Even though I buy new clothing I still end up wearing older clothes in which I feel most comfortable.
I frequently go shopping for new clothes but more often then not end up wearing older more comfortable clothing that have been in my closet for a long time.
I buy new clothing all the time but always end up wearing my older clothes.
To convey that one frequently goes shopping but always ends up wearing older clothes you may say that you often shop but nonetheless end up wearing your older clothes that you feel most comfortable in. You may go further and say that they fit more nicely.
comfortable-providing physical ease and relaxation.
fit nicely- To compliment the physique or be flattering on one.
買い物によく行くが、いつも結局古い服を着てしまうことを伝えるには、
you often shop but nonetheless end up wearing your older clothes that you feel most comfortable in.
よく買い物をするが、それにもかかわらず、結局一番落ち着く古い服を着てしまう。
ということができます。 they fit more nicely（よりよくフィットする）と言ってもいいでしょう。
comfortable-身体的に楽でリラックスさせてくれること
fit nicely- 体格にぴったりあうこと
I don't know why I'm buying this. I'll just end up wearing that black dress!
I have so much new clothing but I always end up wearing ***.
This is something that I am VERY familiar with. I often go shopping for something new, but I always end up wearing something that I've had for ages and that I am the most comfortable in!
I always end up wearing the same thing! - This means that you always wear the reliable, comfortable dress/jeans/top that you already have!
これは私も非常に同感します。よく新しい服を買いに行くのだけれども、結局長年着たものや一番着心地いい服を着てしまいます。
I always end up wearing the same thing!
（結局いつも同じものを着てしまいます！）
これは、あなたがいつも既に持っている確かで着心地よいドレス／ジーンズ／上着を着るという意味です。
Even though I usually by new clothes; I always end up wearing my old clothes
Even if I but new clothes, I often end up wearing that I have been wearing for a long time
When you want to explain that even though you usually buy clothes, you always end up wearing clothes that you have been wearing for a long time; then you may explain this in the following way:
-Even though I usually by new clothes; I always end up wearing my old clothes
-Even if I but new clothes, I often end up wearing that I have been wearing for a long time
「新しい服を買っても結局いつも昔から着ている服を着てしまう」は次のように言えます。
-Even though I usually buy new clothes; I always end up wearing my old clothes
（新しい服を買っても、結局いつも昔から着ている服を着てしまう）
-Even if I buy new clothes, I often end up wearing that I have been wearing for a long time
（新しい服を買っても、結局昔から着ている服を着てしまう）
With clothing, I prefer comfort over being pristine
I feel more comfortable in clothing I am used to wearing
Even if you buy new clothes, you often end up wearing clothes that you are familiar with (that you have been wearing for a long time). It's not that you don't like the new clothes, just that the old clothes feel good and you know how to wear them. you can explain this phenomenon by using one of the above suggested comments.
I end up using my old clothes cause they're comfortable even after I buy some new ones.
I resort to my old clothes as they're comfortable even after I buy some new ones.
Whenever I go shopping for new clothes, I always end up wearing my old comfortable clothes.
The phrase "I end up..." or "I resort..." means that 'in the end' or 'conclusion is'.
The word "comfortable" means that is it nice to wear maybe because it's soft or, as you said, know how wear it.
"Whenever" means at whatever time.
"Even after" is used in comparisons for emphasis.
"I end up..." または "I resort..." は「結局は」や「最終的には」という意味です。
"Comfortable" は、着心地が良かったり、あるいはあなたのおっしゃるように、着方を知っている服をいいます。
"Whenever" は「～するときはいつも」という意味です。
"Even after" は物事を比較、強調するときに使われます。
Even if I buy new clothes, I often end up wearing my usual clothes
I buy new clothes all the time but still end up wearing my older clothes
Sometimes the clothes you are use to are more worn so you are used to them and they make you feel more comfortable so might wear these anyway even if buying new clothes
both if the sentences would explain this
南アフリカ 
アメリカ合衆国 
アイルランド 
イギリス 
