How to Wear An Oversized Sweater

How to Wear An Oversized Sweater + Oversized Sweater Outfit Ideas
From Top: & Other Stories Alpaca sweater | tradlands fisherman | L.L. Bean cotton fisherman | sezane sweater | Hatch knit

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 (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 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

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  1. Rach wrote:

    Oversized sweaters are the best! And thank you for the ideas on different ways to wear it!

    10.30.19 | Reply
    • Jess wrote:

      You’re so welcome! Happy sweater season. xx

      10.30.19 | Reply
  2. Ashley wrote:

    Jess thank you for this awesome post! I love all the different ways to wear these! Definitely going to need these this New England winter!

    10.30.19 | Reply
    • Jess wrote:

      You’re welcome Ashley. Definitely a must for winter in New England. xx

      10.30.19 | Reply
  3. Jessica Camerata wrote:

    Needed this post! I struggle with sweaters because I’m a bit busty and I find that I feel even bigger in them. But think I just need to try some more styles!

    xo Jessica
    My Style Vita

    10.30.19 | Reply
    • Jess wrote:

      It is definitely tricky and a bit of trial and error, it has been harder for me finding styles I like with a much bigger chest (and stomach) but I find the longer styles that aren’t too bulky tend to be the most flattering. xx

      10.30.19 | Reply
  4. Jada wrote:

    Thanks for sharing these tips! I love oversized sweaters but sometimes struggle to make them look stylish.

    10.30.19 | Reply
    • Jess wrote:

      You’re welcome! I hope it’s helpful for chilly weather xx

      10.30.19 | Reply
  5. Lynn wrote:

    Love all of those looks on you! I really want everything , lol but it’s just too warm here now. I couldn’t find the same style backpack that you have that I been loving for years, so I found one in a deep Cocoa color with a beautiful braided leather on one side and alligator leather on the other side on sale from the Brahmin Shop right in Newport on the Wharf! They were so nice! It’s on the way!

    10.30.19 | Reply
  6. emily yelencich wrote:

    Hey There!

    Love these sweaters! Was looking for suggestions on tissue tees and long sleeves! I have one from BR from about 5 years ago and can’t find anything thin like that anymore! Any great finds?!

    10.31.19 | Reply
    • Jess wrote:

      I like Everlane and Boodywear!

      10.31.19 | Reply
  7. Lisa wrote:

    Is the code for the boots? I tried to use it, but it wasn’t working…expired? Thanks!

    11.7.19 | Reply
  8. Thank you for writing such an amazing post Jess! These are some amazing tips. I feel oversized sweater go really well with tailored bottoms. I feel it balances things out and gives a chic look.

    6.17.20 | Reply
  9. Astora wrote:

    I love cozy sweaters! They all look amazing and stylish.

    Thanks for sharing some ideas.

    9.20.20 | Reply
  10. Baguio wrote:

    Interesting! with such cold weather in my hometown, this comes in handy. couple of week before December, I’ll be preparing some outfits. Got some ideas already. Thanks 🙂

    11.10.20 | Reply
  11. Marc wrote:

    I have a lot of sweaters that are too big for me. I’m glad to hear that I am not alone. Thanks for this post.

    10.25.21 | Reply
  12. Thanks for the ideas.
    I love big sweaters because they are super comfortable

    6.17.22 | Reply