29 Most Iconic Womens Shoes, Sneakers, and Boots of the Girl World Generation

I know what you’re thinking…what’s “girl world”? Basically, it’s my fun way of amalgamating that whole Britney Spears concept of “not a girl, not yet a woman”. If anything, that interesting case of which today’s twenty-something girl that somewhat remembers the original episodes of MTV’s House of Style with Cindy Crawford or when getting a belly button piercing was actually a rebellious act, but acknowledges, whether or not she agrees, that Rihanna is the new fashion icon. That in-between state of generations. Honestly, some of us here actually experienced the return of bell bottom jeans (cue: the brand Mudd).

When it comes to shoes, some of the most iconic of the last twenty years, the average woman may not have in her closet (and not because she doesn’t work hard for the money, but unlike Nicki Minaj, we will double check to see if there’s a comma on the price tag), she’s fully aware as to why a particular pair of heels have been deemed so awesome (here’s to Sex and The City). I came up with a list of super memorable shoes about two years ago after going through an entire slideshow of what anoter online magazine considered to be the top sneakers of the ’90s or the best Jordans ever. These lists were always devoid of any sneakers that girls loved however. Even on women’s fashion sites I hadn’t seen similar vestiges of the footwear that had women either blowing whole checks on or filling up that ol’ piggy back in hopes of eventually getting their dream pair of shoes. So I had a little fun brainstorming and came up with what I can honestly say are the most iconic shoes of the female aesthetic. Some shoes were purely designed for editorial purposes, others were just a sign of the times. Either way, many of the shoes listed have been duplicated, imitated, and immortalized from the moment we saw them. There are also nods to our childhood and flirtations with tomboy style, so this capsule is not just about the world’s most revered fashion houses. It’s in homage to the fancy footwork that throughout the years got us from the playground, to classes, to work, and after work, and sometimes gave us that extra pep in our step because to move on, you must move forward.

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