Dressing Casual at Home: Comfy Work from Home Outfit Essentials

As more and more people join the work-from-home taskforce these days, I can’t help but pay closer attention to the outfits I have found myself wearing day after day while I work from home running my own business. I like to think I’ve found that nice balance between completely given up and comfy/cozy. To help inspire others to find comfy work from home outfits, I found some inspiration to gather 20 essential pieces to the work-from-home wardrobe.

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Know your style

I’m embarrassed to admit that even though I used to have way more clothes than I do now, I never really used to know what my style was.

Taking a 3-year spending pause on buying clothes definitely helped, but the biggest change I made in order to understand my particular style was to stop scooping up other people’s style.

Knowing your own unique style and knowing who you are on a deeper level can help you truly feel at home in the clothes that you wear. Snag The Coaching Kit to help you really uncover who you are.

It might sound silly, but have you ever tried to buy something just because other people were wearing it and you never really felt comfortable. You didn’t see what all the fuss was about, yet you continued to try to like it because it was “trendy”?

Please don’t tell me this was just me.

One major game-changer to this can be to start recognizing when you are buying into fads and trends in the first place.

Dress it up

Even if you are covered in loose, comfortable clothing all day, why not dress it up a little with a gold minimalist necklace. This can be such a great way to make your cozy work at home outfit seem a little fancier.

I’m a big believer in the broken window theory. This is a theory that says when you have buildings that have been vandalized continuing to exist in a broken down state, it encourages more vandalism.

How the heck does this relate to a gold necklace? Well, if we are walking around in sweats all day, we just might be tempted to let the rest of our self care slide. Throwing on some pretty jewelry can remind us to continue to value ourselves and our worth.

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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The oversized cardigan

I am so glad I’m not the only one who has become obsessed with the “librarian sweater” as I like to call it. This oversized cardigan looks easily pairs with any kind of pants. Like, for real. Leggings, sweats, jeans, or dress pants. It’s like wearing a blanket all day.

After having done the work to truly understand who I am and what my style is, I have officially determined I am an over-sized cardigan kind of girl. When I stopped buying clothes for 3 years, I lived off mostly hand-me-downs and one of them was a brown librarian-like cardigan I would have never bought for myself — and I loved it!

Living in Minnesota, I cannot tell you how nice it is to have something to snuggle up in all day while still looking like I sort-of tried.

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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The t-shirt tuck in

Instantly you become more work-appropriate when you tuck in your shirt. Right? I saw DJ Tanner do this on Fuller House and decided if it’s good enough for her, it’s good enough for me.

So wake up, tuck your shirt in and you’re basically wearing Prada. (Is Prada even cool anymore? I don’t know.)

See more at My Kind of Sweet

Going with the flow

These amazing pink flowy pants are the perfect balance between comfort and workwear. It’s a great way to dress up any cozy work from home attire.

Years ago, I probably wouldn’t have had the body confidence for these (having such a small booty and all). These days, thankfully, I have learned to embrace all that God gave me (or didn’t give me) and just wear what feels comfortable and fits my style despite what any style gurus might tell me.

See more at Lady Fashionizer

Matchy-matchy

Finding adorable matching “sweats” allows you to be completely comfortable at home while still looking a little more put together than if you were running around in your favorite Van Halen T-shirt and bleach stained sweats.

Then again, maybe you’re all about the Van Halen T-shirt and bleach stained sweats. I bet that look totally works for you.

At the end of the day, the only person we need to be “on brand” for is ourselves, right? If you’re being true to yourself, then…you go girl.

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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Office casual

Who says you can’t actually dress a little work casual from home? If dressing a little nicer makes you instantly feel better when being trapped at home, then I say, do it!

These days the trendy thing to do seems to be embracing sweats and leggings, but there are some people that just can’t do it. Not all day at least.

I used to have a girlfriend who felt obligated to like sweatpants in college. While I appreciated her efforts to still find curve-hugging sweats, at the end of the day I’m glad she realized they just aren’t for her.

If you are the type to prefer being a little bit more dressed up, go you. Don’t apologize for it. Knowing who you are is never something to shy away from.

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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Comfy footwear

Lounging around the house is so much better when your feet are happier. Plus, that cozy, sherpa-lined slipper look is something you can get away with just about anywhere.

Personally, I have been sticking to thick “boot socks” to wear around the house. Maybe it’s a Minnesotan thing. If you don’t take your shoes off the second you enter the house, you just might not get second helpings of goulash. That would be a nice passive-aggressive way for a person to let you know you had broken the cardinal shoe rule.

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
See more at Who What Wear

Business on the top, party on the bottom

Have a Zoom call? No problem! Just dress up your top and stay crazy comfortable on the bottom! This simple grey blazer paired up with a T-shirt and sweats is ideal.

This look just might be my favorite. It’s like the work-from-home woman’s version of the mullet. Business up top, party on the bottom. People know you’re laid back but must also be taken seriously.

