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A Beginners Guide: 16 Essential Style Tips For Guys Who Want to Dress Better Part 2
Date Posted: 06/Oct/2017
Here’s the truth. Dressing well is a skill. And like any other skill, you can learn it and improve. Don’t believe me?
Why are some cashmere sweaters $100, and other $1,500? Is the $1,500 one really 15x better?
Are higher quality clothes “worth it”?
No doubt these questions have crossed your mind. And my answer is…
It depends.
It’s hard to make anything good for a low price. Whether that’s a pair of jeans, a laptop, or a steak dinner at home. When you have a limited budget to work with, there has to be some compromises.
There’s an assumption that because higher quality or designer clothes are expensive, “you’re getting ripped off” as a customer. You’ll sometimes read guys on blogs and forums proclaim you’re just “paying for the marketing costs”
I can tell you having worked 11 years as a menswear designer, it’s just not really true.
Better materials, better construction, and better design cost more to make, so it costs more for you to buy.
A perfect example: Cheap jacket zippers can be low as $0.50 a zipper. They’re light, can be frustrating to use and, of course, break easily.
When I was making leather jackets, I was using high end RiRi zippers. They’re heftier and nearly impossible to break. When you zip up your jacket, it was buttery smooth.
The downside? They can sometimes cost as much as $20 per zipper for me as a designer. That means by the time the jacket hits you in the stores, that single $20 zipper adds $60 to the price of the jacket thanks to a standard 3x markup.
That’s not marketing, that’s math.
But it’s hard for you to grasp how much better that zipper or $1,500 cashmere sweater is without trying it. The same way I can tell you one of the best meals I’ve ever had cost $220, per person, no matter how well I describe it, you can’t truly understand until you take a bite.
Go to a store that you would consider out of your budget. A place that might even be uncomfortably expensive for you. You don’t have to buy anything. Just walk around, touch the clothes. Maybe even try something on. Make mental note of how things fit, feel, and how you feel wearing it. Then go to a fast fashion shop like Zara or H&M and try similar items on. Make note of what’s different and what’s similar. Anything surprising?
This leads us to the question, how much should you spend on clothes?
Simple: My recommendation to all my clients is to buy the best quality that fits in their budget.
If you’re making mid 6-figures a year, then a $200 pair of jeans might not be a big deal. But if $200 is barely what you make a day, there are plenty of great options at lower prices.
To start, I always recommend J.Crew. They’re in almost every major city, are classic with a touch of trend, and they have solid prices. For more store recommendations, check out my post “Where I personally shop (and what I get there)”
Whenever I’m out shopping, I always see people pulling one size, then going back and forth from the showroom to the dressing room.
It drives me crazy! It’s such a waste of time.
Imagine cooking a meal at home where you took out one ingredient at a time from the fridge.
I’m going to show you how to cut your shopping time in half with one trick.
When you’re pulling clothes to try on in the dressing room, “Pull 3” of the same item:
One in the size you think you are
One size up
One size down
So if you’re shopping for jeans and you think you’re a 33, pull a 32 and a 34 and take all three to the dressing room. It saves you a couple trips, and is a bit of insurance in case it’s a new cut or the brand changed their sizing.
Use the “Pull 3” trick when you’re out shopping
There’s no change without stepping outside of your comfort zone. But it doesn’t have to be terrifying.
I teach my clients what I call “The Swap Trick”. It’s a way of introducing something into your wardrobe – a new trendy piece, a new color they thought they could never wear, or an item of clothing they never considered before – gradually.
Here’s how it works.
Think of it like trying out hot sauces. You wouldn’t go from a mild hotsauce straight to a super hot ghost pepper sauce. You would try something slightly hotter than the last and work your way up.
It’s the same thing when you’re trying something new with your style. You probably don’t want to jump from a black leather jacket to a neon green one. The next step up would probably be a brown leather jacket.
Here’s another example:
You want to start wearing more colors and patterns for summer.
I’ll start with an easy outfit: linen oxford shirt, navy lounge pants, sunglasses, white sneakers. The color palette,while perfectly fine, feels a little boring and safe. So let’s swap out the shirt for something a little more colorful. We can go two ways, a brighter color, or a pattern/print.
Even though the choice of a light blue shirt isn’t so crazy, you can already see it feels a lot more colorful than the outfit we started with. With the print, it’s even better and more in the spirit of summer.
But notice how one simple swap can change the entire mood of the outfit! This is really the key to starting to wear more color. You don’t have to wear a lot to brighten up your look.
As a starting recommendation, I always advise to start with just one swap per phase. When you get more comfortable with wearing some color and patterns, take it a step further.
Each time, swap out one more item in your look for something a bit brighter and colorful. The great thing is, if you feel like you went overboard, you can always pull it back a level or two and still have a great outfit.
Think about something you wanted to add to your style that you’re nervous about. How could you break it down and gradually introduce it into your wardrobe using “The Swap Trick”? If you need a specific example on how to use The Swap Trick for something like trends, check out this post I wrote on Effortless Gent.
Think about when you first started learning how to drive a car.
You were probably terrified.You were pretty sure within the first 10 seconds of hitting the road, you were going to crash.
You weren’t confident. Yet, as you kept driving, your confidence grew. Driving got easier. Now you illegally Snapchat on your phone while sipping your coffee and playing with the radio as you steer with your knee, and still get work in one piece.
It’s the same with your style.
You don’t need to start with confidence to improve your style. Your confidence grows as you work to improve your style. 
Just like with driving, the more you do it, the easier it gets.
