J.W. Hulme Mini Legacy Shoulder Bag ($370)

Rating: Trust It! 

I've had this J.W. Hulme Co. Mini Legacy Shoulder Bag for at least four years, which for me is practically a lifetime. I rarely ever splurge on bags, so shelling out $370 for it at the time was a pretty huge deal.

However, whenever I'm going anywhere that doesn't require a laptop, I grab this. The leather truly is buttery—an adjective I rarely use for things other than food. It's practical, made exceptionally well, and just gets better with age. I like to think of it as the fine wine of handbags.

... as worn by Racked NY editor Tiffany Yannetta.