39 + Easy Everyday Winter Outfit Ideas You need Try

With winter quickly approaching, it's time to start thinking about your cool weather wardrobe.

From wintry layers to statement jackets and accessories, discover my range of casual winter outfit ideas that are perfect for transitioning into the cold-weather season.

Today I am going to answer all of your winter outfit questions! 

Let's dive right in! 

casual winter outfits

Layer Up With Chunky Sweaters and Jackets

Layer up with chunky sweaters and jackets to stay cozy during the coldest days. You can never go wrong with a cozy & classic cable knit sweater.

Chunky knit cardigans are also a great way to keep you warm while still looking fashionable. They are easy to throw on over your look and be ready for the day.

To complete your look, opt for a statement-making winter jacket that will help you stand out from the crowd.

Try a cute leopard print jacket to make a statement this season. 

If you are looking for more ways to style chunky knit sweaters be sure to check out my full guide on HOW TO STYLE CHUNKY KNIT SWEATERS

Go For Chunky Knit Sweaters 


casual winter outfit ideas


Keep things playful in this relaxed-fit pullover with flirty woven paisley print ruffles and stunning two-tone jacquard knit. With banded long sleeves and outseam reverse stitch details, make a statement with this trendy piece!

casual winter outfits


The Bundle Of Love Dolman Sleeve Sweater will bring an instant smile to your face! This adorable sweater features a multi color popcorn knit that shapes a round neckline falling into dolman long sleeves, ending at ribbed cuffs. A Loose fit bodice slightly tapers at the end with a slightly cropped fit. 

For that cute casual winter look, go for distressed jeans, boots and a chunky knit sweater. It's an easy and effortless way to get that easy going casual winter look your after.





Hanging out around the house? Try a cute laid back casual loungewear look with distressed joggers and a soft comfy sweater for casual winter look around the house.

This is a cute look for walking the dog or baby around the neighborhood too. If you love comfort, this look is for you! 




Style with distressed denim

Jeans are definitely my go to for everyday casual style. There are so many cute ways to style jeans and with such a variety its really a fun way to dress up or down your casual winter looks. 

Try a babydoll blouse layered with cardigan and jeans for a cute casual winter outfit.  

Go for loose fit dolman tops or chunky knit sweaters with jeans too. Keep your feet cozy with closed toe booties and chunky low rise socks (or wherever the boot stops)


casual winter outfits


Style with black jeans 

Black jeans are really cute and versatile. I love these jeans for a wintertime casual look. You can easily dress them up when you need or keep them casual for an everyday easy go to look. 

The Kortney Mid Rise Straight Leg Jeans In Washed Black are going to become a repeat all year round-especially in wintertime!xs

These amazing jeans features a mid rise waist, with a five pocket cut and zipper fly. A slim fit through the thighs flares out slightly before ending at ankle length hems.

Lived-in fading through the legs creates a classic and timeless casual look- perfect for wintertime. 

casual winter outfit

Style with high rise straight fit destroyed jeans 

"The perfect jeans don't exis-". Hold that thought, because the perfect jeans actually do exist! Let me introduce you to the Meadow Hi Rise Straight Fit Destroyed Jeans.

These amazing jeans feature a light wash stretch denim that forms a hi rise waist with a five pocket cut and a zipper fly. Perfectly faded pant legs have slight distressing at the knee, ending at a side slit hem.

A perfect addition to your casual winter wardrobe. 

casual winter outfits


Style jeans with cute winter tops

A satin blouse is really fun to style in the wintertime. You can make it casual with jeans and booties, or dressy with the right accessories like high heels and jewelry. 

A good knit top will keep you cozy and casual with jeans in the wintertime anyday. Play around with different denim washes to match your outfits. 

casual winter outfits




If you are trying to figure out what to wear to a casual party in wintertime and your not sure what to wear, I have a few cute casual party ideas for you.

A winter party could vary so greatly, from NYE, a birthday party, wedding guest or a work party. Since a casual party can mean several different parties, there's one thing you can count on when your not sure. 

