Cool Hunting || Best Handbags

I’m on the hunt for a new bag and I have maybe never been more particular about anything in my life.  Last summer we were at Disneyland and I saw this super chic woman with the Celine large trio bag and fell a little in love.  Luckily, I bought the $20 Old Navy version first to give it a test drive and realized it’s not the bag that I want to make that kind of an investment in.  The three different compartments is actually kind of annoying because I never know which compartment the item I am looking for is in. I also bought an inexpensive leather backpack only to realize that it’s a total pain dealing with the leather drawstring and not have a real shoulder strap.  So what are the best handbags? Don’t even get me started on the oversized tote that I carry my computer in that becomes a total black hole.  Oh and I was also tempted last week to buy world’s most impractically small rose colored fringe Elizabeth and James bag.  My wallet didn’t even fit you guys. It would have made a great evening bag if I was someone who went out often enough in the evenings to justify a $200 pink fringe evening bag that can barely hold a cell phone, but it did not fall into the best handbags category.  So here is what I have decided I am looking for: A mid-sized bag that is either a tote bag or a cross body, without too many compartments.  I don’t want it to be black. (Although, a lot of these bags do come in black if that’s what you’re looking for.) I do want it to be leather. I want it to be of a quality that will last for 5-10+ years and I want to pay between $150 and $750 for it. I also want it to be pretty… obviously.  Specific, I know. Here’s what I have found in my ongoing search:


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  1. If you want something for the short term while you find the perfect thing, I’ve had a Madewell Transport tote for YEARS and still use it. It’s aged beautifully, to the point where I get compliments on the leather all the time. And I am ROUGH on it – think gross airport floors, bleacher seats, etc. I don’t treat it preciously at all, and that seems to work just fine. It fits a ton (including a laptop/files easily) and is great for travel.

    Downsides: I wish it had more than one pocket, or a bigger one. And I’ve had it so long that the straps are splitting, but I’ve just put off taking it to the cobbler for an easy fix.

    • Jen Pinkston


      This is so good to know. That’s one of my dilemmas, too, is that right now I carry a purse separate from the bag I take if I need to bring my laptop. Trying to decide if I should consolidate into one bag. I sure do shlep my laptop often.

  2. Michele Spivey


    I love the Teddy Blake bags. It looks like the Hermes Birkin and the quality is so beautiful. the price is right also. I LOVE mine!

  3. Lauren Horton


    I just went through this SAME dilemma! Ended up with this one in taupe (it looks more greyish in person than it does on the site). It’s big enough to hold all my stuff plus a couple diapers and wipes (I’m over diaper bags these days), without being too big. I like that I have the option of carrying over my arm or as a crossbody.

    • Jen Pinkston


      Oh my gosh, I’m so over diaper bags and never going back! This bag is great– thanks for sharing! (and update: still haven’t pulled the trigger on one of these!)

  4. melanie


    Ooh – I have #15 (the Allsaints Paradise). It’s an upgrade from my Madewell transport tote – structured enough to stand upright on its own. I love it, but I will that the single strap is hard to get used to – I’m used to dropping on strap and letting the bag fall open while it’s on my shoulder – but with just one strap you actually have to take it off your shoulder. The price point made it a reasonable short-term solution, but I’m also on a quest for a 5-10 year investment bag (this isn’t quite it).

    • Jen Pinkston


      Oh that’s so good to know. Agreed about the single handle– I hadn’t even thought of that. The gray Claire V bag is kind of calling my name. I need to go try it on in the store though.

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