While writing my latest review for my Onderhoud boots, I reflected on the fact that the real sign of how much I love an item is how much I wear an item and what events I would wear the item to. Actually, this is something I have mentioned in several boot reviews. It is an idea that I always considered in the back of my head, but never really thought about actively. People see pictures of me on Instagram, in my reviews, and on internet forums. These pictures show what I wear at the time, but they are not taken every single day. It may not be clear to everyone, or even entirely to myself, what items I wear the most often and what items I wear when it counts.
I feel that these two measurements best show what my favorite clothing items truly are. The standby, comfort picks and the special items that get worn when I want to look and feel my very best. In this article, I will go over both types of ‘favorites’ for all types of clothing. That includes hats, sunglasses, accessories, wallet, jackets, shirts, belts, jeans, trousers, boots, and sneakers. Hopefully, this will give you an insight into what items I truly love the most and why.
Casual and Everyday:
Hats: This is a mixed bag because I wear quite a few different hats regularly and also style my hair instead of wearing a hat on a regular basis. My most worn hat now though is my custom beaver fur felt Art Fawcett fedora. This was custom fit to my head so it is wonderfully comfortable. If I’m not wearing black, this is usually my go to hat unless I’m dressed extremely casually in which case I will wear one of my baseball caps from Ebbets Field Flannels. My second most worn hat is my Tatton Baird beaver fur hat in silver belly which is a fantastic hat.
Sunglasses: My most worn sunglasses by far are my Oliver Peoples Clifton shades in gold with G15 polarized glass lenses. These are my only sunglasses/glasses that are not made in Japan, so I wear them daily to work because I don’t mind if anything happens to them. They are still high quality though, being made in Italy and having incredibly clear polarized glass lenses. I also still try to take excellent care of them and despite owning them for over 5 years, the lenses still do not have a scratch on them. My daily prescription glasses are the Globe Specs Reggie. These are made in Japan sunglasses that I had regular prescription lenses put into.
Accessories: I used to accessorize far too much. In fact, I’m actually pretty embarrassed when I look back at photos of me and I see how much stuff I have all over me. Now, I just wear my rings from The Flat Head/Real Japan Blues and my keychain from The Flat Head that has a couple of silver dice that are also from The Flat Head, my keys, and a leather fob from Wild Frontier Goods. To be honest, I used to over-accessorize so I could feel like I looked cool and stood out, but now that I’ve lost weight, I’ve gained enough self-confidence to feel that all of that is unnecessary. When it’s enough to need a scarf, the one that I use the most is my burgundy scarf from Marumasu that I bought in Tokyo during my last trip there. It is made of tencel fabric, making it warm enough while being extremely soft and comfortable.
Wallet: Right now my most used wallet is my Wild Frontier Goods Makimono wallet. This is a great little wallet that fits everything from bills, to cards, to even coins. It’s small enough to bring to work easily while also carrying everything I need. I also just think the design is really cool. When travelling, however, I would use my Mill Handmade Japanese wallet as it fits more cash and coins.
Belt: This depends on what boots or sneakers I am wearing because I do match my belt to my boots as well as I can. This is also difficult because I have lost enough weight that my belts are not fitting me as well and many will need to be replaced. Right now, I wear my Wild Frontier Goods hand painted Kakishibu belt the most often because I love the buckle, it goes with the largest amount of my boots, and fits me the best. My Hollows Leather belts are my other favorites. I need new ones because they are too big, but I will be getting replacements from Hollows as I do like his work.
Jackets: OK, now we’re getting to the stuff that you came here for. As far as leather jackets go, I wear them all fairly consistently. They’re all from Freewheelers so I never have to use quality to determine my choice because they’re all from the best leather jacket manufacturer in terms of design and quality and all have leather from my favorite and arguably the best tannery – Shinki Hikaku. Even the deerskin is from Shinki. If I had to pick one that I wear the most, it is probably the Sunset in deerskin. It’s my favorite design and it is so incredibly comfortable that I reach for it the most often.
In terms of my other jackets, these usually get worn when it’s too warm for leather jackets. The most worn are my Conners Sewing Factory WWII Type I jacket because I love the unique details of it and it is the denim jacket that I have had the longest so I would like to get it to fade some more. My other most worn cotton jacket is my LVC Triple Pleat Blouse. The design of the jacket appeals to me greatly due to its vintage, yet casual look. However, the reasons that I wear it so often now is because it is so light at 9oz and the fact that it fits me so well. The fact that I’m not very tall and that I wear high waisted jeans and trousers with my shirts always tucked in, short jackets work best with my wardrobe, making this jacket perfect for me. I would say that since I got it, it has been worn more often than even my CSF jacket. Recently I acquired a moleskin cossack jacket from Ooe Yofukuten. This is now my favorite non-leather jacket that I own. It fits me better than any jacket that I own, is beautifully made and designed, and is light enough to wear in slightly warm weather, though I do wish it was a little lighter. Still, it is getting a lot of wear recently.
