outfits i wore on my imaginary boat
six days, six looks, and exactly zero yacht memberships
Back in high school, I desperately tried to pull off the preppy lacrosse-player look on a blue-collar budget. Spoiler: it was not cute. So you can imagine my surprise and reluctance when I heard boat shoes were making a comeback. They immediately reminded me of those days and of the shoes my four-shirted husband packs for “fancy” dinners on vacation.
And yet, somehow, they made their way back into my wardrobe.
But these aren’t the hot-pink-polo, skinny-jean boat shoes I once wore. The boat shoes I’m spotting in the Substack wild are versatile. Think loafers meet slippers. Multifunctional. Cute even!
I spotted Katelyn Cnossen wearing her gorgeous new Sperry boat shoes in a recent Substack post, which made sense after her observations of preppy style trending hard following Copenhagen Fashion Week.
Then I read Substack posts by Evonne Sturm (re: preppy style as grown-up BTS energy) Lindsay Sword (re: trendy khakis as a pillar of prep) and Sogole Kane (re: plaid as a cornerstone of preppy fashion & so much more). Collectively, their observations made me see preppy fashion in a new light: playful, elevated, and easy to wear.
Boat shoes are no longer just the footwear of fraternity brothers or Conrad and Jeremiah Fisher from The Summer I Turned Pretty. They’re evolving into something more dynamic, polished, and sleek. I’ve seen them popping up as incredibly expensive designer versions, fun collabs (like Sperry x Aritzia), and in luxe materials such as leathers, suedes, and lug soles. Some are accessorized with paracord laces (S/O toJennifer Klee who shared these adorable paracord laces from Etsy).
Who knows, at this rate, maybe next they’ll be accessorized with mini sailor-inspired (absolute new fear unlocked). What’s really interesting is that instead of the predictable nautical styling, boat shoes are now being paired with satin pants, skirts, athletic shorts, colored crew socks, and more.
The algorithm must’ve read my mind because then all of a sudden this post by Lucy Williams popped up on my Instagram feed. And to be honest, I wasn’t mad. I felt inspired and in need of a lobster roll ASAP.
So, what did this millennial gal do next? Obviously, I made a Pinterest board for boat shoe inspiration. I widened the search to “taupe suede shoes” and focused on color combinations. From there, I played around on Indyx, creating tons of outfits using pieces I already own. It was so easy to style them in a gazillion ways. Suddenly, these shoes didn’t feel like the preppy, imposter-syndrome nightmares I remembered. They felt… wearable and intriguing.
So, I put them to the ultimate test: wearing them in real life for an entire week.
What I Wore: Boat Shoes Edition
I was torn between the gorgeous dark leather boat shoe versions and the suede. I narrowed it down to suede. Then it was color: do I go with taupe or a chestnut color? Taupe had the most versatility for my wardrobe (IMO), so it was the clear victor.
After extensive research in the boat shoe department these were my rankings:
WINNER (!!!): The pair I went with were these. I ordered my regular size (9.5) and the size below (9) — and for me they were TTS. (Also available here, here, and here)
Honorable Mentions: This pair looked so cute, but was a bit out of my price range. I also loved these, but they didn’t make the final cut.
I wish I could tell you I wore these shoes somewhere wild and glamorous, but my life is neither of those words. A fellow Substacker, Sarah Lowery, wrote a note asking for everyday outfit inspo— grocery store runs, doctor’s appointments, birthday parties, etc.
Lucky for you, I don’t go anywhere more interesting than what was listed above! While I don’t have a boat (nor friends who would invite me to fake it for the internet), I can show you the outfits I’d wear on my imaginary one.
Here are my six favorite looks from last week, featuring the star of the show, “THE BOAT SHOE.”
Look 1: The Sporty Boater (Worn To: Camp Pickup & a CT Scan)
The Mood: Part athlete, part sailor. Dressed to sprint and catch “the ferry” because I’m perpetually late… and probably forgot there’s some sort of spirit day for my kids wherever we’re going.
Notes: Loved it. When I got hot I tied the sweater around my waist. Boat shoes are comfortable and didn’t need to be broken in. I struggled with the tie, got frustrated, untied them both, and luckily my husband came to the rescue before I had a full meltdown on day one.
