6 years ago I decided to make a change.
I made the decision to stop dressing like a boy and more like a man.
I simply didn’t like the way I looked (or felt).
It was a year after losing my Dad to suicide (read the story here) and I’d fallen into depression myself. I needed something to uplift me, something to boost my confidence and something to help me become the person I wanted to be.
Improving the way you look through your style is almost like losing 10kg when you’re overweight.
It makes you feel good again, you feel more confident going to social events and you enjoy the attention and compliments.
As with any before and after photos, they show the transformation but they don’t show the journey it took to get there.
It didn’t happen overnight and it took years of experimentation. Most importantly I made a lot of mistakes. I bought the wrong clothes, I tied my tie wrong, I ignored the principle of ‘fit’, I overcomplicated things and I tried to dress like someone I wasn’t.
These are all mistakes I learnt from, but mistakes I wanted to highlight in todays article.
Learn From My Mistakes
If you’re someone looking to improve your style it’s important to learn from the mistakes I’ll share in this article.
They may also be mistakes you’re making right now, mistakes you’ll need to overcome.
With anything in life failure is a lesson and it isn’t something that should hold you back.
I made mistake after mistake when improving my style but I learnt from it rather than giving up and reverting back to baggy shorts and printed t-shirts. I’ve made mistakes in business, again to learn from them rather than giving up.
A famous quote by Thomas Edison sums up the importance of learning from mistakes rather than opting to give in.
I was lucky enough to not make 10,000 mistakes when it came to improving my style, but those mistakes helped me simply see what did and didn’t work.
These mistakes I share below.
Learn from them and use them to improve your style in the process.
1. I Didn’t Dress For My Lifestyle
If I had to highlight the one mistake I made that cost me the most it would be this.
In fact if I totalled it up I probably wasted thousands of pounds from this mistake.
Dressing for your lifestyle is something we often shy away from when we first look to improve the way we dress.
Typically (like I did too) we start improving our formalwear. Straight from the off I took inspiration from the smarter guys and decided to start buying suiting.
Why? Because everyone looks good in a suit right?
The issue was this picture I had envisioned of me looking like a boss in a suit and tie all day didn’t exist in my current life. I worked from home.
As time progressed and a lot of experimenting my formal style started to improve. As you can see from some of the photos shared in this article the majority of the things I wore were formal.
Although this wasn’t a bad thing the mistake meant in my day to day life I still dressed pretty appallingly.
I filled my wardrobe with 80% of formalwear but dressed up probably 10% of the time. I quickly found that if you work from home or you have a job which requires a more casual approach you don’t need to fill you wardrobe with 20 suits.
Dressing to your lifestyle is all about building a wardrobe around what you do each day.
It’s about thinking of your day to day life, defining a style which will make you look the best in that situation and then introducing occasion-wear into your wardrobe.
I use the Pareto principle.
80% of your wardrobe should be items of clothing that you can wear (and make you look good) in your day to day life and 20% of your wardrobe should be for occasions (suiting, loungewear, gym clothes).
Spend some time thinking about your existing lifestyle and the clothing you’d feel most comfortable wearing. Now start defining the style you want to achieve gaining inspiration from magazines, Instagram, blogs and more.
This approach will speed up the transformation as well, applying your focus to mastering your day to day attire first and then improving your occasion-wear.
Dress for your lifestyle, don’t dress like someone you’re not.
2. I Bought Too Much Clothing
A key principle for menswear is quality over quantity but it really took me a while to get my head around the idea.
I was a big fan of high street shopping and often neglected quality for the sake of saving some money.
The issue with buying more inexpensive items is you end up hoarding your wardrobe alongside actually spending more in the long run.
Let me break it down for you…
I’d head to a high street store and buy a £20 dress shirt.
I’d wear it a few times and after a few washes it would start to look shabby.
With the shirt looking shabby I’d either hoard it in my wardrobe (but never wear it much) or throw it away.
I’d then head back to the high street and buy another £20 dress shirt.
The same thing would happen again…
Over the space of the year I’d probably buy 3 or 4 dress shirts to make up for the fact they only looked good for a short period of time.
The other approach (and the approach I now take) is to invest in quality from the beginning, to save time shopping and in fact save money in the long run.
Instead I’ll buy a dress shirt that may cost me £80. It seems pretty steep at first but I pay attention to the brand, the way the shirt is made and most importantly the care instructions.
This £80 shirt costs a lot more at first but typically it’s going to last at least a few years (saving me money in the long run).
We don’t need as many items of clothing as we think we do.
In fact I bet you only wear 20% of your wardrobe if you do take the quantity over quality approach.
Stop buying so much and instead opt for quality.
I also want to point out that ‘quality’ doesn’t mean expensive. There’s a lot of high street brands that in fact create good quality, well manufactured clothing. You just need to know what to look for.
