I have to admit, when I first heard that boat shoes were trending this spring, I wasn’t exactly eager to jump on board. They didn’t seem like my style, and unlike some of you, I don’t have nostalgic memories of wearing them back in the day. To me, they felt a little too rugged, and I wasn’t sure how I’d make them work in my wardrobe. But in the name of ‘blog research’, I figured I had to at least give them a try—so I ordered a couple of pairs to test the waters.
J.Crew Icon Trench in Vintage Khaki (6) // LOFT Striped Shoulder Button Wedge Sweater (S) // MOTHER Dazzler Flood Fray (29) // Reformation Kyla Boat Shoe in Rum Suede (also at Shopbop) (8.5) // Tom Ford sunglasses // Jenny Bird earrings & bracelet // Freja Caroline Bag (also at Revolve)
Much to my surprise, I ended up loving both styles I tried! They each have a different vibe—one leans more casual, while the other feels a bit more polished. So today, I’m sharing how I’m styling boat shoes for now while it’s still chilly. And when the weather warms up, I’ll follow up with a post on how to wear them for later with shorts and cropped jeans.
The Reformation Kyla Boat Shoe in Rum Suede is an elevated take on the classic Sperry Top-Sider many of us remember from the ’80s. In fact, it’s more similar to Sperry’s Slim Boat Shoe, which I also really like. I was drawn to these because they feel a little dressier than the traditional styles, and the luxe suede is just gorgeous.
They’re also incredibly comfortable—soft and flexible right out of the box. My only hesitation was the color—it has a slight orange cast rather than the rich caramel tone I was expecting. But once I put them on with this outfit, I decided that wasn’t a deal breaker. They’re truly beautiful shoes.
I love the contrast of brown shoes with darker denim washes, which just so happens to be making a comeback this spring! These jeans are the MOTHER Dazzler Flood Fray—a slim straight ankle style with a raw hem in a mid-blue wash. The subtle whiskering and fading give them that perfectly lived-in look, and the hem hits right at the ankle, making them a great match for these boat shoes..
With a medium vamp (the part that covers the top of the foot), the shoes expose just enough skin to be flattering without interfering with the hem of the jeans. A longer inseam would work too, but I like that these don’t hit the top of the shoe.
LOFT Striped Shoulder Button Wedge Sweater (S) // MOTHER Dazzler Flood Fray (29) // Reformation Kyla Boat Shoe in Rum Suede (also at Shopbop) (8.5) // Tom Ford sunglasses // Jenny Bird earrings & bracelet // Dragon Diffusion Santa Croce Big Tote
To play into the subtle fisherman aesthetic without going full-on nautical, I added a classic navy and white striped sweater. I feel like the combination of boat shoes, dark denim, and stripes has that effortless, slightly rugged maritime feel, but in a way that still feels modern and wearable.
By the way, this sweater drops to just $24 in-cart today! Such a great deal for a 100% cotton knit.
Sizing note: I’m wearing the small, but I might prefer a medium for a little extra wiggle room. If you’re in between sizes, you may want to size up.
I topped off the look with a classic trench from J.Crew, which happens to be on sale today. Unfortunately, my J.Crew affiliate links are redirecting to the homepage, but if you’re interested, you can search New Icon Trench. I’m wearing the Vintage Khaki in a size 6, but it’s a bit snug—I may reorder in an 8 for a better fit.
I also carried my new Freja Caroline east-west bag in Oat. The ‘90s-inspired horizontal silhouette is trending right now, and I love how it adds a refined touch to the outfit.
You might notice I carried my Dragon Diffusion Santa Croce woven tote earlier when I wasn’t wearing the coat—I wanted to show the look both ways. While I often like to match my shoes and bag for a cohesive feel, it’s also fun to mix things up sometimes.
I also wanted to show you these Jeffrey Campbell Boast Boat Shoes for a more casual (and more affordable) alternative to the Reformation pair. I threw them on with this same outfit, and while they work here, I can also see them pairing well with even more relaxed looks—especially shorts once the weather warms up.
J.Crew Icon Trench in Vintage Khaki (6) // LOFT Striped Shoulder Button Wedge Sweater (S) // MOTHER Dazzler Flood Fray (29) // Jeffrey Campbell Boast Boat Shoes in Camel Suede (8.5) // Tom Ford sunglasses // Jenny Bird earrings & bracelet // LV Neverfull
These have a more laid-back feel, closer to the original boat shoe aesthetic, and the light brown suede gives them an easygoing vibe that leans more casual. I also ordered the Brown Brush to try (a dark brown leather), but I have a feeling the Camel Suede will be more versatile for what I have in mind. They also come in Cheetah Suede and Dusty Pink Suede—both on trend and a fun twist on the classic boat shoe.
For this look, I carried my Louis Vuitton tote since the shades of brown played nicely with the shoes.
To wrap it up, I have to say—I did not expect to be into the boat shoe trend, but here we are! I think the key (for me) is to find styles that feel a little more polished or laid-back, depending on the look I’m going for, and pairing them with pieces that keep things modern without leaning too preppy, which can sometimes feel a little frumpy or stuffy to me.
If you’re thinking about trying boat shoes this season, I’d love to hear what you think! Are you team classic, or would you go for a fresh take like these? Let me know in the comments!
