Reader Request: What to Wear for Yourself When You Work From Home

What should you wear if you work from home? Do you need to get dressed up just for yourself?

Long-time reader and all-around amazing gal Ruth sent me this question:

What do I wear when I am on my own? I know that you have written about who one dresses for, and the correct answer is always ‘for myself’ (although having got into a relatively new relationship, I am delighted to be with somebody who finds me attractive, and love to dress in a way that he will like). But I live alone and work almost entirely from home. So there are some days when I see either nobody or only the local shopkeepers or the postman. So what to wear? I do have some standards. Occasionally I exercise in the morning and stay in my workout clothes all day (not a good idea – nothing is more uncomfortable than a sports bra worn all day) but normally I dress in ‘proper’ clothes, but the rather worst of them. And no jewellery – which for me is the signifier of being ‘properly’ dressed. I like clothes and probably have too many of them, and sometimes miss the opportunity to wear them. But there doesn’t seem any point in being anything more than decent and comfortable if I am on my own. I know you work at home but you are married so you have a husband to see you. But how does one resolve the problem of what to wear on one’s own? (If a tree falls in the forest…).

Her question has become even more interesting and relevant to me now, as I begin to take on more writing work and less out-of-the-house client work, and I’ve struggled with the same concerns. I really do believe it’s down to personal preference: I have a friend and colleague who also works from home and holds herself to strict standards of being up, bathed, and dressed by a certain time of morning. Without this personal parameter, she just feels lousy about herself. I used to be the same way … but have changed my tune after more than five years of freelancing.

I love getting dressed up to go out, even if “getting dressed up” just means a graphic tee and jeans. But if I KNOW I’ll be home all day and come in contact with zero human beings? I see no reason to put on delicate clothes or a lick of makeup. Especially since I have two needy cats whose fur and claws interact with everything I wear while working at home, and who can inadvertently ruin my good duds.

Long ago, Angie wrote about loungewear. Up to that point, my clothes were relegated to three main buckets: Work/good, sleep, and gym. It had never occurred to me to cultivate a wardrobe of items that weren’t pajamas but also weren’t street clothes. Extremely comfortable outfits that the cats could climb on, but that would be more passable as actual clothes if I had to sign for a delivery or run an unexpected errand. So now, on days when I’m home, I wear my lounge duds. A couple of pairs of fancy-ish joggers, smart hoodies, a few simple sweaters, nearly everything in charcoal gray to match the cat hair. (I know that sounds bonkers, but I had to get rid of a few black lounge items because every time I pulled them on, I looked like I’d rolled in glue, then rolled in cat hair. Yech!)

I will also admit that going 100% makeup-free is one of my great joys in life, and my skin thrives on a couple of days each week with naught but moisturizer. I will usually pencil in my brows in case of unexpected visitors, but the rest is au naturel. And I don’t do jewelry or accessories, unless I’m adding a scarf for warmth.

In Ruth’s specific case, it sounds like finding some sort of lounge-y happy medium could work. Downgrading a few items to lounge and maybe adding a few more, and considering those her “working by myself” clothes. Since jewelry is a personal finishing touch for Ruth, I encouraged her to nudge herself to add a few small pieces even if she would be the only one who’ll see them.

In terms of having a nice wardrobe that’s “going to waste”? I struggle with that a bit, too. My overall style has become more edgy/casual, so I don’t have loads of pencil skirts and button-fronts languishing, but I also don’t wear my “real” clothes more than three days per week most of the time. Strategies that help me:

  1. Making lunch dates that force me to get dressed and go out, even if just for an hour.
  2. Working in cafes instead of at home.
  3. Keeping an outfit list and actually using it. This forces me to remember all the lovely things I have, and wear them when I do go out. (Instead of reaching for the same 3 easy outfits all the time.)
  4. Making sure my lounge outfits are aligned with my “real” style.

But I feel like this may be something that gradually bothers me less and less. I love clothing and style, so I have cultivated a wardrobe I adore. I don’t wear everything in it all the time, but I am very mindful of wearing everything in it as often as I can. Someday I may pare down to a much smaller wardrobe that focuses on clothes I wear while working, but I’m not ready to do that just yet.

My impression is that many, MANY people who work from home or telecommute stress over and struggle with dressing. Lots of us worked in offices for decades, and feel like doing real work in sweatpants is some sort of sartorial sin. But lots of us also get over it. Eventually. There’s usually a transition period – often several years – in which we insist on being dressed for work before beginning work, even if that work takes place on our couches. Dozens of articles recommend putting on your best work clothes for phone interviews to get yourself in the right frame of mind, and that philosophy can shift over to daily work. But it doesn’t have to. If you are just as productive in your yoga clothes as you are in your suiting, what’s wrong with choosing the comfier option? Working from home is a new frontier, and many people still consider it a perk or privilege. That attitude can carry some guilt with it. I think that some self-employed folks and telecommuters feel like working strict schedules and wearing business casual while we type away in our basement offices is some sort of penance. Personally, I’m over it. But I definitely understand where that urge comes from.

