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!
Find Your Perfect Pair: Boat Shoes for Spring
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52 Responses
I’m eager to find the just right pair of boat shoes for me! I am drawn to the dv perforated one you show. Thank you!
Also, I’ve eyed the J Crew trench for about a year and have considered buying. I’m stunned its final sale!? So risky when the tones in khaki need to be spot-on to be pleasing. Your pictures make it seem much lighter than I would’ve thought the Crew website portrays.
I think it’s a really pretty shade, but I realize beauty is in the eye of the beholder… and I didn’t notice that it’s final sale. Boo.
Standing corrected on the FINAL SALE part I shared. On the J Crew app, it does show all colors are final sale. On the standard website it does not. Probably an app glitch. Sorry to share incorrect information 🙂
Interesting, thanks for clarifying!
That is one trend I am skipping. Besides, I need a shoe with more structure at this point.
I’m right there with you, Maggie. I’m skipping this trend, too. I’ve never liked boat shoes.
I’m glad to see that I am not the only one skipping the boat shoe trend. Jolynne they look cute on you, but I just feel frumpy in them. Like slippers as others have said
I’m skipping this trend too. Too flat for me. I have to have at least an inch height and more than support.
I’m skipping this too. I stick to classic styles that’ll be around awhile as investing in good orthotic shoes that are stylish is a challenge in itself. Jo-Lynne looks great in her boat shoes tho. 🙂
I’m excited to see boat shoes coming back into style. I have several pairs that I’ve worn for years and I love the casual look of them. Thank you for styling them today! Do you think a navy pair would be too dark for cropped jeans? I have long feet, and don’t want them to look like real boats!
Dark colors tend to recede and make those areas look smaller, so I think they’d be a great choice if you’re worried about your feet looking like boats. 🙂
Thanks!
Do you think this shoe and style would work with a knit midi skirt? I have to wear business casual. Thanks!
Yes, for sure, but it’s definitely ‘a look’ that is intended to be unexpected and a little bit quirky. If your office leans more traditional, loafers or ballet flats might be a safer bet.
Is suede the only option for boat shoes this season? I notice both the pairs you show are. I live in the Pacific Northwest, where it rains a lot. Suede isn’t great in the rain. The other thing I don’t like about it is that the toes sometimes get shiny with wear.
I’m one of those old enough to have sported Sperry Top Siders (in chocolate brown) back in the day. They weren’t that comfortable. Hopefully the modern ones are!
Not at all – in the round up at the end of the post, I linked a bunch of options that are leather, not suede. I think I’m drawn to the suede because it’s a little more of a refined take on the look.
I won’t be doing the boat shoe trend. They are not my style and I think they look like slippers. I don’t care for the nautical look either. Too preppy for my style. It’s so funny how trends start huh? You look great in your photos. I’m going to be looking for a grey trench coat.
I like them but they read like moccasins to me.
That’s the name I couldn’t remember. Moccasins.
Skipping this trend. They look like slippers to me and not my style at all.
PS So sorry for two post. I thought my first didn’t post. lol
Stay safe in the wind. Calm and light rain here in NW Oregon
I’m not a boat shoe person, per say, BUT as I’ve mentioned before I do own nearly every color in the sperry “tennis” style shoe that is boat like. I feel like, although both shoes you mentioned are nice looking, to me they feel more like “casual loafers” vs boat shoes as I’m not sure most boat people would wear suede in case they got wet but maybe I’m splitting hairs 🙂 – – needless to say I actually might rob some items from my poshmark closet because they are actually back in style – both an “east west style bag” and a pair or two of this type of “boat shoe”.
Yeah, you just described why I like these – they’re not a literal boat shoe, but an interpretation of the original. And yes, it’s a type of loafer. Speaking of which, loafers, especially ruched styles, are also trending again. That’s kind of the point of it being a trend — there are lots of variations to choose from. 🙂
I realize that the Women’s “Loafer Casual On Flat Shoe Classy and Comfortable” as it’s described (aka boat shoes) on Amazon are not leather however, at $34.00 they look a lot like the Sperry AO2 Eye Boat Shoe at Evereve for $100.00. Yes, maybe they will only last from spring to fall (depending how much you wear them) but at that low price they are certainly worth a try. I found them to be true to size, stylish, very cushy and they have a rubber sole. Plus, they are quite pretty – white and silver with some gold accents. I have expensive shoes and low priced shoes so it’s nice to be able to enjoy both depending on your needs.
Thanks for the tip! I’ll add them to the shopping widget.
I’m suddenly feeling very good about keeping my A02s around, even though I bought them probably 11-12 years ago. My problem with them is that the sole is very thin and doesn’t provide much support.
I agree, they look too much like slippers, in any interpretation. Sorry to be negative, but I think this trend will be short-lived.
