Dressing to Please Yourself

Dressing to Please Yourself

Within seconds of seeing us, people make assumptions about our financial situation, sense of humor, education level, socioeconomic status, happiness level etc. We all know that’s true but at our age and in this era of wearing what we like, how many of you feel pressure to conform? Do you let other’s perceptions affect your fashion choices? Even in a subtle way? Do you dress to please yourself without concern about how you are seen?

I asked a question on my Facebook page, (do you follow me there?) earlier this week which sparked a lively discussion. I asked, “What does frumpy look like to you?” Notice I said look like to you. Not feel like.

Women mentioned brands and types of garments they think look frumpy. There were lots of generalities but few made the connection personal. Some mentioned things which other women defended as not frumpy.

It’s not surprising to read how vehemently women feel about looking frumpy. It’s not a look many women would intentionally put together. There was no consensus and opinions varied widely which demonstrates why frumpy is one of those things that’s hard to describe, but you certainly know it when you see it.

If dressing and feeling frumpy is the terminal look no woman wants for herself, (and that certainly appears to be the case) what would or could cause you to feel frumpy?

Could another woman style a garment you think of as frumpy and make it look chic?

What role does your confidence play in appearing frumpy to others?

Does your size play a role in whether you feel or appear frumpy?

If you don’t feel frumpy, do you care if others see you as frumpy?


Please share your thoughts. Be kind and thoughtful in your comments because this is a sensitive topic for many of us.








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  1. March 30, 2019 / 9:01 am

    I’ve read many of the comments above, and while most resonate with me with regards to how I define a “frumpy” appearance, I think it is really all about the rest of the picture. Do you smile? Do you walk with confidence and head held high? Are you physically clean? Is your hair brushed? Have you made any attempt at respecting yourself with how you’ve dressed? You can take the same baggy sweatshirt and put it on two different people — it’s frumpy on one and not the other. The frumpy one has most likely NOT “put on” good character as well as basic pride in her general appearance.

  2. March 21, 2019 / 11:41 am

    We never do know what struggles another woman is dealing with so should never judge. Sadly, it’s human nature to judge. I think many here are pointing out what appears frumpy to them. What matters most, is how we feel.

  3. Margot
    March 21, 2019 / 4:05 am

    I can’t tell you how horrified I am reading the comments here. They sound so judgmental and not very empathetic. I do try to dress neatly and attractively because it does my mind and psyche good but my appearance doesn’t tell the whole story. Some of us are self conscious about physical features (my neck that I seem to have inherited from my father) and struggle with ways to dress in ways that make us comfortable with those features. Daily I deal with chronic disease and am often achy and stiff so I mostly dress for comfort and convenience. Most days no one sees me – I’m at home by myself except for the hour or two my husband and son are home in the evenings. I tend to not wear scarves or necklaces because they get in my way in my daily activities. I mostly don’t wear makeup. My skin is fragile and makeup irritates it. I use prescription eye drops to deal with a condition. I don’t wear eye makeup as liner and shadow irritate my eyes. I don’t wear mascara because the eye drops cause even waterproof mascara to run. I do get my lashes dyed and my brows waxed in an effort to be at least well groomed but my lashes are thin compared to my younger days. The daily things I deal with aren’t apparent when you look at me but I’m sure many of you would consider me to be frumpy. My situation has lead me to be a little slower to judge because you never know what the other person is dealing with.

  4. Janey
    March 21, 2019 / 12:52 am

    I have seen more frumpy men than women. Frumpy to means not caring, stained and crumpled clothes. My friend (who I adore and don’t care what she looks like) always looks frumpy and doesn’t realise it. Her clothes are way too big and baggy because she thinks that hides the fat, she loves wearing tatty turtle neck tops under short sleeved shirts because she thinks it hides her red menopausal neck.

  5. Heidi Davis
    March 20, 2019 / 6:01 pm

    I think it’s all about how YOU feel. If you dress appropriately for the occasion and are in clothes you love, you’ll feel great. How can you be frumpy if you feel great about yourself??

  6. Su
    March 20, 2019 / 5:31 pm

    How interesting. From the comments above frumpy in the U.S. seems to belong in the same family as sloppy and unpolished. In the U.K. it means dowdy and old-fashioned (whether smart or casual.) I’ve learned something today!

