One Outfit for the Rest of Your Life: The Desert Island/Cartoon Character Outfit

In the previous article, I discussed my ultimate capsule wardrobe. This involved choosing a few items in each category that all worked together. Such an exercise was not easy, but was rewarding nonetheless. Additionally, I said that I would also discuss an even smaller capsule wardrobe- one single outfit. With how long that first article was, I decided to split up the two concepts. The capsule wardrobe was covered in the previous article and in this one I will cover the single outfit while also bringing along some friends to help me.

The desert island/cartoon character fit is a concept that I have always been fascinated with. In the first place, it is difficult to nail down because one’s style can change so often and quickly. Additionally, even if you do have your style locked in, it usually is not easy for any of us to pick one exact outfit to wear. The other additional complexity is the fact that the concept of “one single outfit” can change depending on the criteria. 

In my mind, the desert island fit and the cartoon character fit are not the same thing. Allow me to explain:

The desert island fit to me is more like the idea of wearing one outfit for the rest of your life. If you were trapped on a desert island and had one outfit to bring, what would it be? To start, a desert island is not necessarily hot, it is just deserted. Most of the largest desert islands are in Canada, Norway, and Russia. However, they also can be in much warmer climates such as the Caribbean, Polynesia, and more. Basically, this means that your one outfit has to take you all over the world and be as versatile as possible, being ready for anything because it is literally all that you have. It can include favorite items, but still needs to be ready for essentially any weather. 

I think this is one of the best outfits I have ever worn, but it only works for warm weather.

The cartoon character outfit is different. This outfit concept of course comes from the fact that most cartoon characters, comic book characters, and anime characters tend to wear the exact same outfit day after day, week after week with little to no exception. It is such a trope that some cartoons even make jokes about it. These famous characters are not just identified by their physical characteristics and art style they are drawn in, but also by the clothing that they wear. Shaggy Rogers wears a baggy green t-shirt, rust colored pants, and black shoes. Homer Simpson wears a short sleeve white shirt, light blue pants, and black shoes. Calvin from Calvin and Hobbes wears a red and black horizontal striped t-shirt, black pants, and red/mauve and white sneakers. Superheroes are pretty much the same as well. Their outfits make them more recognizable than their actual physical appearances as proven by the transition from comic books to the big screen. Therefore, the cartoon character fit is more of what defines you and what you are recognized by rather than what is most versatile or even necessarily your favorite.

My desert island outfit is not all that difficult to choose. However, because I have to think of it as an outfit as a whole, it does not include all of my favorite items in each category. That is a huge mistake that a lot of people make when putting together outfits. They simply throw together all of their favorite or most expensive/exclusive items and then think that will look good and instead, it usually ends up looking atrocious. I know this because I used to do that. Instead, the desert island outfit should be your best outfit overall, should be versatile in terms of occasion and weather, and of course be comfortable as well as durable.  

Here is my desert island fit/one fit for the rest of my life. I will start with the building blocks first and then move to accessories.

Boots: Clinch engineer boots in dark brown overdyed horsehide

Trousers: Buzz Ricksons WWII Chino trousers

Shirt: Stevenson Overall Co. loopwheel ecru henley t-shirt

Jacket: Freewheelers Bodie in vintage brown deerskin

Belt: Hollows Leather Rail belt in black cherry bridle leather with brass double prong buckle

Hat: Wellema Hat Co custom beaver fur felt  fedora in rust

Sunglasses: Jacques Marie Mage Torino in agar

Accessories: Wild Frontier Goods Ogawa shell cordovan Makimono wallet, The Flat Head and Neff Goldsmith rings, The Flat Head key holder, and A. Lange & Sohne Lange 1 moonphase in rose gold (lol I wish)

This is the outfit that I listed with my Role Club engineers instead of the Clinch boots

All of these items individually were included in my previous article on my capsule wardrobe so I will try not to ramble on too much. For more information, feel free to read that previous piece that I wrote. This outfit just makes me feel the most “me.” The leather jacket is my favorite and my most comfortable, the chinos are nice and wide and just fit me superbly with a wonderfully high rise, and engineer boots are certainly a signature item for me as are a good hat and a pair of sunglasses. I do enjoy styling my hair, but I do wear full brimmed beaver fur felt hats quite often as well and I am rarely outside without a good pair of sunglasses. All of this is quite functional as well. The jacket is warm enough for most weather and taking it off allows me to survive heat fairly easily as well, plus the sunglasses keep my eyes covered and the hat protects from both sun and cold. 

