I've bought some stuff from realreal. You can always return things if they don't work out. I wanted a new work wardrobe so I bought a fuck ton of stuff from them and returned about half of it because I'm really picky and didn't like how it fit or whatever.
But it's a mixed bag, most of the stuff is not vintage and it's probably only a few years old. Designers also make cheap shit like everybody else nowadays. You have to learn how to tell if an item is quality regardless of its brand or price tag. But you have to see the item to really do it. Though it's generally true the secondhand expensive item is better.
I would buy the bag that you like, though I ask myself the same question a lot. The idea of an expensive bag that holds it's value somewhat is really intriguing. But the area I live in, people kind of look down on designer bags, and I'm not really sold on any one in particular so I don't buy them.
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but thats good to hear about sinner, because i absolutly love the bottles that there in, thank you!
