The Return of the Boat Shoe
I've been long-awaiting the glorious rebirth of Sperry, one of my teenage favorites
I’ll get right into it. I’ve always had a knack for forecasting trends but I don’t always bet on them — I’m changing that today.
While I do a lot of product research and online shopping for my job, I’m not a professional when it comes to trend forecasting; I wouldn’t even call myself a “fashion expert” because I don’t know all the fancy terms and couldn’t recite the history of Chanel.
What I am familiar with is building my own personal style around buying secondhand, and at 31, I’ve been around long enough to see things go in and out of style again and again. Honestly, I’m just going off my gut vibes here.
This year, I’m betting on the rebirth of the Sperry. It just makes sense — all the context clues prove it. Sofia Richie is bringing back “preppy” and people are clawing to get their hands on J.Crew’s ‘90s archive drops that romanticize life on the water.
I attended Catholic school for 13 years, which meant wearing uniforms and dress shoes every day — and everyone (I mean everyone) wore Sperrys to school during my high school years (2007-2011, to be exact).
Aside from freshman year when my mom bought me off-brand boat shoes from Payless, I would get a new pair of Sperrys at the beginning of each school year. But this dark brown leather pair ($30 on Poshmark) was my absolute favorite. Plus, I loved that they were on-trend while being a little different than everyone else’s. Most peers went with the classic light tan colorway.
I should have also mentioned I went to school in Kansas, a landlocked place where only the lucky ones that knew someone with a boat were able to get to a lake during the summer. We were not East Coasters who grew up sailing and actually had a need for good boat shoes.
But let me tell you something: We took Sperry culture very seriously. There was even a point my junior year where the school administration wanted to ban Sperrys because they weren’t “dressy” enough. We literally made signs, went on strike, and protested. Spolier: we won and got to keep wearing our beloved Sperrys.
During my middle and high school years, Ugg boots were all the rage. They’re all the rage again. In terms of timeline, it only makes sense it’s Sperry’s turn to make a comeback, so I went ahead and bought a pair (planning keep them forever this time). I wanted the Authentic Boat Shoe in dark brown to pay homage to my favorite 2010 pair (shown above), but $110! Girl’s on a budget.
So, I scanned my favorite secondhand sites and on Depop found a brand new pair in my size for $80 with tax and shipping, so I pulled the trigger. One thing about me is if I find something I like online that’s new, I’m always going to look to see if it’s available secondhand first — you’d be surprised how often it is.
Here are other secondhand pairs I love that are still available. Stock up while they’re cheap!!
Amazing metallic ones for $14 — size 8.5
Cute new-in-the-box Oxfords for $15 (I also had these but in beige suede) — size 7
Le Classic in good condition for $13.50 — size 7.5
Like new medium brown Intrepids for $12 — size 5
Honey leather Authentic Originals for $13 — size 6.5
Lined leather chunky mules (I’m obsessed with these??) for $33.75 — size 8.5 and 9
Green and pink leather colorblock (I would have killed for these back in the day) for $24 — size 7.5
Red, white, and blue Authentic Originals for $30 — size 9.5
Classic honey leather Originals for $21.25 — size 7.5
Good condition classics for only $10!! — size 9
These $17 ones would be cool with colored socks — size 6.5
Rare-ish all-black pair for $40 — size 8.5
Suede leather sneaker hybrid for $30 (I had a canvas/plaid version)— size 7.5
Burgundy leather with gold accents for $20 — size 7.5
Brown leather with hot pink accents for $37 — size 5.5
Dark green leather Authentic Originals for $25— size 7.5
Cream leather and braided jute for $40 — size 6.5
Green and navy tartan (would have matched my grade school uniform lol) for $40 — size 7.5
Two-tone dark brown and cream with toggle laces for $22 — size 9
Might also buy these if no one snaps them up! for $35 — size 7.5
And these black leather ones with a white sole for $40 — size 7.5
All aboard the Sperry Ferry ⛵︎