Do you dress Casual? or Scruffy?

posted in: Style advice | 21

Karen wrote to me recently (and I have reproduced her letter, slightly edited, with her permission):

As a tall woman in her sixth decade, pale skinned, blue eyes, white hair who is reluctant to wear much makeup, on the slim-to-thin side, following your advice on color and dress/clothing shapes has been so useful.  My transition out of dark suits is complete!  I donated all of them, and my closet has much more color.


But something happened that puzzled me … I recently went to a neighbor’s 77th birthday party (more a late afternoon tea) where the other ladies present made such a fuss over how I looked – I found it more than a little embarrassing.  The food was elegantly presented, wine was served, we ate on one of the patios in the host’s lovely garden, etc.  That evening I mulled their reactions and tried to understand why the fuss over how I looked.


I had worn a sleeveless red linen dress with a cropped black knit silk 3/4-length sleeved cardigan, bare-legged, red clogs, a beaded bracelet, simple silver earrings and only mascara and a dash of red lipstick.  I wore my hair twisted up and held with a clip. I wasn’t “dressed” up – I certainly wouldn’t have worn it to a wedding or evening dinner party but I had put a little though in.  BUT most of the other guests were wearing clothes they could have gardened in. I have noticed the same thing when out shopping.


Anyway, it all made me wonder how “casual” morphed into slovenly and why it is so accepted.  (Of course, I recognize that Brits may be more formal than Americans.)

Are you all imagining how nice Karen would have looked in her red dress and lipstick with a little cardi, her hair in a twist? And clogs! That is an interesting feature and if I had been at the party I am sure I would have admired her footwear. I have been thinking about her question for a week or two and I wonder what you think? I do believe that people should be absolutely free to dress as they prefer, but I like to dress up a little and I like to look at people who have taken some trouble with their appearance.

Here is a red sleeveless dress that looks quite smart with beige heels – probably for an occasion.

Any item can be dressed up or down. With summer sandals or trainers (or even clogs) this dress would be different. With a chunky belt and thick tights it would be suitable for a weekend outing. With lively jewellery or cardigan it would be nice for an informal evening event. For work I would put on a jacket.

Hobbs smart dress

For me the answer lies in the difference between under and over dressing. I discuss this in my book as I think it is a challenging topic, especially as many of us have plenty of clothes and spend a considerable amount acquiring even more. There is also the interesting distinction between fitting in and standing out. With no real rules of fashion or etiquette many of us flounder and fall back on the “I want to be comfortable” which includes soft jersey fabrics but also implies feeling comfortable in your environment.

Personally I do what I can to look good, but I don’t want to stand out too much. We have a couple of guys at work who wear three-piece suits and they stand out as being rather overdressed (our customer group is generally poor and very diverse). But I don’t like to be underdressed either. Today, as it is very hot in London I am wearing a yellow dress. It is nicely made with a few interesting features and I have added a red leather belt. The dress itself could be worn for a formal occasion with a hat, jacket or flashier jewellery. Today  I am accessorised to some extent (earrings, necklace, nice shoes, colourful glasses, rings, watch). On Fridays we seem to have moved towards “dress down Friday”. Many colleagues wear jeans but often with a smart top or something colourful. I would say on the whole that the average colleague looks good on a Friday, perhaps more so than the rest of the week as they feel freer to be themselves. I wear jeans very occasionally to work. But only when I have no external meetings. If I am meeting a tenant, board member or partner organisation I would generally dress a little more formally so they would never feel that I was disrespectful.

And there is another consideration  – do we want to be approachable or authoritative ? At a tea party for an older lady I would want to show respect but also to be approachable. I wouldn’t want to wear a formal suit or a stiff dress and gloves – unless the old lady was the Queen!

The key for me is to try to get a balance – just enough authority to be able to do my job as a senior manager, but sufficient approachability so no one feels uncomfortable around me. I want to look stylish and slightly cool, but I certainly don’t want to draw too much attention to myself. I would go for relatively subtle details rather than cutting edge fashion. I like to get a few up-to-the-minute items each year – which may be a T-shirt, or a pair of shoes or an accessory, and combine this with more classic items.  My advice is to go down the middle. Not too dressy and not too dressed-down. Not too authoritative but not so casual you could be gardening (eg shorts, flip-flops, torn or paint spattered clothing). Not to0 stiff and not too slobby (PJs, elasticated things). Not too different, but not too samey.

