37 Casual Winter Outfits

If you are like me whether midweek or for the weekend, a winter casual outfit is a must. They are not only comfortable on the weekend, traveling for your winter vacation or working from home. They can also be more than just sweatpants and bulk sweaters. You can create stylish winter outfits while staying comfortable and casual for the winter months. Today, I’m rounding up 37 casual winter outfits to give winter season inspiration for your business casual attire for work and everyday casual for cozy weekends and winter getaways.

Everyday Casual Winter Outfits

Winter season is one of my favorite seasons to style. All the layers make for a stylish winter outfit for running errands, casual date nights, and a coffee date with your girlfriends.

casual date night outfit

Wearing your high-waist denim with your ankle boots is the perfect cold-weather combo for casual winter outfits for date night. To keep it casual, opt for a long sleeve turtleneck or hoodie sweatshirt under your sweatshirt or leather jacket for extra warmth in the cold weather.

Casual Weekend Getaway Outfits

If you are headed out for a snowy day or looking for some stylish winter outfits for your next ski trip, here are a few winter outfit ideas. Style your puffer coats and teddy coats and snow boots during the winter season. Layer long sleeve base layers for extra warmth. Opt for skinny jeans for black leggings and a jogger set for cozy nights by the fire or your travel outfit.

Lunch Date with Girlfriends Outfit

Whether you have a quick coffee date or lunch date with your girlfriends, a few ways to get a stylish winter casual style is to add a blazer over a casual graphic tee or sweatshirt or pair your black faux leather leggings with a casual hooded blazer.

Workout to Casual Running Errands Outfit

Adding some sherpa jackets for the winter months is key to creating a stylish outfit after the gym in the colder months.

Business Casual Winter Outfits

Business Meetings Outfit Ideas

Winter work outfits can get harder as the cold weather approaches. One of my foolproof looks is trousers, boots, or a pump and a wool jacket. When you have these winter wardrobe pieces it makes getting dressed easier and allows you to mix and match for numerous outfits throughout the winter season. Simply change out your winter scarf, bags and ankle boots to create new stylish winter outfits. These trousers are high-waisted and slim fitting and are great winter work outfits.

Casual Fridays at the Office

My staple for casual Fridays at the office is a blazer, high waisted jeans, ankle boots or pumps and adding some winter accessories such as a scarf for extra warmth. The winter work outfits give you a slim fitting look for your business casual outfits.

Blazer, jeans, and boots business outfit

Business Casual Travel Outfit

Business casual outfits can be difficult when you are traveling and heading straight to the office. An easy combo for me is my high waisted jeans or skinny jeans. Pair with long sleeve top and wool coat or trench coat. Finish the look with ankle boots that have a block heel or low heel. If you don’t prefer an ankle boot, opt for ballet flat or loafer to keep it comfortable yet stylish.