Do You Feel Frumpy?

Believe it or not, some still think that being a grandmother is synonymous with looking frumpy. That passing 50 or 60 means turning the style corner to dowdy and getting on the fast train to unstylish. I don’t know about you, but turning 60 wasn’t even a small speed bump for me, my desire to dress stylishly didn’t change and I don’t feel frumpy.
Jennifer Connolly of A Well Styled Life wearing a column of black with checked duster

I have pictures of my grandmother at 60, and her style looks very different than mine. She wore her gray hair in a bun every day, with no makeup, housedresses, and clumpy looking shoes. So did all of her friends because that’s what was in style. She didn’t feel frumpy because she took time with her appearance and felt confident the way she looked.Jennifer Connolly of A Well Styled Life wearing Everlane sweater over checked pants and snakeskin ankle boots

I am a proud Granny myself. It’s important to me that I look current and wear what I feel is appropriate…for me. Does that mean I listen to rules others have made up about what I shouldn’t wear because of my age? Nope! I use my internal radar to guide me.Jennifer Connolly of A Well Styled Life wear cropped wide leg crop pants with denim jacket

I’ve had a few readers comment that I’m too old to wear a particular look. My response is always, “according to whom?”. I’ve also been told the outfit I was wearing looked frumpy. I respectfully disagreed each time. I felt confident wearing those outfits, and what’s important is how I feel.Jennifer Connolly of A Well Styled Life wearing leopard blouse with denim pants and black sweater duster

Many women our age are interested in remaining stylish and are finding advice online. Since print magazines have long abandoned our demographic, we use blogs, Pinterest, and Instagram to fill that gap. They provide style ideas, inspiration, instruction, and encouragement to keep us informed,White shirt tied at waist and skinny jeans on Jennifer Connolly of A Well Styled Life

We need to follow our internal guidance about what feels right on us. What looks frumpy to me, may not look or feel frumpy to you. Frumpy is not always about fashion. It’s often a state of mind and a nasty feeling that robs us of our confidence.

Have you ever felt frumpy…what did you do about it?

Thanks for reading, and remember to wear what makes you feel confident.

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  1. Lisa DeLille Bolton
    July 1, 2020 / 6:22 am


    “We need to follow our internal guidance about what feels right on us. What looks frumpy to me, may not look or feel frumpy to you. Frumpy is not always about fashion. It’s often a state of mind and a nasty feeling that robs us of our confidence.”

    Women all ages are always struggling to be approved and judged attractive/pretty/hott etc as compared with advertising’s ideal of the 23yo barbie-like beauty with long blonde hair and disproportionately huge breasts — vs — the wildly divergent standards of beauty as created by God and found in different global cultures and reverence by artists in galleries and museums.

    Not to mention Inner beauty shining through.

    Thank you for making it about feeling beautiful for ourselves rather than the hopeless dance of pleasing others with our “look” — love this empowering message!!

  2. Sheila-Merle Johnson
    November 19, 2019 / 1:54 am

    Brava! What a great post! I dress to please myself and if there are some days I feel ordinary, I may dres a little frumpily (word?). mostly I feel special and dress to fit any of my style words. What are the white and black snakeskin boots you are wearing? Are they still available? I would love to know.

  3. Kathy
    November 18, 2019 / 5:44 pm

    I can feel frumpy with my shoes. I noticed you have cute shoes in all the pictures.
    Well fitting clothes, a good haircut, shoes and updated makeup call all help beat the “frumpies”

    • November 18, 2019 / 6:44 pm

      I struggle with shoes because I have very painful feet. I may have to spend more for my shoes but I keep them for many years.

  4. Téa
    November 18, 2019 / 1:08 pm

    I think all of the comments are so excellent! I feel my good posture keeps me from veering towards “frumpdom” – even though I do carry 40 extra pounds and have a large bust and and jiggly bits. I do exercises daily to keep my core strong and avoid lower back issues, and try to remember to stand tall. Another thing that helps me is the advice of Marie Kondo, I do not “downgrade clothes that don’t thrill me to “loungewear”…I put them to Good Will or the like. I have 2 beautiful and cozy winter “lounge” outfits, and when they no longer “spark joy”, they, too will be donated. MK’s philosophy, “what you wear in the house does impact (your) self-image” really resonates with me…when I look good, I feel good – even if I’m just home watching “The Crown!”