I will probably skip the boat shoes, although I like the look of the more elevated ones in suede a bit more. I do think the suede may be why some people are saying they look like slippers—they remind me a bit of the LL Bean slippers my daughter & her friends all wore to school several years back! The darker colored leather ones are a definite pass for me. I SO badly wanted a pair when I was in college (when preppy was big), then finally got them & found them really uncomfortable. Those Jeffrey Campbell suede ones are pretty though!
I’m curious what you binge watched. I’ve been looking for something new to watch.
I love everything about the first outfit you posted!
Younger – It’s on Neflix. It’s a little raunchy in parts, just as an FYI, but it’s well written and light and fun.
I’m watching that too. I think it’s because yiu mentioned it in a previous post. It’s good!
Can you wear boat shoes with socks? My feet are always freezing.
You can… it’s sort of like the skirt question. It’s more of a quirky, intentional look, so make sure that’s what you’re going for. If you just want the warmth and don’t have a quirky style, I would go with something simple and subtle, and you probably want it to match the shoe, your skin, or your pants.
I like the look of those shoes on you. I tend to stay away from flats myself, needing a little extra height. Hoping there will be a pair with some elevation for the shorties! 😉
Me, too, on the freezing feet! Socks are always a must. So I wonder about socks and boat shoes also.
I am all in where the boat shoe trend is concerned! As soon as I heard the first bit of buzz about boat shoes coming into style I got so excited! I love the new sleeker style and will be sporting both that and the old school style this spring and summer. I’m waiting on a sleek pair to arrive this week, and I can hardly wait until the weather cooperates enough to where them. Thanks for the great post and styling ideas!
I was the opposite of preppy in the 80s, and prep trends have never appealed to me in the decades since. But last year I found myself buying not one but two striped sweaters with polo collars, and now I’m considering boat shoes! I like the look with the raw hem jeans, and I really like the suede. Considering the Campbells since they’re more in my budget range.
When I was in late high school and early college, I wore Sperry boat shoes (and Bass penny loafers) all the time. When I saw they were coming back recently, I thought I would just pass on them this time around. But….then I came across one of the slimmer styles on Bloomies website. They were a pair by Aqua and on sale for $35, so I ordered them ago try, and I really liked them. A day or two later I was online browsing and saw the Jeffrey Campbell pair you showed above, and I ordered those too:)) I like that they are more of a cross between a driving moc, a loafer, and a boat shoe.
Unless–and that word is carrying a lot of weight here–unless I can find N or S, non-suede, I’m skipping this trend. I don’t “need” them, but the (really) old flashback style in the classic cognac would be so fun. I was trying to remember when the last Sperry’s moment was. 5 years ago? 15? At that time they had a gazillion pastels and color mixes AND they still made N’s. I am no doubt one of your older fans/readers. Maybe the oldest? But I do get a kick when someone comments on retro styles. My “preppy years” were mid to late 1960’s, just before we all became boho hippies.
Thanks for another fun post. I always look forward to email.
I think it’s more like 15 years ago. I remember women wearing them when I worked in an office. I didn’t like them. I was more into higher heels.
I’m intrigued by the Reformation boat shoes. They’re subtle but super cute. I’m also intrigued to know what new show you binge watched!
I look forward to your email every day and have learned so much from you, Jo-Lynne! We are the same size and have a similar style. Thank you for all your hard work and for posting sales information. For some reason, I have not been getting your email the last few days. I even re-subscribed, but it did not come today. I read today’s posting after Googling your website. Could you check into this for me, please? Thank you in advance!
Hi Cheryl. It says you are active and they are delivering. Have you checked spam? Sometimes they get caught in a spam filter – this has happened to a few people lately. I wish I knew why.
I checked and there they were! Definitely not spam! Thank you for your reply and for all you share! 🙂
I love boat shoes! Couple years ago I had a red pair, dear husband scoffed at them, saying you’ll only wear them with one outfit. Proved him so wrong, I wore them with dresses, skorts, all length pants, by the time I got rid of them, they were pretty used up. Boat shoes are suprisingly comfortable and decent foot support.
I love this trend! I’m all in if I see a pair with an inch or so height.
Check out Timberlands Noreen, or the platform version if this is your jam 🙂
I love Sperry Top Siders. I had a light navy pair with blue and white stripes on the toe box and got complimented until I wore them out. They were such comfortable and stretchy leather. I think you will enjoy them.
Have been wearing boat shoes since the eighties. I gravitate to the classic style. These are pretty…I think they would be particularly great in the fall.
I’m a no to boat shoes but that’s just me and the flat shoe thing. With alot of flares and bootcuts running longer I need the heel plus they just aren’t my favorite style. I have some fisherman sandals from Vionic I do love that are tall and work with alot of Spring & Summer so glad I didn’t throw them out. I think clogs are still in too, aren’t they? I love the sweater in blue. Enjoy your day out !! I’m off to the Heathplex.
Love this new trend. The two pairs you show look great with your outfits!
the orange ones would match my Louis! (it has some of that cognac leather) great post, thanks for sharing