How To Wear Oversized Sweaters – Top Style Tips

by Min Lee

There’s nothing as cozy or surprisingly feminine as an oversized sweater. A major hit for casual wear fans, boyfriend to chunky style knits continue to confirm their place as a year-round staple. Great for rainy days and vital for seasonal changes, here’s how to wear oversized sweaters. 

How To Wear Oversized Sweaters

Relaxed sweaters are an undying trend. If we look at fashion throughout the recent decades, street style has always favoured loose knits, borrowed boyfriend fits and baggy sweaters. Many worry that oversized equals sloppy, but there are ways to size up and appear well put-together.

  • Pair oversized knit sweaters with a sleek mini to midi-skirt and some great ankle boots.
  • Go loose all-over and wear your sweater with a pair of distressed boyfriend jeans and some comfortable sneakers.
  • Sport a button-down shirt underneath for a preppier appearance that could work for the office.
  • Skinny denim jeans and with heeled boots or shoes will always be a solid choice.
  • If in doubt, a baggy jumper and leggings is the last word in comfort and the ultimate laid back style.
outfit grid oversized sweaters knits womens style

PHOTO CREDIT: Whistles, Topshop, Alexander Wang Fashion GPS

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What To Wear With Oversized Sweatshirts

When you think of sweatshirts, you’re probably imagining yoga pants and a gym bag, but this basic essential can grab all the attention, and in a good way.

  • Take a cue from streetwear fans and wear a flared skirt with your sweatshirt. Extreme opposites can create the perfect balance.
  • Rock an oversized bomber jacket on top and combat style boots. Think Alexander Wang.
  • If you can get past those times your mum put you in denim overalls as a little one, they actually work with an oversized sweater for cool, urban appeal.
  • Oversized sweaters with skinny jeans is your ultimate fail safe for the transitional period. Balance out the oversize top with a slim fit bottom and voila: you’re blogger style approved.
outfit grid womens oversized sweatshirt sweater style

PHOTO CREDIT: Fashion GPS and Pinterest

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Cute Ways To Wear Oversized Sweaters

You don’t have to limit yourself to borrowed-from-the-boys or street wear inspired looks. There are many ways to create cute outfits with big sweatshirts and baggy sweaters if you prefer keeping it more feminine.

  • Pairing your outfit with bright heels or a colourful handbag will help take away that city edge.
  • Look for beaded and floral-inspired statement necklaces: they’re perfect for making an oversized sweater dressy.
  • Coloured denim is another alternative to create some elegance. Try out rosy hues or oceanic blues and turquoises.
  • Wearing a fitted pencil skirt creates a beautiful silhouette made for date nights and after-work events.
outfit grid oversized sweater womens fashion styles


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How To Wear Sweater Dresses

  • Take the athleisure approach and go for boxier sweatshirt dresses and a pair of kicks.
  • Sweater dresses are a great office option. Wear them with classic heels to dress up your look.
  • Try wearing statement jewellery with solid coloured sweater dresses. A longer necklace or trendier layered style amps up the plainness.
  • Play around with lengths. An ankle skimming maxi or midi skirt can look extremely sophisticated and fashion forward.
  • For patterned dresses, think simple, minimalistic accessories so you don’t look over-elaborate.
  • Ankle to knee-high boots are great for wearing long sweaters, or be a little more daring and wear a mini sweater dress with thigh-high boots.
outfit grid womens oversized sweater dresses style


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Best Places To Buy An Oversized Sweater

Not sure where to buy big baggy sweaters? Here are ten of our favourite styles, from business casual to artsy graphics, at all price points.

  1. Love Moschino Embellished Sweater Dress available here for £190.
  2. Greylin Nami Turtleneck Sweater Dress available here for £34.
  3. Topshop Oversized Jumper available here for £39.
  4. Proenza Schouler Flared Sleeve Jumper available here for £760.
  5. Saint Laurent Distressed Roll Neck Jumper available here for £530.
  6. Belstaff Roll Neck Knitted Dress available here for £689.
  7. New Look Oversized Sweatshirt available here for £12.99.
  8. ASOS The Ultimate Boyfriend Sweat available here for £16.
  9. Zara Oversized Sweater available here for £9.99.
  10. COS Dress With Ruched Hem available here for £79.
outfit grid oversized sweater oversized sweatshirt women styles

PHOTO CREDIT: ASOS, Farfetch, COS and Zara

Celebrity Outfit Inspiration

Around the world, celebrities live in oversized knit sweaters. From airports to casual selfies, they put their own twist into their best-loved basics. Take a cue from Alexander Wang’s muse, the self-proclaimed “baddest female in the South Korean music industry”, singer and rapper Chae-rin Lee. There are no boundaries to CL’s style or her confidence. She takes every look and owns it both on and off the performance stage.

outfit grid chaerin lee cl womens oversized sweater style

PHOTO CREDIT: Instagram @chaelincl

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Christine Andrew, the owner of the popular blog Hello Fashion and ILY Couture, knows how to rock casual looks as she balances her work as a top influencer, mum and entrepreneur. For you mums out there wondering how to wear a sweater and still look chic, Andrew shows that is possible to stay stylish while chasing the little ones around. Classic stripes and cute, graphic prints make up some of her favorite loose sweaters fashion — with every outfit apt for an active lifestyle.

outfit grid oversized sweater oversized sweatshirt womens style

PHOTO CREDIT: Instagram @hellofashionblog

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What to Wear with a Long Sweater: Quick Style Guide

  • Heeled shoes and boots will always dress up the casual appearance.
  • Try asymmetrical or pencil skirts to create feminine appeal.
  • Wear a collared button-down shirt under your sweater for a cleaner, work look.
  • Coloured denim and beaded or floral-inspired necklaces can help add some elegance.
  • For oversized sweater dresses, try different lengths from maxi to midi for more interest.
  • Oversized sweatshirts don’t need to break the bank, so check out our top affordable picks.

Wearing Long Sweaters: Final Note

An oversized sweater is an essential piece for your wardrobe. Don’t dismiss the ease of being able to throw on a sweatshirt and still look poised. Whether you prefer pop-culture graphics or sophisticated sweater dresses, there are big, baggy sweaters out there for all styles and tastes.

Check out more on advice for women’s wardrobe styling.