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 kami 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 (use code JESSANN20 for 20% off). Keep it monochrome for a chic and polished vibe.
CHUNKY KNIT 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 Ever lane. 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.
Credit : https://www.jessannkirby.com/
