Do you consider the popularity and "it" factor?

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I consider it highly and make sure I go the other way. Don't get me wrong. I check out fashion shows as soon as they're out on the web. "It" bags come and go, be it premiere or contemporary designer. Remember Foley + Corinna, Stam and Paddington?
 
Never. I actually usually buy "it" bags that are no longer it.
I never buy them when they are the in thing because they're the in thing. Most bags I've bought have come and gone but I still love them so I buy them later. I bought a fendi spy years after it went out because I liked it, same with the paddington and the miu miu bow bag. May get a stam one day if I still like it and see one in a colour I love. Prefer to do it that way and make sure I still like the design over a few years rather than just buying something to keep up.
 
I pay attention to IT bags because many of them are popular for a good reason. Timeless style and elegance. Not every IT bag is according to my taste though and some I tire of because I see them a lot.

Whichever ones I don't tire of, would probably be a good future investment.

I don't own any IT bags, or classics...but I can imagine to buy a somewhat popular bag in the future. Some bags I like are the Mulberry Alexa, Bayswater, Chloe Marcie and Paraty, different Chanel bags...also like the Vintage styles from the 90's a lot, Givenchy Nightingale, Fendi 2 jours...
 
Normally, "it" bags are expensive. I would not want to buy expensive bags that would soon enough go out of style. If I really like the design/style, maybe I'll get it when it is no longer an "it" bag, and is priced more reasonably. In fact, when I was deciding on my first ever designer bag, an LV, I went for a style that is classic looking and not really the popular one at that time. And it is only now that I got a (mini) Stam, long after it was an "it" bag, because I like its look and I could get better prices now.

Of course not all popular bags are "it" bags. I think I would still like popular bags, for as long as they are reasonably priced.
 
Nope, since I´m not the kind of age/finance/lifestyle bracket that IT brands tend to target - so most IT bags leave me cold and, even if I liked them well enough to give them a try, they look weird on my very petite frame and/or don´t suit my practical needs at all. I do have a (very) few top designer items, like the Vuitton Trevi or the Chloè Paraty, but they´re timeless classics that go unremarked, and not amongst the brands´ IT bags at all, I think.

It´s like being a cottage vs city loft type, or a motorbike vs SUV type, if you know what I mean?
 
Well, if I like an It bag I'd just buy it. Don't care much if it's an It bag or not. But a lot of It bags look so dated now. Like Chloe Paddington and Fendi Spy. This is why I'm happy I bought my Fendi Chameleon. It was made popular by Gossip Girl but Fendi stopped it's production before it became an It bag.
 
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