  7. Penny L. Luckenbaugh
    March 20, 2019 / 3:19 pm

    My mother was a fashionista before there was that word. She always told me that being appropriately dressed and well groomed was a sign of respect for others. It showed that you thought they were worth the effort. I was probably the only teenager in town whose mother asked them to put on makeup!
    I am retired from a job that often required suits and heels. I seldom wear either now, but only an extreme emergency , i.e. at trip to the ER, excuses me from putting on makeup and styling my hair before leaving the house.
    I find I feel better about life in general if I am looking neat and well put together. And a quick spray of Opium always cheers me up. You can be comfortable and still look tidy. Some people think casual means sloppy. To me, sloppy means lazy.
    What do I think is frumpy? Pajama bottoms worn to the grocery store, work-out gear except at the gym, flip flops away from the beach, going out in rollers , chipped nail polish and clothes that obviously belong in the laundry.Keep it clean!

  8. Kay
    March 20, 2019 / 2:41 pm

    Frumpy is my late aunt in her printed house dress that she’d cinched with a plastic belt under her chunky knit cardigan sweater with snags on the elbows, finished off with her nude knee high trouser socks and her pink, dirty bedroom slippers. However, she loved everyone, did endless volunteer work for the church, and she made delicious fudge. I dress much better than she ever did, but she’s still my role model. When I see a “frumpy old lady” somewhere, it always brings back thoughts of her. How I miss her.

  9. Connie
    March 20, 2019 / 2:30 pm

    Funny, I just flew home…Frumpy was everywhere and very common on the passengers. So I see frumpy as skintight leggings that look like pantyhose with a top that doesn’t cover the bum, crewneck tee shirts with sayings, flip flops, velour running suits, sweatpants, and jersey shiny pants and shorts with side stripes and clunky athletic shoes. I don’t wear any of these things, much less as a traveler. I have felt frumpy when I put on jeans and a knit top has lost its shape and looks like I’m sponge bob square pants! I throw it into the give away pile.

  10. Lori
    March 20, 2019 / 2:01 pm

    I asked my daughter what she thought of and saw in her head when I said the word “frumpy”. She said a cat lady with big glasses in oversized knitwear that is beige and pink! I have two visions of frumpy. One is the person who seems to be wearing something they pulled out of a bag on the street. Meaning it is ill fitting, over or undersized, clompy shoes, messy hair and no makeup and made of some horrible material that doesn’t flatter anyone. The other is someone who might be put together and tidy, but looks like they are wearing all of their clothes and hairstyles from another era. It is fine to re-use and keep clothes from the past, but it is vital to keep some part of yourself looking fresh, whether that is your accessories, hairstyle or makeup. Recently, I had a leg injury and was forced to wear nothing but sneakers and wide legged pants to cover my leg brace for 5 months. I never felt so frumpy in all my life! I tried focusing on my hair and makeup and top half of my outfit and that seemed to help a bit by taking the focus off of the lower half. I don’t judge people for how they dress, because we never know what someone is experiencing and it may be that they are just happy to be out and alive, but it is true that first impressions are strong.

  11. Joyce
    March 20, 2019 / 11:07 am

    Frump doesn’t have an age ,gender , or economic level attacted to it, its a mindset. I was told many years ago, we had a beer pocketbook and champagne taste…yup and your point is? You cant count my money but you see my refection! I sparkle. My self image was not always the best. But with reading, watching, finding those i wanted to emulate > i grew,,and so can everyone. Self doubt is a terrible existence…grow, self confidence is weath. Sparkle, smile, respect, uplift, you never know what someone else is going through. Life is short, wear more cashmere, no old shoes, or dull lipstick….Sparkle! ????

    • Deborah boykin
      March 21, 2019 / 6:09 am

      Such words of wisdom … for over 50 years, I have hidden behind my clothes. I have little self confidence so I dress to blend in with the crowd. I want to look nice, but never “sparkle.” Life IS short, I need to learn to love myself and stop the self doubt! ????

      • March 21, 2019 / 11:30 am

        We could all benefit from more self-love and sparkle. Throw that brighter lipstick on and smile.

  12. Denise Walker
    March 20, 2019 / 9:25 am

    I agree with the thought that big scarves are overwhelming to my short, fluffy self. I have started having the tailor cut mine in half and hem them. Then I send the extra half to my skinny, short daughter who also feels overwhelmed in wide scarves.

  13. Janet
    March 20, 2019 / 9:11 am

    I think that frumpy is messy hair & clothes that don’t look like they fit. I have always dressed to please myself. I am 66 & stay fit by walking, Tia Chi, & light weights. My favorite clothes are jeans because I spend a lot of time outside & whenever I can with my Grands. I don’t want to worry about getting dirty or ripping them (they hold up to tough play). I never leave the house without lip gloss, eyeliner & mascara. I keep my very straight hair that is graying in stripes, cut in a bob at shoulder length. I wear a variety of styles but nothing stained, snagged, or faded. If it fits & you like, then wear it!

