Stages of the fashion journey

Simple Style
7 min readDec 12, 2016

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Along your path to dress better you’re bound go past these “landmarks”

As you go through trying to dress better you’ll find yourself at varying levels of confidence. Let’s take a look of some of them phases that you’ve been through, are currently experiencing, or have to look forward to.

Level 0

Fashion doesn’t matter

Ah yes, this is the bottom, the seventh circle of hell. You are at the worst you’ll ever be at because you just say: “Fashion doesn’t matter”. This is where you make all of the mistakes. The pictures you take during this time will make you cringe the hardest, you’ll be ashamed to show off pictures from this period of time in your life.

To you anyone who dresses too well is trying too hard. Dressing up simply means putting on a button up shirt with a tie and you never dress up because you just don’t care enough or some other excuse.

Maybe you do care about fashion so you make a big splash about not following norms, so you take up a staunch anti establishment position. Maybe you go with grungy t-shirts, some odd hat choices, or some very loud colors.

Feel the pain of when you thought a fedora or trilby was a good choice

Level 1

Why do I always feel out of place?

This is it, this is the beginning. You start to really wonder about what you’re putting on everyday. At this level you don’t have an idea about what is quite wrong with what you’re wearing, but you know you feel out of place.

Sometimes this can be caused by changes in your regular social setting. Graduating from college, moving from a small town to a big city, moving to a new country or making new social circles can all trigger this response. Other things such as milestones in your life, a new promotion, becoming recently single or a big event where you have to be the focus of peoples attention can also cause the trigger.

In these new situations what was OK before with how you dressed suddenly feels off. Which immediately leads to the next level.

Level 2

This one or that one?

At this stage you start to think about what you’re wearing when you go out whether it is a social or formal situation. You struggle to put together a reasonable outfit for whatever you’re about to leave home for.

You know what you want to look like, but you can’t quite ever get there

All of those graphic tees suddenly seem dated. The dressy button up shirts you have feel like a safe way to feel like an adult, but they all look frumpy on you, or the colors just feel odd. Maybe you settle on a polo shirt (because those are always classy right?), thrown on some jeans and you feel a little better, but not by much.

Ah ha! You got it, you figured that you just need to go shopping right? It’s been a while since you’ve been shopping, so you move right onto level 3.

At this stage you hate / fear shopping

Level 3

Maybe I should just buy some things

This is the most wastefully expensive stage. You go to the closest store that sells clothes and you buy a few things. Maybe it’s the discount store that has “good deals” as someone once told you.

Or maybe it’s one of the trendy stores with all of the forever youthful models who are always having fun. You walk in those stores and you feel like you could hang out with them if you just dressed like them. You get the ones that “look good” and are at a reasonable price, at least you think it’s a reasonable price. You hope it was a reasonable price.

Maybe you have finer tastes and you go right to the high end stores like GUCCI or Louis Vuitton. If it’s this expensive it must be good fashion right? You get a few things, put them on with pride and consider your fashion journey done.

It could be you never left the house and just ordered some new shirts off that new cool t-shirt site. Also you got some pants on amazon that looked good. For all of your online purchases you just assume you’re a large because “they make all the clothes skinny now, but I like them a size up” or something equivalent.

It finally all clicked on!

Level 4

I see the light

You finally figured it out. It was an expensive trip, but you figured out what you like, what your fashion sense is and how it all works. The things you’d previously ignored like the size suddenly matter. Various fits and materials are no longer just words thrown around, but actual English you can understand.

Maybe at this point you’ve burned a lot of money on some poor choices. Or maybe you’ve just accumulated a series articles of clothing that don’t make up a cohesive wardrobe. You have some odd sizes, colors and fits. You know what’s wrong and you can see the work ahead of you.

You’ve probably also started reading articles like this around the internet. You now how a pair of jeans should fit. It is at this step you realize how far you have to go, how bad you were at level 0 and how much of your clothing you need to donate or get rid of.

Level 5

I got this

You finally start putting together modern, adult, region appropriate outfits together.

It starts off as nothing special: A few shirts that fit right that aren’t too loud and obnoxious. You maybe figured out the few pieces in your existing wardrobe that work when worn right. You know how to tuck in a shirt right, and you know your size. You maybe picked up a new decent pair of shoes to replace that old pair that was old faithful for years.

You no longer own clothes, but a wardrobe instead

As time goes your wardrobe changes slowly. You feel better about yourself because you are wearing clothes that fit for the first time. You have a few different pieces that you can wear interchangeable with each other and still look decent. You started working out because you realize that clothes fit better on a in shape body. Maybe you’re not pumping weights everyday, but you start eating better and being a little healthier.

You may occasionally stumble and wear something not quite right, but you know it now and you never repeat the mistake. The compliment start coming in.

They’re slow at first, maybe from your buddy at the bar going “Look at you all dressed up” giving you a hard time. Next a family member tells you genuinely that you look nice today. It feels good. A few months later the compliments really start rolling in: co-workers, friends, strangers, the fruit lady, the mail man, everyone.

Level 6

Game recognize game

Sharp in any situation

You’re at a point where you always feel confident in what you’re wearing. Maybe you feel overdressed at a few events, but it makes you stand out in a good way.

You have fewer clothes now, but no one would ever know because you have a versatile wardrobe that makes you look like an adult whether it’s just out with the guys, going on a date, formal speaking occasion or just going into work day to day.

At this point you can confidently say you understand fashion. You’ve been to one or two fashion websites or blogs and maybe even follow them. You’ve also invested in a few higher quality items, like some tailored chinos or a blazer. You also are now on a first name basis with a tailor.

You’re getting accustomed to the compliments and you take them gracefully. Along with the compliments you start to notice women checking you out. When you catch their eye you send a smile their way and sometimes they return it.

You also notice when other men are well dressed. Sometimes you just take note of a combination you like and will keep in mind when you go shopping. Other times you both lock eyes and give a polite nod.

Game recognize game.

Level X

To infinity and beyond

Past this point you are master of your domain. You may experiment with things, take risks and break the rules. You’ll fall in love with the routine of getting ready and paying attention to the small details.

Do you remember any of these stages? Have another one to add? Leave a comment and let me know!

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