Skip to Content

23 Winter Outfits To Wear This Season!

Disclaimer: This blog post may contain affiliate links. If you click on one and make a purchase, I will make a small commission, at no extra cost to you. These are products I’ve personally used and stand behind, learn more.

I can’t believe the Holidays have finally come to a close!  Does anyone else think they went by fast!?  January and February are definitely not my favourite months however I do love winter fashion!  To give you guys some inspiration this season I’ve summarized some of my favourite winter outfits below!  Click on the links to shop each look!

1. Cheers To The New Year!

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, sweaters, sweater outfits, striped sweater, striped sweater outfit, pom pom beanie, starbucks cup, prada & pearls, fashion blogger, cold weather fashion

Cheers to the New Year, 2019 I’m coming for you!  In all seriousness though, I cannot wait to see what 2019 holds.  Chris and I have some big plans and I can’t wait to see what new adventures we go on!

This year, my New Year’s resolution is to take more time for myself.  I find there’s always this underlining pressure in our society to be busy and to do more.  No one ever praises relaxation!  2018 was an amazing year however I also worked myself into the ground.  A big lesson I learned was I need to take more time to enjoy life.  I spend so much time working that life seems to pass in a blur!  This year I’m going to stop and smell the roses and actually live in the moment.  Anyways that’s just my opinion!  Leave your resolution in the comments below!

Click To Shop

2. The Perfect Winter Skirt

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, sweaters, sweater outfits, suede skirt, pleated skirt, winter skirt, winter skirt outfit, gucci disco bag, disco bag, suede skirt outfit, button up skirt, button skirt, OTK boot outfit, OTK boots, prada and pearls

I own this skirt in grey and LOVE it (click here to see it)!  When I found out it came in pink I knew I had to get it (it also comes in beige as well)!  I think this shade of pink is perfect for winter!  It’s also made of a thicker suede material which adds extra warmth!  I’ve mentioned before that I don’t usually wear skirts in the winter since we have frigid temperatures in Canada.  However, this one is quite warm!  I paired the skirt with a white sweater and rust OTK boots – they’re the perfect color combo!

I’m a size small in the skirt, small in the sweater and 37 in the boots.

CLICK TO SHOP

3. Stripes on Stripes

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, sweaters, sweater outfits, striped sweater, casual outfit, street style, leggings outfit, legging outfit, leggings outfit winter, gucci disco, pom pom beanie, starbucks cup, prada and pearls, fashion blogger

As you can see from this entire post, stripes have been everywhere this season!  I’ve been jumping on the train lately myself!  This sweater in particular is SO cozy.  I just love the shades of red and pink especially during January and February!  If you’re not a fan of this color combo it also comes in a purple and blue version!

In the sweater I’m a S/M and the leggings a small.

CLICK TO SHOP

 

4. Stripes!..Again!

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, sweaters, sweater outfits, pom pom beanie, starbucks cup, disco bag, gucci disco, ombre sweater, ombre sweater outfit, ombre outfit, blonde hair, cozy outfit, cozy winter outfit, prada and pearls, fashion blogger

Like I mentioned above, I love stripes!  When I saw this ombre grey sweater I couldn’t resist!  Ombre is such a fun pattern.  With that said however, it can overwhelming at times.  I like the grey because I think it’s muted enough and it’s perfect for winter! I paired it with a cozy beanie (these are needed during canadian winters) and rust OTK boots!

To finish the look I had to add a red in the lip!  Lately I’ve been using the Georgio Armani Liquid lipstick and have been loving it!  I usually add a little gloss so it’s not too drying.  It’s the perfect red shade!

The sweater is a size small and the jeans are a size 25.

CLICK TO SHOP

 

5. RED POM POM HEARTS

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, sweaters, sweater outfits, pom sweater, pom pom sweater, red sweater, red sweater outfit, LV bag, never full bag, fashion blogger, prada and pearls

Anyone else obsessed with Pom Poms?  I can’t seem to get enough of them!  This red pom pom heart sweater is SO CUTE!  It comes in a variety of different colours and is so cozy for winter!  This one in particular is the perfect valentines day sweater!!

