Style Essentials for Women Over 50

Style Essentials for Women Over 50
At 25,  it’s easy to shop for clothes and almost everything looks great on you. It becomes more of a challenge as we age and what was essential then, is no longer important. Here are a few style essentials I find important over 50.

Quality Handbag

A quality handbag in proportion to your body. I’m not saying designer/logo and I’m not saying expensive…I’m saying quality. What is a quality handbag? It has even stitching and there are no hanging threads. The seams lay flat with no puckers. The zipper works well and the hardware matches.  Knock off designer bags scream insecurity, so choose well.

Great haircut

A flattering haircut is a necessity over 50. Your hair texture and face shape changes as you age so your hairstyle needs to also. A flattering hairstyle needs to have movement. Helmet hair is fatal to looking stylish. Whether you choose to cover your gray or not is a personal choice and there is no wrong answer. Just be aware that if your hair and skin are the same tones, you may look washed out and need to intensify your make up.

Comfortable Shoes

Comfortable, quality flat shoes that can be worn all day. High heels are great for special occasions, but for everyday running around, nothing beats a classy pair of flats.  Ballet, loafer, flat boots, brogues or driving moccasins…this is where comfort and style collide for the woman over 50. Support is important so if your shoe of choice doesn’t have built-in support, add an insert that does.

Flattering Pants

Few women wear dresses all the time so a flattering pair of pants with a modern silhouette is essential. They could be in classic black, chocolate, charcoal or navy, and are a basic building block that allows you to feel chic when you put them on. They’re tailored to fit your body perfectly, (yes women pay for alterations too) and are in a quality fabric.  If you’re always in casual clothes, these pants could be in a Chino, cotton, twill or a dark jean. If your lifestyle calls for a more dressed up feel, wool or silk gabardine works well.

Great Coat

A coat you love. If you live in a mild climate as I do, it could simply be a trench coat and it needn’t be stuffy. Mine happens to be black with a zip out lining, but I’ve also added a pale green one with gathered sides and buttons up the outside of the sleeves. If you live in a 4 season climate, a quality wool coat plus a warmer weather alternative like suede is a nice choice.


Lovely Robe and Slippers

A lovely robe and slippers. These may only be seen by you but is important for how they make you feel. A ratty robe and scuffed slippers don’t make anyone feel stylish and you deserve better. I’m not saying marabou slippers… but if that’s your thing, go for it. This is to make you feel stylish. If others happen to see you in them, all the better.

Quality Watch

If you wear a watch it should reflect your personality and style. I’ve seen $5,000 watches that are glitz over style and look trashy.  I’ve also seen Timex watches that have a timeless look that speaks quality.  If your taste runs to a more modern aesthetic there are watches at reasonable prices that have clean lines and work well.

Little Black Dress

A classic always appropriate dress which can also be in chocolate, charcoal, navy or any neutral. The idea is to have a reliable, well-tailored dress that you can put on with confidence, knowing it fits your body (alterations key), flatters your coloring and can be dressed up or down.  Mine happens to be black, surprise!  I’ve worn it to a formal affair with a silk scarf and glittery jewelry as well as the local farmers market on a Saturday morning with flip-flops and a big straw hat.

Properly Fitted Bra

We’ve all heard the statistics of how many women are wearing the wrong size bra, and it’s true.  Your bra size changes as you age. You may need a little more support now so get professionally fitted regularly and always when your weight changes. The right size bra can take pounds off your silhouette and be much more comfortable.


Flattering Lipstick Shade

Dry-looking lips are aging but high-gloss goopy looking shine wicks up the lines around your mouth. Aim for gleam in a color that flatters your complexion. Opt for brighter rather than deeper shades which make your lips appear thinner than they are. Know that lipstick draws attention to your teeth so aim for paler colors if they’re not your best feature.

Modern Eye Wear

If you wear glasses every day, it’s the first thing people notice about you. Outdated styles and unflattering shapes can add years to your look and reduce your style quotient faster than anything. Sunglasses also make a huge impact, so a modern shape that flatters your bone structure helps you feel like a million bucks the moment you put them on.


