I have some vintage and early 2000s pieces that have wonderful leather. Some of my favorites are:
1. 2010 Poppy. This is surprising because it was
Coach's budget priced line. This is my sapphire Poppy Spotlight which has the softest, smoothest, slightly sparkly leather.
2. 2009 Parker. This leather was called gelato leather is super squishy and soft.
3. 2007 Bleecker. I absolutely love this collection. The leather is burnished and has a smooth sheen.
4. 2006 Legacy. The leather on these almost glows. This is a favorite among Coach collectors.
5. 2004 Tortilla bags. These are made of lambskin and you can't get any softer than that.
6. 2013 Madison pebbled leather. My Isabelles are soft and squishy, and have the most wonderful leather smell.
7. 1999 Rambler's Legacy. With older bags, the location of manufacture makes a difference. US, Costa Rica, Hungary, Turkey and Italy are some of the best. Anything made in the mid to late 90s through 2002 in those places is probably going to have nice leather.
8. 2006 Sonoma Natural grain. Very soft thick, pebbled leather.
9. 2013 Legacy pebbled drawstrings. Very thick pebbled leather.
The worst leathers I've seen are some of the classics produced in the last few years, the made for factory Zoes made in 2012-2013 (but my 2009 MFF Zoe is wonderful), anything with cross-grain leather... The 2012 Legacy duffles looked and felt nice but didn't hold up, but I still love them. I'm not thrilled with the leather on my 2013 archival Rambler, but I love the leather on my 2012 Legacy bucket bag.