9 Ways Not To Look Like A Slob Even If You Don’t Dress For The Office These Days

We’ve addressed workwear on Privilege, several times. We’ve explored festive occasions that require little black dresses, or designer confections. But some of us require a more relaxed elegance. We wonder, how to dress when retired, or working from home, or, fleeing our suburban haunts for the big city? In other words, what kind of wardrobe is comfortable and without ceremony, but still stylish?

One might well ask. This is my most current and central fashion quest. At my nadir, pressed for time after a brisk neighborhood walk, I entered Whole Foods wearing baggy white basketball shorts, sports bra, white tee printed with Microsoft marketing gibberish c. 1998, and Mizuna walking shoes in pink, white, and silver. We will pause as you guffaw. Urgency is the best teacher. Here’s what I’ve learned.

The difficulty in what we’re going to call “Relaxed Elegance” is that comfort and elegance conflict in their origins.

  • Comfort is loose, durable, and often visually random, because one prioritizes feel over look.
  • Elegance is structured or fragile, a little fierce. Also harmonious in silhouette, color, and relative “fanciness” of pieces.

Clearly, one has to figure out the least uncomfortable determinants of elegance that can be imported to comfortable gear. Let’s look at the answers first, then deconstruct the whys and hows.

  1. If you are going for Relaxed Elegance, Classic Variant, you want to get the basics right. You can’t rely on a fabulous Prada dress to eclipses other lapses. Go with well-done basics, for the effect of subtle style. (Unless you’re an Advanced Styler. Which I’m not, so can’t address.)
  2. In this mode, first, do your silhouette homework. What pieces, what shapes, what proportions, support your silhouette in a way that pleases you. If you haven’t already explored body shape on Inside Out Style, I recommend you do so soon. I like the way I look with bare arms and covered collarbone, flared trousers, fitted waists, and a jacket. If it works, repeat. Good geometry bores no one.
  3. Focus on color palettes for the most effective tweak to sophistication. Go for monochrome, in navy, black, gray, brown, or “off” colors that suit you perfectly. Alternatively, wear shades all in a similar family, or if you’re adventurous, dress across the color wheel, i.e., navy with a flash of orange, purple with mustard. Avoid overly sweet pastels, be chary with pure primaries. Except red, if you can carry it off. You want appear intentional, albeit casual.
  4. Now look at your default casual clothing and upgrade the fabric – from cotton tees to silk, from oxford cotton camp shirts to cotton lawn button fronts.
  5. Buy some go-to pants. Jeans will serve you well. Or good khakis. You can even find drawstring pants that work, if you pay attention..
  6. Align your your shoes and bags with clothing, don’t go up a notch of “fanciness.” That said, also avoid shoes that look cheap.
  7. Keep two or three classic but informal jackets in your closet, i.e. a short trench, a sweatie peacoat, a knit jacket. They will add the touch of structure that elegance requires. In this world, vs. the work world, you are wearing your jacket most of the time, without having to type in it. It will make more impact than almost anything else.
  8. Accessorize with small pieces of good jewelry, or a classic large watch. Statement pieces require statement outfits or they will unbalance you. One can’t make a silk purse out of a sow’s ear by adding big necklaces.
  9. Never forget that you have hair. It must be well-handled.

Let’s say your At Home outfits consist of flannel pyjamas, yoga pants, or loose jeans/khakis. With any old tops. (Some of you may swear by worn out dresses, I wear dresses only to, well, dress up.) You will want to modify your preferred mode for Relaxed Elegance. Let’s look at a few examples.

Let’s say you’re a loose jeans and khaki sort. To a client meeting in the city, wear good jeans in your go-to shape with a top in the same color. Blue jeans, navy top. White jeans, white top. This creates what Inside Out Style calls the Column of Color. Then add a classic (with a twist) jacket in a contrasting color, Complete the picture with really good shoes, real gold jewelry, and a man’s watch. Make sure your hair is impeccable. Mine is long now. I like low ponytails, if the holder has some smack to it.