What would you add to this list?

Thanks for reading and have a great day.

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  1. Susan Athanasakou
    September 29, 2014 / 5:21 pm

    I couldn’t agree more…on all points!
    Especially about flats!

  2. September 30, 2014 / 6:51 am

    I believe that flattering eyeglasses are worth every cent. I have two pair so that I can vary my look.

    • Jennifer
      September 30, 2014 / 7:56 pm

      I totally agree Joanne! They make such a great statement.

  3. Tamera Beardsley
    September 30, 2014 / 2:15 pm

    Wonderfully done my dear! What a treat to see your beautiful stylish self! I most agree with the robe and slippers … as I care as much about how I feel in clothes as what others may think. Dressing bad at home … is such a downer. I pay just as much attention to my lounge/home wear … as I do what I wear out.

    Love your list my dear!


    • Jennifer
      September 30, 2014 / 7:58 pm

      Thanks Tamera!! I couldn’t agree with you more about how “I feel in my clothes”! xo

    • Emnncp
      June 27, 2019 / 9:43 pm

      Agree! If we can’t love ourselves and throw in a bit of pampering – it will surely never emanate for others that are important I your life. 🙂

  4. September 30, 2014 / 5:26 pm

    So much great, common sense advice for us Ladies of a Certain Age. You look like the last word on “chic,” my dear friend. Lipstick, lipstick, lipstick —- it’s the easiest, quickest and most inexpensive way to brighten your face; but, it must be the right shade. As we get older, we need to go brighter not darker.

    xoxo, M-T

    • Jennifer
      September 30, 2014 / 8:00 pm

      Yes, yes, yes about brighter not darker. There’s something rather odd looking about a dark slash across an older woman’s mouth.
      Let’s talk soon.

  5. heather
    September 30, 2014 / 5:35 pm

    This is a great, thoughtful post. I agree with your suggestions–especially the handbag and bra. I also love the photo of you.

    • Jennifer
      September 30, 2014 / 8:00 pm

      Thanks Heather!! You’ve narrowed in on the two crucial ones.

  6. October 1, 2014 / 8:51 am

    I think YOU have ticked all the boxes…………..beautifully stated.XX

    • Jennifer
      October 1, 2014 / 9:26 pm

      Thank you Elizabeth! Can’t wait to hear all about Paris!!

  7. Marcia
    October 1, 2014 / 1:35 pm

    You look fabulous, Jennifer…LOVE the shoes.
    I agree with all your points, cannot stress lighter lipstick and makeup enough, and sadly I see too many women doing the very opposite. Could not agree more with the mark downs…oh dear. I actually don’t even like designer logo ridden anything.
    I’d add NO undergarment visible or detectable EVER at any age, groomed nails, dental hygiene, clean fresh fragrance even to the market … and gracefulness.
    PS- LOVE your new blog design, DARLING. 😉

    • Jennifer
      October 1, 2014 / 9:32 pm

      Wonderful additions Marsha!! Gracefulness is a favorite of mine!!
      I have a very talented women to thank for this blog!! Without her help I wouldn’t even have a blog anymore!! She is amazing. Her name is Lisette and you can find her at http://www.northernbellediaries.com.

  8. Jill
    October 2, 2014 / 8:39 pm

    I really enjoyed this post, nicely done! It helped me identify some things I could easily update/tweak. Your photo is lovely and thanks for putting this all together so concisely. You have such a relaxed and authentic writing style.

    • Jennifer
      October 2, 2014 / 10:33 pm

      Thank you Jill! Sometimes it’s the little tweaks that make all the difference.

  9. Jen
    October 7, 2014 / 2:40 pm

    Great list. I agree with it all (for those over 40 too!)

  10. Mary
    October 8, 2014 / 10:53 am

    Good suggestions all around. I have found a product that has done wonders for my eyes since I have reduced the amount of eye make up I wear. It is called Eyenvy (there are other brand names for this product) and I cannot say enough about how well this works. My eyelashes are now thick and lush requiring only a little mascara for dress up. Love it.

