Ladies, how often do you buy purses and bags? Do you prefer to make one big purchase and buy a quality, name bag — or do you prefer to make more frequent, smaller purchases? Does having a trendy bag matter to you, or do you want a classic style? 

I’ve been thinking about this recently because I’ve been helping a friend look for her first big bag purchase in a while — she’s finally out of the diaper bag phase of her life, has almost 2 of her 3 kids in school, is settled into her “forever” house, etc. Accordingly, she and I have been trolling resale sites like Tradesy and The Real Real, as well as discount sites like Last Call and Rue La La. She’s inclined to make one big bag purchase, and carry the bag everywhere — and she’d like to find a designer bag for around $500.  (We’ve yet to find the perfect bag at that price point — I’ve suggested she look at discounted but new Furla bags for quality, stylish bags, as well as lightly used bags like Mulberry, Ferragamo, and Saint Laurent.

In the past I’ve gone the other way, buying bags frequently but at lower price points. In my lawyering days before kids, there was a steady stream of discounted bags that I paid between $150-$350 for, all with original MSRPs of $500-$700. (You can see a lot of them pictured/discussed in this older post on purse budgets.)  They were all quality, leather bags — lots of Cole Haan, Furla, Botkier, Dooney & Bourke, with the occasional Coach or Kate Spade thrown in — but none of them really qualified as “designer” bags on the same level as my friends with Chloe, YSL, Prada, Chanel, Bottega, etc.  So I’ve wondered over the years — should I have just saved the money up and spent my “purse budget” on a single designer purse each year, instead of four or five little ones? Would that be a better “investment”?

Here’s the interesting thing I’m finding while looking for a purse for my friend: a lot of the designer bags I’m seeing seem incredibly dated to me.  Much, much more so than the fun, sometimes offbeat bags my closet is filled with.  Some of the bags I see are particularly tied to very old memories, such as:

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