This is probably awful advice. Meaningless middle of the road stuff. But I would like to encourage individuality, self-expression, and diversity. I want to say “I care”. About myself and about you. And caring about my appearance is part of respect (of self and others) and caring for others. Give them something nice and interesting to look at when they are talking to you.

The way I try to achieve this approachable yet authoritative, different but understandable, neither over or under dressed is to combine looks and elements.

  • Jeans with a formal shirt or jacket
  • A dressy lace skirt with informal footwear.
  • A miniskirt with thick tights and masculine shoes
  • A tailored skirt with a hand knit jumper or down jacket
  • Pinstriped suit with a corset (I am joking about this one!)

Even something like cargo pants (without the weird phone accessory, carabiner clip and dibber) could look dressy with different shoes, a more formal top and a smart belt. Again the shoes and blouse would be more than fine for a party with a fashionable skirt.

Suitable for the garden

For me “slob” and “slovenly” have connotations perhaps of looking down on people, which is an added complication. I don’t want to judge others – there are many reasons why people dress down – usually due to feeling insignificant, un-confident, and sometimes due to depression etc. Sometimes people are simply natural dressers and really aren’t interested in clothes or dressing up.

Nice clothes can make you feel a lot better but not if you are shamed into changing. Dressing down, and dressing up, sends a message. Sometimes the sloppy look is adopted as an act of rebellion, or to belong to the group. And sometimes you really don’t have the time or money to do much better. When people are ill, or disabled or mentally low having nice clothes, hair, teeth and make up can make them feel better. But getting there may not be feasible. When I had lots of little kids I literally dressed in what I had taken off the previous evening, shoved a spare nappy into my pocket and dragged the children to school. Only after they were gone could I have a bath, get dressed in fresh clothes and try to improve my appearance.

What do you think?


21 Responses

  1. Sue

    This post really resonates with me. I believe that if I am going to visit someone or go to an informal party I want to look like I made an effort. Not so much for me, but out of respect for the person hosting the event. I used to be quite amazed at what people wore to interviews and I have been known to reject a potential employee because he wore jeans and a cardigan, on the grounds that if he didn’t look smart at the interview, he was going to look terrible day-to-day. I was vindicated when I ran into him where he did gain employment, and yes, he was slovenly. I think Karen would have looked perfect at the afternoon tea and she might just prompt all those other people into dressing a little better the next time they go to a function.

  2. Stephanie

    Interesting thought provoking post. How we all dress has got more casual over the years and there are cultural differences. On internal flights in the States my fellow passengers look as though they have just rushed to the airport from doing chores (gardening or painting) but in New Zealand we have a smarter casual look. Regardless of geography, at sewing retreats we all care about our clothes, how they fit and the messages they send even though our style may be different arty, casual, retro etc.
    I live in a country where dress is largely casual, where it is acceptable to wear your pyjamas, slippers and dressing gown to the shops and jandals and shorts out to dinner. Not something I personally subscribe to having a preference for being well presented, appropriate to my environment. Pride in my appearance = pride in myself.

  3. Lisa

    My daughter only wears jeans and t-shirts and refuses to compromise. I’m happy for her to be herself and be comfortable but we’ve had arguments when it comes to more formal occasions like weddings and parties. As a previous commenter said I have told my daughter that when you are invited to something you should show respect to your host and make an effort in what you wear. It doesn’t have to be expensive or very formal or make you feel uncomfortable but it should be more than the norm.

  4. Claire Cooper

    My Saturday attire usually compromises jeans/ shorts and a t shirt. But then I’m often chilling at home, walking the dog or doing housework. But I will go out to the shops like it too. However, most of the rest of the time I’m wearing something me made and want it to look good.

