I was unfortunately not able to compare these two very similar totes side by side since I ordered the Madewell Tote first, didn't care for it so returned it and then purchased the Cuyana Classic Leather Tote. But here are some of the similarities and differences I noticed between the two bags (also you can read a whole reddit forum discussion here).
First the dimensions: The Madewell Transport Tote (in black, with tan handles) measures 14.25(h) x 14.25(L) x 6(w) inches with a 8.25 inch strap drop. The Cuyana Classic Leather Tote measures 13(h) x 18(L) x 5(w) inches with a 9 inch strap drop. So the Cuyana tote is a a little shorter, but a lot wider. However, since the leather on the Cuyana bag is so soft and smooshy, it's quite easy to fold in the sides a bit to make it less wide (like the picture below).
Though the totes are really similar, here are the reasons why I think the Cuyana tote is better:
-First off, the leather on the Cuyana tote is amazing. It's super soft and smells wonderful. The smell reminds me of the leather of Balenciaga bags, even though the textures of the leather are different. The leather on the Madewell tote is stiff and feels and smells like cheap leather.
-The difference in the leather is probably due to the fact that the Cuyana tote is made in the US while the Madewell tote is made in China (plus Cuyana is a brand all about producing top quality items).
-The strap of the Madewell tote is a just a tiny bit shorter, but it can make all the difference when trying to wear a tote bag over the shoulder when wearing a winter coat. I think the Cuyana bag might fit, while the Madewell tote most definitely wouldn't.
The Cuyana tote also comes in 3 different variations: the classic, the tall tote and the zippered tote.
So as you can see, my vote clearly goes to the Cuyana tote over the Madewell tote. But if we were to have a broader discussion about all the totes that I own (including the Mansur Gavriel Tote and the Everlane tote), I would have to say my favorite is probably the Everlane tote. I love the smaller shape, the adjustable straps, and the two deep interior pockets with snap closures. The Mansur Gavriel is good for just piling things in, and it holds its shape really well. I think in general I'm just not a soft tote kind of gal. But if I were to choose one, it would definitely be this Cuyana tote.
Have you guys checked out Cuyana before? I'm in love with their products and their site
I personally purchased all of these totes and were not paid in anyway to make this review (just trying to help fellow-tote lovers!)