Work From Home, Meet In Cafés

Or let’s say you wear yoga pants at home. To take them to Whole Foods, wear layers in shades of the same color. I tend to go for all black, myself, black pants, tee, parka and Pumas. But one could venture out in the purples and lavenders if one were talented with color, and pull it off quite well. Especially if you add one accessory across the color wheel, like an acid green hair tie or tee.

I must note an important rule in the High WASP dress canon is Do Not Add Fancy Shoes To Sports Attire. Same goes for jackets. If you’re dressing for physical activity, and taking that on the road, do it proudly. To us, anything else looks dowdy. As I said above, You Can’t Make A Silk Purse Out Of A Sow’s Ear. So don’t try. Impunity, impeccable impunity.

How To Do Yoga Pants In Public

Fear not, my friends, there’s a Relaxed Elegance world beyond solid colors. To add sophistication, and edge, I recommend that you follow the Artsy strategy – mix patterns in the same figure quality, i.e. small or large, dense or sparse. Just stay in a color family. A classic jeans jacket counteracts all the drape, toughening it up. Remember, elegance, even this far left, requires a smidgen of fierce. And good shoes.

Retiring Artsy

So now, how to guarantee that one actually leaves the house wearing these appropriate get-ups, rather than in the moral equivalent of basketball shorts? We can all shop. But can we implement?

Strategy #1: Make sure your At Home gear is SO DREADFUL that you’d never wear it out. I write in the flannel pyjama bottoms above. Yes. I do. They are my work uniform. The uniform is an honorable tradition, is it not? And I will never wear them out of the house unless my survival depends upon it.

Strategy #2: Don nothing but Relaxed Elegance, even on the sofa. My hat’s off to you, conferring instant Grande Dame status, no matter your age.

So. Now. First things first. Go stare at your closet and consider. Great endeavors require a pause before the leap.

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  • My entire life is casual*. When we retired and started traveling, I had to force myself into Strategy #2. But it is the Sturdy Gal version: comfy, solid color tees, comfy classic bottoms like khaki skirts and trouser jeans. Pop them up a bit with silk scarves. Spend real money on few but top quality shoes.

    Since I had to downsize into the 3 drawers and tiny closet of our motorhome, I got rid of every single free logo-ed t-shirt and sloppy pair of shorts. No old sneakers; there’s simply no room for them. My mantra is “Quality Casual takes up the same amount of room as Sloppy Casual. Why choose sloppy?”

    When space is at a premium, it is much easier to choose only the nicest, most comfortable and (hopefully) most flattering items. I know which necklines and colors suit me best and allow only 1 or 2 trendy pieces. And for a Sturdy, as you know, even a modest ruffle can feel “trendy!”

    *Okay, I have a few outfits for Important Dinners and cruise ship Formal Nights. But very few.

    3:43 pm
    Trystan (the CorpGoth) said...

    “Quality Casual takes up the same amount of room as Sloppy Casual. Why choose sloppy?”

    I love this idea! I’ve been trying to rid myself of junky things, like the free T-shirts that are ubiquitous in the tech industry where I work. I managed to stop taking them (no more thinking “oh, I’ll just wear at the gym / to sleep in / to clean up the garden”). They multiply in closets.

    I’m aiming for Strategy #2 when I work from home, which is often. I’m not there yet, but it’s my goal! If I can at least be as well dressed as the “How To Do Yoga Pants In Public” combo instead of the dreaded flannel PJs, it’s a step up :-)

  • Love this post. I’ve been working from home for two years, and “at home” fashion is a tough one. All my meetings are virtual, so I never have to worry about how I look, but I’ve found over time that’s not a great thing. Often I sit around in ratty clothes, let my hair air dry, forget to put on makeup. So easy to get in a rut! I find when someone calls to have lunch or I need to run out, I am often unprepared. I’m also trying to get myself to do the whole “core wardrobe” thing, because I tend to accumulate tops (worn with jeans or ratty old khaki shorts–bah) just to cheer myself up.