  14. Kathleen O'Brien
    March 20, 2019 / 8:47 am

    To me frumpy is looking like you just don’t care. Also I do think it goes with age and attitude, as young girls can put on jeans or leggings and tshirt and look cool, whereas an older woman can put on the same and look frumpy and old. Ill fitting, stained, and unkempt looks frumpy. I’m a plus sized lady, so fit and proportion is key – hopefully staying out of the frumpy range.

  15. Karen
    March 20, 2019 / 8:42 am

    I agree that frumpy is about not caring. What I battle with are “mom” clothes or now “grandma” clothes. It seems items that fit my apple shape often fall into this category…not stylish, matchie matchie, and shapeless. I don’t want to look like that even though I am 67 (gasp). My coloring is flattered by lavender and mint, etc, but I feel like such a frumpy old lady when I wear those colors! One of the many reasons I treasure your blog is that we fall into the same broad category in terms of looks…similar size, coloring and features. You never look frumpy or like you are dressed in grandma clothes. Sometimes I literally copy your outfits because you are so very good at putting things together. Thank you!

  16. Lily
    March 20, 2019 / 8:25 am

    I can answer this easily because I looked frumpy yesterday. It was because I desperately wanted to wear a new short sleeve yellow top even though the temp was in the 30’s. What went wrong – I layered a longish cardigan over the top. Then I topped that with a short jacket. Added a too big scarf. And athletic shoes. I am 5’2″. The layers hanging out and the gym shoes looked frumpy. I’m also starting to question scarves. They just swallow me up.

    • Veronica
      March 20, 2019 / 8:47 am

      Over the past several years, I have added several scarves of all sizes to wear with certain outfits and I have noticed that oversized scarves also swallow me up. Short and medium size thin fabric ones look fine. But the bulky ones draped right under my jawline look like I have a tiny head and instead accentuate my generous sized chest and make me look like I am at least 5 pounds heavier than what I am. To me that is instant frump!

  17. Gina
    March 20, 2019 / 8:20 am

    I guess I AM frumpy! I think I am in the stage of just not caring right now. Taking care of a ageing parent and dealing with chronic autoimmune disease myself hasn’t left me much time or energy to spruce myself up. But, I know it’s past time to get out of this stage. Thanks ladies for the nudge in that direction. Thanks you Jennifer for all your good suggestions too.

    • Anon
      March 20, 2019 / 8:29 am

      Please give yourself credit for this daunting, exhausting and important work.Few are strong enough to be up to the task. You are not frumpy.You are as woman warrior with very important work. I am with you, sister. Been there. Still am there.

    March 20, 2019 / 7:49 am

    Pardon the autocorrect errors please.

  19. Shirley (GA)
    March 20, 2019 / 7:15 am

    I looked up the definition of “frumpy” and found “dowdy and old fashioned” and “the opposite of stylish”…Also “A female with lack of concern for appearance. Often characterized by sweatpants, frizzy hair, gramma panties and a paisty complexion.” (Typos are not mine – this one came from Google – Urban dictionary. ) In winter, I guess you could say my complexion at times could be called “pasty” (correct spelling) – Webster defines this as “resembling paste…pallid and unhealthy in appearance”. Geez….No WONDER people are touchy about “frumpy”! Let me see – I wear sweatpants. I wear “granny panties”. I can appear “pasty” at times (gray/silver hair, too!) BUT – I really do not consider myself frumpy! My 30 year old daughter is quick to point out to me when she sees something that is not my best look – a lipstick shade, outfit or “Mama, your hair looks so much better when you style it the OTHER way”…She’s got my back! There’s a saying in the South – “There’s a fine line between tacky and trashy”. Maybe there is that same fine line between “frumpy and comfy”? Reading the other ladies comments, they seem to have defined it for their own selves. And I suppose that’s what we should keep in mind – constantly evaluating our look and attitude to stay current! And just because I wear “granny panties”, does NOT mean I’m frumpy! 🙂

    • Didi
      March 20, 2019 / 8:53 am

      ‘fine line between frumpy and comfy’ Cute!!

    • Vicky
      March 20, 2019 / 3:47 pm

      How could anyone possibly know what kind of panties you wear?? Or care??

    • Kelli
      April 7, 2019 / 1:13 pm

      I wear granny panties, too! Bikinis/hipsters feel as if they’re about to always fall off—and there’s nothing sexy about those or, the worst, g-strings!!!

