Attention! Cupshe has so many cute cold weather fashion pieces in stock right now! You probably know Cupshe for their swimsuits that I wear literally all the time, but in the past few years they’ve had the cutest cool weather outfits to shop, too.
I live in San Francisco which means I’m the queen of layers, which comes in handy for putting together cute cold weather outfit ideas. This season is all about layers, textures and staying warm AND stylish.
In this post I’m sharing I’m sharing my favorite cute winter outfits from Cupshe this season that are stylish, affordable and cozy.
The exact amount of layers you’ll need will depend on where you live or where you’re traveling. When I lived in Wisconsin and was facing brutal -20 winters, I left my house with at least 3 layers (even my bottoms) and a giant coat every day.
Most of us don’t need to go that extreme. I live in California now and even when I take winter trips to Colorado or Lake Tahoe, the weather is forgiving enough to wear thick tights and skirts instead of thermal underwear layered under my straight leg jeans.
I love the look of skirts and sweaters for the chilly months, so don’t be afraid to keep wearing them come autumn or winter! Thankfully, Cupshe has it all.
1. Plush Plaid Jacket With Chunky Sweater
Shop the look: plush jacket (wearing XL) / chunky sweater (wearing XL)
This is such a classic street style outfit for autumn or mountain trips when you want to reach for plaid. I don’t want to be dramatic but this plush jacket from Cupshe is literally the softest jacket I’ve ever owned. It feels like a fancy throw blanket and is so dang comfy.
Personally, I’ll be wearing this on my upcoming winter trips (I’m about to face an 11+ hour flight to Germany and this jacket will help me sleep like a little baby on the plane) but it’s perfect for any cold day outfits you have ahead of you.
I paired it with a chunky turtle neck sweater from Cupshe along with tights and boots. Classic, timeless, can be worn anywhere.
11/18-11/21, up to 70% off + an additional 15% off with WHIMSY15
11/22-11/25, up to 80% off + an additional 15% off with WHIMSY15
11/26-11/28, up to 85% off + an additional 15% off with WHIMSY15
2. White Blouse And Brown Mini Skirt
Shop the look: white blouse (wearing XL) / mini skirt (wearing L)
If you’re looking for cool weather outfit ideas for pumpkin patches, Thanksgiving gatherings or even working from home, try tights and skirts!
When the air turns crisp, I love reaching for mini skirts paired with tights and ankle boots (plus a fun blouse like this white one from Cupshe) to frolic around in. They scream “autumn” but aren’t too bulky or hot (who else lives in a place where mornings are cold but the afternoons are chilly at best, but usually kinda warm?)
This brown skirt looks great with this blouse for those sunny winter days, but also looks darling paired with sweaters if it’s a little colder out. And if it’s really cold, top this outfit off with a puffer coat or a nice camel jacket and it’ll look fab as well.
3. Chic Black Jumpsuit & Heels
Shop the look: black jumpsuit (wearing XL)
If you’re on the hunt for affordable New Years Eve outfit ideas for cold weather, you NEED to get this Cupshe jumpsuit for yourself!
I have never worn a jumpsuit so dang comfy, it feels like a warm hug which is exactly what I want when I’m bar hopping at 11pm in December (brrr!) This jumpsuit is affordable but chic – just look at how fun those sheer sleeves are for a little bit of personality.
Here I paired it with simple black heels but for actual New Years Eve I’ll likely go with a faux leather jacket or faux fur jacket like this cute pink one to dress it up.
4. Chic Black Swimsuit & Cover Up
Shop the look: swimsuit (wearing L) / spotted cover up (wearing XL)
YES – your cold winter outfits need to factor in hot tub dips! And a cute cover up. I always pack along a few Cupshe swimsuits on any winter trip I take because you never know when a hot tub (or a hot spring) will be available.
Just last week I was down in Orange County with my friend Justina. The nights were in the high 40’s and nothing felt better than sinking into the hotel’s hot tub with a glass of wine.
I wore this Cupshe black swimsuit and paired it with a cute spotted cover-up which totally doubles as a blouse. (I wore it on the plane down to Southern California!)
5. Brown Pants & Open Back Cream Sweater
Shop the look: cream sweater (wearing XL) / brown pants (wearing XL) / black belt
This sweater has been making its way into all my cold weather outfits lately. It’s all business in the front – standard cream knitted sweater, but turn around and BAM, little party in the back with that fun knot design.
This past weekend I visited my friend Gen in Sacramento, where autumn is still in full force. I paired this cream sweater with these brown pants and a belt. I’m a trousers gal but you could also swap the tan pants for brown leather pants.
We went thrifting and somebody complimented me on my outfit so I knew I had to include it in this blog post! I think this outfit is best for cool days that don’t need a jacket (just a sweater) since the back is too fun to cover up.
6. Green Holiday Dress
Shop the look: Green midi dress (wearing XL)
A couple of weeks ago I had my first holiday event of the season (a fun wine event in downtown San Francisco that had a fab view of the ferry building!)
This new Cupshe dress arrived just in time to wear out. I love wearing the color green, especially around the holiday season. It’s so festive and strong enough to wear on its own.
Here I wore black combat boots and tights, but you could easily pair this dress with heels and sheer tights if you’ll be indoors (my wine event was outside so I wanted my feet to be warm.)
7. Tan Sweater Dress & Tall Boots
Shop the look: Tan sweater dress (wearing XL)
My favorite cute outfit ideas for cold weather always have to include a sweater dress (or two). I love getting all cozy in a sweater dress while working from home since it still low-key feels like I’m wearing a blanket but it’s professional enough for virtual meetings.
This tan sweater dress is a perfect weight (not too thick, not too light) so it’s great for layering all winter season long. Here I wore it solo, but I’ll be taking it to Germany with me and styling it with scarfs and a winter coat.
8. White Sweater Dress
Shop the look: White sweater dress (wearing XL)
The best winter outfits are usually sweater dresses in my opinion. They’re chic yet cozy and are almost neutral palettes to accessories like scarves, beanies and mittens.
Here I styled this cute white sweater dress on its own since it wasn’t cold enough in Sacramento to layer on the knit hats, but come winter this white sweater dress will look so cute with my red winter coat and a holiday scraf!
11/18-11/21, up to 70% off + an additional 15% off with customized codes
11/22-11/25, up to 80% off + an additional 15% off with customized codes
11/26-11/28, up to 85% off + an additional 15% off with customized codes
Shop My Favorite Cupshe Gems From This Season
I hope this helps you feel inspired to try some new cold weather looks from Cupshe this year!
On top of pulling out the Christmas tree every November (yes, I’m THAT person) I always reached for my knit sweaters, boots, cozy dresses and my stock of winter fashion pieces. I’m thrilled to have added a few new Cupshe pieces to my winter box and I can’t wait to wear them out and about this winter.
Especially to holiday parties and on my Christmas trips! You’ll be seeing these outfits for cool weather a lot on my Instagram and TikTok feeds coming up soon.