Since my typical work day consists of sitting in front of a computer all day long, I occassionally sneak in a little break to “window-shop” online. I recently found myself scrolling through Piperlime looking at shoes and was pleasantly surprised to discover the updated penny loafer making a comeback for fall.

My first experience with penny loafers was in sixth grade. My family and I had just moved from Texas to Oklahoma the summer before I would start middle school. As any new kid knows, starting at a brand new school is incredibly nerve-wracking. And we all know that middle school is just an awkward time. Someone in the neighborhood told my mom that all the middle school kids wore Cole Haan penny loafers, so she bought me a pair. Even though it was a pricey shoe for a sixth-grader, she understood the importance of fitting in where I knew no one. And the fashion tip was correct – everyone wore those shoes at my new school, so it helped ease the transition a tiny bit.

Obviously, my style has evolved since then. Although I don’t consider myself edgy, I also don’t consider myself preppy. But the updated look of the penny loafer really appeals to me – it’s classic and fresh and just a little bit funky. Take a peek at a few that I pulled off Piperlime:

"Grippa" by Joe's Jeans

"Abalene" by Nine West

"Hathaway" by True Religion

"Balinia" by Enzo Angiolini

I love that each pair has a bit of a platform and some great details, like the nailhead studs or the buckle. I picture these with some great-fitting wide-leg trousers for a cool spin on menswear, almost a bit of an Annie Hall-vibe. All four styles really appeal to me, but I’m especially drawn to the Enzo and True Religion styles. Looks like I may need to place an order on Piperlime soon. And, each pair is under $200. I believe in buying quality pieces, but I don’t have an unlimited amount of money to spend, so I have to set limits somewhere.

What do you think about this updated shoe? Would you wear it?

All images pulled from