The no longer trendy handbag i find is only a problem when they become overly ubiquitous for a while (and often in mid-range price-point), especially when their look has something
very unique about them. There are trends that die hard deaths, and trends that die slow deaths. Dior Saddle, Fendi Spy, and likely the Celine Luggage (which inspired all types of other flared out bags), die hard. Monogram is starting to die a slow death. These are sometimes also exacerbated by all the less expensive bags that are "inspired" by the more expensive bags, making the look everywhere (remember when everyone was carrying a
coach logo covered demi pouch because everyone else who can afford a
Gucci monogram pochette is wearing one?). When things are everywhere, people are going to want to be different, and then the bags (or sometimes even a brand) become a part of an era. It's hard for some people sometimes to disentangle whether you are buying a bag cuz everyone else has it, or if it's because you actually like it, when the trend is everywhere. Repetition makes things grow on you - cognitive fact.
But personally, I find that as long as the bag hasn't been "everywhere," and you like it, it's less of a problem. I think the embarrassment from carrying out of trend bags comes from not so much that the bags are no longer trendy, but a testament to the fact that you owned something because everyone else had it but can you can't continue to keep up carrying what everyone else is carrying. Therein lies the argument that if you truly do like the bag, to this day, then there's nothing embarrassing about it.
