After a night of searching to the ends of the internet, I have come up with the following. (I will include some messenger bags too because some people might define saddle differently)
My two favorites choices that I will submit for the challenge are -
Rugby Leather Saddle Bag
Rugby is a line by Ralph Lauren, which is known for their classic polo design. It would only make sense that they can do a saddle bag right. Here, Ralph Lauren did a well-made a classic saddle bag which just the right amount of detail on the flap and a tan color that is very versatile. This is a bag you can definitely carry through the summer into fall. It is a steal at $159.99.
See by Chloe Yate Leather Messenger bag
I have a love-love relationship with See by Chloe. It all started with Chloe where I developed a love for their supple leather handbags with the high price tag. You can imagine how excited I was to find out Chloe will have a little sister! See by Chloe always puts fun details into their products, which makes it very easy to recognize. Their quality is amazing for the price. I have a wallet from them that I have used for the past 3 years, every single day, and it is still in very good shape. Here is a messenger bag that displays all those qualities of a See by Chloe bag - nice leather, fun detail of the bows, and amazing price. At 50% off, it'll go very quickly!
Buy it via Net-a-Porter.com for a sale price of $237.50
If you have slightly different criteria, maybe one of the following will fit your needs.
Rough Roses pumpkin leather 'Riley' Messenger Bag
Buy it via Bluefly.com for $199.99
Rebecca Minkoff almond leather 'Mini Rikki' Crossbody Bag
Buy it via Bluefly.com for $285
MARC BY MARC JACOBS Classic Q Natasha Crossbody Bag - available in multiple colors
Like See by Chloe, Marc by Marc Jacobs has a special place in my heart.
Get it via Bloomingdales for $348
Melie Bianco Miley
Not leather but cute for the price of the bag
Get it via Piperlime.com for $68.99
MICHAEL Michael Kors 'Medium' Messenger Saddle Bag
Get it via Nordstrom for $228
This was fun, so if anyone has something that they need to find, I would love to help to the best of my abilities! :)