Pay attention to the fabric, find brands that excel with certain items (e.g. Levi’s and Jeans), pay attention to the finer details such as the stitching and most importantly look at how the item fits you.
Take a more minimal approach to style.
3. I Didn’t Plan My Shopping Trips
I used to go shopping and impulse buy. You probably do too.
We walk round our favourite retailer and buy whatever catches our eye. We wear it a few times then hoard it in our wardrobe.
When you go shopping, or even when you do it online… create a shopping list.
“I need a Blue Button Down Oxford Shirt and I’ve got £90 to spend on it”
“I need a Pair of Dark Denim Jeans and I’ve got £70 to spend”
When you have a clear plan on what it is you need it removes any need to buy clothes impulsively.
I’d advise doing some research before shopping too, looking at the best brands for certain items.
For example if you wanted a new pair of jeans a bit of research into the best quality brands will help you make the decision.
It’s also a good idea to go through your wardrobe and get rid of anything you haven’t worn for a while alongside items that are extremely worn.
Then with your lifestyle in mind start writing down the items of clothing you need alongside how much budget you have for them.
If you end up spending less on an item either save that money back or spend a little bit more on another item.
Going to buy clothing without a plan is a recipe for disaster. You’ll end up seeing things you like (but don’t really intend to wear for more than a few weeks).
4. I Avoided Fit For Too Long
Why did I avoid ‘Fit’?
The number 1 principle to style?
It’s simple… I thought tailoring was too expensive.
The way your clothes fit you is the most important element to improving your style. Whether you dress casually or formally it’s irrelevant, fit still is something you should focus on.
I spent a good year or two with one eye on fit often hunting down items ‘off the rack’ that fit me pretty well. But even though they fitted ‘ok’, there was still something that needed improving.
I was introduced to a cheaper alternative to tailoring a few years in to my journey. Looking back I have no idea why it took so long.
Tailoring isn’t expensive.
Buying a bespoke suit is.
It’s important to understand the difference.
For everything I buy now I’ll always see what areas could fit better. Maybe the trousers are too long, they could be too loose, the waist might be too big…
The list of tailoring options is endless.
I’ll try clothing on, see what can be improved and then I’ll simply pop it into my local tailor.
In fact ‘tailor’ is a word that’s thrown around way too often these days.
Why? Well she simply does repairs and alterations out of her Dry Cleaning shop.
You don’t need to buy a suit jacket from Saville Row to have clothing tailored to fit you. You can buy it ‘off the rack’, see what areas need improving and then get a local tailor/alteration service to make the adjustments.
You also can of course opt for Made to Measure or Bespoke if your budget allows.
The lesson is simple… you have no excuses when it comes to clothing not fitting you as it should.
Use a tailor.
5. I Often Overdid It
Pocket square, Belt, Cufflinks, Collar Bar, Watch, Bracelet, Tie Pin…
I often overdid it on the accessories front.
One of the biggest mistakes I made and I still see men make today is over accessorising.
Accessories are there to add subtle details to a look when needed. They’re not there to transform a look.
I always recommend that you take off the last accessory you put on if you feel like you’ve overdone it.
I also overdid it in terms of prints, pattern clashing and colour. I find keeping it simple is often the easier and best approach.
Don’t overdo it.
6. I Wore Cheap Shoes
Shoes really are an important part to any outfit.
We put together a video asking women in London what they liked on a man. Over 80% of them said good shoes.
The mistake I made was I often avoided quality when it came to shoes opting for formal choices that looked cheap.
Even though it was a brogue (like I was advised to wear) it was made from cheap leather, the sole was thin and it was badly stitched.
All the shoes I buy now I invest in. I typically only get them from Shoemakers (brands that specialise and just sell shoes) and I’m not afraid to spend more on them. Why? They last longer and look better.
I recommend shopping at brands such as Grenson, Duggers of London, Church’s and Crockett & Jones.
7. I Dressed For Others, Not For Me
How often do you dress to please others?
Whether it’s overdressing to stand out or even underdressing to blend in do you find yourself thinking about other peoples opinions of how you dress?
This was something I did for a long time and it’s something that held me back in terms of looking (and feeling) the best I could.
Why worry what other people think of you?
You may look smart but if you don’t feel comfortable it will show.
A stylish man dresses confidently but most importantly acts confidently.
The next time you get dressed dress to impress yourself, no one else.
We overcomplicate style a lot. We try to be someone we’re not.
Why not keep things simple?
A simple approach to style worn by a confident man will always outperform a complicated approach to style worn by a man feeling uncomfortable.
These 7 mistakes are things that held me back from improving my style massively. But I learnt from them.
Now it’s time for you to learn from them too.
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