(Editor’s note: This is a guest article by Robert of Restart Your Style.)

Being a rookie is brutal.

You want to fix your style, but you don’t know where to start. Let’s face it; you don’t even know what needs fixing.

So you go online for help, but you discover an overwhelming amount of information, and it’s all scattered.

It’s like someone ripped out the pages from a style encyclopedia and scattered them all over the floor.

So you pick a random page and try to learn something – because that’s better than doing nothing, right? But deep down you know it’s a random act of desperation because you still don’t really have a clue if it’s right for you.

Hell, you might even end up changing the one thing you were actually doing right!

But it’s not your fault. You’re a rookie and you’ll always make rookie mistakes.

Unless of course, someone who’s already made them all tells you exactly what they are. Then you could just skip them altogether…

Mistake 1: Assuming You Already Know Something

When we first set out, as rookies, to learn how to dress better, we work under the impression we already know how to dress. We just need to learn how to dress better.

But knowing how to put on clothes is not the same as knowing how to dress.

If you want to learn how to dress better, you must stop thinking you already know something. You must forget everything you think you know.

Because what you think you know might be exactly what’s ruining your look.

And when you think you already know how to do something, you´ll skip over information telling you how to do it right.

I skipped over articles on fit for a long time, and my mind exploded when I finally discovered how little I knew about it. Fit was such a basic concept, I thought I had it down. When I discovered I didn’t, I felt like a moron for getting it wrong for so long.

The more basic you think advice is, the more you need to read it. The basics are the most important to learn.

So if you think you have something down, just tell yourself you could use a refresher.

You might surprise yourself.

Mistake 2: Confusing Dressing Up With Dressing Well


Dad’s suit?

Many rookies think dressing better is about wearing dressier clothes. They think they put on a suit, and SHAZAM! Their style issues are fixed.

Doesn’t even have to be a suit. Other guys think blazers have the same magic powers, or hell, others think a simple shirt does the trick.

But wearing a shirt instead of a tee, or a suit instead of casual wear, ain’t no style fix, dude.

You’ll just make the same mistakes as before, just on dressier clothes.

And poorly-worn suits look just as sloppy as poorly-worn T-shirts and jeans.

Because style isn’t about the clothes you wear. Style’s about how you wear the clothes.

Mistake 3: Taking Your Lead From the Fashion World

When you first decide you want to dress better, you naturally look toward the fashion world. They’re all about clothes, after all.

But the fashion world sucks.

The fashion world isn’t about teaching you how to dress well. The fashion world’s about telling you what to wear this season. The fashion world is about selling.

So when you look to the fashion world for help, it’s telling you “buy this, buy that, buy this, buy that”.

And you think that if you just buy what they say, your style will improve. But it won’t.

You’re wearing trendier clothes, but they still don’t fit, and you’re still getting the colors all wrong, and it all still looks like a giant mess, because you never learned how to wear the clothes.

You’re wearing trendier clothes, but you still look sloppy.

You have to ignore seasonal trends, and focus on learning the basics of dressing well.

Because when you know how to dress well, you won’t need to rely on the fashion world. You won’t need to rely on anyone.

You’ll just know what works for you and what doesn’t.

Mistake 4: Settling for Close Enough

When a rookie’s eyes are finally opened to how clothes should fit, rookies often discover how troublesome finding proper-fitting clothes off the rack is.

So they settle for a fit that’s close enough.

But close enough isn’t good enough, dudes.

You want clothes that fit like they were made for you — like their creator had you in mind when he made them.

If you haven’t already, you want to get a grip on this pronto. Getting a grip on fit is priority one.

Without the right fit, your clothes won’t look good on you.

Without the right fit, all your efforts to fine-tune your look will be futile.

You don’t want close enough. You want as close to perfect as possible.

Never settle.

Mistake 5: Treating the Tailor as a Last Resort

tailorMost rookies are reluctant to get their clothes tailored.

They’ll spend hours upon hours trying to find perfect-fitting clothes off the rack, and end up feeling frustrated when they can’t find any.

And you know what?

I totally get it.

I put it off for the longest time as well.

I think when you’re a rookie, the mere idea of getting your clothes tailored is just too foreign. You feel like you shouldn’t have to pay for this service, because you never had to before. You feel like you should be able to find good clothes off the rack, just like you’ve always done.

But then, maybe you should stop doing what you’ve always done, and start doing what works.

And what works is getting your clothes tailored.

Just try it with one shirt, and you’ll see how well it works with your own two eyes.

You’ll save yourself a lot of time and frustration.

Mistake 6: Buying Super-Fancy Designer Duds

Much like the rookies mentioned previously, many think buying fancy designer duds will solve all their issues. They think Versace, Armani or Hugo Boss clothes have magic powers too.

But again, it’s not about the clothes you wear, but about how you wear the clothes.