The items here play well off of each other as well. Tan chinos go with nearly everything and I like the contrast between them and the darker brown leathers that I chose. Along with the ecru henley and reddish-brown fedora, I feel that this outfit as a whole stays with my preferred earth tone color palette while still having enough contrast and a dab of color as well. What I am least attached to here is the shirt. I could see myself replacing it with a button up shirt, especially a chambray one quite easily as well. Still, I think that as of this moment, the henley is my go to and if I feel like changing this over time, I will come back and do that. Aside from that, it really was not all that difficult to choose this outfit. Everything included are pieces that I own aside from the watch which I would love to have one day.

However, my cartoon character outfit would probably be a little more difficult to identify. This is because this outfit requires that I choose whatever most identifies me and technically, I am not necessarily the best person to choose this. In fact, the best way to choose my cartoon character outfit is to have other people choose it for me, so that is exactly what I did. 

I talked to a group of friends that I chat with regularly on Instagram and asked them what they would choose as my cartoon character outfit. The results were interesting. All who responded (around 7 people) said that my cartoon character fit would consist of a leather jacket, an ecru henley, non-denim trousers, and engineer boots. To my surprise, pretty much everyone specifically chose not to include any of my hats with the outfits and instead said that my hairstyle identified me more. For the most part, nobody even chose a specific pair of trousers or leather jacket. What was specific was engineer boots and an ecru henley. To be fair, their choices were quite close to what I actually chose. Obviously, I got more specific with everything, but what they chose was not far off. 

This was one of the outfits chosen by my friends for my cartoon character outfit.
The same outfit listed, just without the hat

This was a fun experiment and I wanted to include others here besides myself. As such, I reached out to a few of my friends that I feel are quite stylish to have them contribute their favorite/cartoon character outfit along with a description from them explaining why they chose what they chose. I hope you find their outfits and logic behind said outfits as informative and fascinating as I did. As you will see, we have a good variety of choices and styles as well as differing interpretations of what this single outfit was supposed to be. Hopefully you enjoy reading about and viewing this assortment of outfits as much as I did!


Jacket – Mister Freedom Mattock jacket

Shirt – The Real McCoys Waffle Thermal

Belt – Hollows Leather custom color 8 CXL belt

Jeans – Mister Freedom Lot 54 

Boots – John Lofgren Donkey Punchers in burgundy CXL

Description: They look good together.


Mister Freedom Ranch Blouse:

This was a game changer for me, it set me on the course for more of a heritage style and fit on jackets having previously worn a longer type 3 jackets. This meant I was tucking shirts on a consistent basis, going for a higher rise jeans and trousers and selecting other garments that worked well together.

The modern interpretation of a denim blouson is also very unique in the niche scene where people are looking for exacting repro’s. For me this is Christophe Loiron’s masterpiece and probably the garment most people identify with the Mister Freedom brand.

Merz B Henley:

I always wear an undershirt, and I have found the Merz B, henleys to be the best both from a style and quality standpoint.

Warehouse Chambray:

When thinking of shirts,  a chambray has to be the ultimate choice in my mind. It is something I wear all year round and is great on its own or layered. It is also the most versatile shirt and pretty much goes with everything.

Warehouse Sweatshirt Oatmeal:

A classic sweatshirt for those colder days is a must and this particular neutral colour is a favourite. Warehouse make my favourite sweats, they are a nice mid-weight and have a great overall cut on them hitting me at belt level which I like. They also wash well and maintain their shape.

Buzz Rickson Early USMC Fatigue Pants:

I know it might sound crazy to not pick a pair of jeans but I thought about it long and hard and the overall fit is more important! These fatigues are my go to pair when not wearing jeans and HBT fabric is always a favourite of mine and which I’m drawn to.   The cut on this pair is also probably one of the best I have seen. It’s well balanced and proportional which makes an easy pair to wear.

John Lofgren Donkey punchers MTO:

These are my favourite boots in my lineup. I love a logger boot with its lace to toe nature. It makes it a hell of a comfortable boot which I can wear all day long and not get tired of. Great for hiking, walking around town or in the motorbike these have served me really well the last few years. This particular makeup was an MTO with Standard and Strange and is a two tone black and olive CXL which gives them a pretty distinct look.


