Prep With A Bit Of An Edge

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…πŸ˜‰πŸ˜‚ 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.”

Let Me Tell You About My Robot Pants


Just writing the title of this blog post got me singing like Butters in one of the best episodes of South ParkΒ ever, so while I try to get that catchy song out of my head let’s talk about this outfit!

Who doesn’t love a critter chino? When I saw these at Original Penguin a few months back I had to have these pants featuring robots, planets (Saturn and Neptune) and rocket ships these were a must buy for me. They were in the window display and I probably looked like Ralphie wanting his Red Ryder BB gun in A Christmas Story. I’m really obsessed with robots and the combination of robots and preppy chinos made this boi jump for joy. However, they were $95 and this boi is a cheap bastard. I ended up waiting two months and scored them online during Black Friday with free shipping for $60.


The first time I wore these, I definitely wanted to highlight the whimsy of the pants, so I kept it neutral with this short sleeve half button chambray shirt that I got super cheap ($8) at Target while buying La Croix. The men’s stuff at Target is hit or miss, especially when it comes to fit (Smalls tend to be a victim of vanity sizing thus too big for my small frame), but this was definitely a home run, because this impulse buy has turned into one of my favorite shirts. This time I paired it with a navy and white gingham self tie bow tie from Tommy Hilfiger and shades from H&M.

Masculine dressy shoes for tiny feet are really hard to find, now I got some tiny ass feet. Case in point, I fit in a 3 or 4 (depending on the style) in Converse. These Wanted brand vegan leather oxfords come in a bunch of colors so I had to pick up a few pairs at Macy’s. Funky socks are always a must; these are from Swedish brand Happy Socks.


The watch is the Game Starter by Swatch, which was apart of their Mystery Vintage 2016. I know it’s called the Game Starter, but I got some awesome motorcycle racing vibes from this chronograph.