  • Great post, and I’m happy to say I conform well with your suggestions. The only thing I might disagree with (for me) is the silk tee vs. cotton tee. I find silk tee shirts a bit “geriatric” usually, but maybe haven’t been looking at the right brands. I love Gap’s v-neck tee from their lingerie section. I always have a lot of clean white ones on hand, a few blacks, a few grays, and a few navy blues.
    James Perse also makes great tee shirts – but they’re much more expensive and I save those for “special” occasions!

  • lose the scrunchie…no matter what color it is…it looks soooo dated

  • Love it. Especially the advice about not making accessories too fancy.

  • I’m glad to see that you’ve not ruled out yoga pants! Personally when I’m not working, I’m living in my Lulu Lemon pants! My girlfriends and I often pair the yoga pants (and Lulu has so many styles some sportier than others) with a longish sweater or tank and tunic combo and ballet flats. Some people will simply not wear yoga pants outside the gym, but I think if they’re pair with appropriate tops and shoes, you can look casual chic without looking like you’ve just come from the gym.

  • On behalf of men, thank you for the yoga pants recommendation!

  • A man’s white cotton shirt, sized to fit you, will dress up drawstring waist khaki pants and dressy sneakers and take you anywhere.

  • oh yes. I fell into serious schlubdom a couple of years ago (working from home + living in Portland + midlife weight gain) and am now digging my way out….

    One observation I have is that “bad drives out good”–thus, unless you are incredibly disciplined to never ever wear that crappy jacket out of the house, go ahead and get rid of it, because you will inevitably put the damn thing on and head to Whole Foods or the bank or…

  • Fun post….I loved having your permission to guffaw. I wasn’t guffawing at you, I was guffawing with you:)

    My rule is this: wear nothing that makes you feel dumpy. Its a burden on your psyche. Because so much of the nice comfort-wear tends to be created for those with svelte shapes, I have to make the better stuff I wear. Fortunately, I can.

  • Nearly everyone at work, even the top management have gone so casual.

    I insist as you as being casually put together and the accessories and color palette make all the difference.

    Yes I go to Trader Joes and CVS in my Yoga pants, I somehow make it work, as you do so well Lisa. Great tips!

    Do come and join my giveaway of a wonderful painting by Mary Maxam!


    Art by Karena

  • Love the scrunchie…we are soooo the same age. “Yoga pants go to the Market” has been my uniform for quite a few years, altho’ in this blazing heat the bottom is generally a short denim skirt. Adorable post.

  • Always ready to learn and to tweak what knowledge I already have! Thank you!

  • One of the perils of working at home is the ease with which one can slip into schlubdom. Some are aghast that I get dressed (jeans, sneakers, light makeup) every day, but for me (just me, not suggesting it’s true for anyone else) too much of a relaxed attitude can spill over into the work product.

    I would have been here writing this comment fifteen minutes ago, but I had to click on the link to Advanced Style. (Yes, it’s all your fault.) What an amazing and delightful site, I can’t wait to show it to my mother!

    Thank you for nailing it in so many ways, I am a believer that yoga pants have a great spot in the closet, they really are an asset in many situations!

  • Excellent advice. I love a short jacket and hate pastels! My favourite outfit is the yoga trousers to the market – which I would wear everywhere.

  • I am so happy you did this post, so much better than my “jeans” post the other day. You always do such a great job, Lisa. I’m jealous!! I’ve worn your shoes with a fab outfit, tan linen mini jacket & long skirt, white tee, my jewelry, D&G straw & white handbag & YOUR shoes. I love the entire outfit. I think I look younger now. xx’s, my friend….

  • I just LOVE the client meeting in San Francisco attire. LOVE it. That’s what I would wear…well, that’s kind of what I do wear whenever I got out (minus the Manolo Blahniks, which I do not own…maybe one day ;)

  • Yoga pants are for Yoga.

    If you stop at the market on the way home from Yoga that’s fine. Otherwise you need to pour yourself into a pair of pants with a waist band. It’s good to remind your waist that it exists and you don’t want it to dissapear.

    The privilege of wearing stretchy comfy Yoga pants is your reward for getting up, getting dressed, spending the time with your DVD or that impossibly lithe teacher who rattles on about the meaning of life…..