Shirts: My most worn long sleeve shirts are from Freewheelers. During winter, the most worn one is my Olive Docker flannel shirt. It’s warm enough, but not too thick while fitting very well and being a beautiful olive color. My other most worn shirt is my blue Freewheelers Neal chambray shirt. It is a versatile color, fits comfortably, and is light enough to be versatile depending on the weather. The sleeves are a little too long, but it mostly gets worn under jackets so that does not matter too much.
During summer, my most worn shirt by far is my Flat Head dobby cloth mechanic shirt. This is easily my favorite shirt that I own. It is the perfect shirt to wear unbuttoned over a t-shirt because it is so short and has a flat hem. The fabric is a little warm, but it is a stunningly beautiful dobby cloth fabric that demonstrates just how great Flat Head fabrics are. It has a great ‘50s vibe that makes me feel cool even during warmer weather, which is difficult to do when I can’t wear my leather jackets.
However, none of my shirts get worn as much as my t-shirts and henleys. If you follow me on Instagram, then you will know that I adore ecru henley t shirts. During colder winter days, I wear my Real McCoys ecru thermal henleys which are warm enough while not being too warm, making them good for socal winters. When it’s not cold enough to need those, I wear my Stevenson Overall Co. and Merz B Schwanen ecru henley t-shirts most often. The Stevenson henleys get the most wear because the fit is a little better for me and the fabric has more character, but the Merz one is great too. I wear these by far the most of any of my shirts of any type. While ecru is my favorite, I do also wear some other colors with my most worn colored t shirts being my Mister Freedom Stanley T in Jungle Green and Warehouse t shirt in burgundy.
Trousers: This is hard to discuss because I have lost so much weight recently that I have had to get a lot of new trousers and unfortunately put many of the ones that I used to wear up for sale. Probably my most worn trousers are a pair that I still have, my Mister Freedom Continental Trousers in cacao chambray. They have a nice high rise, relatively slim fit by my standards, which means they still have a leg opening of over 8.5in, and the fabric is a dark brown that is light enough to be worn in summer while also working well with pretty much all of my wardrobe. Something important to point out is that I wear jeans a lot more on “normal” days and wear trousers and chinos more when I want to look my best.
Jeans: This is a no-brainer. For the past 3 years, I have been wearing Conners Sewing Factory jeans consistently, with the most wear being given to my 1937 jeans. I love the details of CSF jeans, so instead of rambling on about them, I will just tell you to read my review of one of my pairs here and go over to the threads on denimbro and superfuture to learn more about them. This will change shortly because I have joined the TCB ‘40s contest on Superfuture and that will start in September and last for 18 months. I don’t even need to show photos of these.
Sneakers: Despite the fact that I mostly wear boots, I do wear sneakers fairly often, especially during times when I won’t be out very long. My most worn sneakers as of right now are my PF Flyers made in the USA in ecru/off white. I really like the slightly chunkier aesthetic of them and that they fit wider than my other sneakers. However, my favorite sneakers are definitely my PF Flyers made in Japan. I love the look of these as the green accents look incredible. They also are my cushiest sneakers. With that said, my personal favorite pair are my made in Japan PF Flyers. I just do not wear them as often because I bought them used so they do not have as much life left in them and they are half a size too small for me.
Boots: At this point, my most worn boots are my John Lofgren engineer boots in natural CXL I have owned these longer than almost all of my other boots, but I also wear them a lot because of a combination of them being extremely high quality and beautiful looking while being easy to put on and comfortable to wear. Also, critically, I don’t care about the leather. I have no reason to baby these boots because I don’t like CXL very much. They are a perfect balance of being really nice, but also not a pair that I feel like I need to put on a pedestal. Overall, engineers are my most worn boots because they take the least amount of time for me to put on. I hate getting ready in the morning so I wake up as late as possible, meaning that I do not have much time to get dressed. Lacing up a pair of boots is a hassle, so putting on engineers is easier. This means that my other most worn boots are also engineers. My Role Club and Wesco Knuckle Draggers are probably my second and third most worn boots because of this. Like with the Lofgrens, they look great, are well made, and are easy to put on while also being boots made out of leather that I don’t like much so I don’t ever hesitate to wear them. The Role Clubs probably get worn a bit more than the Wescos though because I like them a lot more and because they’re more comfortable.
When I Want to Look my Best:
Everything that I have mentioned up to now has been what I wear the most often on a regular basis. However, what I wear to special dates, hang-outs, parties, and events is sometimes a bit different. Some items may overlap, but not all will do so. There are certain items that I reserve for when I want to look my best.
Nothing changes in terms of accessories, wallets, and belts.
Hats: My Art Fawcett hat is still my go to, though perhaps even more when I am really putting effort into my outfit. However, I do often just do my hair instead. Additionally, I never wear my baseball caps when I really care about how I look.
