There was quite the range of responses! And it helped me realize something. I think a lot of you carry "normal size" by hand or on the shoulder. I am either wearing a dark colored cross body or a gigantic shoulder bag that holds my laptop. I was considering buying a black leather tote to hold my laptop, etc, and obviously it would be overwhelming right *next* to the black leather jacket.
Claire: Monty is the perfect bag to wear with your moto - the pattern/texture contrast makes perfect sense (and I'm ashamed to admit I didn't realize why you picked the name Monty until now)
San: I agree. It's the leather boots that put it over the top for me.
Shiny: I know - I don't want to feel too biker or too cave woman. Wearing different colors of leather is a great solution.
Gaylene: Your rules are the opposite of Shiny's but it makes perfect sense why they work for you. Wearing an unobtrusive bag with a statement jacket is very sensible.
Diana: Aha, a rebel! I will have to pay more attention to the leather components of your outfits.
JAileen: Dark green suede + smooth brown leather gives you enough contrast in my book.
k can shop: No, no, I don't mean to add another item to your checklist
Carole: Post a photo of your jacket with your purse. I for one, would love to see it.
Suz: I know once you have your leather jacket, you'll do a brilliant job of pairing it with the right bag.
BJ111: Thank you for sharing your specific handbag+jacket pairings. That is really helpful! Agree on waxed leather look jeans + leather jacket being a bit much unless you're going for the biker look.
Merwoman: I agree that I can't see matching the color of the bag to the jacket unless it's black. I usually prefer contrasting colors.
Rae: Calf hair - now there's a good idea! (I have a bag with calf hair detail on order)
Kristin: I didn't get Claire's bag reference until your comment, so thank you!
Jayne: I demand outfit photos.
Caro: Another vote for the textured side. Now I really do think I want a suede bag.