When in doubt, reach for a dress! 

A knit dress is almost always more casual than a woven dress. A knit dress generally offers a more casual appearance but can easily be dressed up with high heels and the right accessories perfect for a casual party. 

casual winter outfits


Style with a sweater dress

Couture and body flattening, this soft Hacci sweater dress features a rib knit turtleneck, a banded hemline and side pockets. Touting an elastic vegan leather buckle belt, this dress will be a trending staple this season.

casual winter outfits


Style with a statement blouse

If you are going to a casual party, styling with jeans and a statement blouse can be a perfect fit. And If you are spending the holidays at a relatives house this may be the perfect winter outfit choice. 

I love a statement sleeve because it adds the perfect amount of festiveness to your winter party look while still keeping cool and casual. 

If you're looking for an eye-catching holiday top to ring in the New Year, look no further than this ribbed Hacci round neck top featuring gold foil crinkle bubble sleeves capped with elegant rib bands. Pair with faux leather pants or denim for a stunning look.


casual winter outfits



Dressing casual doesn’t mean dressing boring or plain, or necessarily wearing sweats either. Dressing casually has a few different meanings which can make it kind of confusing.

Generally speaking, a casual dress code means dressing informally, (not suit and tie ) but still clean and well put together. It can also mean "event appropriate" which can slightly change the "casual" dress code meaning. 

There are few different levels of casual attire such as:

  • Casual 
  • Smart Casual
  • Dressy Casual

Example of casual dress code is a nice cute top, jeans and sneakers. Not necessarily sporty like leggins and T-shirt.

Example of smart casual is basically simple, but lovely and elegant. Like a blazer, jeans and loafers or flats. Maybe go up a notch with fitted pants and a a nice blouse or dress, button down collared shirt, etc. 

Examples of dressy casual can mean a dress, with a blazer coat and high heels. Avoid distressing in jeans and jackets. Dressy casual basically means it's not all the way a formal dress code, just skip wearing jeans and T-shirts. Go for something dressier.  

Casual Winter Outfit 

casual winter outfit


Smart Casual Winter Outfit

casual winter outfit

Dressy Casual Winter Outfit

casual winter outfit


You can start wearing winter clothes as soon as the weather allows it. 

Basically, the best time when you should start wearing winter clothes will depend on a few different things, like where you live and your own personal comfort levels.

So basically, you can start wearing winter clothes when the weather begins to hit those lower temps of 50°F (10°C) or below, or whenever you start to feel uncomfortable and too chilly in your fall clothing.

The weather can also be a bit all over the place so you might want to take into consideration your local temperatures. Different location can affect when you start or stop dressing for winter time too.

In California it can be 70 degrees in February while in New York it will still be 40 degrees. If you are traveling, you definitely need to check up on the weather and opt for layering pieces if your not exactly sure how cold it might feel in your location. 

Anyway, it's always better to be prepared for the cold and have a warm outfit ready to go rather than be caught freezing because you forgot to grab warm clothing on your way out like a jacket. 

winter outfit ideas


If you are planning on going out for an outdoor winter date, you definitely want to dress in layers to stay cozy and warm. 

Since there are different types of winter dates you may attend, the appropriate outfit for the occasion is necessary to stay cute and cozy. 

Here are a some outdoor winter date outfit ideas to keep you cozy and cute:

  1. Warm and stylish: A knee-length long coat is a fashionable and reasonable choice for an outdoor winter date. Style it with your favorite pair of jeans, and layer it with a chunky knit sweater, and knee length boots. Accessorize with a scarf and some gloves to stay extra cozy. 

  2. Cozy and charming: A chunky turtleneck sweater dress is also a fab pick for a winter date. Stay warm when you style it with some thick tights, long boots, and a nice long coat for a classic look. Complete your look with a sparkling necklace and a cute beanie.

  3. Preppy and polished: For a more dolled-up winter date, style a pair of stretchy brown pants with a chunky knit sweater and a long peacoat. Complete your chic look with a pair of loafers or oxfords and a beret hat.

