Mimimum Effort, Maximum Style – Casual Dressing Made Easy

Casual Dressing for over 40 womenDear Deborah ,

I am a 49-year-old woman who lives in the Northeast, and while I do dress up occasionally for a 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 ourselves to feel, and look, attractive, year round?


Thank you again,


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. Vests like this leather and faux fur one are very popular at the moment and look great at any age.

Wear one with jeans, a shirt and some real 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 more funky!

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.

What to wear with leggings


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  1. 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.

  2. I’m a 44 year old woman i have little confidence when buying clothes, because im 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.

  3. I love wearing jeans with lace up the 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.

  4. jusbeachin says:

    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).

  5. What can i layer over a black flowy tunic tank, it’s very cute with jeans but i don’t want my arms to show.

  6. mind blowing idea’s. i think soo after 40 you become in routine dresses.you dont like to change your life life.but your idea’s are inspirational.

  7. 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 absolutely 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 sweater, big purse, cool belts thing that is happening now. I think these items suit women of all ages very well. And you can never miss with a well-fitting pair of jeans, t-shirt, blazer and 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. : ).

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

  8. 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!

  9. Lisa Abend says:

    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!!!!


  10. 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!

  11. Bonnie McManus says:

    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.

  12. 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

  13. 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.

    • 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!

  14. 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! ♥

  15. Jennell Thornton says:

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

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