If you are like me, whether midweek or for the weekend, a winter casual outfit is a must. They are comfortable on the weekend, traveling for your winter vacation, or even just 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 casual winter outfits to give winter season inspiration—whether it’s for your business casual attire for work, or everyday casual for cozy weekends and winter getaways!
37 Casual Winter Outfits
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.
Coffee Date with the Girls
A chic but classic winter layered look makes for an effortless casual coffee date outfit. Opt for a cozy, oversized sweater, tucked into a pair of high-waisted and cropped wide-leg trousers—in either dark denim or a charcoal gray. You can layer it with a structured wool coat, and finish it off with an ankle boot. It maintains some much-needed warmth, while the clean lines and refined textures keep your look polished.
casual date night outfit
Wearing 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 look 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. You don’t have to sacrifice warmth or style.
Quick Running Errands Outfit
If you need an outfit for when you’re just running errands, consider going with a cozy, monochromatic look. Start your look off with a pair of black jeans, and pair it with a sweater in the same tone. If you want to elevate your outfit in the slightest (but most impactful) way, add on some black Chelsea boots. This outfit has an effortless touch of sophistication, without feeling like you’re overdressed.
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 pumps), and a wool jacket. When you have these winter wardrobe pieces, it makes getting dressed easier. It also 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, making them great winter work outfits.
Business Casual Work Day Outfit
A wool scarf coat is a great way to begin an outfit that needs to provide both warmth and style. It’s elegant enough to maintain the business aesthetic, while still keeping your outfit stylish and casual. Because this piece will be the subtle detail that stands out, you can keep the rest of the outfit relaxed. Wear a black sweater with a pair of black jeans and pumps to finish it off.
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. Winter work outfits give you a slim fitting look for your business casual attire.
Casual day at the office
When I think of an ultimate business casual outfit that keeps up a chic and comfortable aesthetic, a black leather jacket immediately comes to mind. Pair your leather jacket with a pair of dark denim jeans, and finish it off with a chic pair of loafers.
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 a wool coat or a 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 flats or loafers to keep it comfortable yet stylish.
Which look is your favorite? I’d love to hear in comments below.
Please feel free to email me at thegraydetails@gmail.com if you have any questions! I’m always happy to help with styling or picking out a specific outfit for an event! Have an amazing day!!
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