I feel like my answers might be dull compared to some! This is an interesting thread!
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What bag do you know you overspent for?
Oh, this is tough. I mean, if I sit and think about it objectively I think it is crazy insane how much my LVs cost. I mean, they are just handbags! To carry my s#!t! They do not do any better of a job than my bags that cost a fraction of the price. However, I also
love them and they feel special to me, and that is just what they cost - they don't go on sale, so unless I was willing to take risk of finding on secondhand market with all the fakes, and the often HIGHER than retail final prices from reputable secondhand vendors for in demand items, well, that is what they cost. I love them and use them so I still don't feel I "overspent". They will be mine forever.
I think I would have to say for me the ones that fall in this category then are the bags that even though I bought on sale/at discount, I did/do not use enough. Their CPW ended up very high by time I parted with them (I donate rather than sell). I feel better spending $2,000 on a bag I wear 1,000 times versus one I spend $200 and wear...twice. So, I think there are probably a couple MKs and a couple KSs I could put in here, all around $200-$250 CAD, but that is still $200-$250 CAD that could have gone towards a bag I wore/wear more or something else entirely. The two in next answer are probably are ones that I think I also overspent for based on anticipated future CPW, even though they weren't all that much relatively.
Also, I am thinking of a couple "could have been regrets" here. I have been lucky in that the one
Coach bag I DID pay FP for (an Olive Rogue) actually went on sale within the 14-day adjustment period, if I had missed by a day I might have added that one in there too...though I just adore all my Coach 1941 bags and I could justify paying FP; I would not feel great if I could have saved 50% a week later and could not get that credit.
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What bag should you probably sell/get rid of but still haven't? :
Up to a couple of weeks ago I would have said the three RM Nikkis I had hanging out in storage since January...but I finally gave them to a coworker last week.
So now a couple immediately came to mind. I should probably get rid of this little Cole Haan crossbody I got on clearance. It was like $85 CAD and the leather is sooo soft and smushy, but I just don't use it; I reach for other crossbodies instead. I do really like how nice the leather is, and how under the radar it is though. I am debating cutting the strap on it (which is not detachable)/making a wrist strap and just using it as a pouch/clutch; but it is a bit heavy to be a pouch. I feel bad but I just have not been able to make it work in my life...but I want to! Google image as I don't have pictures on here:
This is the other one, a Kate Spade Small Hayden in Crisp Linen. I have barely carried it, but it is also new so I am not quite ready to part with it. It is so cute & summeey, but I am not using it, and I think I need to take my own advice I give to others and let it go. I just find when I want to carry this particular style, I reach for its twin (I have it in black). I had wanted the black one forever to have a small structured black bag, and bought it when it went on sale as it was being discontinued....this one was on sale at same time and so I got it as well. The black one gets worn, but this one I just don't reach for. If I want to carry a small light coloured bag I tend to go for my Rogue 25 in Chalk. Another Google image, except mine does not have the white sides, it is all the middle colour:
- What bag are you embarrassed to admit you like? : I don't really have anything here? One, I don't think I have any very unusual tastes, and two, I am long past the days of caring what people thought of my likes
There are bags I like but would not buy due to function, practicality, and not fitting into my own lifestyle, but I am not embarassed to like them!
- What bag did you buy, then realize it doesn't work? : Aside from the above two...I suppose my Iena MM? I just got it and I am selling to my sister who does want it, only time I have ever sold, so I won't lose money on it. It is a beautiful bag. Soft and comfy under arm, and straps are wider than NF straps, Outside pocket and interior pockets make it beautiful. But....I really wanted a true tote-style bag I could pack full, something more like my Longchamp, or Vince Camuto tote, and the Iena MM was just a bit too small - more larger shoulder bag for me than a tote. So Iena MM is being rehomed and now I have a new NF MM and loved it right away!
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What is your worst handbag mistake (i.e ink, stain, scratch.....)? None so far when it comes to damage and so on, knock on wood (or leather?). I just hate thinking how much I have spent on bags at times - I can afford it but I could have afforded other things too. My mistakes are really more related to impulse buys and how much I have lost learning the lessons of what works and what does not!
But, I agree. Gucci is amazing! Def one of my favorite 3 brands. 
Maybe the only thing that could qualify is Gucci's velvet bags and to a lesser extent the nubuck bags. Those are insanely beautiful. The color saturation is breathtaking. But I worry the velvet will look worn over time and that the nubuck will get grungy. So I only have one Gucci nubuck bag and am contemplating when to take the plunge again.
I sent the bag off to be cleaned - luckily it's fine. But, it took years off my life. 
