I also own both bags, and I agree, it's a really, really tough choice. These bags both fill different holes in my collection.... the Jumbo is very classic, elegant and timeless, while the Boy bag is young, fresh and a bit more edgy. I can only recommend to really take a look at your wardrobe, which bag leans more towards your daily style? Also, if you're leaning more towards one bag over the other, definitely go with your heart. I spent years desperately wanting a Jumbo, but ended up going for another style (the Easy Jumbo) that looked very similar, but was at a much cheaper price-point. I instantly regretted it, sold it a few years later, and eventually bought my Jumbo. I should have followed my heart in the first place. Lastly, functionality is important. Choose the bag you think you'll get the most use from, and what you think will be a durable choice for your lifestyle. I recently sold my lambskin Square Mini because I was scared of how delicate it was and bought my caviar Small Boy Bag instead. It's way more suitable to my lifestyle, and will get a lot more use because I won't be so paranoid to use it. I hope some of those points help you make a decision. Let us know what you decide!