25 Winter Outfit Ideas

Cheers to Friday, friends, and the long weekend ahead! It feels like the kids just went back to school, and now they already have another day off…but I’ll take the extra time with them! We saw Hidden Figures last weekend, and loved it so much. It’s supposed to rain all weekend, so we’ll probably head back to the movies…what should we see this time? I love any excuse to eat popcorn and milk duds!

In true Texas form, we had frigid, snowy days last week, followed by 70-degrees this week. Hence why we don’t really have ‘off-season’ clothes! It could be wool sweaters and hats one day, and t-shirts the next…we have to stay prepared for both. So pretty much the only thing I pack away during the Winter is shorts and sandals! But I know many of you are in the throes of a legit Winter, so I rounded up 25 (yep, twenty-five!) of my favorite cold-weather styles. Basically, a month’s worth of outfit ideas for you, plus links to recreate them yourself. Now that’s what I call Fri-Yay!

Plaid Scarf | Sweater | Jeans | Faux-Fur Parka | Similar Boots | Sunglasses

Long Cardigan | Long Tee | Distressed Jeans | Scarf
Similar Crossbody | Sunglasses | Hoop Earrings

Camel Peacoat (on sale for $37!) | Gray Sweater | White Oxford | Distressed Jeans
Rainboots | Crossbody Bag (back in stock!) | Sunglasses

Similar VestGingham Shirt | Favorite Leggings | Similar Boots
Watch | Sunglasses | Hoop Earrings | Fringe Scarf

Black Cardi-Wrap | Striped Tee | Plaid Scarf | White Jeans | Rainboots
Sunglasses | Beanie Hat | Earrings

Similar Sweater (love this one, too) | Leopard Scarf | Black Jeans | Similar Boots
Similar Crossbody Bag | Sunglasses | Watch | Hoop Earrings

Poncho | Blouse (on sale!) | Favorite Black Jeans  | Wedge Booties
Saddle Bag | Pendant Necklace | Sunglasses | Hoop Earrings | | Leopard Cuff

Hat | Sunglasses | Fringe Scarf | Striped Tee | Long Cardigan
JeansBoots (worn folded down) | Hoop Earrings

SweaterCamel Peacoat (only $38!) Leopard Scarf | White Jeans
Booties | Sunglasses | Earrings

Sweater Tunic in ‘Pink Fawn’ | Favorite Leggings | Wedge Booties in ‘Beet Suede’
Pendant Necklace | Crossbody Bag | Sunglasses | Hoop Earrings

Striped Tee | Fleece Cardigan Wrap | Jeans | Rainboots
Beanie Hat | Sunglasses | Hoop Earrings

Striped Shirt | Fair Isle Sweater | Crystal Necklace
Puffer Vest | Jeans | Booties | Sunglasses

Sweater | Scarf | White Jeans
Suede Tassel-Tie Booties | Hat | Sunglasses | Earrings

Turtleneck Tunic | Favorite Leggings | Sunglasses | Hoop Earrings | Rainboots

Similar Fur Vest | Gray Sweater | White Jeans | Leopard Belt
Sunglasses | Hoop Earrings | Similar Bag

Jeans | Plaid Shirt | Sweater (v-neck version)
Utility Jacket | Crossbody Bag | Sunglasses | Hoop Earrings | Similar Boots

Similar Sweater | Striped Tee | Jeans |  Boots | Bag |  Sunglasses

Blouse (similar) | Cardigan (similar) | Jeans | Scarf | Pendant (similar)
Leopard Pumps (similar) | Earrings | Sunglasses

Fleece Wrap Cardi | Jeans | Similar Boots | Scarf | Long Tee | Sunglasses

Peacoat Dress | Sunglasses | Earrings | Bag | Scarf | Tights | Plaid Heels

Similar Navy Blazer | Plaid Shirt (similar) | Pearls | Sunglasses
Bag (similar) | Sweater | Jeans | Leopard Heels