  5. Sis

    I hardly ever wear trousers and never jeans because I don’t feel comfortable in jeans. I wear trousers in spring and autumn but otherwise always skirts or if I go to a function a dress. This has been my “dress code” for the past 30 years (I am 61) and I have met a number of people who have told me I am over-dressed and even at family events people of have sniggered at my outfits. 40 years ago you never told anybody that you made your own clothes that is thankfully changing now. I would never question other people as to why they think it appropriate to wear jeans/shorts/gym gear and tees for whatever occasion although I feel it is not “an uniform” I find acceptable for various events in our lives but I can accept their choice of clothing but then I also expect them to accept if not respect that I dress differently. I never wear make-up because my skin is sensitive and that too can be “talking point”. There is a lot of intolerance in our society and sadly standing out is not acceptable by some. I feel sorry for them as they miss out on life not being able to look past the clothing or maybe they are suffering from the green eyed monster called jalousie sitting on their shoulder because they would actually like to dress differently?
    In regards to being approachable to me that is all in the facial expression. I look at a person’s face and hands to judge whether or not they are approachable or not. How they dress is up to them.

  6. Elaine Sabin-Simpson

    Other than slobbing round the house, I prefer to at least look ‘put together’, even when uber casual. My workwear needs to step up a notch for my new job, the ethos being that as uniform for the students is considered of very high importance, staff should reflect these values ion their own clothes. Nothing specific is laid out, and the expectation for male staff is usually as simple as shirt and tie…it’s always more vague for female staff of course!
    I refuse to abandon elastic waists though, you cruel style guru, you!
    So my vague plan is- smarter trousers, more blouses than T shirts, a few smart cardigans as I don’t really do jackets. As long as my colours work together, and I keep my quirky prints under control, it should be fine…I’m not a manager after all [thank gawd]!

    • fabrickated

      I like the sound of your workwear plan, and the idea of setting a good example.

      Incidentally I am working on a range of elasticated waist skirts right now, my dear. Instant Frida gratification, don’t you know!

  7. Diane G

    I always like to look like I made an effort to look pulled together, or I don’t even mind being the overdressed one. I prefer it that way than the other way. There’s a word I like to use and it’s ‘polished’…in other words, I can be wearing really casual gear but still put together, neat, accessorised etc.
    I read an article some time back about a woman that had suffered badly with depression and every day, through small steps of self-care, taking a little time with dress and appearance, she gradually came through the depression…it really does work. I’m a great believer in the effect clothes have on the psyche.

  8. Theresa in Tucson

    Good topic, Kate. My everyday uniform is a pair of jeans and an open neck cotton shirt and I have two separate wardrobes of that. The first one is the “grubbies”; clothes I do physical work in. These are things I’m not afraid to get paint on, climb on the roof, scoot around the floor and subject to getting ripped or torn. The second wardrobe contains the “nice” jeans and shirts that I wear when not physically working. These go dog walking shopping and lounge around the house. Both sets are mostly “me made” so I can vary the pattern, fabric, and style so I’m not running around in an endless succession of blue jeans (how boring). And when things in the “nice” set start fraying they are sent to the “work set”. But I live in a very casual town so the dress is very informal.

    But I do have another wardrobe of skirts and dresses that take me to church, special occasions and out to lunch with my sewing friends. It didn’t used to be like that but once I started sewing again I’m much more pulled together

  9. KS Sews

    I like clothing and I like putting together “looks”. I am not a casual dresser. It’s just not in me. I’m rarely overdressed though.

    I don’t automatically consider knitwear or jeans and tees or whatever “more comfortable”. My comfort level will depend on what I’m doing. I’m generally most comfortable in a dress. And I own a lot of them! Different lengths, different fits (fitted and slim vs loose and flowy), different fabrics…not to mention a host of cardigans and jackets to change the look.

    I love blazers but I have switched out the more serious versions for fun/relaxed versions so I’m less out of place in my casual office. I have a plaid jacket where the less dominant (non-dominant?) color is a brownish-orange. I love wearing it with a bright orange tee and navy trousers. I get to “dress up” a little, feel pulled together, but I don’t think I’m so far off from everyone else.
    And as middle management, I have some room to dress up a little without seeming out of place.

    For example, with regard to your coworkers; I think I were wearing 3-piece suits in the office then I wouldn’t care much if I was more dressed up than everyone else at work. But dealing with clients, I’d certainly want to ensure I’m seen as relatable/approachable.

    When I first started working here it was summer. After a few days someone said, “you’re always so dressed up! You know you can just wear a top and capris!” I caught myself from responding, “I don’t even own a pair of capris…” but I don’t. I have no need for them!

