How to Wear the Comfortable Spring Shoe Trend I Can’t Stop Thinking About
It's as if a sneaker and a loafer had a baby...
Welcome to Style Notes, an occasional column where I share cozy style ideas and take you along on my journey to shop and dress with more intention—missteps and all.
A note before we dive in: Last spring, I went through a phase of writing about personal style, then hit a wall after I got the consumption “ick” and took a step back. But lately, I’ve been feeling the itch to get back into writing about style — how to approach it creatively, intentionally, and with comfort and ease first and foremost in mind — while still being aware of overconsumption and its impact. A tall order, but this post is a part of my effort to revive a topic I care about and find joy in. If this content isn’t for you, you can absolutely opt out in your email Notification Settings here. No hard feelings whatsoever!
In today’s post:
The surprising spring shoe trend I’m into and why
How to style it effortlessly: 6 outfit formulas to try
18 new *and* secondhand picks I love
On the Merits of the Boat Shoe (Yes, Really)
If you’ve been looking for a sneaker alt this season, you’re in luck because the boat shoe appears to be trending. Yes, you read that correctly. I hadn’t thought about them in years—probably since my preppy-leaning middle school days in North Carolina, when Sperrys were practically a uniform. But I remember them fondly: that gingerbread-brown, spongey feel, the burnt caramel patina of accidental water stains, the rawhide leather laces that darkened and softened over time. By the end, they were beaten up in the best way—proof of how well-loved they were.
As someone who loves both classics and comfort, I’m glad to see this heritage shoe making a comeback. With its non-slip sole, easy slip-on design, and leather that’s meant to wear in beautifully over time, the boat shoe is a solid contender for a spring sneaker alternative.
Curious about what’s out there, I went searching for boat shoes and ways to style them for spring—when a transitional, closed-toe option like this feels especially welcome after months of stomping around in boots and sneakers.
6 Outfit Ideas: How to Wear Boat Shoes This Spring
1. With Relaxed or Straight Leg Jeans + Thin Knit + Transitional Jacket
Based on what I’ve seen, the trick is to show some ankle or skin with a boat shoe. Since it has a slightly heavier, more structured look, that bit of delicate skin helps balance things out. But there are exceptions to this guideline, as demonstrated here by Lucy Williams, who wears them with relaxed-fit jeans, the hem just floating above the shoes.
The example above is from Lucy Williams.
I love the textural interest of the suede shoes + leather jacket + light wash jeans to keep things a bit brighter for a transitional season like spring. And if you don’t own jeans that are just the right length, the example below is a good reminder that you can always cuff those bad boys. :)
In the examples below, the wider hems have been taken up to just show the ankle. I love this combo as it feels quite breezy—and again, I love them with the light wash jean.
2. With a Longer Jacket + Shorts or a Mini Skirt
I saw this look on Miu Miu’s site and love the bare legs mixed with a longer coat, balanced out by the shoes.
The below is a similar but different take: a white mini skirt paired with a slightly oversized work / barn jacket that just shows a sliver of the skirt. I love the neutral palette of brown, tan, and white in the look below, again from Lucy Williams (is she perhaps the queen of boat shoes?!). The white skirt appears to be crochet, which again balances out the heaviness of the dark brown suede boat shoe.
I could see myself recreating this look this spring, using clothes I already own (ALWAYS a win to shop your own closet).
3. For Being On-the-Go: With Cropped, Stretchy Kick Flares + a T-Shirt
This is essentially the same idea of “showing some ankle,” but swapping jeans for the trending kick flare, a pant style so versatile you could really wear them with any type of shoe.
I love the styling below from Donni: brown shoes paired with gray pants, and a sweater tied around the waist to add some colorful interest (and butt coverage, as needed!!).
And if you’re in the market for a pair, I won’t shut up about Donni’s version of the kick flare which I find to be petite friendly. They feel like rib knit leggings! I would size up if you’re in between sizes, they can be quite squeeze-y around the waist and thighs. (They also now sell a “tall” version which I’ve heard works great for curvier bodies, too.) You can use ALISHA10 for 10% off. This is not sponsored, I just love them a little too much, ha!
Under the paywall: 2 more outfit ideas, 9 boat shoe picks, and 6 secondhand boat shoe finds.
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