Woman confidently posing in an oversized hoodie streetwear outfit

Streetwear

how to rock the oversized hoodie look: streetwear edition

By Willow Creek

Published: 29 Apr 2025

Hey there, fashion friends! So, picture this: it's a chilly autumn evening, and I'm scrambling to find something comfy yet cool to wear out. My eyes land on my oversized hoodie – the one that's basically a walking, wearable hug. And suddenly, I'm hit with inspiration. This isn't just lounge-wear, this is a streetwear statement! That's when I knew I had to share my oversized hoodie styling secrets with you all.
Woman wearing oversized hoodie, autumn setting

Woman wearing oversized hoodie, autumn setting | Image: Supplied

The magic of the oversized hoodie:

The oversized hoodie's appeal lies in its effortless cool. It's that perfect blend of comfort and style that we all crave, right? Forget those restrictive, clingy clothes; an oversized hoodie is the ultimate in relaxed sophistication. It's forgiving, fashionable, and frankly, incredibly versatile. You can dress it up or down, making it the ultimate piece for any wardrobe. Honestly, I think every woman needs at least one in her closet.

Rocking the oversized look: Streetwear Style

Now, let's dive into the fun part – styling your oversized hoodie for a killer streetwear look!

  • Layering is key: Think a fitted cami or a graphic tee underneath to add a bit of shape and personality. Experiment with different necklines and colors to find what works best for you! A pop of color under a neutral hoodie is always a good idea.
  • Pants that pop: Skinny jeans or leggings create a fantastic contrast to the hoodie's loose fit. But don't be afraid to play with other styles too – wide-leg trousers or even joggers can add a whole new dimension to the look.
  • Accessorize with attitude: Add a bold belt to cinch the waist (great for creating shape!), layer on some necklaces, or try a beanie for a dose of extra warmth and style. Don't forget about sneakers! High-tops, chunky trainers, even sleek minimalist sneakers – it's all about personal style. Oh, and sunglasses are my absolute go-to accessory; they instantly add a cool, mysterious vibe.
  • Play with proportions: Don't be afraid to experiment! Try pairing your oversized hoodie with a mini skirt for a fun, edgy look. You might surprise yourself with how amazing it looks!
  • The unexpected twist: Sometimes, the most unexpected pairings lead to the most amazing looks. Try adding a blazer over your hoodie for a chic, unexpected twist on a casual look. It's a bit high-fashion, but seriously cool.
Various street style looks featuring oversized hoodies

Various street style looks featuring oversized hoodies | Image: Supplied

My go-to hoodie looks:

Okay, let me spill the tea on my personal fave looks:

  • Casual cool: Oversized hoodie, black skinny jeans, white sneakers, and a baseball cap. Simple, effortless, and always chic.
  • Edgy babe: Oversized graphic hoodie, ripped boyfriend jeans, combat boots, and layered necklaces. This screams edgy street style.
  • Unexpectedly sophisticated: Grey oversized hoodie, midi skirt, heeled ankle boots, and delicate gold jewelry. This look is unexpectedly polished.
  • Athleisure Queen: Oversized hoodie (a comfy one!), leggings, and stylish trainers. Perfect for running errands or heading to a yoga class.

See? Endless possibilities!

Four different women modeling different street style looks featuring oversized hoodies

Four different women modeling different street style looks featuring oversized hoodies | Image: Supplied

Finding the perfect oversized hoodie:

The key to nailing this look is finding the right hoodie. Look for quality fabrics – something soft and comfortable, but also durable. Check the sizing – you want something oversized, but not too oversized. It shouldn't swallow you whole; you still want to see your shape underneath.

My personal recommendation is to try a few different brands and styles before settling on your fave. Some of my favorite brands are Champion, Independent Trading Co. and even some amazing ones on Etsy!

Close-up shots of different oversized hoodies, showcasing various fabrics and styles

Close-up shots of different oversized hoodies, showcasing various fabrics and styles | Image: Supplied

Fashion is what you buy. Style is what you do with it.

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