that you’ll get there eventually.
The Rest Is Up to You
Following these 20 rules will help you restart your style, but you’re the one that will have to do the work.
Change doesn’t come from reading things. It comes from taking action. So if you’re serious about developing your fashion sense, then take these rules to heart. Start working on 1 small thing and work your way up from there.
Are you going to take action? Let me know in the comments what small thing you plan to improve about your style first!
Hey guys, I'm Robert, and I used to be a terrible dresser. But after a long time trying to make sense of personal style, I now walk out my door every day, looking (and feeling) my best. I want the same for you, so I'm here to simplify the process. 
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I know that you mentioned white shirts, dark blue jeans, grey sweaters and black shoes, but what if I just altered one thing in this list? Could I replace those black shoes for chukkas or desert boots perhaps? What would you recommend?
Definitely. The items I mentioned aren’t the rule. They’re examples of the rule.
Desert boots are awesome.
Very glad I found this link! I’ve been working on upping my style for a while now, since coming to terms with the fact that I was going to be working in IT for a while yet so I wanted to stand out from my torn jeans and t-shirt wearing coworkers.
To make this journey more interesting, and to hit on a topic you don’t cover, I’ve lost 80+ lbs and counting over the last 2 years. Trying to find pieces that polish my new style, stay in budget, and don’t make me cry when I shrink out of them has been touch and go to say the least.
I’ve settled into a closet that works for me for now, and I have a list of items I will be adding once I reach my goal size and know I’ll be able to keep them around for years.
Thanks for the great post!
Jesse
Congrats on your weight-loss, Jesse!
Have you tried to get your clothes tailored when you shrink out of them? I don’t think your shoulder shrink as much when you lose weight, do they? (I’m not speaking from experience)
The shoulder are the hardest to get altered. A tailor should be able to take care of the rest.
This might be more cost-efficient than buying new ones every time. Look into it.
Yes! Number 1 and 15 ring true for me especially. Don’t worry about the naysayers. They’re just jealous that you have the balls to grow your style while they keep wearing those American Eagle cargo shorts from college.
Epic post!
Thanks Brock!
I believe the prime reason guys don’t work on their style is fear of judgement from their peers. It’s something that you need to learn to deal with.
Getting defensive will only add fuel to the fire. Just laugh it off with them.
Bookmarked!
Awesome post man. Very helpful. In particular, I have struggled with feeling overwhelmed when it comes to choosing new clothes. I am basically as beginner as is possible. But sometimes I think I try and get too creative. Like you say, I need to start with the basics.
Number 18 was a good reminder too… It may take a while
Thanks Izzy!
I think it’s great that you’re a beginner. Guys like you are exactly who I want to reach.
Creativity is good, but you know… Someone who’s never wielded a pencil is unlikely to start drawing a masterpiece. I suggest keeping it simple for now.