    • Jennifer
      October 8, 2014 / 3:59 pm

      I’ve never heard of it. I’ll have to check into it. Thanks

  11. Jen
    October 10, 2014 / 6:04 pm

    Get the hair color right, you are not 30 anymore!
    I see too many women that are still dying thier hair too far in one direction (light or dark). Getting rid of all grey can actually be aging! Someone of “our” age isn’t supposed to have absolutely no grey hair or hair of all one uniform color.

    I know it is hard, but consider being yourself now insteado of yourself from back in your 30’s!

    • Jennifer
      October 10, 2014 / 10:06 pm

      Hair color is a tough one. My color is natural but washing me out. There’s so much silver in the blonde it now looks highlighted. I’m thinking of adding lowlights but haven’t totally decided. Who would want to be in their 30’s again? Not me. This is the best time.

  12. October 11, 2014 / 8:13 am

    Hi Jennifer! I love your style here ~ so chic and sophisticated! The LBD, the sunglasses, the pumps.. everything works perfectly. I believe a woman can be pretty at any age, it’s just takes a bit of tweaking;) Hair color is SO tough because with the increased GREY we have to deal with dryness and “coloring” is more challenging.

    Have a wonderful weekend! xxleslie

  13. Patty
    October 12, 2014 / 2:44 pm

    Push ups and triceps dips.

    • Jennifer
      October 13, 2014 / 12:54 am

      They are tough, but oh so beneficial. It’s making myself do them that is the problem.

  14. Nancy C
    October 13, 2014 / 4:08 am

    Love your list! As I approach 60, I find the lower quantity/higher quality principle is pertinent to every area of my life.

    I would add two things (two since you included makeup):

    1) The RIGHT white top. My fave is a cross-front, 3/4 sleeve in an opaque, damask-patterned good-quality polyester. Classy, versatile, shapely without being too revealing, and wearable almost year-round (a little heavy for mid-summer in the South).
    It goes with everything – clothing and accessories – can be dressed up or down, packs well, hand washes easily & dries quickly… It’s a neutral and a wardrobe staple for me.

    2) The RIGHT mascara. One that isn’t too thick, isn’t waterproof, isn’t “volumizing” or “lengthening”, doesn’t flake, doesn’t irritate my eyes, and is the right color (brown or brown-black for me). If I had to pick lipstick vs. mascara (and I hope I never do!), it would be mascara for me.

    Cheers to all of us who are aging gracefully and beautifully!

    • Jennifer
      October 13, 2014 / 2:29 pm

      Great tips Nancy. It would be mascara for me too!! I always believe in highlighting our best facial feature, and for me as I age…it’s definitely my eyes.

    • Carol
      May 25, 2015 / 11:41 pm

      Ok, that’s exactly the kind if mascara I’m looking for. What brand(s) have you found?

      • LauraBP
        July 11, 2019 / 3:44 pm

        Basic Maybelline in the pink-and-green tube. There are good reasons why it has stood the test of time!

  15. October 13, 2014 / 9:58 am

    Jennifer you look fabulous! I love your chic, classic style, I have a closet full of black and white and it actually drives me crazy. I don’t even notice myself buying these colors over and over, maybe I’m just an incredibly boring person. Thanks for these tips, I agree with them all except the robe. Not with my hot flashes hahaha can’t do too many layers anymore. 🙂

    • Jennifer
      October 13, 2014 / 2:31 pm

      I hear you about the hot flashes Leslie and am in the same camp. Isn’t this fun? I’m trying to branch out from my neutral palette but always go back to my basic black!

  16. November 28, 2014 / 4:26 pm

    Love this post and the photo, think your hair looks fabulous. So agree about a bag being proportionate, I just cannot do the big bags. Our essential here is cardigans or things to stick over as its just never warm enough to wear sleeveless.

    • Jennifer
      December 1, 2014 / 6:35 am

      Thanks Jody!! Huge bags overwhelm me because I’m short…it took many trips to the chiropractor to convince me of that:)

  17. diana thompkins
    December 29, 2014 / 8:13 am

    how about nail care and color to make hands look a little younger.