If I had to pick one kit to be stuck on a desert island with it’d be the following:  

Himel Avro Jacket, Black Sign henley, Mister Freedom lot 64 (Okinawa denim), and my John Lofgren x Standard & Strange Devil’s Causeway engineers.  

Let’s start at the feet.  Nothing can make or break a kit like the shoes.  And there are few kits in my collection that don’t look best with the Devil’s Causeway.  They are my first and only pair of Lofgren engineers and I’ve been absolutely thrilled with them.  The design is very classic and the fit is on point.  What really sets these apart from the rest of the boots in my collection is the leather.  The Horsehide on these is an awesome reddish brown with an incredible amount of 

character.  I love how different they look in the sun vs. the shade.  As with much of my current favorites I slowly came into the engineer game and really preferred lace up boots.  But once you try a pair of engineers there is just something about them that elevates a kit more so than a lace up.  They’ve only done two very limited runs of these and my hesitation on the first run meant missing out on my size.  The second time they were announced I immediately jumped on them.  For me, I’ve never seen a cooler leather on a boot.

The Mister Freedom Lot 64’s I’ve had for years now.  They were my first straight fit jean in my collection as I was wearing slim tapered religiously at that point in my life.  They got a little wear here and there for the first year of ownership until I started to gravitate toward more classic fits.  Since then they’ve been my favorite jeans as, for me, they are a fantastic cut that is still slim enough to be flattering while maintaining a classic silhouette.  The denim also has a ton of character and has really come to life over the past year or two as they’ve become my main pair in the rotation.  Christophe knows how to design a damn good pair of jeans.

Over the past year I’ve slowly amassed a solid collection of cream colored henleys and tees.  And my most favorite is the Black Sign 1920s Amish Henley.  It comes in a nice trim fit, has a great weight to the fabric, and has plenty of subtle details that really make the henley stand out.  The henley is so versatile it really can work with just about any kit, but most importantly, it looks fantastic with a leather jacket.

And that’s really what this kit is all about.  The jacket.  I wanted a Himel Avro for probably close to a decade (ever since I first saw a photo of it it has been the jacket, my ultimate grail piece).  Roughly six months ago I was finally able to get one.  I had the jacket made to measure and the results blew me away.  I love it.  Nothing else in my collection comes close in comparison.  The materials, pattern, and construction are stellar.  It’s one of these pieces that when you get it in your hands you can feel how much thought and care went into designing and constructing it.  I love wearing it and there is no way I’d want to be on a deserted island without it.


Jacket: Glad Hand & Co Migrant Coverall Jacket

The jacket is inspired by the 1930s French hunting jackets, the fabric is a perfect match and the “animal buttons” are an insanely cool touch. 

Watch: 1963 King Seiko 1st Model Ref 15034

I bought this watch as a kind of a gift to myself for moving to Japan and being able to find a job. Even though it’s not pictured in many of my photos, it is always on my wrist. It’s one of my most cherished possessions with a really rich history.

Top: Buzz Rickson’s Chambray Work Shirt

The Buzz Rickson Chambray Work Shirt is probably my favorite shirt to wear, super comfortable and holds up to all different types of weather.

Pants: 1950s Canadian Military Battle Dress Trousers

These battle dress trousers are by far my favorite pants, they fit me perfectly and have the perfect rise that I’m always searching for when I’m on the hunt for high rise trousers.

Suspenders: 1940s French Military

Suspenders: 1940s French Military

I have quite a few suspenders but these are the ones I always reach for, they just have such awesome character and match perfectly with everything I wear. 

Boots: Rolling Dub Trio “Boys” Button boots

These boots are easily my most worn in the past year. They have a well designed side zip that makes taking them on and off a breeze (which is super important in Japan). They’re also designed after the early 1900s Button boots that I’ve always been a fan of, but the real ones just aren’t very practical or comfortable. These boots combine the best of both worlds, in my opinion. 


It’s a little difficult to have a “cartoon character” outfit here in Japan since the weather is so different depending on the season. If I were to wear something too heavy, I’ll have a heat stroke in the summer, but if I wear something too light, I’ll freeze in the winter. With that being said, I think this outfit is something I can wear in all four seasons and be okay. I chose these particular pieces because one, they’re the pieces I probably gravitate to the most and two, it’s the perfect blend of my favorite types of clothing which are actual vintage and really well made vintage inspired garments.