    I firmly believe people should dress in a way that suits themselves and their lifestyle. But I also think people make dressing daily some type of mental hurdle when it doesn’t need to be.

    One more anecdote…a woman called me dressed up when I was out grocery shopping. I was very nice about it, but pointed out how similar the individual items were we were wearing. She had on an oversized hoodie and t-shirt with yoga pants and sneakers. All knits and flat, comfortable shoes. I had on slim ponte pants, a sleeveless knit top, a cardigan (zip front with pockets), and leather flats. I’m certain I put no additional effort into my look that day than she did!

  10. Linda

    Hi Kate – I love this post as it is a constant issue for me. I am retired and live in Florida, where it is very warm most of the year. Too warm for layers, scarves, tights, so some dressing options are limited.No matter where I go, even including many nice restaurants, I see women wearing shorts or capris, t shirts, athleisure. I am at an age where I prefer not to show any more skin than necessary, though many of my same-age friends show plenty. I also like to put thought into what I wear, so whenever I have a meeting, lunch, or date with my husband, I consider what I’m wearing and try to respect myself and the occasion. But I sometimes feel that others think I am trying to be “better” than they are by so doing, kind of oneupmanship. The heck with them, I dress mostly for me and husband and looking good does make me feel good. By the way, I’d love a post on warm weather dressing for mature women. Thanks for listening.

  11. ceci

    Wow, so much reported hostility to commenters who make an effort to look nice – perhaps a feeling of inadequacy on the part of the critics? I haven’t experienced that so perhaps I need to dress up more in my daily life! Or I just have kinder friends and relations?

    One related story, my adorable daughter in law just started a new and much desired job and was attending a meeting of the governing board of the organization. She asked the co-worker she is most in contact with what one wears to these meetings and the woman said “oh anything, shorts and a tee would be fine, its not a dressy group….”. My suggestion was a polished day wear outfit, skirt or pants, coordinating top or light jacket (its very hot here) since as the new kid it pays to be respectfully dressed up – if everyone else has on shorts and tees she can wear that kind of thing to her second board meeting! I will be fascinated to hear how this works out!


  12. Marianne

    I’m wondering if perhaps the commenters reacted on the colour of Karen’s outfit, more than the style. Would there have been the same fuss over a beige or grey linen dress with matching clogs? I regularly get comments about my outfits being so ‘daringly colourful’ for my age. I’m 60 and look and feel best in a cool, deep and clear palette, which can make me stand out regardless of whether I’m dressing casual or formal. I don’t mind and I don’t care but apparently some people think you should start blending in the background at a certain age. I feel Karen’s outfit was very appropiate for the occasion and I hope she keeps wearing it with confidence and joy.

  13. Avril

    Great post Kate.

    In a casually-dressed world, it is very easy to feel overdressed. My formal jackets get little wear now – which is a pity as I love how the shoulders look!

    However, regardless of outfit, I most commonly wear at least three items of jewellery – always earrings and a watch, plus either a necklace or a bracelet. My shoulder length hair ( dyed – trying to work out how to go gracefully grey!) is pinned up with a matching crocodile clip, unless I’m in the gym, on my bike or with hair covered up in the sun.

    I colour coordinate my clothes, even casual wear, although I don’t do so when I’m gardening or doing diy. I think it such a shame when people do not make the most of their best points when they are dressing. Lycra has a lot to answer for, as it has led to an acceptance of the overly tight, sausage-skin look that is only flattering to about 0.001%of the population.

  14. helen

    Interesting post!
    Before I started a new job a few months back I went to M&S for a style consultancy. I had got really lazy in my old job, especially with biking to work. I wasn’t really expecting much but it was free so I thought I’d give it a go. It wasn’t a new look that I wanted but me but just a bit smarter with more colour and to have enough mix and match outfits to have 5 days of clothes. I came away with some great outfits and accessories, there were also a few pieces that I wouldn’t have thought to even try on. Nearly 4 months into the job I’m keeping it up and I always have something to wear. I also wear a couple of really nice printed home made dresses which I wouldn’t have worn to my old job.
    When out with colleagues last Friday night (most of who are 20 years younger) one told me that she really liked my style and they I always wore great clothes – it made me feel great!