Start with one outfit. Just one. Use the advice in the previous tips – stick with neutral colored, classic styles that fit well. You’re going to look and feel great. That quick win is important. Now use that feeling to keep going. Then, read the next tip to learn my favorite trick to help you build confidence even faster.
This is a great technique to use in conjunction with The Swap Trick, and is a KILLER hack for a first date. In fact, it’s something I used when I first started dating my current girlfriend.
Whenever you have a date (or a conference, interview, or speaking event): Wear the outfit you’re going to wear to date for an entire day before the date.
Even if it’s a dressy outfit. Go about your day like it’s any other day. Get coffee. Go grocery shopping. Go to work.
What you’re essentially doing is “breaking in” the outfit. Getting yourself used to wearing it.
I started doing this because I noticed that when I would dress up for a date, even if it’s clothes I’ve had for years, I would always feel uncomfortable during the date. I’d feel self-conscious. I’d fidget a lot.
Then one day I had schedule a date right after work, since I had no time to go home and change, I wore my date outfit to work. By the time the date rolled around, I had spent an entire day in my date outfit and felt relaxed.
WHAT YOU CAN DO TODAY: Whether it’s a new jacket you got or an entire outfit for a date, break it in by wearing it around to do errands. Got a last minute date or event and can’t spare an entire day? I’ve found even wearing the outfit for a few hours before helps.
Need some date outfit ideas? Check out this post: “A beautiful woman lets you know how to dress (and what to do) on a first date”
According to Mint, I spent $7,360 last year on books, courses, and consultants to help me improve my business, my skills like writing, and general knowledge in topics I’m interested in like philosophy.
It sounds like a lot, but ask yourself this question: What’s the cost of bad advice?
Imagine you’re a CEO of a company and you have a marketing budget of $25k. You read some advice from marketing forums filled with anonymous writers. You decide to take some of the advice and it turns out to be bad. Now you’re out $25k. Suddenly, a $7k investment in an top expert seems like a steal.
How many months, even years, will you waste following bad advice when it comes to your fitness routine? Your finances? Your style?
This tweet from Amy Hoy sums it up perfectly:
amy hoy learn from the best
When it comes to learning how to dress, there are TONS of options. From style blogs, Instagrams, Reddit, and Youtube channels.
Some dish out great advice. Most are filled with guys who like to shop and like to talk about it online.
When it comes to style advice, it can be tricky to filter out the good from the bad.
As someone that’s been doing this for over 11 years, I know how style advice can be challenging to teach. Telling someone what to buy isn’t the same as teaching them how to have great style. The same way a cook telling you to buy ingredients doesn’t help you learn the technique.
WHAT YOU CAN DO TODAY: Whenever you read advice online, always consider the source. Do they dress well? More important, is it a style you want to adopt? If they are a stylist or have products, how do their clients and readers look? Good, or terrible? Do they have a background in fashion or style, or are they “a regular guy just like you!”
Once you find an expert you’ve vetted. You have two options:
Pay for their advice
This is the fastest way to learn. Whether that’s a book they’ve written, a course they’ve created, or hiring them for one-on-one time. And while this is the fastest, this is also the more costly option. This is my personal preferred way to learn because my time is limited. I can always make money back, but one thing I can’t make back is my time.
Reach out to them via e-mail for advice
On the flip side, this option is “free”, but is going to take more time on your end. Before you reach out to an expert for advice, make sure you do your homework. Experts are often busy people. Make sure you search if they answered the questions you want to ask before. Skim through their blogs, Twitter, check if they’ve been interviewed on a podcast or magazine. If you can’t find the answer you’re looking for, only then should you consider reaching out to them. For that, I highly recommend reading this post: “How to get the attention of your favorite expert”
I have a confession to make: I don’t read fashion blogs.
Shocker, right?
Sure, I skim sites like Hypebeast and Gear Patrol to see what’s new, but when it comes to blogs, forums, news about the industry, I stay clear. Why?
Well, for one thing, a lot of it’s really boring. It also doesn’t help me with my job.
I do a lot of research when it comes to learning the pains men have when it comes to their style. I often come across forums where guys are endlessly debating selvedge denim vs non-selvedge, having long discussions about the “death of original style”, and share their theories on what “DESIGNER X” was trying to say with his latest collection.
One thing I realized after I went from designing menswear to becoming a private personal stylist: I’ve learned to take it seriously enough not to take it too seriously.
Yes, great style can truly impact your life. I’ve seen it first hand.
Better style can make you get taken more seriously in your job. It can make you an unforgettable brand. And yes! It will make you more attractive! (What woman doesn’t want a well dressed, successful man?)
But the last thing I want you to do is spend hours on forums debating about clothes. I’d rather you put on an amazing new outfit (you learned thanks to me, of course), go out and live your life. Crush it at your job. Go on an amazing date.
Have fun.
Because if you aren’t having fun dressing better, it’s not going to last very long.
To sum it up, make sure you:
Buy clothes that fit – It will solve 90% of your style problems
Focus on the classics first – classics are classics for a reason. They’re time tested essentials that look good on every guy.
Stick to a neutral color palette – Neutrals automatically mix with each other, so you don’t have to worry about mixing colors. They make you look professional and masculine, and when you’re ready to introduce more color into your wardrobe, they serve as the perfect backdrop
Have fun
Want to kickstart your new style even faster? Download my free “Starting Style Triple Pack”. It’s a combination of my 3 best guides to help you get started, and includes my “how clothes should fit” cheat sheets to help you master fit in 10 minutes. Just enter your info below and I’ll send it to you.
Source: The Essential Man.

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