How to Wear An Oversized Sweater

Raise your hand if you love sweater weather. I know I sound like a broken record talking about my affinity for sweaters, but there’s just something special about the season when you can throw on a cozy knit. Maybe my obsession with sweaters was born out of the fact that it’s basically cold here from mid-October through April (that’s more than half the year). Now that I’ve got a growing baby bump and my number one priority when getting dressed is ultimate comfort, oversized sweaters are my new uniform. From sweater dresses to chunky knits they’re the easiest outfit makers that will also keep you cozy all season long. I pulled together some tips and outfit ideas for oversize knits, along with a bunch of my favorite oversized sweater styles right now.

How To Wear An Oversized Sweater

layer it

Under a menswear blazer, long wool coat or a lightweight puffer, pair an oversized sweater with cozy layers. If you’re rocking a cardigan try a silk cami or bodysuit. Lightweight tissue tees and turtlenecks are great for wearing under wool, alpaca and cashmere sweaters.

Go monochrome

Pick a single color palette from head to toe for an easy and chic outfit. I love creamy neutrals and earth tones or shades of grey and black.

size up

I almost always size up with sweaters, even when they’re oversized. If I’m wearing it untucked I like the bottom of the sweater to hit the upper thigh. Check out the men’s section too, there’s some gems.

Check fabric content

I like to go with either 100% cotton (organic is even better), merino wool, alpaca, cashmere and other natural fibers. Some brands are doing recycled wool and cashmere (occasionally with a recycled synthetic blend) which can help lend softness and make a sweater less itchy. But I stay away from acrylic, polyester, and any sweaters that don’t have sustainably made synthetic fabrics.

Oversized Sweater Outfit Ideas

menswear blazer and fisherman sweater

Pair a boxy blazer with an oversized fisherman sweater, jeans and knee high boots (use code JESSANN20 for 20% off). Stick to a similar color palette, like earth tones, for a polished look.

Chunky ribbed Alpaca sweater

I love a big chunky ribbed knit, especially in alpaca or wool. Pair it with skinny jeans or leggings.

Men’s fisherman sweater

Some of my favorite oversize sweaters are from the men’s section. I’ve had this L.L. Bean Fisherman sweater for years (size small). If you can’t do wool they also have a cotton version. I love it with distressed denim and sneakers or booties.

cotton turtleneck sweater

Another great alternative if you don’t like wearing wool/alpaca, a cotton turtleneck sweater is the perfect cozy knit for fall and winter paired with boyfriend jeans and flats. Tuck your hair into the turtleneck to mix it up.

cashmere turtleneck and long wool coat

Pair an oversized cashmere turtleneck sweater with a chic long wool coat, faux leather leggings and ankle booties. Keep it monochrome for a chic and polished vibe.

Oversized Knit Sweater And Hiking Boots

Keep it casual in an oversized chunky knit, leggings and hiking boots. Stay extra cozy with a cashmere wrap.

cashmere sweater dress

It doesn’t get easier than a cashmere sweater dress. I love this one from Everlane. Pair it with ankle boots or over the knee boots and a light puffer jacket.

green & black

I love this color combo, especially around the holidays. Layer over a striped tee or turtleneck and let the sleeves poke out a little.

Oversized Sweater Styles

Chunky Knits

Fisherman Sweaters

Turtleneck Sweaters

Sweater Dresses