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How to Style an Oversized Sweater

I absolutely love an oversized sweater. Whether I’m hanging out at home, running errands with the kids, or heading out with friends, an oversized sweater is such an easy piece to style that also keeps you warm. Don’t get me wrong – I definitely have some lighter-weight sweaters I gravitate towards when it’s not as cold, but for the most part, most of my sweaters lean towards the oversized/thicker side.

I know how hard it can be to find and style an oversized sweater that is warm and cozy but not too bulky and to make it easier for you, I’m sharing my favorite oversized sweater that’s warm and cozy but not too bulky, and how you can style it for those colder days.

Related Post: Casual Winter Outfits

How to Style an Oversized Sweater

When styling an oversized sweater, keep these tips in mind:

  • Opt for a tailored bottom such as a pair of well-fitting skinny jeans (love this pair!) or faux leather leggings. This will give you a more tailored look!
  • Consider your height! There are generally two styles of oversized sweaters. The first is a boxy oversized fit and the other is a straight, but longer, fit. Since I’m on the taller side, I opt for a straight but longer fit!
  • When in doubt, tuck it! This is one of my favorite ways to style an oversized sweater if I’m pairing it with jeans. It gives it a stylish, more intentional look and if you’re on the shorter side, it’ll help elongate your legs.

My Favorite Oversized Sweater Outfit Ideas

With Faux Leather Leggings and Sneakers

the best oversized sweater

casual winter outfit

Keep it casual and layer a big sweater over a pair of faux leather leggings and sneakers. I love this look for running errands, driving the kids around, and getting work done around the house. It’s comfortable and warm but still looks put together.

Tucked Into Your Favorite Jeans

tips for styling an oversized sweater

how to style an oversized sweater

If you want an easy, classic look, tuck your oversized sweater into your favorite jeans. Throw on your favorite booties, grab your bag, and you’re ready to head out the door! When I’m planning on tucking my oversized sweater into a pair of jeans, I will opt for a high-rise style to help lengthen my legs.

Layered with a Wool Jacket and Hiking Boots

how to style an oversized sweater for winter

On days that it’s really cold and I know I’ll be spending more time outside, I’ll create a monochrome outfit with the same color bottoms and my favorite winter boots (love this pair, too!) and add contrast with a wool coat. Since it’s the winter, I typically opt for an all-black look when I do this and add a camel wool coat to add that contrast!

In A Monochrome Outfit

the best oversized sweater for winter

oversized sweater outfit inspiration

I love monochrome dressing, especially when it comes to knitwear. It gives a simple sweater such an elevated look! Pair your oversized sweater with the same color bottoms (give a slightly different hue a try!), and keep the monochrome palette going with a fun pair of boots in the same color. I love pairing my sweater with these heeled booties for warmer days and these lug sole booties when the weather isn’t as great. The pearl detailing is so fun!

The great thing about all of these outfits is that all of the pieces are easy to mix and match to give you even more outfit options when styling your oversized sweater. If you’re still on the hunt for a great sweater that isn’t bulky, I can’t recommend this one from Amazon enough! It’s under $50 and the quality is so good.

A few other places I will shop for oversized sweaters include H&M, Free People, and then Nordstrom and Shopbop.

Thanks for reading! Be sure to follow along with me on Instagram @curlsandcashmere.

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