Winter Outfit Ideas (Casual, Work & Date Night)

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Most people get excited for fall fashion (myself included), but winter outfits are often glossed over and don’t get the attention they deserve. But, they can be some of the cutest looks since I love layers and that’s key in the colder months. So here’s your ultimate guide to cute winter outfit ideas, from casual athleisure to polished work-appropriate outfits.

Winter Outfit Ideas (Casual, Work & Date Night)

Building a winter wardrobe starts with the essentials with pieces that can be styled for different occasions. Think flattering denim, colorful sweaters, puffer coats, comfortable boots, and timeless accessories like scarves and gloves. These staples create the foundation for effortless winter outfits that keep you warm while still looking polished.

Casual but Cute

Most days (since I work from home and have two little boys), I find myself opting for very simple outfits that consist of a sweater and denim. Here are a few tips for dressing casually (but stylishly too) in the cold weather:

Choose comfortable denim: I have over 30 pairs of jeans, no lie. This post has a roundup of my very favorite jeans, and you can find lots of styling tips for different cuts of denim here.

Pair with a flattering sweater: One of the best parts of winter is that we can wear cozy sweaters almost daily. I love affordable Quince cashmere for easy denim looks, and Boden carries some fun, happy patterned sweaters and cardigans if that’s more your speed. I shared my 10 favorite affordable sweaters (that don’t feel cheap) in this blog post. If you want to invest in knits, no one does it better than Sezane.

Throw on sneakers: Fashion sneakers are practical and cute in the winter. I like leather Vejas or these cute velcro Talia sneakers from Sam Edelman when I’m choosing sneakers for jeans. I skip athletic-looking sneakers when it comes to styling denim.

Dress it up with loafers, booties or ballet flats – Lately, I’ve been drawn to dressier shoes rather than white sneakers, which were my go-to with every outfit for years. They just feel a little more grown-up. Booties are, of course, great in the winter. But loafers and ballet flats can work well too. Pair loafers with socks (tips here), and ballet flats can work well with tights. Larroudé makes my favorite ballet flats, Margaux makes my favorite booties, and Sam Edelman and Madewell make my favorite loafers.

Larroudé makes so many other gorgeous shoes I included in this Larroudé shoe review.

Work Appropriate

Dressing for the office in cold weather calls for polished layers and classic pieces. Here are some tips:

Invest in a tailored wool coat: A long wool coat like this belted Bernardo number or the Rafael Coat from Sézane is the perfect layer for work outfits in the winter. Pair it with work dresses, high-waisted trousers, and even dark denim! This faux suede skirt from Amazon is another great piece to wear for winter work days.

Classic blazers layer well: A classic blazer layered over a turtleneck adds structure and warmth. My favorite blazer is from Nordstrom, but I’ve also ordered two different colors in this blazer from Amazon’s the Drop and love it (it’s just not quite as warm).

Polished shoes finish the look: Complete the look with loafers or black knee-high boots. I also love a suede pump for a work setting.

Date Night

I find winter date nights one of the easier things to dress for since a pretty dress and boots can go such a long way! Here are a few other ideas to help you mix it up:

Dresses with sleeves: Long-sleeved dresses are ideal for winter date nights. Even if the length of the dress is short, like this cute Tuckernuck Vivianne dress, a pair of tights and booties or tall leather boots is the perfect look for an evening out.

Mix and match: Elevate your winter date-night look with a maxi skirt and a statement knit sweater. This suede skirt from Tuckernuck is just like the one I have and wear all the time in winter.

Grab a long coat: A long coat in a neutral tone, like camel or black, pulls the outfit together. Again, this Rafael Coat from Sézane will last for years and go with everything, or go for a fun Scarf Coat like the one I’m wearing from J.Crew.

Accessorize: I like to carry a fun clutch and statement earrings (often with my hair pulled back) in the winter months.