Black Peacoat | Similar Gingham Shirt | Ivory Sweater | Jeans
Similar Boots | Crossbody Bag | Sunglasses

Hat | Sunglasses | Similar Vest | Similar Sweater | Similar Shirt | Jeans | Boots
Hoop Earrings | Watch | Bracelet

Pink Coat (similar) | Red Sweater | Jeans | Leopard Heels (love these too)
Pendant Necklace | Pom Pom Clutch | Rose Gold Sunglasses

Faux-Fur ParkaSimilar Vest | Similar Sweater  |  Sunglasses | Jeans |  Snow Boots

I know from my friends up north that the novelty of snow and cold has worn off by now, so hopefully this will give you some fresh new ideas for the coming weeks…and stay tuned for new inspiration later this month! Happy weekend, lovebugs!


Leave a Comment


  1. Jenny wrote:

    Lalaland! I want to see it again! It would make for a perfect rainy weekend treat!


    Posted 1.13.17 Reply
  2. Jennifer wrote:

    I definitely need some winter inspiration! It has been cold and icy here in Michigan. The pink and red is one of my favorite combos!

    Posted 1.13.17 Reply
  3. This makes me not even care that it’s all of a sudden pretty cold here again today! So many great outfits and pictures!

    Posted 1.13.17 Reply
  4. You could make 125 winter outfits! You make everything look CUTE and spontaneous! Love sugarplum style! This weekend is going to be a wet rainy mess…break out the hunter rain boots and bring it on. Go Cowboys! xo

    Posted 1.13.17 Reply
  5. Shelly wrote:

    Your style is seriously my favorite! Love to see how you put outfits together that look so easy.

    Posted 1.13.17 Reply
  6. Love all your outfits and your style! You have the best pieces for winter… Happy Friday!

    Brittany 🙂

    Posted 1.13.17 Reply
  7. Kathy wrote:

    Oh your outfits are darling and so cute on you! I love your combinations. They are all so fresh! Here in Wisconsin only a couple of those 25 combinations are considered winter outfits. The rest were appropriate for fall. GO PACKERS!!

    Posted 1.13.17 Reply
  8. Jenny wrote:

    What a great post! Can you do this every season?

    Posted 1.13.17 Reply
    • Cassie wrote:

      Thanks Jenny, I’m thrilled you liked it! I did one for Fall…you can find it here. I’ll be sure to do more with each season! xo

      Posted 1.16.17 Reply
  9. Colleen wrote:

    Cassie I love your blog, fashion sense and home style. I have 2 questions for you that to my knowledge you have not addressed-does your husband always agree on your choices for home design? My husband and I only butt heads surrounding our vastly different home styles. To make matters worse I suppose we used to share the same style only my taste are changed. And secondly are you familiar with a wardrobe time capsule? While I love your dressing room diaries and fashion, you have a ton more clothes, shoes, accessories than the average person. Please don’t take this as a criticism but I would love to see you do a post about outfits with way less pieces. Just my 2 cents! Thank you!

    Posted 1.14.17 Reply
    • Cassie wrote:

      Hi Colleen!! My husband doesn’t always agree to my initial vision, but almost always loves it in the end! I run stuff past him, especially if it’s really outside the box. But I’m fortunate that he’s a creative soul, and pretty much trusts me to do ‘whatever I like best’ at this point! #keeper But I do consider him when making choices…hence why my house isn’t hosed down in pink paint! 😉

      And yes, I’m familiar with capsule wardrobes…they are certainly appealing! But the nature of what I do is find new clothes and ways of styling them for my readers, so they might not like it if I showed the same 10 items month after month. 😉 I don’t keep the majority of the things shown, usually I’m just trying them on and reviewing for the blog. I’m also a huge purger, so I go through my closet and donate about once a month! xo

      Posted 1.16.17 Reply
  10. Amber wrote:

    Super cute outfits. Thanks for posting a link where you can actually see or buy the clothes. Love it!!!

    Posted 1.25.17 Reply
  11. Darlene wrote:

    Great site!

    Posted 11.1.17 Reply