The sweater is one size and I’m a size 25 in the jeans.

CLICK TO SHOP

 

6. Pretty in Pink

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, sweaters, sweater outfits, pink sweater, pink sweater outfit, pink sweater casual, casual outfit, gucci disco, disco bag, blonde hairstyles, prada and pearls, fashion blogger

One of my favourite colours is pink!  I don’t own too many pink sweaters so I when I saw this one I wanted to stock up!  The shape of this sweater is also really flattering.  It only comes in one size (I would say it’s a small-medium) but I love the form it gives.  I also have this exact same sweater in green – that’s how obsessed I am with it!

Sweater is one size fits all, in the boots, I’m a 37 and jeans I’m a 25.

CLICK TO SHOP

7.Faux Snakeskin!

winter outfit, winter fashion, winter outfits, winter outfits cold, prada and pearls, winter outfits casual, winter outfits canada, sweaters, sweater outfits, winter skirt, winter skirt outfit, faux snakeskin, faux snakeskin skirt, faux snakeskin skirt outfit, OTK boots, OTK boots outfit, pom pom beanie, prada and pearls, fashion blogger

I’ve been seeing faux snakeskin everywhere lately!  It’s such a fun winter pattern to style!  There’s also so many different color combinations that go with this pattern!  I chose a neutral brown sweater for this look to add some additional warmth!  However, another great color combo would be white, black or red!

Sizing wise the skirt is a size small, the sweater is a size small, and the boots I’m a size 37 (in US sizing I’m a 6.5)

CLICK TO SHOP 

8. Cozy Neutrals 

winter outfit, winter fashion, winter outfits, winter outfits cold, prada and pearls, prada & pearls, fashion blogger, winter outfits casual, winter outfits canada, winter scarf, scarf outfit, winter scarf outfit, winter scarf style, winter scarf pattern

I love finding cozy scarves during the winter!  This pink scarf has been one of my faves (it’s more a baby pink in person – the light is making it look more peach)!  Neutrals are one of my favorite color combos during the winter time.  Also – as you can see, I’m totally breaking the “no white after labor day” rule and you should to!  White jeans are a staple in my closet during the winter because they go with so many outfits!

Sizing wise I’m a 25 in the jeans, small in the sweater and size 37 in the boots (in US sizing I’m a 6.5).  The scarf is one size fits all!

CLICK TO SHOP

9.Winter Patterns!

winter outfit, winter fashion, winter outfits, winter outfits cold, prada and pearls, prada & pearls, fashion blogger, winter outfits casual, winter outfits canada, winter scarf, winter scarf outfit, winter scarf style, plaid scarf outfit, otk boots outfit, otk boots outfit black, sweater dress outfit, sweater dress, sweater dress with knee high boots, knee highs, knee high boots

I found Dasher and Dancer but where’s Rudolph!?  In all seriousness though I’m loving all the winter patterns right now!  Also this sweater dress is SO comfy!! Sweater dresses are so easy to thrown on and style!  During the winter I either pair them with tights or OTK boots to add some extra warmth!

Sizing I’m a S/M in the sweater dress, 37 in the boots and the scarf is one size fits all!

CLICK TO SHOP

CLICK TO SHOP WINTER SCARVES

10.Cozy Cape!

winter outfit, winter fashion, winter outfits, winter outfits cold, prada and pearls, fashion blogger, prada & pearls, winter outfits casual, winter outfits canada. winter cape, cape outfit, winter cape pattern, cozy winter

My winter outfits wouldn’t be complete without a cozy cape!  I actually purchased this cape last year and still love it!  I love the plaid print and it’s super cozy during the cooler months!  Nordstrom has so many capes out right now that are the perfect addition to your wardrobe!  This one is now sold out but I’ve summarized my favorites below!

Cape is one size fits all, I’m a 25 in the jeans, size small in the cami and size 37 in the boots.