Sunglasses: My most worn sunglasses when I really want to look my best are my Oliver Peoples Victory and Oliver Peoples Benedict sunglasses. These are both made in Japan, so even though the brand is owned by Luxxottica, the quality is still incredibly high with these two pairs. With that said, Luxxottica has made the brand worse lately so I likely will never buy Oliver Peoples again. However, both of these pairs are perfect for me. The lenses are high quality glass and are polarized, and the design/proportions for each are impeccable. I absolutely adore both of these glasses so much that I have not bought new sunglasses in several years because I am just so happy with these. I also have a pair of Globe Specs Cozumel that I wear quite a lot too, though I consider the two OP pairs more special. Interestingly, the Benedicts were originally Alee’s, but she did not wear them much and instead liked to borrow one of my Globe Specs. I used to only wear square or rectangular sunglasses because my face was so fat and round. However, after my face thinned, I was able to wear different glasses so the Benedict aviators started to work better on my face. I traded one of my Globe Specs glasses with Alee and the Benedicts are now mine.
Jackets: All of my leather jackets are Freewheelers as I mentioned so they’re all as good as it gets. However, my most worn when it really counts is still probably my deerskin Sunset. It just works with everything. However, if I want to feel and look really cool, I will probably wear my new San Mateo. For non-leather jackets, my go to for looking my best would easily be my Ooe Yofukuten moleskin cossack jacket. It fits too well and looks too good for me to pick any other fabric jacket. I feel almost as cool as Han Solo in this jacket. I know that I’m not even in the same universe as Harrison Ford in terms of looks and coolness and I never will be, but this jacket gives me that feeling anyway.
Shirts: My favorite shirt to wear when I really care about how I look is my Orguiel shirt. I do not know the exact model name, but it is an ecru shirt with blue vertical stripes and a unique collar shape. The fabric and design of this shirt is beautiful and is definitely a shirt that I reserve for more “important” days. A close second would be my Rite Stuff Atlas shirt in mint/sage green. It is a beautifully designed and made shirt with a unique color that I am quite partial to. It looks especially good with black leather jackets and boots. During summer, that same Flat Head shirt that I mentioned before would still be the one I wear most often. It’s my favorite shirt so it’s a go to for going to the store or for going to an event. The same goes for my t-shirt choices. They are exactly the same no matter the situation. Ecru henleys are always my first choice.
Trousers: As I said before, my collection of trousers is changing due to weight loss. I would say that during the winter my favorite trousers for important days are my Viapiana Custom Harris Tweed trousers. They are beautifully made out of an impressive fabric with deep character and heritage. I love them so much that I will be sending them back to Ben Viapiana to be downsized so they can still fit me instead of selling them now that they’re too big. In cooler weather, my Stevenson Overall Co. salt and pepper trousers were my first choice for a long time, but with many new trousers in my collection now, that could change. I will say that olive green is a color that I wear quite often because I love earth tones. No specific olive trousers are mentioned, however, because I have owned too many pairs over the years and most of the ones I used to wear a lot do not fit me anymore.
Jeans: It’s still CSF/One Piece of Rock no matter what until the TCB contest starts.
Sneakers: I do not wear sneakers to any important event, date, or anything similar.
Boots: This is probably the category where the difference in terms of choices is most clear along with shirts. My top boots for when I want to look my best and feel the most confident and comfortable are my White Kloud custom boots and my two pairs of custom Clinch engineer boots. These are my best made boots for one thing and that is quite important to me. Not only that, but they are also beautiful boots in terms of appearance and design. The White Klouds and brown Clinch boots also have especially nice leathers with the White Klouds boasting cognac minerva cowhide leather from Badalssi Carlo and the Clinch engineers having brown vegetable tanned horsehide from an unnamed Italian tannery. Simply put, these are the two pairs of boots that make me feel like a million bucks when I wear them.
With that said, I have also owned the Brass engineers for 3 years and the White Klouds for 2 years so I have grown quite attached to them. I have some really nice newer boots that I also like quite a lot, so this category could change over time. For black boots, my black Clinch engineers have been my first choice there, though in fairness they were my only choice for quite some time, so again, this may change in the future. Some may be surprised to read that the boots that come after these first three are my Vibergs. They are not well finished, but the design, details, and leather are so incredibly perfect for me that I wear these quite often when I “dress up.” Being a bit more formal in appearance than my other boots helps this as well. Still, when it really matters, It’s the Clinch and White Klouds all the way.
I wrote quite a lot more about this than I thought I would on this subject. Then again, I had no idea what to really expect given how off the cuff this idea was. It was fun to think about which items I really wear the most and like the most. Hopefully the distinction between what I wear on a regular basis vs. what I wear when I want to look my best gives some insight into how I choose my clothing. This was not even a distinction I planned on making at first, but I realized that I needed to. Also, keep in mind that recency bias has to come into play here and I also do not have a perfect memory so treat me as an unreliable narrator. Either way, this was an interesting exercise for me and I hope you got something out of it as well. I suppose the next thing to do is to finally figure out what would actually be what one single outfit I would wear for the rest of my life if I had to choose.
Also, I want to point out that just because I did not mention a lot of the items I own does not mean that I never wear them or do not think they are good. This is just an article about what I like the most.