10 Winter Outfits to Wear

Time for a little bit something different (than your regular outfit post)! We all know it is coming (winter that is…try not to say it too loudly, you’ll startle it), so why not prepare it for the best way I know how…shopping! ;)

I thought I would round up my 10 favorite winter outfits from last year, and link to some pieces that will help you get ready for winter…because we know it’s only going to get colder and snow-ier.

And if you want to be taken to the original outfit post, just click on the photo and you should be taken there!

Buffalo Plaid for Days

stripes and buffalo plaid print mixing; Style On Target; winter casual outfit

Whether it is hint of the pattern (like in a scarf – here) or a full blown blast of this print (like this coat here), you can’t get much more festive than buffalo plaid!

Mix Those Prints

old navy fair isle sweater, Loft jeans, buffalo plaid shirt, pom pom beanie Target; winter casual style

See Exhibit A (above). I love a good print mixing outfit no matter the season, but let’s face it. It is so much easier with all the layers of winter to make this work. I love pairing a plaid shirt (try this one here) with a fair isle sweater (love this one – here) for a warm, cozy, AND stylish winter look.

Rock Those Christmas Colors


Ahhhh red and green. No matter when or where I see these colors together, I ALWAYS think of Christmas. So embrace it for the next few weeks by pairing these colors together over and over again. Try it with a similar green winter puffer coat and a great red plaid scarf….or reverse it with this berry red coat and this green plaid scarf!

Always Ankle Boots

fair isle sweater + J.Crew Factory camel coat, black tights for work; Style On Target blog

It’s not secret here on Style On Target that I LOVE my ankle boots come fall and winter. I pretty much wear them allllll season long. The ones above are an older pair from Loft (similar), but I’ve replaced them with this fantastic pair from Target (here – available in black and brown). I also love this pair and this pair! Gotta collect ’em all!

Rock Those Classics


Stripes forever (this sweater is similar to mine above)…and neutral color palettes for the win. Because while it is a struggle to get out of bed on those cold winter mornings, getting dressed shouldn’t be. Other classic pieces to include are this black winter coat, this pair of cord pants, and this pair of winter boots.

But Don’t Forget About Color

yellow Old Navy coat, navy stripe tee, navy skirt, navy tights and Sole Society tassel ankle boots

While the weather is gray and drab outside, that doesn’t mean that your winter wardrobe has to be. My favorite way to combat this is with a brightly colored winter coat. This yellow one is similar to mine above, but I also love this bright blue option and this red toggle beauty!

Stay Festive


When in doubt what to wear to a holiday party…put down the ugly Christmas sweater and grab some plaid instead. I promise you’ll look waaaaay cooler, but still look festive. Try this plaid crew sweater (super similar) or this black and white option. 

Free to Fair Isle

fair isle sweater + J.Crew Factory camel coat, black tights for work; Style On Target blog

And while we’re on the topic of sweaters, you can’t beat a fair isle sweater in the winter, and there are so many options out there right now that I had to put together a widget below with all of my current favorites. Give me ’em all!

Embrace the Tights

plaid blazer + navy skirt + Uniqlo rayon blouse + cognac tote; Style On Target blog

I’m definitely one to delay wearing tights as long as possible, but I will admit they add a whole new layer of texture, pattern, or color to an outfit. I wear these ribbed ones (here) from Target allllll the time, but I also picked up these cool diamond weave ones to try out this year. But my ultimate favorite style of tights to wear? Polka dot print (like these)!

Get a Great New Coat

camel coat + gray stripe sweater + black jeans + black ankle boots + gray crossbody purse; Style On Target; winter outfit inspiration

If you live in a cold-weather climate, I would recommend making this a yearly or every-few-years rule…just to keep things interesting! This camel coat was my 2015/2016 winter pick, and it has served me very very well (it’s back again this year – here), and I feel like I have mentioned it 200+ times, but this plaid beauty (here) is my 2016/2017 acquisition, and it might be the prettiest thing I have ever bought. If I had to choose one more to add to my hall coat closet (but I can’t, because The Husband might kick me out of the house), then it would be this gorgeous red print option (here)!

And that’s it for my top 10 winter looks! I hope you found some inspiration for some future outfits or shopping trips, and together, we can make it through the bitter winter chill (with lots of layers and hot chocolate)!

  • I am seriously LOVING ALL OF THESE!! Your sweater and layering game is seriously on point….plus all of those wintery patterns are perfect:)

  • Sarah H.

    I know I’ve already seen the vast majority of these outfits but I still love them!

    ~Sarah of Sarah’s Real Life