So a fancy brand won’t fix your style issues. You’re only making more expensive mistakes.

Clothing in your stage of learning style is practice material. You’re better off getting a lot of practice material for a low cost, than practice on a few super expensive items.

Besides, few people will realize you’re wearing brand clothing anyway. Unless you broadcast it, which makes you look like a show-off… and a moron… and everybody hates you.

So don’t.

Mistake 7: Cramming Instead of Doing

crammingSome guys seem to think upping their style is like a big test they have to prepare for. They stay in research-mode for the longest time, leading to analysis paralysis.

What happens is, you want your style transformation to be perfect.

You want to avoid making a fool of yourself. So you go online to find advice, but you find so much of it. And you feel like you need to study it all before you start your transformation.

You feel like you need to know everything, before you change anything.

And without realizing it, you’re paralyzed.

You just keep reading and reading, but you never take any real action on what you read (save for the small, easily-implemented tweaks).

But learning style is all about developing your eye, and your eye is not developed from reading. Your eye is developed from seeing.

So instead of trying to learn everything, learn one thing, and implement it right away.

That’s all. Just one thing.

And then the next.

And then the next.

Mistake 8: Obsessing Over Details

Everybody says style’s all in the details.

And I disagree.

Style’s all about the big picture. Details can elevate a look, but they can’t make a look. If the big picture is off, the details won’t fix it.

You have to learn how to put an appealing outfit together, before worrying about details. Otherwise you’re just icing the cake before you bake it, which I’m almost sure is the wrong order.

So forget about the details.

Focus on the big picture.

Mistake 9: Thinking “Effortless” Means “No Effort Required”

no-effort-requiredSo a look often advocated recently is the effortless look.

And many rookies use this effortless look as an excuse to keep dressing sloppily. They think they achieve this look by putting zero effort in.

But you don’t achieve the effortless look by looking like you just didn’t bother. You just want to look like you didn’t put a lot of thought into it — like you just grabbed whatever you had in your closet and put it on.

But you still want to look like you know what you’re doing. You still want your outfit to look good.

Just keep it simple. Don’t over-think it. But also don’t stop thinking entirely.

Mistake 10: Going For an Instant Transformation

Many rookies think they have to transform like Optimus Prime and overhaul their entire wardrobe overnight.

But they don’t.

In fact, I recommend against the instant transformation, for the following reasons:

  • You’ll stay in preparation mode for too long (possibly forever).
  • You’ll feel incongruent when you do transform.
  • You’ll be freaked out by the attention.

So even if you do get out of preparation mode, you’ll likely transform back into your old, trusted look. You’ll tell yourself you tried it, but it just wasn’t you.

But when you take your time, change gradually, and learn along the way, the transformation will be a lot smoother, and a lot more comfortable.

So What’s a Rookie to Do?

Well, Rookie, to finally stop looking sloppy, you need to focus.

You need to focus on the right things.

You need to stop randomly reading anything the web throws your way, and focus on the basics, like fit, color-coordination and achieving balance in your outfits.

Effortless Gent has a Start Here page, don’t you know? As does my own site. The articles listed on these pages cover a ton of basic information, and just going through these will help you on your way.

Focus on the Basics

Nothing you do matters until you have a grip on style basics, dude.

No suit, no trend, no brand will look good until you do.

You need to forget about the what, and focus on the how. Because once you know the how, you’ll never have much trouble again. Once you know the how — once you’ve internalized the how, and developed your eye — everything else is easy.

All you have to do is forget everything you think you know, erase your bad habits, and take it one step at a time.

Just one tiny step at a time.

And before you know it, you realize you look pretty damn awesome.

Don’t forget to visit Robert’s site. He’ll get you started on your new style by personally helping you over your current sticking points.


[photo, photo, photo, photo]

Learn a few shortcuts to dressing well

Enter your first name and email, and I'll send you a free eGuide with quick and easy tips you can use today.

33 Responses

  1. JC on

    Great list! I’m still working on reworking my wardrobe/style, and I do #5 and #7 (especially #7) all the time.

    • Robert van Tongeren on

      Yeah, it’s easy to fall into the cramming trap. There’s just so much information out there, but it’s better to apply one piece of info at a time, than try to learn everything at once.

  2. DZ on

    great! definitely still settle for “close enough” sometimes… being really short makes OTR clothes impossible to wear. But I do take certain measures to make “close enough” ok, like rolling my sleeves up because I really can’t afford to get all my short cuffs shortened, that and I learned how to alter my shirts to fit slimmer, that was HUGE. Now all my shirts fit close to the body rather than being a billowy mess like 95% of the people that wear button up shirts.

      • Steve Gordon on

        Great article again Robert!

        Really? Getting shirts slimmed? I’ve tried and it’s not cheap, even here in Hong Kong, the land or sweatshop tailors. If you’re getting a shirt made from scratch it “should” already be tailored to you. But I can’t imagine altering one off the rack is going to be good value for money unless you’re buying Gucci or something.

