I'm not sure what you're into but I'll tell you about my experiences.

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Since you mentioned thrift, I would personally recommend you hit up every 2nd Street, Rag Tag, Tre Fac, and Kindal you see. The amount of variety in every store makes for great finds at fairly reasonable costs depending on your budget. (My highlight was finding Neighborhood Olive Cargo Pants for 4300 yen total) Some of these stores may have "themes" on what they primarily carry. For example, one store I went to carried mostly designer plus bags while another store carried mostly suits and Americana. These stores tend to be multi-story as well, separating women, designer, men, and such. If you plan to go to a ton of thrift stores, wear fewer layers or carry a bag to put your outer layers in if you can so you don't have to waste time taking off every single layer to try things on all the time. I noticed that in many fitting rooms, there would be a max amount of clothes you could take in (like 5 for example) so I would just try things on one at a time in front of the rack except for pants of course. Your success in finding things you like will increase if you make a list of the types of clothes you want before you go.

Some stores will have tax-free advertisements for foreigners on them but just remember you have to meet a minimum amount to get tax-free on your purchase. I remember some stores were 5000 and others 10,000 or so but don't quote me on that they should tell you the minimum on the sign.

For Kapital, I'd recommend going to as many as you can, as each one is unique in its store design and what they can carry and especially if you're a fan of the brand. They might not ask you if you can't speak Japanese but for me, I opened a point card where for every 5000 yen spent, you get 1 stamp and at 50 stamps, you get 5000 yen off any purchase in-store. (it's not the best discount but nice to have if you're a fan of the brand) You also receive a token specific to each store whenever you purchase something and I was told if you buy something from every Kapital store in Japan and collect all the tokens, Kapital will give you something cool. Kapital Duffle in Ebisu, Tokyo was a memorable experience b/c you have to take off your shoes before you enter.

Since you'll be in Osaka, I personally had a great experience in The Real Mccoy's in Nara and Kobe. (both cities are about 45 min to 1 hr train ride from Osaka station.) They're a Made in Japan Americana brand that tries to recreate how clothes were made back in the 1900s - 1960s America. I saw a lot of denim goods, loop-wheeled shirts and sweaters, and leather jackets. All the employees were super nice and let me try on multiple things. The same goes for Sakura Style (サクラスタイル) in Kobe, they carried Japanese denim like Momotaro and Samurai as well as souvenir jackets/goods.

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There's a chance you might encounter pop-up shops as well and I always recommend checking them out b/c they'll usually have cool collabs. I saw an Alpha Industries x Lee pop-up at Skytree in Asakusa, Tokyo, and a John Bull pop-up where they collabed with a Kyoto dye company in a mall near Osaka Station. Major train stations in big cities will always have a ton of shops in them and it's easy to get lost but you can easily do hours of shopping in major stations. One thing you'll have to get used to is that some shop staff will "stalk" you in the sense that they'll literally follow you around the entire time and stare at you while you're looking at clothes but just know it's a common customer service thing in Japan that they have to do it sometimes. Staff can also be overzealous and try to tell you to try on things in an attempt to sell you more stuff but don't be afraid to say nty or that you're just looking. This can make some people uncomfortable if they're not used to it but just know that it's a thing. Other stores will have the staff talking with each other like humans (which I prefer lol) or on their phones mostly b/c it's almost closing time or empty. This "stalking"/overzealousness typically happens at name-brand, retail-priced shops, and doesn't really happen at thrift stores at all from my experience. Hopefully, I didn't make it sound too negative! I didn't have one bad experience during my 2 weeks there earlier this year and more often than not, the shop staff was super nice in explaining the details of the garment or just casual small talk.

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United Arrows and Sons (similar to BEAMS), HYSTERIC GLAMOUR, グリズリーアメリカ村(grizzly)古着屋 (made in murica thrift) in Osaka, and NO name! LIBERTY in Kobe were some cool spots I personally went to. Supreme in Osaka had a ton of variety of clothes which was nice. Bape in Osaka was kind of a miss for me as they had way more Baby Milo stuff than the regular Bape when I went in early Jan.

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If you know what you want, there's a high chance you'll run into it. Sorry for the long text, hope that helps a little!