This last installment of my “Fall” into the 90’s mini-series (check out the previous two here and here) is inspired by the Tommy Hilfiger takeover of the late 90’s urban community. Although hip-hop and the iconic brand have had their ups and downs, the selling power of that magical time cannot be denied. Every “cool” celebrity rocked Tommy Hilfiger and his business expanded as more and more adopted the trend. I absolutely love and adore specifically how the late Aaliyah would wear her Hilfiger gear and it is where I drew my inspiration from for this outfit. She looked tomboy-ish and comfortable but still effortless sexy and urban. I found both the Tommy Hilfiger boyfriend jeans and undies (boy’s size) at my local tjmaxx both on clearance! I spent less than $20 and I couldn’t be happier. In order to give it the “fall” element I wore my sturdy wheat timberlands as well as threw on a sweater crop top that happened to coordinate with my color scheme. Most of the pieces for my mini fall series came from my own closet and were items I could mix and match to get the 90’s aesthetic. Check out similar items below!