Casual Dressing Over 40 – What it Is and Isn’t!

If you are over 40 you’ve probably noticed a huge shift over the years to more casual dressing. This is great because it has allowed us to dress in a way that is more relaxed, fun, and often more authentic to who we are. The only problem is, that it’s hard to know what to wear to dress casually because dress code definitions we all grew up with have disappeared.

What exactly is casual dressing and how do you dress casually without wandering into frumpy-ville?  What qualifies as casual women’s clothes over 40?
Here’s a look at what casual dressing means and some ideas for how to dress casually over 40.

Nailing Casual Dressing
The trick, I believe, to dressing casually over 40 is to dress is to wear casual pieces but keep your look classy.

Casual Doesn’t Mean Sloppy

Let’s be honest ladies, where once we could throw on a pair of jeans and a t-shirt and look fabulous when we reach a certain age, a little (or a lot!) more maintenance is required. If we’re not aware of this, or not willing to make a small effort, it can become easy to let ourselves go. Sometimes it sneaks up on us.

Running out to the grocery store? Sweatpants and an old pair of sneakers will do, right? Going to a movie with the hubby? The flip-flops and hoody you’ve been paddling around in the house all day are fine, right? Who’s going to see you in a darkened movie theatre anyhow?
While it sounds good in theory, this laissez-faire attitude is really just a slippery slope to Frumpville. (If you suspect you’re veering down this road, check out my article, 10 Sure Signs You Are Looking Frumpy After 40.)

Casual Does Not Mean Anything-Goes
Just so we’re clear about this, let me say it again and this time repeat after me: “Casual does not mean anything goes.” That’s particularly true when you’re over 40.
Just because you work in a casual office, or just because you’re invited to a casual dinner with friends, you still should give some thought to things like the formality of the venue, the weather, time of year, and especially your personal style and what kind of message you want to convey.
Just because you’re dressing casually, it doesn’t mean you shouldn’t look chic and classy.

Casual Does Not Mean Oversized, Baggy Clothes
Many women equate ‘casual’ with comfortable and then take it a step further and think ‘comfortable’ means loose and baggy. This is particularly true if you carry a little extra weight. (And after 40, who doesn’t? LOL)
I’m here to tell you that hiding under oversized clothes is not doing you any favors. In fact, it is probably making you look bigger, older, and matronly.
If you want to look modern, hip, and fresh, you’re much better off wearing fitted – not tight – casual clothes.

Casual Does Not Mean Living in Denim
I love jeans as much as the next gal but please know that denim is not your only casual outfit option. A cute pair of cotton chinos or a pretty knit dress are both examples of non-denim casual outfits. Mix it up a bit.

Casual Does Not Mean Juvenile
We sometimes tend to equate casual with the way kids dress. While jeans, t-shirts, and sneakers can and often do figure into the casual wardrobe of an over-40 woman, our version should be chicer than what most 14-year-olds are wearing. Sneakers are great but consider a cute slip-on version in a pretty shade of blush instead of the gym shoes your teenagers might wear.

Casual Does Not Mean Out-of-Touch with the Trends
Fashion is always evolving – even casual fashions – and if you intend to look ‘with-it’, modern and vibrant – what I like to call Age-Amazing – then you should keep up with it.
I’m not talking about being an overly-trendy fashion victim. Even just being aware of the trends and picking and choosing the ones that are right for your body, your lifestyle, and your personal style will go a long way in helping you tweak your chic.




Dear Deborah,

I am a 49-year-old woman who lives in the Northeast, and while I do dress up occasionally for dinner or evening out, 95% of the time I need to be dressed for getting in and out of a car, easily; for walking to and from places on a variety of sidewalks, and for a very casual everyday kind of life.

I’m finding myself at a perimenopausal standstill!  I have run out of creativity, and I am sliding down the slippery slope of jeans, colorful t-shirts, fleece, and turtlenecks.  Yuck!

I also have to wear comfortable shoes and boots to fit my aging feet.  How do women like myself, who live casual lifestyles full of activity and creativity, help themselves to feel, and look, attractive, year-round?


Thank you again, Lori


Casual dressing over 40

Hi Lori,

Your letter was so heartfelt and your question so common! Many women see their lifestyle change once they are past 40. Casual wear becomes something they wear a lot! Here are a few tips to get you started:

1. Do you have a Cute Faux Fur Vest?

Many women don’t think about buying a vest to dress up their casual wardrobe, but I bet if you do you will be hooked. faux fur vests are very popular at the moment and look great at any age.

Wear one with jeans, a shirt, and some really cute books, and you have a showstopper casual outfit.

2. Have you tried a Sweater Dress?

A sweater dress with some patterned tights and knee-high or over-the-knee boots works.  Don’t feel like you have to wear pants all time. Why not snuggle into a sweater dress and feel more feminine and a little funkier!

3. Try a Dash of Color

Lord knows we wear far too much black after 40 and it’s not always so flattering. All those years of black can really drag a woman down now that our skin is not as vibrant as it once was. Read all about ABD, and you will know what I’m talking about.  It’s time to put some color into your casual wardrobe. A coat is a great place to start.

4. Have you considered Leggings?

You say you want to be comfy. Stretchy leggings are the most comfortable thing you can wear. The key to looking good in them is to make sure they cover your bottom and more. Buy some thick black leggings and pair them with a long loose sweater like this. Add some jewelry and glam accessories, and you have a chic, casual look.

