I've been really happy with most of the stuff I've bought but here are a 5 that stand out.
1. Garmin 220 - I love this watch! I got it as a birthday gift from my parents about 6 months after I started running. I had been using Runkeeper up until then but it was pretty inaccurate as my runs got above 3 miles. The watch has been trusty and reliable and is still holding up well more than 2 years later.
2. Flip Belt - I love my flip belt and in fact, have bout it again since I thought I had lost mine at one point. It is comfortable and holds pretty much everything I need while running. It fits my Iphone 6 with no problems and nothing has ever fallen out.
3. Saucony Guides - shoes are obviously very personal but these work really well for me. And I have bought them multiple times since I keep replacing my old pair with a new pair of Guides.
4. Rain jacket - I love this jacket. It's great for wind and rain, and it's convertible into a vest. I took off the sleeves mid run one day and the sleeves tied easily around my waist and didn't fall off or loosen at all. I really wish I had had this jacket during the RnR DC half in 2015 when it rained the whole time.
5. Under Armour Marbella sunglasses - these have also lasted more than 2 years. They fit so well and I never have to push them up while running. They also fit on the top of my head while running and don't slip so they're great for those days when you may need sunglasses for part of the run. And somehow they manage to still feel comfortable and never tight. I was worried because they're expensive and I have a problem with losing sunglasses, but I've kept a tight hold on these because I love them so much. I would be sad if I lost these. and would definitely look to buy them again.
So those are my five things I'd buy again, and have in some cases :) Any favorites you have that you'd buy over and over?