  15. Suzanne

    I enjoyed reading this post. I’ve noticed that few people seem to make an effort when out doing “ordinary” things. Still, when I went to NYC this past weekend, the (non-tourist) women were dressed very smartly, liked they cared. As a prof, I’ve gotten comments from students who say they appreciate the effort I take to prepare for class, both in terms of the material and my appearance. They say it shows respect that I try to avoid the “traditional professor look”. For women, that often translates to frumpy. As an aside, when I first started, I wore suits all the time – and was criticized for being unapproachable. I’ve moved to separates and dresses and my approach-ability scores soared (correlated with getting more comfortable in the job, naturally). In the end, I prefer to be on the slightly overdressed side of the spectrum, as long as the colors/styles/fit work for me. When that happens, my confidence soars and I don’t mind standing out. As I enter my 5th decade (in a decidedly hot/humid climate), I’m reassessing what colors/styles/fit work for me. I’m glad I sew so that I may experiment.

  16. Ellen

    Great advice and insights as always! I shared this post with my son who (in two weeks!!) is about to start university in Washington DC, as your authoritative / approachable spectrum really resonates with me. It’s fun to be brainstorming with him about how to look professional, polished, and youthful for his internship (hopefully on Capital Hill where he will get to watch the midterms unfold). Coming from Seattle, where everyone dresses like they’re ready to hike a mountain at the drop of a hat, he’s going to have to adjust to the far more formal dress style of the Capital.

    PS. Where can those of us who missed the launch order a copy of your book??

  17. SweatyKnitter

    I like your suggestions re how to dress up/down nice basic pieces – basic pieces that are part of one’s capsule wardrobe you discuss in your book. That said, my eyes lit up when you mentioned a lace skirt. My daughter convinced me to buy a knee-length black skirt with a fluffy-ish black on black polka dotted chiffon overlay. I didn’t know what to do with it – what it pair it with etc. It hangs in my closet unworn … but not for long!

    • fabrickated

      Yes, SweatyKnitter, I do think you can combine those very special items you made, or are “evening dress” or occasion-wear, with casual items for a nice, original look. Personally I like a dressy skirt – otherwise they are perhaps too simple or plain – with a soft, hand knit, or smart T shirt. I imagine your black skirt will look fabulous with a more casual top. Or clogs!

  18. PsychicSewerKathleen

    When I first met my husband he declared that he didn’t, “really care about clothes”. Although he wore jeans and a Tee or shirt most of the time, I noticed his clothes always fit him great (right fit across the bottom, length of pants, arms long enough on shirt etc), so I knew I had a work in progress 🙂 Over a period of months I convinced him to take more care with his dressing. It wasn’t THAT hard b/c he even though he said he didn’t care, there was evidence already to the contrary.

    I said, “People judge you by your appearance whether you like it or not. If you want people to respond positively towards you, to feel comfortable with you, smile at you, chat with you, you must dress like you care about YOURSELF.” That’s just a fact of life. If you deny this reality YOU are the only one who will suffer and I wanted people to see this beautiful man as I did – to smile at him, to LIKE him because I knew he would, in response, start to like himself more and others more as well. His life would just keep getting better. Just yesterday (we’ve now been married for 28 yrs) he had me order $500 in clothes from a clothier we both like (eco/natural fibers, made in Canada etc) which he didn’t really need but do update some of his other wardrobe pieces. And he has no where special to go! He’s retired 🙂 but when he does go out, he does like to look good. I agree that too many are dressing sloppy – meaning the fit is poor, the fabric is worn and faded, un-pressed, hem half hanging off, missing buttons – the clothing looks sloppy on them. Or worse they look like they ARE wearing their PJ’s. As if they slept in it or left it in a heap by their bedside the night before and jumped into it before leaving the house. Come on!! That is just laziness.

    Didn’t their mothers teach them anything I wonder? Did their mothers care so little about them? Did their mothers give up the arguing and belly aching when they were teens and just let them do what they want? Oh well this is obviously a topic that sets me off on a tear 🙂 The bottom line is that if you LOOK like you could care less about the garments you are adorning yourself with, people will care less about YOU. You will suffer for that attitude.

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