Hello! Thanks for the question!This question falls under the “how formal do you want your kimono kitsuke to be” category, I think.
There are really two major schools/branches of kimono these days, like so many other Japanese crafts (like sushi!). There’s the Formal ©, Correct ™, Traditional © way of wearing kimono, that is proper and serious for things like tea ceremony, coming-of-age ceremony, 7-5-3 Festival, formal family portraits and kimono school.
And of course there’s the modern fashion branch of kimono (just like a California Roll) that’s just as valid, it’s just modern, creative and completely understood to be worn as a fashion choice.

One really quick way you can signal that your all-black yukata (and black is a very valid yukata choice, see here: https://lifulu.shop-pro.jp/?pid=78345074&view=smartphone) is for fashion is in the treatment of the accessories. Fluffy, fashionable obi, a hat, hair accessories, purse, jewelry, all will show that of course you know all-black is uncommon and you’re OWNING IT.
Compare to this all-black furisode that, by all laws of Traditional Kimono, should not exist: (https://sokid.exblog.jp/29242002/)

It’s absolutely stunning, goth and looks fresh as hell!
As you can see, it’s absolutely acceptable as high fashion (or High Fashion, if you will), so have confidence and show that you know precisely what you’re doing and subverting it with grace and purpose. :)
Thanks again!
Yes, it will be quite difficult! Kimono are cut in a shape that you could describe as a “column”– absolutely flat, intended to be worn absolutely flat. The obi should properly be the widest point of the body when seen from the side, never the bust. And if your waist is slimmer than your hips and ribs, the obi will collapse, wrinkles will form above and below it, and there will be too much fabric, the collar will slip etc. What to do?
Put simply, everything is either bound or padded!
Wearing kimono is never as simple as throwing a kimono on over a slip (unless you’re wearing a male kimono). If you have a bust, it’s bound–traditionally with a long roll of cotton fabric, these days with a binding bra.

(Image here http://xn–4buq53cmyl.xyz/240.html)

(Bra available on Rakuten )
What if you have a waist?
You gotta wrap it up! People use a dishtowel or a face cloth to pad the small of the back, the upper chest, shoulders or ribs as needed. Check out the following diagrams at https://yukatamusubi.com/contents_02.html .





Further instructions for padding here: https://yukatamusubi.com/contents_02.html
If that sounds pretty hot and slightly uncomfortable, you’ve put your finger right on it. Kimono is definitely suitable for cold weather! You’ve got layers of silk, cotton and towels wrapped and tied tightly around your whole body. Of course, this padding and arranging is used primarily for very proper kimono, in formal situations, when you can’t afford a single wrinkle. But when you get it just perfect it’s great!
You can always get a proper binder MADE for flattening the chest! As with all binders, make sure to take it off now and then, massage, stretch, etc. They have options in lots of colours and price ranges, many as little as $20-35, cheaper than a regular bra and WAY cheaper than a fancy ‘kimono bra’!
DO NOT USE ACE BANDAGES. They are NOT the same as sarashi, and can cause a lot of immediate health problems.
You’re darn right!
Kimono bras are typically designed for small chests (around an A–B cup) and made of many layers of padded cotton quilted through in a vest. They often have some extra padding at the upper breast (as seen below in the moon-shaped cushions) that will smooth the front of your chest so it doesn’t dip down toward the bustline. The kimono collar will lie flat and diagonal up toward your throat. There is also some padding on the shoulder straps.
In some cases you may still have to add a towel around the collarbones or shoulders, depends on your body.

