Waypoint: A Winter Roadie

Waypoint is built for the roads less travelled, the unexpected detours, and the moments in between. It’s a collection inspired by classic Kiwi winter roadies.

Because great men’s winter style isn’t about having a different outfit for every occasion; it’s about having the right layers for every stop along the way. Warm knits, easy fleeces, relaxed denim, and practical pieces that can handle four seasons in a single day (because, well, New Zealand).

So whether you're heading north, south, or completely off course, consider this your map. Five stops, five fits, and plenty of winter outfit inspiration for wherever your next roadie takes you.

The roadie officially begins.

It’s dark, it’s cold, and nobody’s really speaking yet. The only thing standing between you and happiness is a flat white and the hope that your car's old heater will eventually kick in.

This fit is built for early starts and questionable weather forecasts. A solid knit, a lightweight puffer vest, and the kind of pieces that work just as well at the first coffee stop as they do six hours later.

Easy, warm, dependable. Much like the mate who remembered to bring the aux cord.

Shop The Essentials

✅ Anti Series Search Puffer Vest | Rip Curl
✅ New Retro 1.0 Sweatshirt | Oakley
✅ Charter Pants | Just Another Fisherman

You weren't planning on stopping here.

But somebody spotted a lookout, somebody else said "bro, trust me," and suddenly you're twenty minutes behind schedule taking photos you'll chuck on your story.

The best roadie moments are never on the itinerary, which is exactly why this fit keeps things simple. Easy layers, practical pieces, and enough versatility to handle a quick wander, a gravel track, or an impromptu mission to find "the better view just around the corner."

Because somehow, there’s always another hill.

Shop The Essentials

✅ Everything OS Box Crop Tee | Thrills
✅ Yumiori Vest | The North Face
✅ Step-Stone Cacoon Pants | Rusty
✅ Built To Win 5 Panel Cap | Thrills

Fuel for the car. Fuel for the people.

By this point, someone needs a toilet break, someone wants another coffee, and everyone suddenly agrees that a $7 saussie roll is absolutely essential.

The fit? Casual, comfortable, and pulled together without trying too hard. A classic tee and loose denim keeps things relaxed, paired with neutral kicks that keep you ready for whatever the next stop throws at you.

Looking put together while operating on nothing but caffeine and optimism is a skill in itself.

Shop The Essentials

✅ Immortal System OG T Shirt | Billabong
✅ Billow Chino Pants | Volcom
✅ Immortal Arch Beanie | Billabong
✅ SB Force 58 Shoes | Nike

The energy has shifted.

The playlist is getting softer. The windows are fogging up. Someone’s asleep in the back seat with a hoodie pulled over their face, and "surely we're close" gets thrown around every fifteen minutes.

This is where comfort wins.

Relaxed sweats, heavyweight layers, and pieces that feel like a wearable blanket without completely giving up on looking good. Because yes, we want to be comfortable - but no, we refuse to look like we surrendered halfway through the journey.

Road trip survival mode, but make it stylish.

Shop The Essentials

✅ Cherub 1/4 Zip Sherpa Fleece Sweatshirt | Worship
✅ A5 Loose Jeans | Abrand
✅ One Star 95 Shoes | Converse

✅ Shesh Besh Fleece Hoodie | Rusty
✅ Topper Elastic Cargo Short | Worship
✅ SB Force 58 Shoes | Nike

You made it.

The bags come out. The coffee cups finally leave the cup holders. Somebody immediately claims the best room, despite contributing absolutely nothing to navigation.

And just like that, the road becomes the reward.

The final fit is all about winding down - warm knits, easy layers, and the kind of pieces that work around the campfire, at the bach, or wherever the road decided to take you this time.

Because the best trips aren't always the ones you planned, but the ones where you took the scenic route, stopped too many times, yet still ended up exactly where you needed to be.

Shop The Essentials

✅ Awake Polar Fleece Polo | Abrand
✅ A5 Loose Jeans | Abrand
✅ 480 Numeric Shoes | New Balance

✅ Griffin Flannel Shirt | Rip Curl
✅ Nailhead Miner Jacket | Rollas
✅ A4 Relaxed Jeans | Abrand
✅Boston Oiled Leather Clogs | Birkenstock