Side note: At one point a friend who works a 9-5 job said, “I really hope you sleep in and kick off early sometimes. What’s the point of working for yourself if you don’t?” I had quite literally never thought of it that way, and it was so liberating to get “permission” from someone who worked in an office.

If you work by yourself and just don’t feel right if you’re not fully dressed in non-lounge clothes, stick to your guns. If you secretly wish you could just work in your PJs, try it out and keep an open mind. If you need a happy medium, chic lounge clothes might be the way to go. There’s no right answer except the one that works for YOU.

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  • Allison

    As a long-time reader and a recent work from home-er, thank you for this! Where are your favorite lounge outfits from?

  • Nebraskim

    Allie over at Wardrobe Oxygen talked a little about this recently. She said she once had the three buckets — work/good; sleep/home comfy; and workout. She now has a fourth bucket — spiffy but casual weekend wear. I feel like as I have switched from a fairly business casual office wear wardrobe to a work from home/freelance wardrobe, that the nice but casual weekend wear look is becoming my “uniform.” I’m huge into wearing leggings with a long tunic or dress over them with footwear like dansko clogs or boots. This looks pulled together for just about any situation. i can walk the dogs in this look, go to the grocery, go to the dentist, go to almost all my free-lance meetings. It’s very easy, very comfortable and casual but still pulled together. It looks fresh and just professional enough for what I do. I am not one to wear “lounge” clothing but i am guilty of wearing workout gear for long periods during the day. I actually wear sports bras all of the time as regular bras don’t work for me.

  • Sarah Gaunt

    I’ve been working from home for almost 5 years now and what I wear runs the gamut from skimpy nightie (all good as long as I don’t hit the webcam button by accident when I’m on a call!!) to workout clothes with heels (I have so many pretty shoes, I just want to wear them sometimes) to jeans and t-shirts and sometimes dresses. I live in Australia and work for a US company so I often stumble out of bed at 4 or 5am to do conference calls. There’s just no way I’m worried about what I look like that early in the morning! I’ve read the articles about sounding different depending on the clothes you wear and, for me at least, that’s total bull. I never put makeup on when I’m at home either.

    I’m finally figuring out that I don’t need business clothes anymore (in fact, because I’m not going to work functions either, I hardly need many going out clothes) and am trying to buy clothes that are more suitable to my lifestyle now – that part I find super hard TBH.

    I do like your idea of going out to cafes to work – unfortunately that’s not a big thing here. Plus, I like my 3 big monitors at home… 🙂

    BTW, I think most people who don’t work from home think we’re all just sitting around in our sweats and watching TV, when, in my experience anyway, it’s the exact opposite and because there is no line between home and the office we tend to actually do MORE work, certainly not less! Having said that, one definitely has to be self-motivated…

  • Jessica M.

    When I was writing from home, I liked wearing the same kind of clothes I feel best running errands on weekends in – jeans or weathered chinos with a little stretch, long sleeve tees and thermals and henleys with a vest or scarf for warmth, earrings occasionally just for fun. Maxi skirts and graphic tees in summer. I was comfortable, casual, and didn’t feel like it was a lot of effort (I would have felt totally foolish in business casual), but it still gave me a lot of room to combine interesting colors and textures, and I always had trouble focusing in pajamas and sweatpants. As a bonus, everything on that list has been very easy for me to thrift.

  • Ruth Slavid

    Great answer Sally, thank you. Yes, i am sure we are all ‘on a journey’ to our final freelance style. Luckily I don’t have the cat hair problem…

  • Mercy Morris

    This is gold. Thank you.

  • I’m so glad you’ve answered this; I’ve been thinking about emailing you the same question! I have a strict bathe and dress in outside clothes rule, but I get so discouraged by the amount of cat hair that I end up wearing only t-shirts, which turned into only wearing free t-shirts from client projects or 5Ks—but they don’t really fit my sense of style. I always feel disappointed when I put them on. But you’re right; cat claws are a real problem.

    A couple of weeks ago I decided that it was worth investing in nicer t-shirts, so that they look pretty but can handle frequent washing and cat love. I hit up Lands’ End and got a few good items, and I’ll be phasing out the free shirts. It makes a difference.