Hi, and welcome to my secret world of obsession and indecision. I’ve been looking for a new handbag and although I think I know what I want, I decided to go through what I have to help me make a decision. Here’s what I have:

  1. Black Banana Republic Top Handle Bag (similar): This is my go-to everyday bag. It has multiple pockets and zippered compartments, a top handle and a shoulder strap. It’s a bit heavy though and quite boxy/structured.
  2. Black Liz Claiborne Shoulder Bag (similar): I love this bag. It’s made with a really great quality leather and has a relaxed shape. It used to be my number one bag but now I don’t use it much. It is a great bag…
  3. Brown Madewell Transport Tote: I was thrilled to get this as a Christmas present a few years ago. I love the look of it, but it’s heavy and much too big for what I need to carry most days.
  4. J. Crew Straw Tote (similar): This is my tried-and-true go-to summer bag. I choose it over the others most of the time. So good.
  5. Multi-color Le SportSac Nylon Tote (similar): I don’t know when or why I bought this. I’ve seemingly had it forever. It is really good as a beach tote or if I’m going shopping. It’s lighter weight than the brown leather one and it’s a great choice if it’s rainy. I really like it, but it’s not very chic.
  6. Black and Tan Element Backpack (similar): Why is this even included in my handbag collection? I mean who uses a kid’s school backpack anyway? But, I think it’s good. I actually bought it at Disney World. It’s pretty indispensable for traveling. It carries a lot comfortably. I took it to California last month and I was really glad I did.
  7. David Bowie Ziggy Stardust Canvas Tote: This bag sort of checks off all the boxes. The perfect size. Kind of goes with everything. Not pretentious. It’s the sort of bag Rita would have as her handbag. It was $15 at Target. It’s cool but not very grown-up.
  8. Black Canvas Barney’s COOP Tote: This was the bag I got when I bought a pair of J Brand jeans at the COOP. It was free but I liked it so much I kept it. I often use it to carry my laptop (in neoprene sleeve that fits in the tote perfectly.)
  9. Hawaiian Print Tote: I got this on my honeymoon in Kauai so it’s pretty sentimental. It’s funky and on the small size but good for summer and goes with black better than my straw tote.
  10. Brown Lucky Crossbody Bag: I bought this a couple years ago because I became convinced I needed a bag this color and shape. It’s nice but very stiff and the flap closure kind of annoys me. Also, it’s a little too small for an everyday bag.
  11. Black Banana Republic Crossbody Bag (similar): I like the look of this bag. I like that it’s black and has the gold chain. It’s quite small and not practical for everyday.
  12. Light Blue Coach Crossbody Bag (similar): So cute but so small. I almost never use it and wonder what I was thinking when I bought it. However, I did take it on my last trip and it worked out quite well.
  13. Black J. Crew Clutch (similar): One has to have at least one clutch, so I have this.

My conclusions:

  • I could choose to keep one or the other of my two black bags (or find one that I love.)
  • The Madewell transport and straw tote are both keepers…
  • …as are the nylon tote and backpack. Very functional.
  • I could probably do with just one cute, casual canvas tote.
  • I really only need maybe two crossbody bags – one black and one not black (and the brown one isn’t really working for me.)
  • I really want a Spring/Summer bag that is leather, light colored, medium sized, that’s not too structured and makes me feel like a grown up.

I’m considered one of these:

Everlane $235

Madewell $158

Mark & Graham $199

Cuyana $375

Banana Republic $178

I decided in the end to purchase the Madewell medium tote (in “Linen”). I bought it through Poshmark so I got a great deal.

What’s your go to bag style? Do you change them every season?