Admittedly, I had a pretty hard time with this.  I rotate through clothing pretty frequently, and while I feel like my style has some pretty consistent elements, there are days that I feel I lean hard into the casual spectrum, and other days where I put together more Ivy-inspired fits (although I’ve been slacking on those lately).  I tried to think of some items that I’ve worn consistently, or at least ones that I’d pick the most given the chance.  It ended up being a little jumbled, but I think it works out.

Jacket – Taylor Stitch Cuyama

This is just a really good jacket, and I think it’s one that has become pretty recognizable on my feed.  I’ve worn it in casual situations, dressed it up for work, and a number of fits in between.  It wears well, it looks good, and I like how I feel in it.  If I had to pick one jacket from my closet, I think it would be this one pretty consistently – and I’m a very, very big jacket guy.

Second/Mid Layer – Dehen Cardigan

I’m a big layer guy, so it only makes sense to include a layered fit here.  I had a very hard time picking a mid layer.  I’ve come to realize that at this point, I’ve been wearing a hoodie about 75% of the time – so it probably would have made more sense to pick one of those (my current favorites are by 3Sixteen and American Giant).  However, if I’m only getting one mid layer going forward, it’s gotta be one that I can wear in a lot of situations – and a cardigan from Dehen 1920 is a great fit.  It looks good on its own, and it works well with the Cuyama too.

Shirt – Orslow Chambray Workshirt

I don’t really think that I pull one collared shirt out from my rotation very consistently, but this one is a great choice for a huge number of situations.  Work shirt styles wear casually extremely well, and I’ve actually thrown a tie on this one before to dress it up (slightly).  I think it would work well on its own or under either of the layers I mentioned above.

Tee – Taylor Stitch Heavy Bag

Had to include a tee shirt.  Had to.  I don’t consider myself much of a tee shirt snob, but I like my tees to have a little weight to them.  The heavy bags that I’ve gotten over the years from TS have held up well, have a nice drape, and definitely don’t feel flimsy.  I’m sure there are better tees out there, but I find myself reaching for these pretty consistently.  Honorable mentions are my 3Sixteen Heavyweight tees and my Taylor Stitch merino tees.

Pants – 3Sixteen CS-100x

Had a very, very tough time deciding whether or not jeans were the right call here – but honestly, these are my favorite pants by far and it just made sense to pick them.  They’re jeans, so they can only work in so many situations, but honestly, the fit, construction, and style of these is just too good to not choose here.  Honorable mention is the OrSlow Fatigue.

Shoes – Whites Boots Stevens in Natural CXL

Again, pretty tough choice here considering I have a large, large number of boots and shoes.  My Stevens boots by Whites are “rugged” enough that I’m not worried about getting scratches or scuffs on them, but dress up super well and can elevate a number of fits.  This was probably one of the hardest categories for me to pick – so honorable mentions include Whites Ramblers, Whites MP-Sherman, and Thursday Chelseas (seriously).

Hat – Baseball Cap by Ebbets Field Flannels

It was either a baseball cap or a watch cap here, but I’m going with the vintage/ivy look from Ebbets.  I have a few different ones from them, so I’m not sure which one I’d pick honestly – at the time of writing this, I have a replica 1957 University of Connecticut hat on the way, which probably would get my pick overall.

Watch – Bremont A10 Series Watch

Honestly, the easiest choice of the list for me.  I just got this watch from my dad, but it’s easily one of the most important items – not just clothing- that I own.  It’s based on the U2 model watch that Bremont makes, but it’s a limited run that was only offered to pilots who flew the A10 Warthog.  It has his call name and logged flight hours engraved on the back, and, of course, it’s gorgeous.  I’m going to treasure this thing forever.


Like many others, my style has changed a lot over the years, but I still like garments that are versatile.

Paul’s Hatworks x AB Fits Lightweight Beaver Fur Open Crown Hat

The hat is extremely comfortable and easily shaped from bowler to fedora. It can also be rolled up for travel which is a huge plus. The dress weight beaver felt is great for San Francisco Bay Area weather.

MHL French Deck Jacket w/ Custom Alpaca Liner and North No Name Patch

I love Margaret Howell’s minimalist patterns and I love deck jackets. Deck jackets are typically way too warm for the area. MHL’s take has a really clean design with removable liner and faux shearling collar which solves that issue for me. Originally it came with a thin wool vest liner that did pretty much nothing for warmth and I eventually found a nice alpaca fabric from a luxury teddy bear manufacturer and had a liner made from that – now it’s absolutely fantastic in colder climates. I also had a North No Name ‘Stanky’ patch added to the back. It’s lightly waxed which makes it great at resisting noodle splatter and it manages to have an inner chest pocket that’s usable with and without the liner. I love how practical this jacket is, and how this version has no buttoned placket for a more streamlined look.

