So it’s cold now (what the heck happened to fall?) We are gearing up for our first winter here in Chicago, and I’m not sure I’m quite ready for it. But I have a plan. A work-from-home winter uniform that’s going to get me from computer to school drop off (or errands or a coffee run) without having to change outfits. I wouldn’t say these are the most fashion forward outfits I’ve ever created, but they are practical and I can put them together with as little decision making as possible (and when your brain is operating at hibernation levels, that’s all we can ask.) In this post, I’m giving you ten pieces I’m keeping at the ready for my winter work-from-home uniform. I’m keeping these front and center in my closet for dark mornings! Plus, I’ve got five outfit variations for each type of work-from-home day whether you need to be zoom-ready or you’re planning to run errands during your lunch break.
Winter Work-From-Home Uniform
Ten Wardrobe Items
A base layer long sleeve tee.
A good quality layering tee acts as a base layer in the colder months. You want something that fits slim so it doesn’t bunch up when you wear it under knitwear. Being able to wear it on it’s own if the weather takes an unexpected upturn (we live in the Midwest, this happens regularly!) If it’s really cold where you live, I would go with something warmer like these Ultra Warm tees from Uniqlo.
Options To Shop:
Everlane Luxe Rib Long Sleeve Crew
Uniqlo HEATTECH T-Shirt
A heavy-weight turtleneck.
Sometimes that little bit of extra fabric on the neck is exactly what you need to keep your body toasty in the wintertime. It really makes all the difference. As with the tee, I recommend one that’s slim enough to layer under sweaters and cardigans when the weather’s freezing.
Options To Shop:
Quince Organic Cotton Micro-Rib Turtleneck
Everlane Luxe-Rib Turtleneck
Relaxed cashmere crewneck sweater.
A cashmere or wool crewneck sweater is a winter wardrobe staple and looks elegant for all those work-from-home video calls. You could also try a v-neck sweater (it looks modern when layered over a crewneck tee!) Cashmere also isn’t bulky and sits more nicely on the body when compared to other wool sweaters or even cotton ones.
Options To Shop:
Quince Mongolian Cashmere Oversized Crewneck Sweater
Everlane Boxy Crew in Cashmere
Elevated cardigan.
A basic cardigan with a hip length fits like a sweater but with buttons down the front for added interest. A cashmere or merino wool option is best for winter, but you could go with cotton if you live in a warmer climate. I like layering these with a long sleeve base layer for added warmth (see above!)
Options To Shop:
Sézane Emile Cardigan (I take a size down)
Reformation Clara Cardigan
Pull-on pants.
A pull-on pant with a stretchy waist is a WFH necessity. You can sit down in them all day without discomfort. If you get a nice pair, you could also wear them to the office as well. If you live someone where it snows often, you may want to choose a cropped pair that won’t drag in the slush. Otherwise, a full length pair is a good option. You could also try a knit pant (I just purchased these), a track pant, or silk pants layered over leggings.
Options To Shop:
Spanx Ponte Wide Leg Pant
Quince Ultra Stretchy Ponte Wide Leg Pant
BRF Straight Mid-Rise Pull On Pant
Straight leg denim (with stretch).
You don’t have to swear off denim if you work from home (I don’t!). Just look for a pair with stretch, ideally with less than 95% cotton content (rigid denim is usually 98% – 100% cotton) with the addition of other fibers such as elastane, spandex, Tencel, or polyester. Stretch denim, although super comfortable, tends to bag out more quickly than rigid denim, but the two pairs I’ve listed below I actually own and can confirm they hold up to multiple wears without washing.
Options To Shop:
Frame The Mellow
Quince Bella Stretch Relaxed Straight Jeans
Thermal base layer legging.
If you tend to run cold like me (even when inside!), a base layer on the bottom half will help in keeping you warm in the winter. I’ve heard from many people who live in cold climates that Uniqlo’s HEATTECH line works amazingly for the price so that is what I’m recommending here. I’ve linked two different options – one for mild winter days and one for extreme cold days.
