Why I Created the FlyFiftyFive Challenge

When I was a teen, I bought what I had been sold from large companies. I always felt the need to have more.  This carried on into adulthood where I grew a wardrobe that was massive, thinking I needed all this stuff to keep up with others in the business world.  I ended up being fortunate enough to sign with LA Models, NTA models, as well as a few other agencies and model for amazing brands including Louis Vuitton and Coach.  I had the honor of rocking the most amazing Tom Ford suits, all while getting paid for it!  I met all kinds of people and learned a lot along the way some of which I will share with you in this post.

As a brand ambassador and model, I was expected to sell the lifestyle and image of these brands, all while not living that lifestyle at all.  Models often lead lives that are far less glamorous than the ones that are portrayed in magazines, on billboards and in commercials. We usually end up cramming things into suitcases, sharing small spaces with other models and always looking for the next job or paycheck.  And when models get a job, it’s not unusual to wait around three months to finally get paid.  I’m by no means complaining, but this is just how it works behind the airbrushed dream.  As an insecure kid raised in a small town in Idaho, I never thought I would be able to do all of this and meet so many interesting people.  I feel so fortunate that modeling supplemented my income while I worked other jobs and wrote.  This image of a jet-setter lifestyle full of wealth that is created by a team of people when shooting is how brands make money. However, we can all love what we have and get a model-esque wardrobe that doesn’t break the bank.

So I’m here to spill a secret…

Models are required to show up looking very sleek, in form-fitting clothing without logos at go-see’s (meetings with clients where they choose which models they will hire to represent a brand).  They may wear logos when they are paid, but — in normal life — models I know don’t wear anything loud or loaded with labels typically. So to dress like a model is actually quite easy.  Wear something timeless that fits your body well and shows your style off.  It turns out it’s also a very inexpensive way to create a great wardrobe for yourself that is easy to manage and travel with. To skip ahead to what the challenge is and the rules, check out my previous post that explains it all (FlyFiftyFive Challenge Rules) or read this post to take a more in-depth look at why I think this challenge can help so many people like myself.

The mission was to get down to 55 articles of clothing, not counting underwear, socks, a few pairs of shoes, hats and other accessories. The number 55 seemed good to me because I knew it would be a challenge, but that I would have what I need.  I created Fly55 because I loved that when I would travel and open up my suitcase, I would have everything I needed.  With 55 items, I wouldn’t be over the 50lbs checked baggage weight limit at the airport and I could even  bring back a few souvenirs from my travels.  I knew it would be less overwhelming and stressful to live this way all the time, even when at home. I wouldn’t have to rummage through my packed closet anymore. With The FlyFiftyFive Challenge, everything can be neatly arranged and I have something for every occasion with me.

Many of us are clothing hoarders and we don’t even realize it. 

Downsizing to 55 pieces of clothing meant I would be getting rid of at least a couple hundred articles of clothing from my current closet.  While that was exciting, it was also a bit challenging to do.  I found it easiest to pull out my favorite things first and then edit it down to the final 55.  It took some time, but it was well worth it.  In order to keep the number at 55 in the future, I will get rid of something each time I add in a new piece.

After choosing my initial 55 pieces, I decided I wouldn’t buy another thing for four months. For me, 55 items felt like the right number because I travel to different places quite often and need clothing for all climates and I also work out a lot so I also needed my gym wear (including a swim-suit).

I think the important thing here is to start with a number that feels limiting enough, but not like torture or you might not stick with it.  So if you absolutely don’t think you can bring your wardrobe to 55 items, this time around do it over time. Take note of what pieces you aren’t wearing after you downsize and continue shrinking it if your goal is 55.  The point is to become aware of what you need, reduce stress, simplify your life, save money in the process and enjoy the extra time you have when you’re not looking into a packed closet for something to wear among so many things you don’t even love.

Some tips for downsizing your wardrobe to upgrade your life- 

Avoid Loud, busy pieces with large logos or crazy colors- these will stick out to people and they will remember, that shirt or whatever, whenever you wear it. If you opt for simple, less busy pieces, odds are people won’t even notice when you wear something multiple times. This will make having fewer pieces easier for you because you’ll still have a world of possibilities when it comes to creating different looks. Now, if bright clothing is your style, you can do that as well, but just love each piece enough to want to wear it over and over again. Bright shirts or sweaters are a great way to go if you love bold color because you can always layer them with different neutrals (black, brown, gray, white, tan) pants, jackets, sweaters, etc. I have kept a few graphic cut-offs and Nike pieces for the gym and casual “out and about” clothes. I find this allows me to still have some graphics mixed in, but I would limit these pieces to just a few.

Quality over quantity- Is key when building a wardrobe. You want nice, well-constructed pieces that will last you years and not fall apart. When you buy things that are poor quality, be ready to toss it after a month or two.  You’ll also never get the same pleasure of watching something like a great leather jacket, change color over time as it ages.  I’ve seen a rising pressure for people to not be seen wearing the same thing more than once, which I think is ridiculous. I understand if you are on the red carpet or where things are loaned to you, but it makes no sense in day to day life. Celebrity and Instagram culture have aided in the public perception that clothing should be disposable.  This is not only bad for your wallet, but also terrible for the environment because it’s so wasteful.  I really enjoy having a few things I call “signature pieces”.  These are the things that give you your unique style and should each be something you absolutely love. If you don’t love something, why keep it?

Avoid fad clothing- Anything that comes in and out of style will most likely continue to do so.  Don’t buy a piece because other people are flocking to it unless you love it and can see yourself wearing it for a long time to come. This will save you a lot of money and will ensure you enjoy your clothing much longer.  We, as a society, are often ripped off when buying the latest trends because these styles come and go so fast.

I downsized my closet to this:

This includes my work clothing, evening clothing, workout wear and daytime clothes… I also have a medium-sized tote with winter clothes so I can trade some pieces out when the time comes.

When you whittle your clothing down so much, you will instantly notice yourself weighing the effects of bringing something new in.  I love everything I wear now and when I go to the mall and see something I like, instantly I ask myself, “Do I like this enough to be a part of the Fly55?” The answer is almost always no and, because I decided to not buy anything new for four months, I don’t have that impulse to purchase.

My entire wardrobe can now fit into one large suitcase, which is great when you don’t know where your adventures might take you.

With my new wardrobe, I am prepared for just about anything at a moment’s notice.  It makes me feel like Indiana Jones, only without the hat and whip… Unless it’s Halloween…

Try downsizing for a few months and see how great it feels…

Take the FlyFiftyFive Challenge

Kaden JamesComment