You can take the boi out of New England, but you can’t take the New England out of the boi. No matter how I’ve evolved when it comes to my style, sexuality, and gender identity I’ve always been drawn to classic preppy looks. I’m not talking about circa 2005 Abercrombie prep (Although, yes I was rocking Moose polos back in high school), I’m talking about old school Letterman-style sweaters and penny loafers.
I found this vintage-style prep school sweater at a Tommy Hilfiger outlet in the “women’s” department back in 2015. When it comes to choosing what I like and what to combine to make an outfit, I shop from all departments. Masc presenting folx, it’s TOTALLY FINE to wear clothes from the women’s department. If it looks nice and fits well, who gives a fuck what department you got it from. *Gets off soapbox*
I wanted to “theme” this outfit a bit so underneath I wore a white microprint motorcycle button up and incorporated the moto-theme with red checkered flag socks. The skull print bowtie tells the world that I’m cute with a bit of a naughty side…😉😂 On my feet, I have on a pair of Florsheim KIDS oxfords and for shades I went with my red wayfarer-style glasses that are literally straight out of the mid ’80s. A few years ago, my mother was going through an old dresser and found these and was going to donate them to the Goodwill, I scooped these bad boys up from her faster than you can say “Frankie Says Relax.”