G’day, fashion legends! Winter in Australia is a bit like a choose-your-own-adventure book—chilly mornings, sunny arvos, and the odd rainy day that catches you off guard. But let’s be real: it’s also the perfect season to flex your streetwear game. Whether you’re strutting through Melbourne’s laneways or chilling in Sydney’s Inner West, nailing that winter streetwear vibe is all about blending style, comfort, and a dash of rebellion.
As a streetwear obsessive who’s spent way too many hours scrolling Insta and hunting for the perfect fit, I’ve rounded up the top 5 winter streetwear must-haves for Australia in 2025. These pieces are straight-up fire, backed by the latest trends, and guaranteed to keep you looking sharp while braving the unpredictable Aussie winter. From local heroes like The Unrivaled Brand to global icons, this list has you covered. Let’s dive in and level up your wardrobe—your mates will be jealous, and your mirror selfies will thank you.
1. Oversized Puffer Jacket – Your Winter MVP
Nothing screams winter streetwear like a puffy jacket that’s equal parts cozy and cool. In 2025, oversized puffer jackets are dominating the scene, with Aussie brands like Carhartt WIP and The Unrivaled Brand dropping bold designs. Think vibrant colors like burnt orange or olive green, or keep it classic with black for that sleek urban edge.
Why it’s a must-have: Puffers are the ultimate layering piece. Pair one with a hoodie and baggy cargos for a laid-back look, or throw it over a tailored fit to mix high-low vibes. Plus, they’re practical for those frosty mornings in Canberra or Tassie. Look for water-resistant ones to survive Sydney’s random downpours.
Style it: Rock a Carhartt WIP puffer with loose-fit jeans, chunky sneakers, and a beanie. Or, check out The Unrivaled Brand’s outerwear for affordable, high-quality puffers that nail the oversized trend. Peep our winter layering guide for more inspo.
2. Checkered Flannel Shirt – The Retro Comeback King
The ‘90s called, and they want their flannel back—but we’re keeping it. Checkered flannel shirts are making a massive comeback in 2025, and they’re a streetwear staple for good reason. Brands like Obey and Above the Clouds are serving up fresh takes with bold patterns and heavyweight fabrics that scream quality.
Why it’s a must-have: Flannels are versatile AF. Wear them open over a graphic tee for a grunge-inspired fit or buttoned up with chinos for a smarter edge. They’re perfect for layering under a puffer or denim jacket when the temp drops. Plus, that lumberjack aesthetic is giving major Aussie bush vibes—ideal for a weekend in the Blue Mountains.
Style it: Pair a red-and-black check flannel with Agolde baggy jeans and Nike Dunks. Toss on some retro sunnies for that effortless cool factor. Want more throwback vibes? Check out The Unrivaled Brand’s graphic tees to layer underneath for a bold twist. See our retro streetwear guide for more tips.
3. Baggy Denim – The Fit That Never Quits
Denim is having a moment, and baggy jeans are the hero of the 2025 winter streetwear scene. Forget skinny jeans (sorry, millennials—Lattitia Taylor called it at Daily Mail); loose, relaxed denim is where it’s at. Aussie labels like 108WAREHOUSE and The Unrivaled Brand are nailing the vibe with premium cotton and vintage washes.
Why it’s a must-have: Baggy denim is comfy, stylish, and screams streetwear attitude. They’re perfect for layering over thermals or pairing with oversized tees for that skater aesthetic. Plus, they balance out chunkier winter pieces like puffers or hoodies, keeping your fit proportional.
Style it: Go for a The Unrivaled Brand relaxed-fit jean with a tucked-in graphic tee, a Les Deux hoodie, and some New Balance 9060s. Finish with a bucket hat for that ‘90s revival nod. Need more denim tips? Check our denim styling hacks.
4. Oversized Hoodie – Cozy Meets Statement
Hoodies are the heart of streetwear, and in 2025, oversized hoodies are stealing the show. Brands like The Unrivaled Brand and Song for the Mute are dropping bold, comfy designs with graphic prints or minimalist vibes. Think plush fleece, vibrant colors like cobalt blue, or classic black with statement logos.
Why it’s a must-have: An oversized hoodie is your go-to for warmth and style. It’s perfect for layering over tees or under jackets, and it nails that effortless, relaxed vibe. Aussie winters aren’t Arctic-level, so a quality hoodie can carry you through Melbourne’s chilly evenings or Perth’s crisp mornings.
Style it: Layer a The Unrivaled Brand graphic hoodie over a white tee, paired with wide-leg chinos and Adidas Sambas. Add a subtle chain necklace for that extra drip. See our hoodie styling tips for more ideas.
5. Waterproof Chelsea Boots – Step Up Your Shoe Game
Aussie winters can be wet and wild, so a pair of waterproof Chelsea boots is non-negotiable. Brands like Blundstone and RM Williams are Aussie icons for a reason, but they’re also getting a streetwear glow-up with sleeker silhouettes and bold sole designs.
Why it’s a must-have: Chelsea boots are the perfect mix of rugged and refined. They’ll keep your feet dry during Brisbane’s rainy days while adding a polished edge to your streetwear fit. Pair them with baggy jeans or cargos for a look that’s equal parts practical and stylish.
Style it: Rock Blundstone 550s with rolled-up baggy denim, a The Unrivaled Brand graphic tee, and a puffer vest. Add a beanie for those extra chilly days. Need more boot inspo? Check our winter footwear guide.
Why These Pieces Are Your Winter Wardrobe Goals
These five must-haves aren’t just trendy—they’re built to handle Australia’s wonky winter weather while keeping your style on point. From the rebellious roots of streetwear to the high-quality craftsmanship of Aussie brands like The Unrivaled Brand and Song for the Mute, these pieces let you express your individuality without freezing your buns off.
Pro styling tip: Layering is your best mate in winter. Start with a breathable base (like a graphic tee), add a mid-layer (flannel or hoodie), and top it with a puffer or denim jacket. Mix textures and play with proportions—baggy bottoms with fitted tops or vice versa—to keep your fit fresh.
Shop the Look and Join the Streetwear Revolution
Ready to upgrade your winter wardrobe? Head over to theunrivaledbrand.com to shop these must-haves and more. Their curated collection of bold hoodies, relaxed denim, and statement tees is perfect for nailing these trends without breaking the bank. Don’t sleep on their limited drops—stock sells out fast, and you don’t want to be that mate stuck in last season’s gear.
Got a killer winter streetwear look? Tag us on Insta @theunrivaledbrand or drop a comment below with your fave piece from this list. Let’s keep the Aussie streetwear scene thriving!