I Didn’t Realize an Oversized Sweater Could Look This Chic Until I Tried These 8 Outfits

This post may contain affiliate links, which means we’ll receive a commission if you purchase through our link, at no extra cost to you. See our disclosure here.

Being a girl in the fall means you have the excuse to wear all the oversized sweaters your heart could dream of. Whether I’m meeting a friend at a coffee shop, running errands to grab my favorite Trader Joe’s goodies, or taking a stroll through the park, a large-fit sweater will always be my cozy staple for the season.

However, sometimes I lack the creativity to know how to style such a simple piece. That’s where Pinterest and Instagram come to the rescue. In an effort to find new, trendy ways to wear an oversized cozy knit this year, I thought it would be fun to share some of my favorites with you too. Below, I’m breaking down 8 oversized sweater outfits and where to shop similar pieces to get the look.

Which size sweater should I order for an oversized look?

Every brand differs in how they size different clothing products. However, my general rule of thumb when deciding what size sweater to purchase always stays the same. 

I recommend sizing up one to two sizes bigger than what you normally wear. If a sweater looks like it’s more form-fitted on the model, you could even go up three sizes from your typical size.

1. Oversized V-Neck Sweater + White Tee + Wide Leg Jeans

Looking for a cozy, minimalist outfit? This one checks all the boxes for being cozy, chic, and simple. Start with your base of wide-leg jeans and a white tee. Then, layer your oversized sweater over the tee and complete the look with black boots, a bag, and sunglasses.

2. Oversized Roll Neck Sweater + Wide Leg Jeans (Cuffed) + Red Flats

I love a classic sweater and flat combo in the fall. It makes you feel like you’re dressed in Ralph Lauren but for a fraction of the price. Pair the iconic J.Crew Rollneck Sweater with some dark wash wide-leg jeans. Complete the look with a pair of red flats and your favorite suede bag.

3. Oversized Cable Knit Sweater + Poplin Shirt + Bootcut Jeans

An oversized sweater outfit like this one is so timeless year after year. You’ll start with some bootcut jeans to give someshape to the bottom half. Then, layer a cable knit sweater over the poplin shirt. Complete the outfit with a pair of pointed-toe boots and a medium-size shoulder bag. 

4. Large Turtleneck Sweater + Slip Skirt + Flats

If you’re looking to dress up your oversized sweater for a date night or to wear to the office, this is the perfect look to recreate. Pair a large turtleneck sweater with a midi slip skirt. A brown silk skirt for fall is always a great staple piece to have. To complete the look, add some ballet flats and a suede shoulder bag.

5. Fair Isle Sweater + Straight Leg Jeans + Ugg Slippers

As the days get colder and the holiday season approaches, I love pulling out a few of my oversized Fair Isle sweaters to wear. They are so chic and cozy for the season. To create a cute, casual outfit with one, pair the sweater with straight-leg jeans and platform Ugg slippers. This is the perfect fit for grabbing coffee on the weekends or traveling somewhere in the mountains this fall.

6. Oversized Cable Knit Sweater + Poplin + Mini Skirt + Boots & Socks

I am actually obsessed with this oversized sweater fit! It’s such a chic way to create an effortlessly styled look. Start by throwing on a poplin shirt and your oversized cable knit sweater over top. Add a mini skirt to the mix and complete the look with scrunched tall socks and some brown moto boots.

7. Grey Oversized Sweater + White Tee + Grey Jeans + Sneakers

I absolutely adore a monochrome look. It’s stylish no matter the time of year. To create a look similar to this one, layer a grey oversized sweater over a basic white tee. Add some grey colored jeans and some white sneakers to complete the outfit. So simple and chic.

8. Slip Dress + Oversized Sweater + Cargo Pants + Salomon Sneakers.

I think this is the perfect for a weekend around the city. It may seem like a lot of layers (and it is), but each is intended to help the look come together. The mix of the silk texture, the raw cargo pant, with the cozy sweater blend seamlessly together. Start with your base of cargo pants and a slip dress on top. Then, layer a white tee and oversized sweater over top. Complete the outfit with some gorpcore sneakers and a large shoulder bag.