  20. Eileen
    March 20, 2019 / 6:38 am

    I agree with the others. When my grandmother started wearing pants and tops instead of dresses in the 70’s, I remember thinking how ordinary and dull she looked, somehow she lost her “spark”. Maybe loosing our spark, is the first step to frumpy. The bigger question is why as a society are we choosing to downgrade/ casualize our look?

    • BeeeBeee
      March 20, 2019 / 7:48 am

      I’ve also thought about why dress has become more casual. I think that economics certainly is a contributing factor. In the USA, wages have been stagnant since the early 70s. The cost of consumer goods has gone down, but the cost of education, housing, transportation, food, and insurance has not. The dot com boom and the dominance of young men in the tech sector also have contributed. I think I’ve in the last two centuries, we have certainly been a much more casual. I enjoy public television and have often marveled at historical series placed in a time where some men wore nicer pants and vests to do manual labor. I think the trend is a global one.

    • March 20, 2019 / 5:52 pm

      That’s an excellent question. I wish we weren’t heading that direction.

  21. Mary
    March 20, 2019 / 6:17 am

    “If you don’t feel frumpy, do you care if others see you as frumpy?” HELL NO!

  22. Linda
    March 20, 2019 / 6:15 am

    I certainly try to look my best when I go out and find that a stylish jacket can project that image.

  23. Carol
    March 20, 2019 / 6:09 am

    I feel frumpy in my clothes when I perceive they do not fit right. In my mind, the colors may be off, or the style is not to my liking, or I am just tired of a certain look. The individual pieces of the outfit my be great, but not the way I may have put them together. So appreciate the views given by Jennifer and others on this blog to open my eyes to fresh looks, and be confident, not frumpy!

  24. Wendy Dunbar
    March 20, 2019 / 5:56 am

    I believe ‘frumpiness is in the eye of the beholder’ regarding style, but also agree with multiple readers who said things like ‘baggy, ill-fitting’clothing or ‘dirty, worn-out’ pieces project frumpiness. I have seen looks on other women from time to time that I would feel frumpy in – although they carried them off beautifully. Ultimately it come down to how you feel when you look in the mirror. What message does your look convey to you? Does it make you feel/ look confident, dressed for the occasion, approachable? I am blessed to have a group of women in my life who have helped me to ‘up my game’ (albeit slowly! ????); they’ve taught me that I’m worth taking the time to think about what I want to wear and how I project myself to others. That may sound like a ‘no brainer’ to many women but for some of us it is a lifetime struggle to ‘feel worthy’. I can usually tell when another woman has taken the time to put herself together and feels good about how she presents herself to the world, too.

    • March 20, 2019 / 5:50 pm

      I agree. It’s very personal. One woman’s frumpy could be a another woman’s comfy.

  25. March 20, 2019 / 5:50 am

    Frumpy to me is looking like you just don’t care. Oversized clothes, worn out, stained. And for goodness sakes, put on a good bra. I totally agree with Marnell that in general, we have become too lazy in how we dress and our self-care routines. This is a great topic for me today as I am preparing for a move and need to purge my closet. I will be ruthless!

  26. Laurie
    March 20, 2019 / 5:30 am

    I agree with Lisa G. that with my newly natural colored hair, makeup is a must. And, it’s a different makeup than I previously used. I’m still searching for lip colors that I love with my new hair coloring. I have always worn mascara, but didn’t start using eye liner until my 60s!

    I feel that I am always on the border of frumpy because I love my clothing to be soft, comfortable, and somewhat flowy. To avoid the frump factor, I try to limit the amount of “flow” in an outfit to just one piece. Also, the colors of clothing that I like can read frumpy. I wear soft colors for accents and neutrals. I now prefer to wear mostly neutrals with smaller amounts of accent colors. Too much soft pink or soft lavender starts to up the frump factor for me.

  27. Susan Gowan
    March 20, 2019 / 5:29 am

    Frumpy to my mind is looking out of style, not bothering to enhance your appearance. A few years ago I hosted a family reunion and wore a paisley shapeless dress. Was glad there were few pics of me that day. Looking at the few, reminded me of my grandmother who at 75 to 80 wore shapeless dresses.Can’t wear that dress now. I like to add pizzazz to my wardrobe. I like the comments about not judging.So important to dress to feel good about oneself. Though a touchy sibject, thanks for bringing it up, Jennifer!

    • March 20, 2019 / 5:45 pm

      We must dress to please ourselves first and foremost.

  28. Sara Dubman
    March 20, 2019 / 5:20 am

    I can not tell you exactly what looks frumpy. I think it is different for each person depending on your size and shape. I know when I try something on if it looks frumpy or not. I know that flowery, oversized things and prints are not the best for me. I am 5’ 3” so solids and more tailored and slim fitting items suit me best. I also do not leave the house without doing my hair and putting on my make-up.

