It has always been true, that what was old is often once again new. That does not mean it works for everything. Some clothes needed to be discarded as a fashion disaster the day after they were first made. But for some items older pieces called “vintage” fit in very nicely with modern wardrobes. If you really want to make a fashion statement, find something that is about 40-50 years old but still in nice condition, that hopefully you will not have to pay a fortune to buy it. You may have to pay for it in the time hunting to find it in second hand stores, but hopefully you will not have to part with a lot of hard cash. That is the fun of vintage.
Finding it is a treasure hunt. You will have to look through piles and piles of nonsense and mostly garbage to find that rare piece, but if you happen to find it, you will know it when you see it. Pray that it is any size bigger than you are when you first spot it. You can always get it tailored to make it smaller if it is too large for you, but you cannot make it bigger if it is too small for you. You cannot make something out of nothing. What kinds of things can you find that are interesting?
How about old high school jackets, band uniforms, bowling shirts, and definitely all kinds of hats. You may also find a nice tweed jacket, or a sweater that has an interesting pattern. Forget about shoes (except maybe boots) or underwear, those things are best worn by only one person. Whatever you get make sure you dry clean it first before wearing it and of course have it taken in as necessary to fit you properly.
For old high school jackets if there is a name on it of the person, you best remove it unless you want to be called Bob when your name is actually Larry. Band uniforms, especially the jackets can be really cool. Don’t wear the full band uniform, just wear the jacket with a brand new pair of jeans so it looks like you made a fashion choice on purpose. Ties can be re-purposed as well. If you are lucky you will never pay more than a dollar for one and it will be wider than the current trend which is about 3 1/2 inches. That means if the tie is 4 inches wide, has a nice pattern, you can have a tailor take it in, and get it to match current widths that are preferred.
On the West Coast of USA we are very lucky to have many inexpensive tailors associated with the dry cleaners. Many people do not know that they can be invaluable in this effort of repurposing. You can pay for a nice jacket at a second hand store and have it taken in for around , dry cleaned for , so for about fifty bucks you can have a new look that you got for a bargain and have fun while you went searching for it.