HOW WE’RE STYLING TIMBERLAND’S BOAT SHOES THIS SUMMER

You heard it here first: boat shoes are on a major comeback arc. Once reserved for preppy Ivy League students and actual sailors, the tides have turned, and they’ve quickly risen to summer staple status for 2025. The humble boat shoe has transcended yacht club to become an essential styling piece in workwear and streetwear – and no brand is steering the revival quite like Timberland. Wondering how to wear them? Take some style cues from your favourite creators Natalie, Nile, Hannah and Josh. Trust us, they know what they’re doing. Get on board.

NATALIE

Streetwear isn’t just a trend to Natalie – it’s a lifestyle. She never strays from her vast collection of streetwear essentials: think hoodies, tracksuits and heavyweight basics – even when she’s swapped the sneakers for boat shoes. While she’s paid homage to the old-school combo of boat shoes + chinos, she’s added a street spin with help from a camo-print hoodie, crisp tee and her signature gold jewellery. Updating your top-siders with modern prints and pieces is always a good idea – Nat’s proof of that.

GET THE SHOE:
Timberland heritage noreen boat shoes in brown full grain leather, £180

NILE

Nile’s a Y2K kinda guy – he’s got baggy jeans, jorts and jerseys in spades and isn’t afraid to pick the loud pieces from the clothing rack. He didn’t sacrifice making a statement when it came to styling his boat shoes either – just look at the mocha pair with his floral jacket and duffel bag. If you’re the type to keep your foundations basic and dial them up with one or two bold pieces, Nile’s your go-to for ‘fitspo, and you can count on these Timberland boat shoes to complete any look.

GET THE SHOE:
Timberland Classics 2 eye boat shoe in mid brown leather, £130

HANNA

Hanna’s dedication to elevated basics is exactly why she’s a mainstay on our moodboards. While the oversized T-shirt + shorts combo is famously failproof for everything from coffee catch-ups to city adventures, accessorising with boat shoes and a sweatshirt hanging off the shoulders results in some seriously preppy feels. If you haven’t already secured your Timberland boat shoes for SS25, Hanna’s your sign to lock in.
 

GET THE SHOE:

Timberland heritage noreen boat shoes in brown full grain leather, £180

JOSH

If British street style could be distilled into a person, it would be Josh. Harringtons, trench coats, tartan and high-low dressing are his forte, and while he tends to keep his palette more muted, he let his boat shoes stand out against vibrant pastel pieces. We can totally see these cargo shorts and pink shirt rocked by Tyler, The Creator and The Kid LAROI – a quirky and preppy pairing that doesn’t lack in style points. The striped socks are the cherry on top and position the shoes as the centrepiece in this ‘fit. 10/10, no notes.

GET THE SHOE:
Timberland authentics 3 eye classic boat shoes in burgundy full grain leather, £180