  29. Yvonne
    March 20, 2019 / 5:02 am

    What an interesting topic! I always dress to my own personal style, and have never felt frumpy in my life. Why are men not described as frumpy? I see lots of men who are dowdy, out of date and sloppy dressers LOL

    • Anon
      March 20, 2019 / 8:05 am

      Good question. Is this phrase reserved for women only?

      Yes, it is. I have never heard of a frumpy man. Time to stop using judgmental, ageist language against other women and ourselves. We are not ornaments. We are 21st century citizens. We have intrinsic value beyond our age and looks. Yet still, harsh judgment is meted out for age and looks. We deserve better as women of experience.

    • March 20, 2019 / 5:40 pm

      I have seem men that appear frumpy too

  30. Lisa G.
    March 20, 2019 / 4:38 am

    I have found with my now natural silver/white hair at 58 that make up is a must. Mostly mascara which I did without for most of my adult life! Skimping on those final finishing steps leaves me feeling like I look older than my years. Oversized clothes can also make me feel frumpy and not as confident. Hard to describe that feeling or look of frumpy, but you know it when you see it! Thanks for this topic of discussion.

    • March 20, 2019 / 5:39 pm

      I have a hard time describing it but I know it when I feel it

  31. Marnell
    March 20, 2019 / 4:36 am

    Frumpy to me is anything that doesn’t fit, worn out and stained. Dirty shoes, rubber flip flops and old gym sneakers. And don’t get me started on “give away t-shirt” Anyone can wear leggings and a t-shirt regardless of size or shape or age. Tie a scarf or throw on a long necklace.. no more frump, you look finished. On me personally, midi length skirts. Maxi is beautiful on me and still some shorter lengths. Put me in a midi or, even worse, a midi with pleats… big no.

    I understand personal style, I get that we shouldn’t be judged by our clothes, but we are. If I want peace and quiet and not be pestered by pushy sales people, I dress the part of not looking like I can afford it. But we have become too lazy in our dress, and in our valuable self care routines, and honestly, I believe that it effects our mental state and eventually leads to self destructive thoughts of self, fostering low self esteem, further leading to self destructive thoughts and opinions of others. I reference the person who says to a skinny woman “go eat a sandwich” as a horrible example. If we feel good about ourselves we are less likely to project our negative comments on others.

  32. Monica
    March 20, 2019 / 4:34 am

    Jennifer I follow your Facebook page but this latest discussion never came up on my feed. For me frumpy is sloppy and not well groomed. I always style my hair and put on a little makeup everyday. Some days I do stay in yoga pants and sneakers but everything is matching and neat looking. I don’t think that’s frumpy. Frumpy is just not caring and it could apply to any age . I have also seen some frumpy men!

  33. Deede
    March 20, 2019 / 4:31 am

    I dress for an audience of one….ME..I select my clothes with one design in mind to make me happy…No second guessing…no does this meet my age…no is this over-dressed…Just…does this make me happy..Do I look in the mirror and smile…I have been a long time coming to this place..It feels good…smile…
    As for defining frumpy..that is just too subjective…I wouldn’t dare to say wearing this is frumpy or that hair style is frumpy…or whatever…We are all just trying to make it in whatever way we choose…

  34. Sondra
    March 20, 2019 / 4:15 am

    For me, feeling ‘frumpy’ is wearing sweats and no make-up which I ONLY do around the house in the winter, some days. Otherwise, I NEVER leave the house without make-up and looking nice….whether I’m headed to church or the grocery store. My one pet peeve is that NO ONE dresses nicely to go to church anymore…at least not where we go! It’s jeans and sweat shirts, etc. I refuse to do that so I’m sure everyone considers me ‘over dressed.’ Everything is so casual now, everywhere you go, so I’m sure most of the women don’t feel like they look frumpy when actually, they do! This is just my opinion.

    • Konda
      March 24, 2019 / 9:27 am

      I totally agree with you!

  35. March 20, 2019 / 4:13 am

    So far, in my early 70s and retired, I am trying to keep my hair and skin in top,notch condition…no short roller curls here, but a mid short bob type cut. Next, my weight has crept up 5 pounds, mainly around the waist , so trying all of Jennifer’s and other bloggers suggestions— to hide those extra pounds. I’ve also joined yoga and tai chi and walking more to keep myself somewhat fit! I eat very healthily and have for decades, so that’s not my problem. It’s about being more sedentary…must move more!

    Frumpy would be too large clothes, disheveled appearances. I hope to never let myself get to that point.

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