Cold-Weather Athleisure

Winter weather can sometimes make it hard for me to put on real clothes most days (vs. just wearing athleisure). However, I’ve found a few things that help me feel polished and pulled-together, even in my comfy clothes:

Buy matching sets: Finding a few cute lounge sets that have matching tops and bottoms has made the most significant difference in my athleisure game. A set feels like an intentional outfit, and I always get questions and compliments when I wear one out! I’m currently loving all things AirEssentials by SPANX.

Grab fun pullovers: If I’m not in a matching set, I wear leggings with an oversized pullover. I have a handful of pullovers in different textures and colors which helps me change it up from time to time. Here’s how to style leggings for all sorts of outfits.

Opt for cute sneakers: while I like to wear leather Vejas with athleisure, I find that sporty sneakers like the New Balance 327 work well for athleisure, as well. They aren’t workout shoes, but they’re a little sportier than Vejas.

Do your hair and makeup: The key to making athleisure feel like an actual outfit is to style your hair and apply makeup. Even on days when I don’t leave my house, I try to wear a little makeup and do something with my hair to feel more alive. Here’s my hair care routine, and this post has my simple makeup tutorial.

Add a hat: I used to think a hat read at lazy, but I’ve actually felt lately that it pulls a casual outfit together. Chord makes my favorite hats, by FAR. So if you’re a hat person, invest in one of theirs. Otherwise, Madewell makes my favorite budget-friendly hats.

Here are more of my favorite loungewear sets.

How Do You Dress Elegantly in Cold Weather?

Dressing elegantly in winter is all about choosing classic pieces and layering thoughtfully. Opt for neutral tones and high-quality fabrics, such as a wool coat over a cashmere sweater. Add polished gloves, a scarf, and sleek black boots for a refined finish. Here are a few winter wardrobe essentials:

Winter Wardrobe Essentials

Outerwear

Your winter wardrobe starts with outerwear that’s both functional and chic. Opt for puffer coats, wool coats, long coats, and classic blazers when you’re building out your coat closet. Next, getting an oversized puffer in a neutral shade will work well for casual looks. I have a full blog post with the best winter coats here, and if you’re a puffer coat girl, you’ll love this puffer coat roundup.

If you were to only order one coat for the winter, I recommend this down coat from Lands’ End. It’s affordable (and often on sale!), the quality is 10/10, and the black color works for most outfits.

Shoes

Shoes are obviously important in the winter since they need to be weather-appropriate. Black boots, knee-high boots, ankle boots, loafers, and sneakers are must-haves for winter. Knee-high boots pair beautifully with skirts and tights, while loafers paired with socks are cute and functional for the office. My favorite winter boots this year have been the Downtown boots from Margaux. They’re a splurge, but if I were breaking it down by price per wear, they’re worth every penny. Chelsea boots are also a great winter shoe option (styling tips here)!

Knits

Make a statement with cozy knits. Oversized sweaters, textured cable knits, and base layers are ideal for creating layered looks. Pair an oversized sweater with skinny jeans or leather trousers for casual days, or tuck a fitted knit into a maxi skirt for a refined look.

Warm Bottoms

Denim, tights with mini skirts, and maxi skirts form the foundation of winter outfits. Jeans and tights are obviously great for extra warmth, while skirts can be paired with boots for a dressier (but still warm) option.

Accessories

Accessories are what make an outfit go from “I just put clothes on” to “I tried and I look great.” And in the winter, they’re definitely necessary for practical reasons. But think beyond delicate jewelry and bags, you need accessories that keep you warm.

• Scarves: Add texture and pattern with chunky knit scarves for a cozy vibe or sleek wool scarves for a tailored look.
• Gloves: Choose leather gloves in neutral tones or opt for fingerless fur gloves for warm but practical luxury. (I love these rabbit fur ones.)
• Earmuffs: I actually love earmuffs, honestly. They’re warm, fun, and don’t mess up my hair like a hat. Look for fur or knit earmuffs to complement your outerwear.
• Socks: Layer thick socks with ankle boots, thinner options with loafers, or knee-high styles for extra warmth under tall boots.

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