Leggings, duh

Leggings are starting to be something I love more and more. Yeah, I’m way behind the curve, I know. Personally, my favorite is the American Eagle, Aerie leggings. I have yet to find a pair that don’t fit fantastically. Spanx also offers amazing, comfy leggings that keep all the things tucked in.

I think I rebelled against leggings for so long because I was so glad to have actually found “my jeans” after years of searching. Is there such a thing as a person who can just wear any brand of jeans and feel totally at home? I doubt it. We all go on the perfect jean quest, right?

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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Sport the crop

Have you ever considered maybe wearing a crop top but it makes you crazy uncomfortable? Well, now is the time to test it out. Grab yourself a pair of high-waisted leggings and pair them with a cute crop top. You just might end up loving how you look!!

When the big Covid quarantine hit in 2020 I decided it was time for me to try the crop top. I had gotten more comfortable with who I am and what my body had become after kids and I really liked the way crop tops looked gosh darnit.

Sometimes we see fashion trends that we love but we tell ourselves we’re “too old for,” “too big for,” “too tall for,” I say, knock it off! If a style fits your personality then it is a crime not to wear it. Need more help feeling like yourself?

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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The little black PJ set

I love the idea of a completely sleek, black pj set. It looks dressy even when you’re just being totally comfortable! Plus, black just never goes out of style!

This reminds me of the perfect example of a minimalist outfit. Black, simple, interchangeable. Heck, she might not even be staying home, maybe she’s going out to brunch with girlfriends. Who can even tell?

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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Dressing down

I love dresses! People instantly assume that you put effort into your appearance if you’re wearing a dress. In reality, you threw on one piece of clothing and you were done!

Plus, if you choose wisely, you get way more comfort and breathing room out of a dress than you do pants! A cute T-shirt dress is perfect to transition from in the house to running errands.

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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Jeans, please

Loose-fitting, distressed jeans are one of my favorite go-tos whether I am working from home or not. It’s a great way to be comfortable around the house while still getting you out of your sweats for a day.

Again, this is me finding my style and not caring what people think. I might be a mama of 4 on the outside, but on the inside I am still just that wild and crazy 18 year old, Holister obsessed chick that still loves her ripped up jeans.

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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Oversized sweater

Just like with our oversized cardigan, don’t let yourself believe that a sweater can’t operate as work from home comfy! As an added bonus…that lace bralette underneath is so dang cute!

Side note: do people’s homes actually stay this clean, organized and well lit? Does she not have kids that would rip all those things right off her shelves in a heartbeat? No? Just me?

Also, I would have totally killed those plants in the corner by now.

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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The white tee

Classic. Like the little black dress but for work at home people. Sticking with a classic white tee instantly makes you match pretty much any bottoms you decide to put on!

Also, I love the curled hair. Even on days I dress down and opt out of makeup, I truly love when my hair is done. You can take that as a bonus suggestion.

Dressing Casual at Home: Comfy Work from Home Outfit Essentials

His dress shirts

Why not go oversized dressy casual by sneaking into your man’s side of the closet. No man? Just buy yourself one! Because how cute is this?

Dressing Casual at Home: Comfy Work from Home Outfit Essentials

Cozy jumpers and rompers

Rompers and jumpers have always been the epitome of comfort (so I hear). If this is the case, you may as well bring that comfort to work (at home)! Not to mention I am a big fan of the off-the-shoulder look.

I don’t know if it’s a short girl thing or just a personal style preference, but I personally have never felt at home in a romper. But, I am always secretly a little jealous of any woman who does.

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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Faux-get about it

Put on leggings that look extra sexy? Spanx faux leather leggings are all the rage right now and it’s pretty easy to see why. So if you really want to combine comfort and cute, they just might be worth the investment.

Not to mention, I have found, after a lot of Pinterest scouring, that you can literally pair these with just about anything. T-shirt, sweaters, slinky tanks. There are so many ways to style them and it’s like wearing leggings in disguise. Talk about a win/win situation.

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
See more at Lady Fashionizer

Fuzzy feet

You didn’t think I was going to make it through an entire post without mentioning the comfy socks, did you? Something about fuzzy socks just instantly makes you feel better about yourself.

Like I said, these are my go-to’s around the house, but I’m still picky about which ones are my favorites.

If we take a quick minute to glance away from the socks, you’ll notice the exact style I would hope to have for my at-home office someday. Maybe I’d be a little more cliche and add toss up a photo of Audrey Hepburn too. Who am I kidding?

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
See more at Who What Wear

Styled up-do

Yeah, we can’t leave out the messy bun either. These messy updos are done right with a scarf or headband/scarf. And let’s be honest, we all want to cover up the fact that we didn’t shower. Right? Right.

I have somehow managed to nail the effortless messy bun up-do. It’s partially why I’m afraid to ever cut my hair again. What if I lose the super power for good?

Anyone else used to spend hours in front of the mirror trying to get a perfect bun only to freak out and leave the house feeling like a failure?

Dressing Casual at Home: Comfy Work from Home Outfit Essentials
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Dressing Casual at Home: Comfy Work from Home Outfit Essentials
Dressing Casual at Home: Comfy Work from Home Outfit Essentials