  • You do good work! I could do the Client Meeting in San Francisco in Santa Barbara–it is my look completely. I would wear that every day. But I never thought of wearing top and bottom in the same color-I always contrast. For one thing, whites never are the same, and I have a thing against navy tops with jeans. But I will give this a try. Thanks for the great post.

  • Great topic. I need an apron tho, or in truth need to wear one of the ones I have. I hate to think how many tee’s I’ve ruined with a grease spot.

    Don’t think I’m ready to go out in yoga pants but there are other good options.


  • Daily wear here is most days white man’s shirt,beige linen pants,one of my 2 Cartier watches always,Chanel or French sole flats + for shopping my thick linen khaki blazer.

    A great well fitted jacket is a must have in this gal’s life…what ere the weather. Ida

  • Lisa, this is perfect, thank you so much. I am sitting applauding ” good geometry bores no one” it’s such a perfect expression.
    I adore that you write in those flannel pj bottoms, I have a terrible lust for flannel, my skin cries out for it!

    I am now saving this post and will start to address my slovenly at home/local errands wardrobe.

  • Great post. I’ve worked from home off and on for 15 years, with occasional client meetings, plus I sometimes teach at the local primary school. I’ve found that I have to shower, dress and put on light makeup to feel human – yoga pants are only for yoga (for me). But I do live in jeans and khakis, with dresses only for teaching or meetings …

  • Thank you, Lisa. I was so looking forward to your take on this look. You never disappoint. In my world, “the Skype” has creeped in and requires one to step it up a bit. I agree that quality of both fabric and construction are keys to the city of “Relaxed Elegance” as are hair, accessories, and good shoes. Speaking of hair, I say Yes to a nice hairband or lovely hair clip/barette. I must say No to the scrunchy – even when covered in velvet. Only the very svelte (or super confident) can get away with yoga pants at Whole Foods, et al. Personally, I would feel so…exposed which is neither Relaxed nor Elegant. Love your poly’s.

    6:20 am
    beacuz said...

    I must say NO to the scrunchie as well. There are really nice hair bands and ties available now.

  • Your jammie pants look very comfy. Have never been tempted to go out in my nightgowns, have taken to wearing skirts in summer and probably like my cheap flip flops a bit too much.

  • “One can’t make a silk purse out of a sow’s ear by adding big necklaces.” What a memorable line. Great post, too, by the way. My husband and I have our offices in our home and this was great information. Thank you!

  • Lisa,

    This is perfect. I am retired, and spend a lot of time with my German Sheperd and two horses. So I am very casual. And often covered with horse and dog hair. I keep a lint/hair roller in my bag! But I always wear black, either black cord riding pants, or black cargo pants from North Face. I do wear cotton tees, but am attentive to the style and cut. V-neck works well for me, black, of course. I get creative with silver jewelry, layered necklaces from John Hardy, David Yurman, and Sundance catalogue, silver earrings with semi-precious stones. And add a little color with fleece jackets in Winter–Pacific NW is more casual, outdoorsy.

    At home, I live in my flannel PJ’s :-). Especially leopard. Good to know I am not alone!

    When I go out at night, it’s in tailored, pressed jeans, a good jacket–Chanel or Armani, and good shoes, either heels or ballet flats. Again, black, except the jeans.

    I keep things really simple.

  • Thank you for mentioning flannel pyjamas, Lisa. They are a special case and you will be relieved to know that I follow your rules about them already :-)

    SSG xxx

  • I love this post. I work from home most of the time, and my criteria for what I go out in is dictated by the answer to this question: How would it be to bump into someone I know in this outfit? If the answer is “embarrassing” , I am not wearing it past my front door
    . Great tips for making casual work in terms of comfort, authenticity and use of your existing knowledge and pieces.

  • I love your collages. As a direct result of your style posts a while ago I bought that Lipstick Queen Medieval red you like. It is a great color, now I’m on my second tube and I credit that lipstick with the best driver’s license photo ever taken.

  • “One can’t make a silk purse out of a sow’s ear by adding big necklaces.” Thank goodness I’m not alone in THAT sentiment; I loathe big, clunky jewelry.

