How To Dress Well – First 7 Steps For A Style Rookie

Style 101If you’re just starting to learn how to dress well –

you’re probably overwhelmed.

So much info – where do you start?

You’re not alone. I’ve been there.

It took me YEARS to get past beginner level.

Why? Because I didn’t have a roadmap. Don’t worry – you don’t have to struggle like I did. Today I’m going to spell out the first seven steps for a style rookie.

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If you keep having to tuck in your billowing muffin top… these will save you from sticking your hand down your pants in public. Click here to check out KK & Jay and use code RMRS for the best discount on the internet.


Click Here To Watch The Video – How To Dress Well

Click Here To Watch The Video – First 7 Steps For A Style Rookie


Read on to start learning how to dress well in 7 easy steps.

#1. Dress For The Body You Have – Not The Body You Want.

I always get emails from guys saying, ‘I’m going to lose 50 pounds in the next six months –  so should I hold off on buying clothing now because in six months I’m gonna have that ideal body?’ The answer is no. You’ve got to dress for the body you have.

The goal of dressing your body type is to bring balance to your overall look. You want people to focus on you and the message. If you wear something that looks jarring or odd or unflattering, it’s going to grab people’s attention and they’re going to be thinking about it instead of thinking about the words that you’re saying and the message that you’re trying to get across.


kk-jay-shirt-stays#2. Know The Name Of Your Tailor

You want to get almost all your clothing adjusted by a tailor so it fits you better. The mistake most people make when they’re learning how to dress well is that they only get their suits and maybe their jackets adjusted. No – take your casual button downs to your tailor. Take your jeans.

When you buy something off the rack it’s made to fit a wide range of body types. When you take your clothing to the tailor they’ll work with you to fit YOUR specific body type. When a tailor does their job correctly, your clothing will actually fit your body – and clothing that fits on your body always looks better than clothing that’s overly baggy or overly tight.

But even if you get a garment perfectly tailored, you can still have issues. If a dress shirt is a little bit short, your tailor can’t make it longer – it’s going to keep coming untucked throughout the day. And any shirt will puff out into an ugly muffin top if you move around a lot. No matter how perfectly your shirt fits, if you want it to LOOK like it fits perfectly all day you need to own shirt stays.


style-pyramid#3. Learn And Live The Style Pyramid

There are three corners to the style pyramid: fit, function, and fabric.


Fit is king. All of your clothing has to fit your body type. If you look around my website you’ll find tons of infographics to help you with that – you can see how a shirt should fit and how a suit should fit.

When you wear clothing that fits you, all of a sudden it looks great. If you don’t nail the fit, nothing else matters.


Function means wearing the right outfit for the occasion. If you’re going to a job interview for warehouse work, you don’t need to show up wearing a suit. It’s the wrong item – it doesn’t function properly.

Take your cues from what other people are wearing in the same situation. You can dress a step above, but don’t dress like you’ve walked onto the wrong movie set. Make sure whatever you wear is serving the function of sending the message you want to send to the world.


I put this last because I do think you can compromise on the fabric and the build of clothing when you’re first learning how to dress well. But when you start to make more money, look at what you wear on a daily basis and start to invest in it.

It may be casual clothing – high-quality denim or nice button-down shirts. Whatever your uniform is, whatever message you want to send the world, start to spend more on better fabric and better construction – the actual build of clothing. You’ll end up with better quality clothes that will last longer, so you’ll get your money’s worth out of them.


#4. Build An Interchangeable Wardrobe

Did you play with Legos as a kid? What’s great about Legos is that you can take a Lego from 1985 and a brand new Lego and they’ll work together, because Legos are made to be interchangeable.

Buy clothes with an interchangeable mindset. You can take three pairs of shoes, three trousers, three shirts, and three jackets – twelve items – and if they’re all perfectly interchangeable, you can create 81 outfits. So you can own less and get more mileage out of it.


#5. Develop A Uniform

I can’t tell you exactly how to dress well – it depends on who YOU are and what you stand for. Think about what message you want to send to the world and dress to send that message. Find something that works for you and have it as your default.

So if you’re a young up-and-coming lawyer maybe you’re going to dress better than everyone at your firm. If you’re a lawyer at a construction company, I still expect you to dress like a lawyer. You have to wear a suit, but you should be better dressed than most of the men there because you’re supposed to pay attention to the details. That’s your job – it’s who you are and what you stand for.

If you’re an artist think about how you can send the message that you’re someone creative. Maybe it could be your glasses – you could choose an unusual frame or have a wide variety of frames.


Trench-Coat#6. Know When To Spend And When To Save

Most men who are learning how to dress well are starting out with a limited budget. If you don’t have much money to spend, be very careful with it. Spend a little bit more time saving up for this investment. I call it an investment because yes, you may want to go buy that big-screen television – but if you spend the money on dressing well, you may get a promotion. Then you can buy your television and a house.

Focus in on your outer clothing first. If you wear a suit on a daily basis, spend good money on at least one to two suits. Go for something classic and conservative that doesn’t draw too much attention and is interchangeable.

Also spend good money on your shoes. If you spend a lot of time on your feet,
buy something that’s comfortable. If you wear work boots then find a company like Thursday Boots, which makes a great Goodyear welted boot.

Finally, think about coats and jackets. If you’re in a cold weather area, spend good money on a jacket, because you’re going to be meeting and talking with people who will look at this jacket and make a split-second decision on whether you seem competent or out of your league.


#7. Perfect Your Grooming Routine

Notice I said ‘routine’. A routine is a system that you can adjust and improve. If you wake up in the morning with no routine and you just get dressed, you can’t improve that.

Set up a system so instead of being reactive you’re already prepared. If you go for a last-minute haircut the day of an interview and get a bad haircut that kills your confidence, you’re going to blow your interview. You want to show up prepared. You do that by having a system – a routine that you don’t have to think about.

Let’s say you’re getting razor rash – if you have a shaving routine, you can adjust and improve it. Try changing to a different razor or shaving cream and make a note of how that changes things. Because you’ve got a routine that you can actually adjust and measure, you’ll find what works for you to get rid of those bumps.


Most men don’t know the first thing about how to dress well – if you just follow these seven steps, you’ll already have the edge over 90% of men. Those steps again are:

  • Dress for the body you have – not the body you want.
  • Know the name of your tailor.
  • Learn and live the Style Pyramid.
  • Build an interchangeable wardrobe.
  • Develop a uniform.
  • Know when to spend and when to save.
  • Perfect your grooming routine.


And finally – don’t forget to check out KK & Jay. I WISH I’d had their shirt stays in the Marines – the ones we had were poor quality and always falling apart. The first pair KK & Jay sent me three years ago are going strong after over 100 wears – and so comfortable you hardly know you’re wearing them.

You can choose stays that clip to your socks (so your socks stay up too) or an innovative design that you can wear with no-show socks. Seriously – click here and check out KK & Jay – and remember the code RMRS for a fantastic discount.

The post How To Dress Well appeared first on Real Men Real Style.


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