Freewheelers Delta Blues Shirt in Gray Check 

I grew out of my Neal Cassidy and needed a replacement. I quickly fell in love with the texture, weight, and pattern of this shirt along with it’s large shell buttons.

Rolex Submariner

A hand-me down from my dad. It’s the classic Rolex. I’m not super into watches though. I had the bund strap made for it from Horween CXL by Greg Spitz of 922 Leather. It makes it much more comfortable for me to wear since I have a really small wrist, also it just looks cooler to me.

Belafonte Ragtime Clothing Belt

I wanted a black tea-core belt to match my boots and this fits the bill. It’s the perfect width for me and I like the buckle. Not much more to it than that.

Mister Freedom Mechanic’s Trousers 2×1 Denim

I like the darker shade of blue these trousers have and the roughness of the 2×1 weave. The trousers also have side cinches that work well for me. The ankle pocket is also oddly useful – I’ve been using it for either keys or hand sanitizer!

Makers Vinch Italian Horsebutt Boots

Selecting that ‘one outfit’ was really difficult for me, but one thing was for sure, these boots would be on my feet. I first fell in love with black tea-core horsebutt field boots from The Real McCoy’s, with their N-1 field boots. Except, I wanted something taller, with a soft-toe, with half-soles, and a woodsman heel. There’s actually not that many choices that meet all of those except for the Makers Vinch. They also have a soft heel which is really interesting. These lace-ups are based on their engineer boot last, so the shaft is rather generous for a lace-up, but somehow it just works for me. It’s crazy comfortable and my gait feels really natural in these boots, more so than any other. The leather is a bit irregular with scratches and bitemarks, but it also has a really nice sheen. In certain light, there’s a beautiful gloss, and in other light, it can look very matte. The boots have a lot of character that I really enjoy and they keep getting better.


Hat: At Last & Co. Salt & Pepper Newsboy Cap

Ever since getting my first newsboy cap a few years ago I’ve steadily begun choosing to wear them more frequently over baseball, mechanics style & beanies. They just have a classier feel to them. To me, At Last makes the classiest clothing in the heritage scene.

Jacket: Freewheelers Brakeman Coat in Tatanka Brown Horsehide Leather

The Brakeman coat was the first Freewheelers leather jacket that I acquired. The thing that I love about this jacket is that it is all leather, and has those big panels. You truly feel like you’re draped in Shinki goodness.

Vest: Freewheelers Conductor Vest in Indigo Wabash

One of the things I love about Freewheelers is that they often offer clues to fabrics that pair well together. For instance, the interior pocket of the Brakeman coat is lined with a wabash fabric. This indigo wabash vest plays well next to the Tatanka Brown Horsehide of the coat.

Shirt: At Last & Co. White Button Up

It’s a single pocket white button up that fits the style. I think that every great fit has an item or two that do not overwhelm or distract from the more extravagant pieces in the look.

Belt: Hollows Leather Natural Chromexcel Belt

This is a thin leather belt with a brass buckle. The thinness of the belt gives it a really classy look.

Pants: Freewheelers Prospector Overalls

These are probably my most worn pair of pants. They are a wide leg early 1900’s style with a cinchback waist. I mostly love the wideness of these pants because they give my fits the proportions that I am looking for. The Brakeman in particular looks best with wide leg pants.

Boots: Clinch Brown Overdyed Engineer Boots

I often describe Clinch as boots that look like they were crafted by a master bootmaker from the 1930’s. I feel that description fits this pair of engineers well. As a bonus, the overdyed Horsebutt leather is a near dead match with the Tatanka brown of the jacket.


The items in the fit

My The Rite Stuff white tee

Red ‘Two Ears Brand’ Bandana as an accessory 

TCB 40’s denim 

Wesco ‘Mister Lou’ engineer boots in brown 


I think the simplicity but understated beauty of the items I picked would never get old for me. Maybe I’m a bit basic, but I love simple silhouettes and fit is king for me. So having my nice fitting, high quality pieces that I love and find very comfortable would be ideal if I was picking an outfit to be stuck with permanently. Maybe a coat in there too for some special wintery scenes or episodes of this made up cartoon!

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