  • Erm, dare I say it? I often wear leggings with a tunic or a dress, but then I lean towards artsy so…
    Sandals, ballet flats, Converse make it easy to get around on foot since I don’t drive often.

  • OMG!! THANK YOU (!) for turning me on to Advanced Style!! What a treasure!!!

  • Oh, hey! I’m an instant Grande Dame. I only have pajamas/loungewear that could pass for street wear. I don’t wear it as street wear, but I would not be embarassed to answer the door or get the mail in it.

    Now I’m a Grande Dame, I’m going to have to make my kids respect and fear me a little more. :)

  • THRILLED BEYOND! I employ each suggested outfit, some more than others and sport my large, bossy men’s watch to boot. Glad to know I’m on the right and relaxed path =) THANK YOU!!!

  • I am a stay at home wife/used to be stay at home mom. I ALWAYS put on makeup, shower, do hair, etc. I never leave the house looking slobby. I only wear workout clothes on my way home from working out/exercise class. My life is mostly casual, so I really appreciate these pointers. I like the the column of color approach and use it often. I need to work on employing neutral colors and more basics. I’m getting there. Thanks for this post–very helpful.

  • Louise – Oh I know, the impact of a ruffle! I think that living life as though space is constrained, when it comes to wardrobes, can really help one find the core set. Nothing wrong with expanding, subsequently, but the discipline around small space is really useful. And one should always have a few outfits for VID:).

    Priscilla – Thank you very much. The accumulation of tops is a brilliant observation. So many people have the same issue. Doing casual well takes even more focus than doing dress up well, I find, because it’s all in the details.

    Kathy – I am not surprised you have similar classic taste. I should hasten to add that I do not mean woven silk shells, unless in very interesting colors. I’m thinking about silk knits, silk and linen weaves, etc. I love James Perse. I own a sweatie peacoat of his that is one of my most-used pieces. Have to find a way to get his tees on the blog soon:).

    Frances – I respectfully disagree. Having lived through the 80, and the 90s, I think scrunchies get a bad rap.

    Susan – :). That’s why I like your scarf initiative. Especially if everything else, pants, shoes, top, are pieces you really really like.

  • Princess Freckles – Long sweater, tank and tunic, yes! Ballet flats, as long as they aren’t too structured or logoed, i.e. they are very close to REAL ballet flats, yes. Repetto, for example. I actually don’t mind people looking like they’ve just come from the gym, as long as it’s a gym where people wear tasteful clothes.

    Alan B. – Always happy to help:).

    Valentine – I’m a huge fan of men’s white cotton shirts. I agree completely. Gets a little tougher as we get older, since our silhouette converges on the male shape, but still, looks fantastic.

    Jean S. – Ha. Love the thought of a Portland effect:). And I agree completely about bad drives out good. I think I once called the bad actors “closet gremlins.”

    Lara of Long Beach – Thank you. I’ll guffaw too. And yes, your rule is lovely. Why contribute anything at all to one’s own distress?

  • Karena – Very interesting about top management. I’l see you at CVS;).

    Rosie – I thank you. Scrunchies get a bad rap. And I am HUNTING for a skirt, but have this urge for a floaty one, and it’s hard to find something longer than a handkerchief.

    Shelly Gregory – My pleasure. I enjoy your Lush picks, BTW.

    TPP – I hope your mom enjoys Advanced Style. Strikes me that they ought to seek out a few Advance Preps, what do you think?

    That’s Not My Age – Thank you so much!

    Marsha – I think the Artsy and the Grande Dame wear jeans less often, unless the jeans are white. And I’d say the world needs some Polyvores from you!

  • Marcela – Oh thank you. And here’s to your future Manolos. I have to say, on cost per wear, those things now cost me negative money.

    RoseAG – I love your focused, no-nonsense approach. Of course, I respectfully disagree, but I love your thinking. And I suppose keeping yoga pants as a reward for physical activity could be very good for us all.

    Marcy Simmons – Thank you. I get compliments almost every time on the navy with jeans plus khaki trench look. And it’s not fancy at all.