  4. Relaxed and comfortable: A pair of joggers or leggings can be dressed up for a relaxed winter date by styling them with a soft knit sweater, a puffer jacket, and some chunky ankle boots or sneakers. Complete your look with a beanie and some gloves for a laid-back but put-together look.

No matter where you are going or what outfit you end up styling, be sure to dress in layers to keep warm and cozy during your outdoor winter date. Don't be afraid to try different styles and textures to create a cute and stylish look for your fun night out. 

winter outfit ideas



If you're feeling lately like you have nothing to wear in wintertime, I have a few outfit ideas to help inspire your next winter look: 

  1. Mix and match your basics: Sometimes styling a simple top, jeans, and a your favorite pair of boots can be a good basic wintertime look. You can easily dress it up or down with the right accessories. Finally, complete your look with a shacket and a beanie for added coziness. 

  2. Layer up: Layering is key to staying warm in wintertime. Try styling a chunky knit sweater with your favorite jacket and completing your look with a blanket scarf for added warmth. 

  3. Dress it up with accessories: You can totally make an outfit feel extra special by styling it with some jewelry or accessories. A statement necklace, a scarf, or a fun pair of earrings can add some fun and liveliness to an otherwise basic outfit. Have fun experimenting with unique styles and colors to find what fits you best.

  4. Break out the holiday outfits: If all else fails, maybe it's finally time to pull out your christmas or holiday themed tops and accessories. Sometimes you just need to get a little festive and add some cheer to your outfits. Try adding some sparkly sequins to your next look for a little dazzle and fun. 

winter outfit ideas


The truth is, sometimes you just need a bit of a closet re-fresh when feeling like you have nothing good to wear.

Bonus tip: Mixing and matching different pieces can help create new outfit combinations with what you already have in your closet. You can always order new clothes to incorporate with older pieces and create completely new outfits. 


winter outfit idea


I have 4 cute winter outfit ideas for your next night out: 

  1. A velvet dress: Take the classic LBD (little black dress) and try a little velvet dress instead for a fun twist on a classic look. Dress it up with some thick tights or leggings, boots, and a long coat for a pretty winter look. Complete your look with sparkling jewelry and a mini crossbody bag to glam it all up.

  2. Stay cozy with a sweater and jeans: Wear a chunky knit sweater with your favorite pair of HI-waisted JB jeans and ankle booties for a cute and comf look. 

  3. Go for sparkle: Winter time is all about the sparkle. Style a metallic blouse with a skirt and heels for a dressy look or jeans and boots for a casual look. Add a shacket for warmth. 

  4. A midi dress: A midi-length dress ( which is a dress that hits from the knee to the top of your ankles)  can be good for a night out in winter. Just wear some a cozy pair tights and a fitting pair of boots along with a coat to keep warm. 

No matter what outfit you decide to style, be sure to wear lots of cozy layers to keep warm and comfy all night long. 


winter outfit ideas

You can find some super cute styles to shop HERE for that wardrobe refresh. 

You can also ask a friend who is your size to do a closet swap with you. More on that later. 

And honestly, just remember to have fun! Because that's what is important here.  The key is to ultimately enjoy your clothing and not take it all too seriously.

And If you're still feeling stuck, be sure to subscribe to my newsletter. I send out a weekly letter with lots of cute new outfits and outfit idea blogs regularly. 

You can also join my FB group where we play a daily THIS or THAT game on helping you discover your unique style.

Look me up on facebook groups: Forever Dolled Up | Women's Clothing Boutique 



Every outfit tells a story and I am passionate about helping women discover their unique style through the Forever Dolled Up blog and boutique. 

Hi, Im Caroline! A boutique owner, style journalist, wife and mum to two littles!

Discover everything you need to stay in style for every season, special occasion, and everyday good fashion. Above all, I hope to delight you.

Check back every Tuesday to get your daily dose of style and inspiration ♡