I’ve been working on pulling together an apartment introduction post, but I’m not quite finished. Hoping to have something to post this weekend. Progress is being made!
Anyone who knows me knows that I don’t make big decisions lightly. Really, I don’t make too many decisions lightly, and have a knack for (over)thinking all sorts of things. Online shopping makes this much worse. Reviews! Blog posts! So many places to research every.little.thing. I doubled checked the prices for sink strainers* yesterday from the Target aisle before committing to all 8 dollars of the thing.
But because I enjoy weighing in on decisions made by strangers, and I like hearing feedback from others (shopping with the right partner is my idea of bliss), I thought I’d start a little mini-series called Decisions, Decisions. I hope you’ll consider weighing in—either with your expert opinion on my uncertainties or with decisions you’re considering in your own world, shopping, decorating, or otherwise. It’ll be fun.
So, the leather tote debate. I’ve wanted a basic leather bag—big enough to carry a laptop, small enough to still be considered a purse when getting on a plane—for many years now. I ogle them at airports. A few chic classmates carried bags closely resembling what I want, though not quite the same. I go back to this specific Olivia Palermo street style shot (carrying a discontinued Zara bag) with some regularity and fantasize about my fashionable life if only I had that bag. And possibly a metrosexual man wearing purple socks.
Requirements: basic, not too embellished, with at least one interior zip pocket. Not too preppy. As much as I like Olivia’s forearm sling look, I need one with straps long enough to slip over a shoulder. Although I am tempted by colors because I always am, and I wear a lot of black, I think a basic luggage brown is probably the best bet in terms of versatility, as Ms. P shows in the image above.
I’m headed to New York for work soon and realizing that a) I’ll need to bring my laptop to and from the office each day/into and out of meetings and b) my laptop-sized bag options include a massive Radiant Orchid Patagonia messenger bag, a Lowe Alpine backpack I’ve had since my senior year of high school, and…I think that’s it. The New York office seems a little Devil Wears Prada-lite and I am a touch intimidated.
So, it’s time. I need to up my professional game.
I’ve basically narrowed down my options to two extremely similar bags: The Madewell Transport Tote in English Saddle and the Cuyana Leather Tote in Caramel (which comes in two sizes).
Quite a few bloggers are singing the praises of the Cuyana bags, but I get the impression they might have been gifted free ones in exchange for their posts—the extent to which that is happening on almost every blog I read is kind of a bummer. Some people say the Cuyana straps don’t look as good for as long, some people say the Madewell bag ages better, others say the Cuyana leather is higher quality. For sure, they all have the option of gold monogramming—I’m thinking MLE since my initials (EEB) and monogram (EBE) are both pretty lame.
So I’m leaning toward the Madewell bag since I can more easily see it in person (there’s a Madewell store in Austin, while Cuyana’s only brick and mortar is in SF), I can buy it and then take it back later to get it monogrammed if I decide I love the bag, and it appears to be a bit more structured and thus stand up on its own, hopefully reducing the number of times it falls over and spills things everywhere.
But…it’s so hard to choose! Decisions, decisions, I tell ya.
So, which would you choose? Do you have your eye on a “timeless” splurge? Do you have tricks for making up your mind in a less dramatic fashion? Inquiring minds want to know.
*I actually think the funniest David Letterman skit I ever saw was a series of Halloween costumes that are terrifying to adults. One of them was a dude dressed up as a sink strainer basket looped with spaghetti and full of unidentifiable chunks. Yep! Adulthood!

Madewell bag, EBE monogram.
Madewell!!
It depends on what you like. Cuyana seems thinner but the leather does not scratch so easily. I have that in the tall, grey tote. I thought at first I wouldn’t like the Madewell because it does scratch easily but after putting the leather conditioner, (bee oil wax type conditioner), I feel like I’m loving this one even more. I got the cognac color, it feels thicker and has that aged, timeless look to it. I got them both monogrammed. I would say to go in the store for the Madewell one since I went through a good amount in the store before they brought out one in the back that was still in the plastic w/ no scratches. The others on the shelf had some scratches. The leather conditioner which darkens it a bit works miracles!
Hi Mg – I ended up going with the Madewell (still no monogram – that’s on my to do list!) so thanks for the tips about the leather conditioner. I’m OK with some scratches/aging but want to keep it looking good for as long as possible…
Does it stand upright on its own?
It does! That was one of the final deciding factors for me to get the Madewell. Also, almost a year later, with daily use and getting caught in a couple of rainstorms, it still looks almost new.
I own the Cuyana tote in the short size and I love it. I bought it in stone, and am thinking of getting a tote in black, but considering getting a madewell transport tote in black. How is the inside of the madewell tote? Are there any internal pockets in the Madewell tote? The cuyana has a zippered inside pocket and a smaller nonzippered pocket that can fit a phone.
The Transport was just on sale last week – worth taking a look. The inside is the rough side of the leather, with one zippered pocket. Other than a few little spots where I’ve spilled something, mine’s still looking good, and I use it every day (plus as my plane ‘personal item’). I expect to have it for years, so it was a good investment piece for me.
(Stone and black are both tempting options…)
Hey! I’m thinking of the Madewell bag, too! but I’ve been reading around (decisions, decisions 🙂 ) and it seems people are finding that the unfinished underside of the straps bobbles and stains their shirts.. Have you experienced this?
How are you liking the bag after this time?
Thank you!!
I’ve read that some of the darker colored Madewell bags stain badly – mine rubbed brown (a little) on light stuff when I first got it, but then it went away after not too long. I’ve had mine for years now and, other than a bad run-in recently with taco grease, it’s still in great shape. I’d recommend it.