    Darla – Yes! I need an apron too. My real problem is that I don’t want ruffles, as per the Sturdy Gal canon. I want one kind of like a blacksmith’s.

    Ida – That sounds great. Very refined, but practical.

  • Tabitha – I have only begun. I know you are surprised by nothing I said here, and I have to up my game and source some good stuff. I’m looking, as we speak.

    Tiffany – Thank you so much. Even the shift from lipbalm to lipstick has an impact on me these days.

    Sylvie – Oh yes, the Skype:). I am exploring other hair accessories, but I am going to cling to my scrunchie for dear life. It doesn’t flap, or anything.

    Terri – I love my Havaianas. Not cheap, as flip flops go, but so comfortable and come in so many colors.

    Mary Anne – Thank you!

    Mary Jane – Great strategy. Do your black jackets have any tweed/pattern/etc. to them? Or more strict black?

  • SSG – I am deeply, profoundly, enricheningly relieved.

    Erin – Thank you very much. And that’s a very good screening question indeed.

    Beacuz – No! No! I must keep mine. I’m expanding my repertoire, but still….

    Jan – Well phew.

    Fuji – Yes, the tunic and leggings often look great. I simply never started on leggings and skinny jeans, so have no expertise. I try to only give advice I have some experience with:).

    Lara – Hahahahaha! My pleasure.

  • rb – Come back and give us some tips on that Grande Dame respect and fear, will ya? I could use some, now and then.

    Mags – My pleasure! And if you even have the bossy (we say authority, I mean, we’ve earned it, no?) men’s watch? Batting 1000 in the lookbook:).

    Susan – I think with neutrals the key is to find the color family that works best on you. I can’t wear gray to save my life. But at least I figured that out before it was too late:). My guess is that you look extremely well-put together.

  • Thank you so very much!

  • I too wear scrunchies. They’ve not been improved upon.

  • Great post and you pretty much nailed my basic wardrobe, at least when I’m not feeling the overwhelming urge to dress a little more. I love scrunchies and think they are perfect, and thanks to you now have a pair of Havaianas, which are perfect with shorts and capris, and the first thing I look forward to slipping my feet into. I also agree about the jewelry, and I am basically drawn to statement jewelry, but not with casual clothes where it offends; simple and discrete is so much better.

  • What exactly *is* the moral equivalent of basketball shorts? One shudders to think…

    But seriously, this is exactly what my stay-at-home-mom wardrobe needs, LPC – thank you. I’m slowly working on the upgrading quality / keeping my style/silhouette aspect of this.

  • Dear Obewon,

    Great post. :)

    Your Padewon

  • Hahahaha! How tawdry I am amongst those peering! Let loose the guffaws. I’m owning it with authority! =))

    a discrete yet purposeful, ‘many thanks’

  • Great post! Like Strategy $2, b/c #1 makes me feel like someone with no place to go and no life force.

    I cannot get scrunchies and elegance into the same thought.

  • I love leggings in black, grey and mink. I’m 50+ and in good shape, so fie! to those who say you can’t wear them past a certain age. I buy good quality jersey leggings from my favourite tall woman shop here in England (proportion is important)and dress them up or down as I please.

    I’m working on upgrading my bijou/wear a proscribed uniform for work so that’s my excuse for having nothing decent in the closet wardrobe. Articles like this help me move forward with more confidence. Thanks!

  • I wish my wife would dress up some when she is at home. Married 46 years and she hasn’t worn anything nice. She wears old sweats or old granny type pajamas all day, she even goes to the store looking like some one hasn’t washed there hair or changed clothes. I won’t go any where with her, I won’t sleep with her and I gave up sex with her 40 years ago.
    I explained my feelings many times and bought her some nice clothes! She takes them back to the store and goes and buys more frumpy clothes. She just grosses me out. I try and dress decent around the house. I don’t understand

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  1. […] I absolutely loved these tips for dressing well and maintaining your style standards as as self-employed or work-from-home woman. […]

  2. […] wear things you will not wear in the outside world, which may mean you have a set of “working pajamas” or “work yoga pants.”  I usually just wear regular clothes, but I have noticed […]