    • November 18, 2019 / 6:46 pm

      That’s wonderful advice!! I think we’d all be better off donating more clothes.

  5. Jane
    November 18, 2019 / 7:53 am

    Thank you for the always interesting blog as well as your fashion insights. My hair makes me feel frumpy. It was large, thick and perfect for the 80s. But now, it has thinned out so much on top I feel like Larry from the 3 stooges! No matter what I do, scalp shows through. So just try to compensate with decent, contemporary clothes, shoes and handbags. Just can’t seem to find the right style or something.

    • November 18, 2019 / 6:51 pm

      Have you looked into a topper? They’re for exactly what you describe.

  6. Janet
    November 17, 2019 / 6:41 pm

    I couldn’t agree more, Jennifer and that’s why I follow you! You are an inspiration! I feel frumpy when I’m tired and don’t make an effort. I also think extra weight and a pear shape don’t help in achieving a flattering look. I have noticed that most (all??) Bloggers don’t appear to be pear shaped. I don’t think that is a coincidence.

    • Eileen
      November 18, 2019 / 6:56 am

      Hi Janet, I am a pear shape, and I noticed that also, not many pear shaped women bloggers. I’m not sure, but, I think Lady of Style ( German), or Chic at any age ( British) may be pears? I do find I need more adjustments to my clothes, and right off the rack is difficult. I do think having broad shoulders , a chest, and a straight shape, must be closer to the norm, my friend who is built like this has a much easier time. Any ideas anyone?

      • Susan Gowan
        November 18, 2019 / 10:08 am

        This is a great topic, Jenn! As a grandmother of four. i just turned 69 a few weeks ago and feel frumpiness is purely a state of mind. You can wear comfortable clothes and be stylish at the same time. Confidence is a factor in looking andfeeling youthful. Never wanted to beanold person trying to look young but I dress theway I like for the most part. Would like less belly like most gals but there are ways to conceal. And exercise like walking around a large block or swimming at a salt pool
        regularly also helps my confidence. You truly are as young as you feel. Some days I feel 26; a few days more like 75 but not often .

      • November 18, 2019 / 6:49 pm

        That’s a great way to look at it!!

  7. Doris Harding
    November 17, 2019 / 6:11 pm

    Thank you, thank you Jennifer for this post. You always look great, but at age 76 years and with chronic health problems, Yes, I often feel “frumpy”…clothes shopping is tiresome and availability of suitable affordable fashions can be problematic, not to mention difficulty of traversing back and forth to the tailor to have alterations made. I love fashion and love reading your blog-advice…Please continue!!

    • November 17, 2019 / 7:00 pm

      Thanks for being here Doris! Keep on keeping on

  8. Eve
    November 17, 2019 / 5:50 pm

    Comfortable and appropriate for the ocassion even if the ocassion is hanging around home is my style as I get older. I don’t teeter sround on heels or wear fitted clothing when I really feel better in a looser fit now. I love the casual chic of your clothes and if I manage to pull off anywhere near the way you look, I feel good.

  9. Elaine D
    November 17, 2019 / 2:25 pm

    You never look frumpy Jennifer, you always look stylish but never ‘mutton dressed as lamb’ ( as we say in the UK) either.

  10. Mary Lee Robinson
    November 17, 2019 / 1:54 pm

    Excellent point about fashion mags that abandoned us. And you are right on point, I turn to Pinterest, Instagram, and a few (very few) catalogs to stay on trend appropriately. Great post! Thank you.
    BTW, I often re-pin your pins for my followers.

  11. Kathleen O'Brien
    November 17, 2019 / 1:46 pm

    Hi I’m just turned 65 and I do feel frumpy some days. But I’m working on not feeling like that most days. I have jobs that get me outta my house most days and long evenings. I’ve been embracing my grey hair and have highlighted it to look more gray, sort of like the youngsters are doing coloring their hair grey! I try to dress my age – in that I don’t wear the short stuff anymore, too tight things, too many ruffles and “characters” across the chest and rear – that sort of thing. I dress appropriate for events and even have been known to wear jeans! I searched until I found some that fit. I do wear makeup, not every day but when going out to church and work. I don’t go overboard, but just try to be nice looking and presentable. I’m not as fit as I’d like or have time to be, but dress for the body I have and the events I go to. I do care about how others view me but don’t care if they don’t like everything I wear – I dress to feel good and express myself. I love reading your blog and love your sense of fashion and style.

