I have wanted a leather weekender bag for the longest time. I love the classic look of them, and the fact that they will always get better with time. With a few trips coming up this year, plus quite a bit of traveling next year for interviews, I figured now was as good as time as any to get one. I had saved up some Shopbop credits, and pulled the trigger on the Madewell Transport Weekender Bag (no longer available at Shopbop). You guys know how much I love the Transport Tote - I've had it for over three years, and still use it almost every day - so I was excited to get something that I knew I was really going to use and love just as much.
I used the bag for the first time two weekends ago, and it was the perfect size for a three day trip. I had four different outfits, a pair of wedges, and all of my personal items in there, with room to spare. The bag itself is surprisingly deep - I was worried at first that it wouldn't fit everything (which is why I initially left the tag still on it!), but was pleasantly surprised by how roomy it is. I plan on using this for my five day trip to NYC in October as well, now that I know how much it can hold.
The leather is of course beautiful, and so soft. It has two top handles, and a shoulder strap. If you buy it through the Madewell site, I highly recommend paying the $10 for the monogram! It's the one regret I have, since I didn't by it directly through Madewell. The inside is lined (unlike the transport totes), has one larger zip pocket on one side, and two smaller open pockets on the other side.
Overall, $300 is a lot of money for a bag that I'll use a half a dozen time a year - but the quality of the bag means that I use it for years and years and years. If you are looking for a genuine leather weekender bag, I would recommend this one to anyone.