Options To Shop:
Uniqlo HEATTECH Leggings
Uniqlo HEATTECH Ultra Warm Leggings
Weather-proof lug sole chelsea boot.
Although I love the look of a sleek heeled ankle boot, they’re not always the most practical option for winter, especially if you live somewhere cold. I’m still keeping my ankle boots on deck just in case, but I’ll be keeping my Chelsea boots by the door. If you live somewhere mild, I recommend these water resistant boots from Frēda Salvador (pricey but functional!) For those of us who live in a colder climate, I’ve linked two lined boots that work well for everyday (I just ordered the ones from Maguire which come highly recommend; the brand is Canadian so you know they know cold!)
Options To Shop:
Maguire Cortina Black Lined Boot
Blundstone Heeled Boots
House slippers or chunky socks.
You probably won’t be sitting at your WFH desk with shoes on so you’ll need some comfy house slippers or thick socks to keep your feet cozy while you’re working. I own a pair of slipper socks from Bombas that I wear while I’m home in the wintertime, but I also just purchased some chunky socks from them as well. I’ll probably end up layering the two and swapping the slippers for boots to grab the kids from school or run errands.
Options To Shop:
Bomba’s Gripper Slippers
Bomba’s Chunky Ragg Calf Socks
Wool coat or puffer coat
For running out the door, I’m keeping two coats on stand-by. A long wool coat that’s a bit more stylish when the weather is above 20 degrees F, and a long puffer coat for anything colder. You could adapt this for your climate – you might be warm enough with a short puffer coat and a light wool coat. Below are the ones I own and recommend for cold climates like Chicago.
Options To Shop:
Aritzia The Only Coat
Aritzia Super Puff Long
Work-From-Home Winter Outfits
Minimal & Easy – Mild Weather
This outfit is super basic but also super cozy and professional. The secret sauce is the elastic waistband of these pull-on pants. For home, I would wear this with house slippers and slip into these loafers for stepping out. For really cold days, swap the loafers for Chelsea boots and the wool coat for a long puffer. You’ll probably want to keep a few cold weather accessories on stand-by as well.
Layered & Cozy Yet Zoom Ready
This is what I would wear if I had a day of video calls to attend – business on the top, cozy on the bottom! The layers on keep you warm but are also professional. For leaving the house, thrown on some boots, add a coat, beanie, and gloves. Add some base layer leggings if it’s really cold, too.
Running Errands Over Lunch
I love wearing jeans in the winter – denim is thicker and keeps me warmer – however, if you’re going to be sitting all day, choose a pair with some stretch to them (I linked two favorites above!) If you plan on popping out over lunch to run a few errands, I would wear a warm base layer under a cardigan (nice for work!) on top with my jeans and a belt which adds some structure. To leave the house, I’d put on my boots, a puffer coat, sunglasses, and a scarf if needed. A puffer coat will always read more functional than fashion, but I think wearing a nice leather bag like this elevates it a bit.
Creative Day
I recommend dressing for how you want to feel, and if you need to boost creativity for your work project, try reflecting some creativity in your outfit. For this WFH friendly outfit, I paired a leopard print sweater (any print or bright color is nice here!) with some trendy track pants (these have an elastic waistband!), a wool blazer, a slouchy bag, and some statement jewelry. Add a base layer if it’s cold and, for leaving the house, a long wool coat.
Day to Night
Note that this is the night version of this look! For daytime, I’d throw on a cashmere sweater, lose the belt, and swap the heeled boots for a pair of Chelsea boots. I think black jeans feel a bit more evening than blue denim, but they work for daytime, too which is why I included them here.
I hope you found this post helpful for dressing for winter on your work-from-home days. Warm layers, comfortable pants, and good outerwear on stand-by are the key pieces you need. I plan to add some leggings under my pants when it’s really cold as well. I’ll also keep my snow boots at the ready as well (we certainly need them now!)
Read More:
Ten Tips for Breaking Out of a Winter Style Rut
French Girl Winter Outfits to Copy
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