    • Jennifer
      December 30, 2014 / 8:48 pm

      Agreed! Even a clear coat of polish, makes hand look cared for!!

  18. December 29, 2014 / 8:21 am

    Great list! I would add an essential that I always suggest my clients over fifty have in their closets, and that is a jacket or blazer or two. A jacket pulls any outfit together and gives your body a slimmer silhouette. Jackets or blazers can be made of cotton, wool, knit for a stretchy fit, leather, denim, crepe, linen, tweed, etc. There are a variety of colors and fabrics that take a put-together woman from daytime to nighttime.

    • Jennifer
      December 30, 2014 / 8:46 pm

      Great tip Linda! Jackets are a great staple, depending on the women’s style. You’re so right about it pulling an outfit together. Almost like the icing in a cake!

  19. Dawn
    December 29, 2014 / 9:41 am

    I agree with your suggestions especially the flat shoes. However, I think fewer people are wearing watches anymore because they carry cell phones that give them the time.

    • Jennifer
      December 30, 2014 / 8:42 pm

      Very true, but I’m one of those strange people who really needs to “see” the hands of the watch or clock to internalize the time. Strange but true. I detest digital clocks. I guess I’m just old fashioned.

  20. Robyn Williams
    December 30, 2014 / 11:09 am

    All very good points, BUT, most important to most any outfit would be some body shapewear, like Spanx, especially when wearing that LBD, and shapewear pieces for any areas that are specific to you, tummy, back fat, saddlebags, ekkk!

    • Jennifer
      December 30, 2014 / 8:24 pm

      I agree shape-wear can make the world of difference. Some women will just not endure them so dressing around the need for them is an alternative.

  21. June 11, 2015 / 9:06 am

    Every one of your posts suggests something I only thought was important to me: it was lovely robe this time. Because, yes, it does make you feel elegant.

  22. June 11, 2015 / 2:35 pm

    A watch, really? They are nice, but I use my iPhone so much, it’s always there for the time. Grrr. I just can’t wear lipstick, and I would really like to. Too many lip lines, I’ve tried everything. Good list though.


    • Jennifer
      June 17, 2015 / 11:42 pm

      Many of us use our phone for the time. And for many of us our watch is a statement accessory that holds memories. For me I enjoy actually seeing the hands. Old fashioned perhaps. But I am 59.

      • Carol LaRochelle
        March 23, 2016 / 1:50 pm

        I agree, still wear a watch every day even though I use my I phone for everything. Would be lost without it!

  23. June 12, 2015 / 6:11 am

    What I love most about your round up of tips here Jennifer is that they ooze simplicity. Brings to mind this quote “Simplicity is the ultimate sophistication.” – Leonardo Da Vinci

  24. June 18, 2015 / 8:06 am

    Great style advice, Jennifer! I love that you included robes. Too often we schlep around the house in things we’d be embarrassed to be seen in.

  25. Elizabeth Tierney
    September 13, 2015 / 9:31 pm

    After reading all the comments about getting the time from one’s phone, I feel a burning need to go buy a classic watch (with a tiny bit of sparkle)!

  26. Nicki
    July 29, 2019 / 4:48 am

    Fantastic post Jennifer. The robe and slippers did it for me. How about adding robes and slippers to the blog sometime?
    Have a great week.

    • Pat Dickerson
      January 5, 2020 / 7:54 am

      I would like to see a few of the robes and slippers you are referring to.

  27. MaryBeth
    September 20, 2019 / 4:35 pm

    I am new to your site and am enjoying it so much. My big thing is finding the right panties a wide waist band they seems to be hard to find but are worth the search no more rolling over for those of us who don’t have much of a waist.

  28. Sandie
    February 10, 2020 / 4:55 am

    Looked every where for help with cruising I’ve done a few and learned what’s not comfy. I’m 75 and these tips are spot on , the old adage LESS IS MORE is brilliant thanks for helping us graceful 😂 ladies out

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