The anchor pieces…
Look 2: The Yacht Rock Boater (Worn To: Target)
The Mood: Looking like I belong on a yacht, but probably just circling the marina lost. But have no fear, “Brandy”1 is playing on loop.
Notes: The cropped polo felt key to completing this look. Long-live boxer shorts, SO comfortable.
The anchor pieces…
Look 3: The Riviera Boater (Worn To: Ubering my kids)
The Mood: I’ve never been to Italy…. but I have stayed in a Holiday Inn Express.
Notes: The scarf completely elevated this look. These boat shoes are ridiculously comfortable.
Couldn’t decide which way to wear the scarf was my favorite…
…Went with this one for the final look!
The anchor pieces…
Look 4: The Didn’t Read the Dress Code Boater (Worn To: Errands—dry cleaners & nail appointment)
The Mood: Were jorts not allowed on the yacht? Sorry not sorry.
Notes: I knew they were a keeper when they passed the CRITICAL jort test!
The anchor pieces…
Look 5: The Breezy & Basic Boater (Worn To: A children’s birthday party)
The Mood: Casual, polished, and low-key hoping no one asks me to participate in a relay race.
Notes: Love how they can be dressed up and dressed down. A skort is such an unsung hero piece. I think next time I’d pair this look (breezy linen shirt & skort) with my new leather croc embossed bag to achieve Fanny Adams’ Breezy + Breezy + Structured (B+B+S) formula!
The anchor pieces…
Look 6: The Comfort > Everything Boater (Worn to: Camp pick-up & library visit)
The Mood: Not worried about being too trendy. Comfort is king. And if seasickness strikes, I’m ready to spring into action.
Notes: Love how boat shoes pair with track pants. Feels like the perfect airport/travel outfit. Not sure if the extra layer was necessary, but I loved the pop of color. If I had one, I’d probably add a cute beaded necklace like this!
The anchor pieces…
Honorable Mentions (have not worn yet)
Here are some other fun ways I styled these boat shoes for the upcoming cooler months. These are all via the Indyx app using what I already have in my wardrobe.
Outfit ideas to continue wearing my boat shoes into the fall…
…even more outfit ideas to rock these bad boys well into the winter!
I definitely want to add some colored crew socks to my wardrobe to wear with these! I’ve been loving green, grey, and cobalt blue. (S/O to Danielle, my color guru, who introduced me to these fun colored socks in her post here)
Dropping Anchor
In conclusion, I do not have a boat. I do not belong to a yacht club. And I have no plans to be on a boat anytime soon… especially after watching Poop Cruise on Netflix.
That said, I loved wearing my boat shoes. They’re going to be really fun during the transitional months and even into colder weather.
I hope this gave you some inspiration! What I’m learning is that the greatest creativity and style ideas often come from what you already have in your wardrobe arsenal.
Maybe boat shoes are for you. Or maybe they give you PTSD, like they did for me at first. Whatever you choose, choose it because you love it! Not because someone on the internet said you needed it.
What do you think… are boat shoes a yes or a hard pass? Which look was your favorite? How would you style them?
This captain is off duty, see ya on the next adventure!
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I can’t explain it, but if I were ever to experience torture, it would be sitting in a room with this song on loop.
Boat shoes were made for you! Every one of these looks should win the America’s Cup (not totally sure what that is but it sounds boat-y)! I love the crop polo and also the rugby in your indyx round up! I also laughed so much at your boat life vs real life events. Life is all about how we frame it 😂
Honestly this lewk really works for you! I especially love the sporty pairing and the skort pairing bc skorts are THE single best fashion invention in history. This is a trend that I love so much but I cannot do myself; certain corners of Prep Americana just don’t look right on me even though I love pops of prep and even full on prep cosplay. Maybe it’s bc I’m 52 and it feels like a step too close to my ‘driving moccasin’ years. The looks you’ve planned on Indyx are terrific; please share when you wear the white jorts with the rugby, that’s my favorite! Also YES these are going to be AMAZING with colorful socks. And don’t you need plaid socks with these? I mean if you’re going all in….