CLICK TO SHOP THIS OUTFIT

CLICK TO SHOP CAPES

11. NYE Sparkle

winter outfit, winter fashion, winter outfits, winter outfits cold, fashion blog, prada and pearls, winter outfits casual, winter outfits canada, velvet outfit, velvet top, velvet winter outfit, sequin skirt, sequin skirt outfit, sequin skirt party outfit, party decor, NYE decor, NYE party decor

Even though NYE just passed you can totally still sparkle into January and February!  I absolutely love red velvet this time of year.  It’s such a rich fabric!  I paired this velvet t-shirt with a sequin skirt to add some sparkle.  Both these pieces are from old seasons so I’ve summarized my favorite red velvet and sequin pieces below!  They’re such a great combo!

CLICK FOR OTHER OUTFIT DETAILS

 

RED VELVET ITEMS I LOVE

 

CUTE SEQUIN SKIRTS

 

12.Pink Teddybear Coat!

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, prada and pearls, prada & pearls, fashion blog, winter outfits canada, pink teddy coat outfit, pink teddy coat, pink teddy jacket, pink teddy jacket outfit, teddy bear coat, teddy coat, teddy coat outfit, teddy coat outfit winter, teddy coat 2018

Teddybear coats are one of my favorites styles during the winter and the holidays!  This pink one is also super unique!  Usually I only see these coats in a tan/brown so when I saw it in pink I had to get it!  I took this picture while finding a Christmas tree with my family – it kept me warm the entire time!

CLICK TO SHOP

13. Lace Dream Dress

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, lace dress, black lace dress, lace party outfit, , black lace dress outfit, party dresses classy, party dresses short, prada & pearls, fashion blog

This dress gives me all the winter vibes!  I love the black lace, it gives such a polished look!  This dress is just the right length so it can be worn to a wide range of events!  It also has so much movement which is really flattering on many body types!

CLICK TO SHOP

14. All That Sparklewinter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, prada and pearls, prada & pearls, fashion blogger, sequin dress, sequin outfit, NYE outfit, sequin outfit ideas, sequin outfit for women, sequin outfit new years eve

I couldn’t summarize winter outfits and not include sequins!  This dress is seriously a dream!  It’s entirely made of sequins which makes it a stunner!  It also pulls at the waist which gives a great silhouette!  Below I’ve summarized some of my favourite sequin dresses for you guys!

CLICK TO SHOP

 

15.Winter Cozies!

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, holiday outfit, casual outfit, casual look, winter outfits canada, green cardigan, green cardigan outfit, green cardigan outfit olive, knee high boots, OTk boots, knee high boot outfit, OTK boot outfit, white scarf outfit, white scarf outfit winter, white scarf winter, pom beanie, black pom beanie, disco bag, gucci disco bag

I don’t know what I like more, the outfit or the holiday decor behind me!  This entire look is so cozy!  The scarf is one of my favourites, since it’s so chunky and warm!  Also I love this green cardi!  It goes with so many different outfits!

CLICK TO SHOP

16.Cozy Knits

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, casual look, comfy look, cowl neck sweater, cowl neck sweater outfit, cowl neck, cowl neck sweater, leggings outfit winter, legging outfits, leggings outfit, leggings, sneaker outfit, sneakers outfit, sneakers women, disco bag, gucci disco, prada and pearls, fashion blogger

Another cozy favourite of mine.  I don’t know about you but I’m obsessed with Cowl neck sweaters.  They’re the coziest in the winter time!  I’m also all for any outfit that has leggings!  This is how I’m usually dressed on weekends!

CLICK TO SHOP

17. Jewelled Romper

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, romper, rompers women, romper outfit, fuchsia romper, party romper outfit, prada and pearls, fashion blogger, party outfit, going out outfit

Okay you guys, this is one of my favourite rompers of all time!  The jewel color is just so gorgeous!  It fits really well, however I would suggest wearing it with some tape on the chest area to keep it closed!  Other than that it’s perfect!  I wore this on NYE and got so many compliments!

