Winter Lookbook: 12 Winter Outfits I’m Wearing Right Now

Winter outfits to get you excited for the season!

Winter Lookbook - 12 outfits to inspire you

Winter is one of the most challenging seasons to dress for, where it’s not just a matter style, but also a matter of warmth, and sometimes the two just don’t go hand in hand. But with the woes of winter, also comes outerwear fashion – which is one of my favourite items which really comes out to shine this season –  along with that comes all the fun frosty accessories like hats, scarves and more. So to get you excited for winter, here are 12 winter outfits I’m wearing right now to help inspire your own cold weather style. 

Fall Winter Outfits - Pink teddy coat, black sweater dress, OTK boots and floppy hat

This look right here is one of my go to winter outfit combination: Sweater dress, OTK boots, and a furry teddy bear coat. It’s such an instant chic look and an easy combo to throw together whenever you’re stumped for a winter outfit. 

Shop the Outfit:
Outerwear: Pink Teddy Coat c/o SHEIN
Dress: Black Sweater Dress c/o SHEIN
Shoes: Grey Over the Knee Boots (similar)
Accessories: Tassle Necklace c/o Olive + Piper
Hat: Black Floppy Hat from J. Crew (similar here)

Get 10% at SHEIN.COM with code YESMISSY

Winter outfit ideas - long camel coat, sweater and white jeans Winter outfit details - long camel wool coat with white jeans and ankle booties


There’s just something that’s always so refreshing about white denim, especially in the winter! Here I’ve paired down this ripped white denim for a minimalist look with a simple grey turtle neck sweater,  long camel coat, and pointed to ankle booties. 

Shop the Outfit: 
Outerwear:  Camel Split Hem Long Coat c/o SHEIN
Top: Turtleneck Bell Sleeve Sweater c/o SHEIN
Bottom: Mila High Waisted Jeans from Citizens of Humanity
Shoes: Utah Chelsea Boot from Chinese Laundry
Accessories: Tassle Necklace c/o Olive + Piper
Hat: Black Floppy Hat from J. Crew (similar here)Snow day winter outfit - Teddy bear coat and winter boots from Cougar shoes

Now it’s time to get cozy! Here’s a look to prove it’s possible to look warm and cute at the same time. First off, can we talk about how cute these winter boots from Cougar are? Plus, they’re waterproof and have a cold weather rating of up to -11. And with this plush white teddy coat, I’m ready to be a snow bunny for real! 

Outfit details:
Outerwear: White Teddy Coat c/o SHEIN
Top: White Turtleneck  c/o SHEIN
Bottoms: Black Rocket Jeans from Citizens of Humanity
Shoes: Venora Suede Boot c/o Cougar Shoes
Accessories: Monogram Tote Bag from Gucci
Hat: Fleece Lined Beanie from Amazon

Fall / Winter #OOTD - Checkered sweater dress and beretWinter lookbook - 12 winter outfits to inspire you


This printed sweater dress is the perfect little number that takes you from the office to date night and even family gatherings. It’s made a cozy thick material that makes it a great item for cold weather season and so easy to dress up or down by changing up accessories.

Outfit details:
Dress: Button Fron Sweater Dress c/o SHEIN
Hat: White Beret Cap  c/o SHEIN
Bag: Eartha Bag from ZAC Zac Posen
Shoes: Black OTK Suede Boots from Goodnight Macaroon

Fall Outfit Ideas - Sweater dress and checkered scarf with hat

I wasn’t kidding when I said this was one of my go to outfits. Here is that first outfit again with a little accessory change to give it a whole new look! 

Shop the Outfit:
Dress: Black Sweater Dress c/o SHEIN
Shoes: Grey Over the Knee Boots (similar)
Accessories: Tassle Necklace c/o Olive + Piper
Accessories: Plaid Scarf from Necessities 
Hat: Floppy Hat from J. Crew (similar here)

#OOTD - leopard midi skirt, white sweater, waist bag and headband#OOTD - leopard midi skirt, white sweater and waist bag with headband


I’ve been wanting to add some leopard to my wardrobe and this leopard midi skirt is the perfect piece. It’s versatile and goes with so many things. Here I’ve styled it with a white sweater and  some OTK black boots with a waist bag to finish off the look. 

Outfit details:
Top: White Drop Shoulder Sweater  c/o SHEIN
Bottom: Leopard Pencil Skirt c/o SHEIN
Shoes: Ellis OTK Suede Black Boots from Goodnight Macaroon
Accessories: Knotted Head Band c/o SHEIN
Bag: Vara Crossbody/Waist Bag from Ferragamo

Fall Outfit Inspiration - pleated skirt and sweater tucked in . So cute!

Shop the Outfit:
Top: Turtleneck Bell Sleeve Sweater c/o SHEIN
Bottom: Pleated Skirt from Forever 21
Tights: OTK tights from FromRachel
Shoes: Suede Ankle Boot from Marc Fisher

P.S. Get 20% off cute tights like these at with code YESMISSY

#OOTD - black polka dot dress from Cupcakes and CashmereHoliday dress ideas - Cupcakes and Cashmere dress

This cute little dress from Cupcakes & Cashmere is perfect holiday outfit for those family dinners and festivities. It has a playful print of stars and moons to bring out the whimsical spirit of the season. 

Shop the Outfit:
Dress: Milan Dress c/o Cupcakes & Cashmere
Shoes: Strappy Sandals from Marciano (similar)

Christmas Outfit - Red dress with puffed sleeves

This is another great dress for the holidays parties with its bell sleeves and ruffle hem. It’s girly and pretty and the red is perfect colour for holiday festivities.

Shop the Outfit:
Dress: Ruffle Trim Red Dress c/o SHEIN
Shoes: Ellis OTK Suede Black Boots from Goodnight Macaroon

LOOKBOOK outfit ideas for the office - yesmissy#OOTD for the office - grey dress and purple Kate Spade bag
Of course it’s not always about holiday parties, I had to include one workwear look at least in this lookbook. This dress is from eShakti, which makes customized dresses made to your measurements as well as customized to your liking. I choose to have a longer elbow length sleeve for this dress, plus I adjusted the hem to knee length so it would be the perfect work dress. To order your own made to measure dresses and clothes, check out

Rocking this classic look with Guess here! I’m loving how Guess brought back their classic logo tee, and I’m wearing one here paired with a denim jacket with faux leather leggings for a casual look to head out for dinner with the girls! 

Shop the Outfit:
Top: Classic Tee c/o Guess
Outerwear: Denim Jacket c/o Guess 
Bottom: Faux Leather Leggings c/o Shein 

Fall lookbook - leather jacket and floral dress

And finally here’s and oldie but a goodie. I’m pretty much wearing the exact same outfit as this post here, and it turns not that not only does this make a good spring transition outfit, but it’s  also a great fall/winter transition outfit as well! 

Shop the Outfit: 
Dress: Ruffle Insert Leopard & Flower Print Tea Dress c/o Shein
Jacket: Kenya Jacket from Mackage
Shoes: Ellis OTK Suede Black Boots from Goodnight Macaroon
Bag: Vara Crossbody/Waist Bag from Ferragamo

Which look here was your favourite? Let me know in the comments below!

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1 Comment
  • Zeba
    December 24, 2019

    It’s so hard to pick a fave bc everything is so cute! But I’m especially loving the white teddy coat and the f21 pleated skirt. You seriously take the prize for making affordable look designer <3

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Winter Lookbook: 12 Winter Outfits I’m Wearing Right Now