        Or do you mean actually doing the sewing yourself? Now that would be VERY useful to see a ‘how-to” article. My wife tried on one and the results were a little funny!

        • Robert van Tongeren on

          When buying shirts off the rack, you’re better off spending your money on getting a good fit than on getting something expensive. You shouldn’t see tailoring costs as extra cost, but part of the cost.

          If getting your shirts tailored gets too expensive, maybe you’re buying too expensive shirts for your budget. A cheap, well-fitting shirt will look better on you than an expensive, poor-fitting shirt.

          Fit is priority one.

          Learning to sew yourself is a great idea. I haven’t learned it myself yet, but I plan to in the future. You can save a lot of money if you can do it yourself.. But I recommend you practice on old shirts you no longer wear.

    • brockmcgoff on

      Yo DZ – you heard of TheModestMan.com? Helping short gents find clothes that fit since 2012. Check it out!

      Robert – great article as always! Also, never too many “dudes”, and I hear you about TMNT. I always wanted to be Raphael…


  3. Lived Through It on

    Overall some valid points but the use of “dude” in this article (four times) makes it a little childish. I get it – you’re talking to “rookies” who we assume to be young gents. And I say dude more than I would like to admit. But in writing, it doesn’t translate to “conversational,” it translates to “dumbing down.”

  4. TJ on

    Yes, yes, yes to #2. I see so many guys wear suits and think they look good just because of that, without paying any attention to fit or style. Don’t get me started on the square toed shoes they wear with the suit.

  5. Tom on

    Excellent, excellent, excellent. Over the years, as I started realizing I shouldn’t only have outfits of tennis shoes and extra baggy jeans…and had no idea how to possibly change that…I’ve made almost all these mistakes. I particularly like the “dressing up is not dressing well” comment, that’s a perfect description of what I haven’t been able to put into such a catchy phrase.

    If you are on the fence about whether to believe what Robert wrote in this article is true or not, trust me as someone who has been there and done that. It’s spot on. And fit is indeed King.

    • Robert van Tongeren on

      I’ve made almost all of them too! I spent so long trying things that didn’t work that I gave up a couple of times.

      Sometimes you just need the right piece of info at the right time to make you see the light.

  6. Dave Hahn on

    Good list. #3 and 6 are so important. When I got my first decent paying job, I thought I’d finally move away from my thrift store clothes and up my game. I’d gravitate towards labels like Penguin, Ben Sherman and Ted Baker and it was just a random mess of too tight shirts with garish designs. Go cheaper and basic in the beginning – focusing on fit of course.

  7. Bea on

    This is amazing! And what’s more, you’ll just as often find so called stylish girls commiting these mistakes! I intend to quote these tips on my blog, I hope that’s ok with you guys 🙂

  8. Gaz on

    I agree pretty much with everything written here. But I do feel some people obsess unnecessarily over fit. They agonize over that centimeter here and there, and never seem to be happy. Sure fit is vital but if your sleeve is a cm longer than optimum so what? Where your clothes with confidence.

    • Robert van Tongeren on

      Well, I agree you can take it too far, but if you’re going to obsess over anything regarding your style, obsess over fit.

      And y’know, I don’t think I’m as obsessive as the guys you describe, but when I see something that’s off about what I’m wearing, it just bugs me and I can’t ignore it. You know that feeling?

      If you do, you may also know that you’re not going to feel great about what you’re wearing until you fix what’s off. So you’ll need to fix it in order to wear it with confidence.

      And maybe a cm extra sleeve length doesn’t tick you off that much, but it might do the trick to someone that’s ja little more of a perfectionist.

  9. Gabriel on

    I really enjoy this article. I especially like no. 10. When I started to learn about style, I was so overwhelmed that I want to change my wardrobe instantly. Your advice on not to rush is good remainder for me.

  10. drjayphd on

    “So a fancy brand won’t fix your style issues. You’re only making more expensive mistakes.”

    Delete “style” and send this to Buzz Bissinger until he gets the message. Ye gods.

  11. Suits and Skirts on

    Can’t tell you how many guy “dress up” thinking they look good, but the clothing makes them look like a child swimming in his dad’s clothing. Embarrassing a great point. It’s probably the number 1 mistake I see. Good call.


  12. Sarah Johnson on

    I totally agree with everything you’ve said! Another thing that I think is important is poperly caring for your clothes once you’ve gotten them to fit. Especially shoes. You can have some amazing shoes, but unless you take the time to polish them and keep them clean, you’ll look like a hobo in no time.
    One of my guy friends just bought a new pair of shoes to wear to a wedding (similar to these: mens Stacy Adams dress shoes) and he spilled a drink on them and didn’t clean it off. When he went to wear them again, they were ruined. Rookie mistake.