What to Wear to Look Smart in a Casual Environment


what to wear in a casual environment

Paola wrote to me an asked:

I’ve been reading your blog for a little while now – I really enjoy your writing and your tips.

I have a suggestion for a post about a style question that leaves me a bit flummoxed. I am a mother of two kids, live in a rural area on small acreage and work as a relief primary school teacher. My lifestyle is casual, yet I have problems doing “casual, but professional” look for school, while not being overdressed when compared with the people I associate with. A conundrum I haven’t yet got my head around. Any tips?

My Top 10 Tips to Looking Smart in a Casual Environment

what to wear so you are looking smart in a casual environment
  1. One of the tips I’d give is not to spend time worrying what other people are thinking.  If you want to dress up nicer than the average for your town, no worry about what anyone else thinks!
  2. So if you tend to wear jeans choose a dark wash with no distressing, as this is dressier than lighter washes.
  3. If the weather isn’t too hot, try a pair of boots over you jeans and a tunic top with a low, hip slung belt.
  4. Tops that have a little structure, rather than just wearing knits will make you look smarter, even when teamed with jeans.  Can you throw a casual style jacket over your t-shirt?
  5. Adding a necklace to a plain t-shirt will dress it up, even a skirt and t-shirt with a denim jacket creates a more polished look.
  6. Choose flat shoes that aren’t too chunky, this will make your look more elegant.
  7. You can still look stylish with kids wearing t-shirts and jeans, adding accessories, from belts to jewellery, and keeping your shoes more refined will help to add some extra style.
  8. Think about fabrics being very easy – wash and wear like drill or denim
  9. add a cotton or wool scarf rather than dainty necklaces
  10. Knits are great and look relaxed and comfortable yet can still be smart with the addition of an accessory or funky casual jacket
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  • This is always my dilemma too. I am seeing more clients these days directly and feel the need to look more professional, but still need to be casual and I need to wear pants for the most part. Summer is the hardest. It is hot and humid so too many layers is out. I do not wear what you guys call trainers I think, we call them sneakers, running shoes, etc. I go for a sport shoe or flat and right now a comfortable sandal. I usually have to walk a property with the client so flats are essential. I always wear some sort of necklace and earrings that are not too light, and if it's a cooler time of year I will layer the necklaces. I have a knit jacket with lapels that is more structured than the usual cardigan, but I don't have the summer equivalent. I don't usually wear jeans this time of year but nice linen and cotton trousers instead. I wear knit tops that are not just t shirts usually. I am planning some more structured blouses in cotton too.
    I was thinking a short sleeved jacket or vest might work, but honestly I get really hot for layers!
    I too live in a small town, though I wouldn't classify it as rural, this close to NYC! I am usually more dressed than most people, but as you say, who cares?!

  • To me the outfit on the very left doesn't look professional at all (tights!). The middle and right look good.

    I'd recommend neutral cotton pants (gray, brown, black, beige – could be clean khakis or jeans) and a shirt *with a collar*. The shirt could be worn over a tank top or not; it doesn't have to be stiff, but it must have a collar to look 'pro'.

    What do other teachers wear?

    – tall & slim anon

  • I wonder if an easy way to look well dressed but not "stick out" is to wear the same sort of clothing others wear, but a nicer, better fitting variety. For instance in summer shorts are helpful for me to wear – but I got some pinstripe black ones. If everyone wears T-shirts, wear one with some embellishments and in a style that is flattering.

    This is of course only if you are not going to be as brave as Imogen recommends and just not worry about the others!

  • Ditto not worrying about what others think!! I'm still a firm believer that dressing a little nicer gets you treated a little nicer. With more respect. Especially love that middle outfit and red flats!!

  • I love your blog, Imogen!

    I have the same problem. Here in Germany in many towns women always wear sneakers, jeans and t-shirt and don't use make-up.
    When I first moved here I wore the usual, for example in the summer a skirt, some pretty ballet flats and a shirt with ruffles/a collar.
    Also a little blush,lipstick and mascara.

    I noticed that people stare at me all the time, especially the other women.

    I didn't think about it a lot but then a friend told me, that I was considered to be not a respectable woman because of my clothes and make-up. They felt I was "dressing up to get men attention".
    (I was not, the skirt was knee lenght, the shirt didn't show cleavege and the shoes were flat.)

    As the years went by I just started to wear what they wear, always jeans and t-shirt but I couldn't go for the sneakers. I hated them. So I still wear my sandals.

    I have to admit that I don't feel very good with this. People still talk about me (although not that much) and I felt better in my clothing before… but I just don't dare going back. It's the staring at me all the time – I just can't handle this.

    I wish I could be as brave as you say, Imogen.

  • Tall and Slim Anon – they're not leggings but slim jeans on the left.

    Some great ideas coming through here!

  • Anonymous: Be your beautiful, well-dressed self! Let them look, they might learn something. As Marianne Williamson says, "Your playing small does not serve the world. There is nothing enlightened about shrinking so that other people won't feel insecure around you".

    Reject a culture of collusion that holds people down.

    I agree with Nancy K,, would add, get a manicure and pedicure, DIY is fine.

    Handbag: not a saggy, fabric tote given free by a store or conference. Does not have to be status, but leather or nice fabric.


  • The ladies from academichic.com have great style – looking professional in all manner of lovely casual outfits, and not a suit to be seen 🙂
    In my workplace we have to be professional but only the senior staff and admin wear suits…it's a dilemma when you are looked at strangely for over- or under-dressing when there's such a fine line.
    Accessories and nice shoes are a good way to dress up an otherwise casual outfit without feeling too overdone.
    Dr Mel.

  • My mom is a kindergarten teacher. She really gets a lot of use out of tall boots with her pants tucked in. They instantly make even the sloppiest outfit look a bit more pulled together. Her school doesn't allow denim, so corduroys in neutral colors are a standby. Fitted sweaters in bright colors or with nice details are handy as well, because they are less restricting than jackets. When I'm helping her out, I like knee-length jersey dresses with 3/4 sleeves for ease of movement, bright opaque tights and my hair tied back with a silk scarf. Flats are a must, and a cute WARM jacket for playground duty.
    P.S. I have to agree w/ Anonymous #1, the outfit on the far left would not cut it for my mom. While another tunic and jeans might work, I'm afraid that particular combination (unrelieved dark colors, very body-conscious bottoms, and a top that is slouchy and looks like it would constantly need re-adjustment) doesn't send a great message to parents. It's probably a better outfit for an assistant or volunteer in the classroom, not for the head teacher.

  • Sorry it's taken me a while to catch up with the answers to my question. Thanks to you Imogen for your post, and to all the commenters for giving me lots of food for thought.

  • Must admit, second time I read this article, but first time a read the comments below. 🙂 I really recognize the problem as I live at the countryside on a farm. I am a 40+ staying at home mom who wants to look stylish everyday. I find it hard to find the perfect balance between ‘not being overdressed’ and ‘not looking sloppy’. I like to dress up but very quickly I feel overdressed and when I dress a bit down, in my eyes it’s boring, very common and maybe even frumpy…… I do use accessories but that is not the issue..

  • This is a problem I have with working in a lab environment. It’s certainly not a place to wear your best business suit but I’ve seen people come in wearing pajama pants and Uggs! I mean come on you could at least put on pants right?

    I long since stopped caring what people think about how I dress at work. I’ve found that it benefits me to dress more polished because it makes me stand out which results in people remembering me better. It’s a lot easier to get a favor if people can put a face to a name.

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