  12. jmp
    November 17, 2019 / 1:34 pm

    So well said! And I couldn’t agree more that magazines etc. have deserted the over 50/60 crowd. Thank goodness for your blog.

  13. Suzanne Nicolson
    November 17, 2019 / 1:26 pm

    My mother and two Aunts were very stylish dressers through out their lives. I felt frumpy beside them, even in my 40s.. sadly, the first sign of dementia for the three of them was a significant deterioration into frumpy dressing. they lost their whole identity and I really missed those stylish ladies. I really miss the inspiration to be your best self that these wonderful women gave me. I really value this site as it has helped fill that gap in my life. thank you.

    • Alison
      January 1, 2021 / 7:35 am

      That is interesting that you say that. My mom never went anywhere without her hair-styled, makeup on and dressed to the nines. Even as a child I remember this- it drove me crazy- haha. She never wore a pair of jeans in her life- again crazy to me. I knew her mind was going when this all changed. By the end of her life, she dressed nothing like the mother I knew. It was very sad to me. In my mind, I have my memories of how I want to remember my mom- and she is always dressed to impress. 😀

  14. Julie Anne
    November 17, 2019 / 12:09 pm

    get up and decide that it doesn’t matter what you look like because you’re not going anywhere today.

    Shower and put on at least a minimal amount of makeup to show you care. For me, that’s tinted sunscreen, eyebrows, blush, and a lip moisturizer. It took me a long time to realize the old adage of when you look good, you feel good and when you feel good you look great. You can be your own worst enemy.

    I’ll be wearing my work clothes for home; if I run to the store, it’s a quick change of shirt and some lipstick. No point arriving and feeling frumpy when others have put a little or lot of effort in to it.

  15. Lea
    November 17, 2019 / 11:38 am

    What makes me feel frumpy is: clothes that are too big, not the intentionally oversized trapeze shirt or harem pants… those are in my closet and I love wearing them. I mean jeans that are a size too big, tops that are too big and cover up too much of me, tunics… any clothing that hides me. And dainty jewelry. But, that’s subjective to my sense of fashion and body style. Someone else may feel good in what makes me shrivel up. And vice versa 🙂

    • Peggy
      November 17, 2019 / 3:53 pm

      Ditto clothes that are too big. Take them to a tailor. If they have stretch in the fabric, buy one size smaller. Comfort does not equal clothes that are too big.

  16. Katrina
    November 17, 2019 / 11:33 am

    Love the PJ day comment! We call it a Mental Health Day! Anything I own that is frumpy has been relegated to the “yard work, painting” pile. When I wear those, it’s because I have work gloves on and actually am WORKING. Everything else had better make me feel classy & confident or it goes into the “donate” pile. I so enjoy your posts, dear Jennifer. I think we may live near each other. Coffee sometime????

  17. Pam
    November 17, 2019 / 11:22 am

    I am 66 and still want to look as good as I can. I am inspired by your looks, your picks and your suggestions. Because of your blog, I have several new outfits for fall that I enjoy wearing and feel good in – thanks, Jennifer!

    • November 17, 2019 / 6:59 pm

      I’m so happy to hear this Pam! Thank you

  18. Lydia
    November 17, 2019 / 10:37 am

    I am six months shy of my 80th. I never feel frumpy, dowdy or otherwise. Love smart (not fast fashion) garments, boots, jeans, sneakers, sometimes a sweatshirt w/accessories. Hair is silver w/highlights – could stand to lose a few ###, but maybe and maybe not! Love your advice – my body type is figure eight – though the waist seems to have disappeared! Love every day and make the best of it. As a disclaimer: sometimes I have a PJ day. Need this once in a while.

    • November 17, 2019 / 6:58 pm

      Way to go Lydia! Your confidence jumps off this page. Thanks for sharing

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