I have a few things from when I was thinner before. My Rupert the Bear trousers (I'm sure you can imagine) are a size 14 and in the last week I have just managed to get them done up, cant breath in them mind and I 'spill' quite spectacularly over the top but the zips up so it counts! Not sure they are anything I'll ever wear out socially again, I loved them at 19 but they're a bit too quirky at 29. But they were definitely a goal.
Another item is a short brown skirt (it's nice but unfortunately the word brown makes it sound blurgh!), again from 10 ish years ago, again a size 14 but still cant get this one done up.
But the ultimate is a pair of Ted Baker jeans I brought from a charity shop about two years back. They were so gorgeous and only 3.99 I couldn't resist. They were a size 3 (not the foggiest, why do they have to try to confuse me?), which holding them up against other clothes in the shop I guesstimated to be about a 14. I thought fine I'll get into those one day (I was a 20/22 at the time). Turns out a size 3 is like a size 12. I've never been a size 12, not since I was about 12, but I am determined I will get in these jeans if it's the last thing I do. Already made progress, can now get them up just about but there's about 6 inches of flab between either side of the zip at the mo. I will do it!