Let's talk about handbag mistakes!

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Hobo bags. Everything settles to the bottom like a trash bag. I love the way that they look with certain outfits, but I find the very impractical.

Red handbags. I own two and rarely carry them. I like the bags but not the color.

Black handbags. BORING. I got rid of them all except for one Karl Lagerfeld and some clutches. I love color and don’t care about matching my handbag to my outfit.
 
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My biggest regret is pricey bohemian-style bags. I like the idea of being at a high end bohemian event carrying one, but in reality, I don't know if high end bohemian events even exist and certainly wouldn't carry an expensive bag to most "bohemian" events in my world. I think I like the idea of being Gwyneth Paltrow at a fancy, but of course earthy, event, but the best bag for my actual lifestyle is entirely different.
 
My biggest regret is pricey bohemian-style bags. I like the idea of being at a high end bohemian event carrying one, but in reality, I don't know if high end bohemian events even exist and certainly wouldn't carry an expensive bag to most "bohemian" events in my world. I think I like the idea of being Gwyneth Paltrow at a fancy, but of course earthy, event, but the best bag for my actual lifestyle is entirely different.
Lol I’ve been trying to figure out an excuse for this bag and that’s it! A high end boho event needs a sardine!

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Most of which you guys mentioned I have experienced, especially since having kids.

  • Heavy bag is a huge nono (the older I get the less I seem to be able to carry) - I'm looking at you Chloe paraty.
  • No xbody strap bags I can no longer do (I seriously admire people with clutches..even before kids I couldn't deal with clutches) - I'm talking about the neverfull with also its uncomfortable straps. Not gonna lie, my Bal city and day are not getting much mileage these days either
  • Small bags (when I lived in North American and drove everywhere this was fine, but with kids and walking/metro, small bags are tough) - lv felicie...I never know what to put in it!
  • Non-adjustable straps, especially chain - the Félicie and Chloe paraty has once again made my mistake list. Neither have comfortable straps either. I'm short and a lot of bags are just too long even crossbody! (Bal vélo has the same problem for me!)
  • Cloth bags (mostly because they get dirty, and it's impossible to clean.)
This last one is a big one for me:
  • Bags I cannot resell: so I have come to the realization, when I was purging bags, was that bags that have no brand, cheap quality, or fall out of trend, getting rid of them is tough. Sure you can fool yourself and donate them to some bin if no one you know want them, but even if you "donate" them, they'll probably end up in the bin anyway.

I always always before I buy a bag now, think about what I can do with it when I no longer wear it.
 
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I have these two small bags I bought that I don't really use? I thought it would be a good substitute for something else but I didn't think more about the capacity or usability. I mainly use other bags, for all occasions.
 
Round bags. Everything I can imagine putting in a bag is angular so it drives me crazy that I can‘t get anything organized in these bags.

Noisy bags. One of my worst purchases was a Chloé Tess bag and the rattling and squeaking was so annoying.

Bags on sale. My biggest mistakes were nearly always bags I bought in a hurry because I thought I would miss a good deal.
Of course, they mostly are on sale for a reason and that’s what I didn’t realize.
Sale might work for others if they enjoy exotic colors or unusual sizes of a certain bag. But if I wanted a black Chanel it would be dumb to by the baby pink one.

From time to time I am still tempted but I can resist. Unfortunately sometimes I still regret these missed opportunities though I know it was the right decision.

The Chloé Tess was a combination of all three: it was round, it was noisy and I found it on sale - large, dark brown; I originally wanted the small in cashmere grey.

Lesson learned.
 
Round bags. Everything I can imagine putting in a bag is angular so it drives me crazy that I can‘t get anything organized in these bags.

Noisy bags. One of my worst purchases was a Chloé Tess bag and the rattling and squeaking was so annoying.

Bags on sale. My biggest mistakes were nearly always bags I bought in a hurry because I thought I would miss a good deal.
Of course, they mostly are on sale for a reason and that’s what I didn’t realize.
Sale might work for others if they enjoy exotic colors or unusual sizes of a certain bag. But if I wanted a black Chanel it would be dumb to by the baby pink one.

From time to time I am still tempted but I can resist. Unfortunately sometimes I still regret these missed opportunities though I know it was the right decision.

The Chloé Tess was a combination of all three: it was round, it was noisy and I found it on sale - large, dark brown; I originally wanted the small in cashmere grey.

Lesson learned.
I have gotten much better at resisting and generally I rarely buy sale bags for exactly the reasons you mention.

But… once in a while something comes along that must be snapped up. I did this recently and it has worked out really well and I anticipate that it will be a real “keeper” long term.
 
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Round bags. Everything I can imagine putting in a bag is angular so it drives me crazy that I can‘t get anything organized in these bags.

Noisy bags. One of my worst purchases was a Chloé Tess bag and the rattling and squeaking was so annoying.

Bags on sale. My biggest mistakes were nearly always bags I bought in a hurry because I thought I would miss a good deal.
Of course, they mostly are on sale for a reason and that’s what I didn’t realize.
Sale might work for others if they enjoy exotic colors or unusual sizes of a certain bag. But if I wanted a black Chanel it would be dumb to by the baby pink one.

From time to time I am still tempted but I can resist. Unfortunately sometimes I still regret these missed opportunities though I know it was the right decision.

The Chloé Tess was a combination of all three: it was round, it was noisy and I found it on sale - large, dark brown; I originally wanted the small in cashmere grey.

Lesson learned.
Sorry for the lesson. Sometimes a lesson is painful, though if it wasn’t too expensive, learning these kinds of lessons is part of the fun for me. I won’t buy a pricey thing just because it’s on sale, but if I wanted it anyway, sales are great!

I have a small bag that scrapes my hand every time I reach into it. It’s also a little too small for how I thought I’d use it. But it’s cute, and buying it was still fun
 
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