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Cute Sweater Outfit Ideas for Staying Stylishly Warm

In This Post: From sweater and jean outfit ideas to a cute cropped sweater over dress look, here’s how to style a sweater outfit for fall and winter 2020.

While I’m always sad to say goodbye to summer, I am excited every year to pull out my cute sweaters and to add a few new ones to my collection. Thank goodness there is never a shortage of cute sweaters to choose from each fall season to help us brave the brisk temperatures that are currently beginning to hit. There are so many different ways to wear a sweater that I couldn’t possibly round up all of them, but I do hope some of these looks inspire you with cute sweater outfit ideas to try throughout the colder months of 2020.


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Trendy sweater outfit

When it comes to cute fall sweater outfits this year, I’ve been styling my favorite pair of jeans with this on trend bobble sweater over and over again (full blog post and review on this Madewell bobble sweater here). The sweater gives a fun statement with its trendy bobble texture and big balloon sleeves. Plus, pairing it with cropped straight leg jeans (seriously, did your read my review on this pair of denim yet? BEST. JEANS. EVER.) makes it such an easy outfit to reach for!

Marled sweater with jeans outfit

Another current sweater trend I can get behind is the marled look. It’s such a fun way to swap out a solid color sweater while still maintaining an elegant, classic look. The threads of the marled fabric can contrast a little (like in this cable knit lavender sweater for a more subtle marled look) or a lot (like with this more contrasting turtleneck sweater) depending on the look you gravitate towards. You can also search the term “spacedye” to find sweaters with a similar blend of color.

Cream cropped sweater over dress outfit

As soon as the weather started to cool down this fall, I became determined to successfully style the sweater over dress look. This sweater outfit idea came together with a slightly cropped cream sweater (similar here) and a pair of classic blush loafers. I have a full blog post with tips and tricks on how to create a sweater over dress outfit here.

Pullover sweater with grey jeans

I wasn’t kidding when I said I’ve been wearing this Madewell bobble sweater all the time! Another recent sweater outfit I used it for was with these perfectly fitting Wrangler jeans (I can’t find the grey version anywhere, but here’s a black pair in a similar Wrangler style) and a black chucky heeled boot. I really love how the grey and purple look against each other in this look!

Colorblock sweater with leggings outfit

I love an elevated casual outfit, but one of the ways to style a sweater that you’d see me wearing most in everyday life is with leggings. My favorite dressier leggings of all time are the “Perfect Black Pants” from Spanx (full review here). They are a cross between a pant and a legging and they are just the worth every single penny. Paired here with a pink, red, and white colorblock pullover sweater (similar here) and my favorite nude heels for a put-together winter outfit.| photo below by Alex Barone

Athleisure Sweater Outfit Ideas

I love laid back sweater outfits just as much as I appreciate a dressier take on the look, like in the outfit above. During the fall and winter months (and even spring!), one of my go-to sweater outfits becomes styling activewear leggings (here’s review of my Beyond Yoga spacedye leggings featured in this outfit) with a thinner, lightweight sweater under a denim jacket. This makes my look feel a bit more put-together and intentional than just wearing an oversized top with leggings. Plus, I love that a stretchy denim jacket adds a comfortable, removable layer for days when the temperature fluctuates.

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