CLICK TO SHOP

18. Cozy Basics

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, white winter scarf, white scarf, white scarf outfit, casual look, casual winter outfits, casual outfits for winter, leggings, legging outfit, black leggings, sneaker outfit, white sneakers, leggings casual look

Another cozy favourite of mine!  What can I say, I love my comfy cloths!  This is totally a go to winter look for me, it’s so easy to pull off while still being super stylish!  I’m trying to wear my white shoes as long as possible until the snow comes!  They’re just so comfy!  I wear OTK boots a lot, but I love throwing on sneakers from time to time!

CLICK TO SHOP

19. Pretty In Pink

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, sequin skirt, sequin skirt outfit, sequin party look, sequin skirt party outfit, sequin skirt and sweater, pom beanie, pink pom beanie, otk boots, Knee high boots, knee high boot outfit, prada and pearls, fashion blogger

This is one of my favourite looks I have styled this winter!  This skirt is stunning!  In this look I dressed it down by pairing it with a sweater.  However, you can also dress it up by wearing a lace top or cami with it!  Even a crop top would work!  It’s now sold out but I found a super similar one that still have some sizes left!

CLICK TO SHOP SIMILAR LOOK

2o. Snow Much Fun

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, otk boot outfit, otk boots, knee high boots, knee high boot outfit, casual look, pom beanie, pink pom beanie, striped shirt outfit, striped shirt, stripe shirt outfit winter, white pants outfit, white pants, black cardigan outfit, black cardigan, prada and pearls, fashion blogger

Anyone else enjoy throwing snow?  Since I live in Canada, I’ve grown up with this white fluffy stuff.  I have a love hate relationship with it at this point.  It can be SO pretty but when those snow storms hit, I instantly regret my appreciation for it!

This picture on Instagram actually has falling snow in it, check here to see! I did this effect by using VIDLAB!  It’s an app in the app store!

CLICK TO SHOP

21. Sequin Stunner

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, sequin skirt, sequin skirt outfit, sequin miniskirt, bodysuit with skirt, bodysuit outfit, prada and pearls, fashion blogger, disco bag, gucci bag outfit, party look, NYE outfit, NYE party outfit

Sequin skirts have been so in right now!  I just love how unique they all are.  They also add such flare to a basic outfit.  I think sequins are one of those patterns that can be pulled off all winter not just during the holidays.  Winter is so dull so if you can add a little sparkle I say go for it!

CLICK TO SHOP

22. Braids On Braids

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, twist back sweater, grey sweater, french braid, french braid hairstyles, hairstyle, blonde hair, blonde hairstyle, prada and pearls, fashion blogger

So I’m not going to lie this was probably the third time I’ve ever done a french braid on myself!  Somehow it turned out quite well…I’m still not sure how.  Even Chris was shocked I pulled it off!  On another note, this twist back sweater is so fun!  I’ve had it since last year and I’m still obsessed!  It comes in so many colors and it’s so unique!

CLICK TO SHOP TWIST BACK SWEATERS

23. Perfect Party Stunner

winter outfit, winter fashion, winter outfits, winter outfits cold, winter outfits casual, winter outfits canada, red suede shoes, high heels, suede heels, sequin dress, sequin dress outfit, designer dupe bag, dupe bag, design bag dupe, sequin outfit, sequin party outfit, party outfit, party look, party style, short sequin dress, prada and pearls, fashion blogger

Got any party’s coming up?  I know some holiday parties happen after NYE so if you’re someone who is still looking for a dress look no further! This sequin stunner is SO gorgeous!  Now it’s a little short, so if you’re under 5’5 it works as a dress but if you’re taller, I would pair black faux leather leggings with it!  To get all the details click here 

THAT’S EVERYTHING!

To see more outfit inspo click on the links below!

XO Jenna

20 Winter Outfits To Style This Season

UGG-Look-A-Likes For LESS!

Amazon Accessories Under $25!