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If I were really and truly ambitious about this 90s thing, I’d be at swing-dancing night as we speak. Rumor has it, the cool cats still meet up in the same spot they did a decade ago to jive and wail. I tried a few times, back in the day, but never really took to it. I got frustrated with my inability to remain suspended in midair. I wanted to be just like the matrix-defying little pixies in The Commercial and when that didn’t happen, I sort of threw in the towel.

Nevertheless, I was quite the khaki lover. And for 90s week, I had to snag a pair of real Gap khakis. How I wish I could style them up in classic form. With nothing more than a beater tank, as they’re meant to be. However, as you may gather from the whiteness behind me, it’s quite chilly here. Layers it is.

Truth be told, I think these are the first real Gap khakis I’ve ever owned and they’re thrifted. My 90s wardrobe was perpetually at odds with my allowance or lack therof. Tried as I might, to keep up with my peers, I could never quite cultivate the designer look to match my tastes. Instead I just read my fashion magazines longingly and loitered the local mall in hopes of someday affording the real goods.

While my friends reeked of authentic Sunflowers perfume, I wore designer imposter fragrance. Maybe some Gap Heaven, when the birthday money Gods were kind to me. Whenever, I did manage to scrape together enough fundage for a splurge, I still lurked the clearance racks. I once scored some sweet Calvin Klein jeans. In the children’s section. I outgrew them about five minutes later.

As much as I longed to be a Tommy Girl with a different pair of Docs for each day of the week, I never quite pulled it off. But I do think that I learned from it. All my years as a walking fashion mishap, eventually led me to develop my own personal style, not dependent on name brands. I still struggle with wishing I had exorbitant amounts of money to spend on labels, but I think I’ve long since learned to live without.

If I could go back in time and tell 90s Jenny anything, it would be that confidence is what actually makes the outfit. Thirteen-year-old me would have then roll her eyes at me. So I’d have to put it in to more succinct 90s lingo. It’s okay little Jenny. Metaphorically speaking, you just need to rock rough and tough with your afro puffs. Rock on with your bad self. Everything is going to be alright.

Khakis – Thifted (Gap)
Blue pinstripe button-down – 5.7.9
White boy tank – F21
Navy long sleeve – Work
Brown beaded necklace – Claire’s
Belt – F21
Shoes – Payless

Title courtesy of Reel Big Fish – “Sell Out”