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21 thoughts on “Casual Dressing Over 40 – What it Is and Isn’t!

  1. I have a very hard time finding anything to wear and I’m in great shape yet I’m tall and most items are proportioned wrong for me. I wear leggings and a t-shirt or sweater, not the long kind it just doesn’t suit me. I often feel frumpy. Jeans forget about it they don’t fit properly either.

  2. My issue is that I don’t work outside the home and spend my time cleaning, working on the computer, homeschooling, bathing dogs, etc. so I tend to wear clothes that I don’t mind spilling some Comet on. Yet I also run errands during this time and go to the gym most days. I do tend to look nice when I make special plans, or for church, but during the day it’s hard when I do so many varied activities. So the bottom line is that I often look somewhat sloppy during the daytime.

  3. I’m a 44-year-old woman I have little confidence when buying clothes because I’m big at the top and smaller at the bottom, sometimes I really struggle to buy clothes I wear jeans all the time to work and going out I have dresses some are too short. I felt more comfortable wearing long maxi dresses.

  4. I love wearing jeans with lace-up front low-heel boots. a cashmere cowl neck sweater ( turtlenecks just don’t look good anymore) and a fur-lined vest… just so comfortable and chic.

  5. When wearing boots with jeans, is it better to tuck the jeans into the boots or leave them over? I don’t want to look like a teeny-bopper or lady-of-the-night. lol And, I’m terrified of wearing leggings with a long sweater–I thought that would be too young of a look for 43 (even though I can rock sweaters of all kinds).

  6. I’m a tad late to this thread, but I have to chime in. I’m 47, and I think that after 40 you should be aware of trends and follow the ones that suit your body type! This is something I have done since I was a working teen shopping for myself. If you like something that’s happening out there, and it fits you, give it a try. Otherwise, you will get stuck in a rut. I love the boots in jeans, scarves, cascading open sweaters, big purses, and cool belts thing that is happening now. I think these items suit women of all ages very well. And you can never miss a well-fitting pair of jeans, a t-shirt, a blazer, and a scarf. These are classic pieces that you can embellish with the latest accessories. I have been wearing some combo of jeans, top, blazer/sweater for 20 years! Typically with boots. I guess it’s my casual signature. : ).

    1. Hi Elle,
      Always great to get your comments! So glad you did chime in… and I am with you on liking the trend of long sweaters, boots, etc…
      You will have to send me a photo of yourself so I can share it with everyone!

  7. IN RESPONSE TO THE WONDERFUL ARTICLE “What about casual dressing after 40?”….
    I LOVE that vest. I have seen some similar ones in stores as Deb and JoJami replied to another inquiry but none near as chic as that one.
    If anyone can find one like that online please let us glam gals know! It is gorgeous! Thanks and Happy New Year to all the glam girls out there!

  8. Thank you for all the inspirational ideas and terrific feedback; I’m getting myself a lovely new vest this weekend. OUT with feelin’ bleak; IN with feeling’ CHIC!!!!


  9. Love your articles! As a woman in the UK working with women 35+ (I’m 45!) around confidence and living full lives I think clothing plays an important part on feeling more confident, be it leisure or business. I rarely follow trends and tend to wear what I love and what feels good.
    Must add that I love those snakeskin cowboy boots…

    Keep on inspiring & thank you!

  10. I have this same dilemma. As a retired lady over 50 my lifestyle has become much more casual . . . and yet I still want to be fabulous . . . not frumpy. I find it is a fine line in “casual attire”. Thanks for the tips (and I love the pictures) . . . they help a lot. Two questions . . . where do you find appropriate sweater dresses and can a petite lady wear the long cardigan? Love you . . . keep this great infomation coming our way.

  11. Oh yes, can I support the lady from Florida with questions about cas dressing!! We have about 3 days of winter and we stretch anything under blaring tropical as an excuse to wear boots, scarves etc etc as you feel like there are a few weeks a year you can feel stylish!! What do you do when it is hot hot hot… and really boxy elephant knees and batwing arms, let alone the lined decolletage in a skimpy top is far off stylish… a few cute combos like your advice for the Mid West lady would be great!!! Thanks gals! Jen

  12. So that’s how to wear a vest! I fell in love with a vest, but until now didn’t know how to combine to make it into a chic casual outfit. You have such a great fashion sense.

    1. Thanks Deborah! Sometimes fashion trends come up and we don’t know how to put it into our wardrobe and end up passing up a great trend that can be something new to add to our wardrobe and help us get out of a rut!
      One warning…we have noticed that some faux fur vests seem to “shed” a lot, so make sure you test it before you buy!

  13. You always have so many great ideas! I guess I need to ask a question about retired ladies that live in Florida! lol We see everything here…but I want to dress casual without looking bummy! heehee! Thanks for all of your great advice! ♥

  14. Great letter, I can sooo relate. Love the advice given. Where did the vest come from? Also which store carries those cute boots???

    1. Hi Jennell,
      These are just examples from vintage pieces and are easy to find in stores now. I hope to serve as inspiration!! Good luck and glad that you find the tips useful. I will try to put in actual pieces you can find next time! Thanks for writing in!

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