This is one of the cheaper kimono bras with padding I found during a quick Rakuten search, but as @thurisazsalail mentioned, if you need more serious binding power, you should get an actual binder or sports bra!
Many people also recommend the classic Underworks binder though that one is made of nylon/spandex and gets very, very sweaty. A good sports bra can do wonders for you and is less restrictive. I know there are many other brands out there (try asking cosplayers and transgender people, who know!) so do lots of research and pick one that fits your needs.
When choosing a binder or sports bra, pay attention to the materials it’s made of, size CAREFULLY (do not choose a size smaller than the sizing charts on the site, even if you’re tempted– usually the sizes measure around your ribs, and wearing a binder too small can hamper breathing and even cause injury), drink water, move slowly especially at first, and take care of your body! :)
This is a difficult question that could probably be more accurately answered by your local community (considering the local ethics, sentiments etc. around Japanese culture and how people are likely to react).
When making a decision like this, you should consider things like:
1. Will other people likely be in kimono? Will you look like an organized group (such as a kimono display/explanation event), or perhaps will enough kimono be present to not look out of place?
2. Will the other people at the con be able to tell the difference between a regular kimono and a cosplay costume? If not, can you explain it many times?
3. Even at weddings in Japan, kimono are very rare. When I attended a wedding with about 150 guests only 3 people were in kimono, all of them women. It’s an uncommon thing for Japanese people to wear kimono in Japan except yukata at festivals, or a rented furisode for graduation or your own wedding, or very specific traditional-culture events (koto, tea ceremony, workers at certain bars, etc). When a kimono is spotted “in the wild” people tend to react with excitement. :)
4. It’s got to be mentioned– is there a worry of cultural appropriation? Again, this is best decided by analyzing your own local culture and community to find out if wearing a kimono will be tolerated, celebrated, reviled, rejected, or enthusiastically accepted. I’d also put it out there that kimono in and of themselves are not a religious or holy garment.
5. Although kuro tomesode are formal and intended for married people, many kimono teachers & enthusiasts have told me, “kimono are meant to be worn!” They don’t do any good laying in a box in your closet! Can you provide educational answers to curious passersby and spread good info and the love of the craft of kimono?
In the end, I’d say that a kuro tomesode would be ‘way overdressed’ for a con, and a yukata would be tonally appropriate, but on the other hand, if you are wearing it as a demonstration piece to show people a beautiful example of Japanese textile they’ve probably never come across, that educational opportunity might be too good to pass up. Again, consider carefully the culture around you and other people’s feelings when encountering a flagship example of Japanese culture, and do your best to conduct everything with care.
Best wishes!
Yes, it will be quite difficult! Kimono are cut in a shape that you could describe as a “column”– absolutely flat, intended to be worn absolutely flat. The obi should properly be the widest point of the body when seen from the side, never the bust. And if your waist is slimmer than your hips and ribs, the obi will collapse, wrinkles will form above and below it, and there will be too much fabric, the collar will slip etc. What to do?
Put simply, everything is either bound or padded!
Wearing kimono is never as simple as throwing a kimono on over a slip (unless you’re wearing a male kimono). If you have a bust, it’s bound–traditionally with a long roll of cotton fabric, these days with a binding bra.

(Image here http://xn–4buq53cmyl.xyz/240.html)

(Bra available on Rakuten )
What if you have a waist?
You gotta wrap it up! People use a dishtowel or a face cloth to pad the small of the back, the upper chest, shoulders or ribs as needed. Check out the following diagrams at https://yukatamusubi.com/contents_02.html .





Further instructions for padding here: https://yukatamusubi.com/contents_02.html
If that sounds pretty hot and slightly uncomfortable, you’ve put your finger right on it. Kimono is definitely suitable for cold weather! You’ve got layers of silk, cotton and towels wrapped and tied tightly around your whole body. Of course, this padding and arranging is used primarily for very proper kimono, in formal situations, when you can’t afford a single wrinkle. But when you get it just perfect it’s great!
Hello, thanks for the ask!
About 8 years ago, I met Mod2, who was taking Koto lessons at the time here in Nagoya, and she introduced me to kimono kitsuke. For the nest 2 years she and I practiced kimono regularly, wearing them on weekends and shopping for used kimono at various shops in Nagoya. At the time my collection was at its largest (about 25-30 kimono and a similar number of obi), and also helped friends dress in yukata and kimono, so needed many to loan out– but later, I whittled it down to just several pieces of male and female kimono each. Now I keep some iromuji and some komon kimono for my partner, one furisode, and 3 or 4 male kimono. They’re very reasonably priced if you can get them in the used shops, the trouble is storage space! >_<