Dressing With Confident Style

Dressing With Confident Style

Do you feel confident with your style choices? How well do you accept a compliment on your appearance? Many women aren’t comfortable with them but sadly find it all too easy to accept criticism. Pardon me while I rant about people who assume they’re entitled to comment on our appearance, and not always kindly.

Jennifer Connolly of A Well Styled Life dressing with confidence

I’m not talking about helpful comments when a blouse is askew or a zipper is down. I’m referring to condescending comments about how you look or why you’re wearing something. Well-meaning friends and loved ones can put a bullet in a women’s confidence faster than any stranger can because we care what they think and trust them to have our best interests at heart.

FYI- Taking the time to dress nicely to go to the supermarket is a matter of personal pride and not cause for criticism from others.

While packing for our upcoming RV trip I’m reflecting on how I want to look. You know what? I want to look like me. I intend to dress to please myself. I will wear makeup, style my hair and pay as much attention to my appearance as I do at home because it pleases me. I don’t use RV travel as an opportunity to stop putting time into my appearance. If another woman wants to take that opportunity, I support her!  We all should.

Our style choices are personal decisions that need to make us happy. Offhand criticism is a subtle put down that dampens creativity and can wreak havoc on your confidence. You deserve to clothe your body any way that makes you feel happy and confident. Don’t let anyone steal your confidence, including well-meaning friends and loved ones.

Have you noticed subtle or not so critical criticism of your style choices? How do you respond?

Thanks for reading ladies and have a great day!









  1. January 10, 2018 / 4:40 am

    I agree 100%!!

  2. January 10, 2018 / 5:00 am

    I’m with you! I enjoy dressing and caring for my appearance. I’m free to make that choice without being considered vain or superficial. My physical appearance is only one aspect of who I am.

    • Jennifer
      January 10, 2018 / 7:32 am

      Exactly!! If folks don’t like it, that’s their business.

  3. Miwi
    January 10, 2018 / 5:16 am

    Well said! Because I change my hairstyle every several years, I’ve been on the unfortunate end of friends’ comments such as, “Oh, you cut your hair.” (Can I please respond, “WHAT? I didn’t know that!” with only a wee bit of snark)? Or, “You look better with short hair;” and when I finally cut it, I’m met with, “Why’d you cut it?” by the same person. And, possibly the worst of all: I’ve friends who completely ignore any major hair change, like color, significant cut, an/or curls. *sigh* Yes, silence can also put a bullet in our confidence. It’s not that difficult to compliment one another!

    • Jennifer
      January 10, 2018 / 7:36 am

      You’re exactly right!! Friends can be the worst. How about responding with, “No, I didn’t change it, what makes you think so?”
      Or, “ I’m glad you have a preference for my best hairstyle, I do too!” Depending on the friend, snark may be called for. Let it rip.

  4. Konda
    January 10, 2018 / 5:23 am

    I agree with you also. Now that I’m retired, I don’t necessarily ‘dress ‘ every day, but most days, yes. I have heard from a couple of friends comments of “Oh you’re so dressed up” when really, I’m not. I just paid attention to what I put on and used makeup. I feel if I don’t dress for my own approval and self esteem, then who do I dress for since I’m not necessarily being seen by someone else on that particular day. Thank you for your support. It’s because of you that I do try to look nice ‘most’days

    • Jennifer
      January 10, 2018 / 7:38 am

      Good for you Konda! I’ve got your back. One persons dressed up is another’s sloppy so we must do what makes us happy!

  5. jodie filogomo
    January 10, 2018 / 5:37 am

    I don’t understand why we wouldn’t dress nice to have pride in ourselves??
    But then again, I have learned we are all so different. Yet we should embrace that, instead of tearing each other down…

    • Jennifer
      January 10, 2018 / 7:39 am

      I totally agree Jodie!!! xo

  6. Martine
    January 10, 2018 / 6:08 am

    I agree. I have a friend who dresses up a bit for everything. Even after golf, when most of us go into lunch in our golf clothes, she goes to the locker room, showers, does her hair and makeup, and changes into a smashing outfit. I am shocked by how many ladies make, “Who do you think you are?” comments.

    • Jennifer
      January 10, 2018 / 7:43 am

      Any person who would comment, “who do you think you are” about a woman’s appearance is just plain rude! I also suspect they’re the mean girls from high school all grown up and nastier than ever. They’re trying to make her feel bad about herself and shame on them. I would speak up and tell her how nice she looks.

  7. Deede
    January 10, 2018 / 6:23 am

    Jennifer, Good Morning…Quick question:…Do you have an UH-HUH BUTTON?…If not put purchasing one on your TO DO for today…When you have an UH-HUH BUTTON that works…You will not be subject to these WELL-MEANING critiques…The well-meaning will be said and you will respond with UH-HUH…You don’t have to ingest every word that these people put out…You have an audience of one to please: YOU….Forgive me for sounding preachy but I am suspect of someone trying to steal your joy with these remarks…Over time I have been able to perfect uh-huh and let it run off my back like water on a duck…Dress to make you smile…That is what I do and it is SO much more fun…
    Best to you and Lucy….Deede

    • Jennifer
      January 10, 2018 / 7:47 am

      I love that! I also say “Really?” That usually makes someone either defend their position or notice they’ve said something out of line. Of course total clods will continue to be clods, but I like to let them know they’re comments are unappreciated. Have a great day Deede! xo

  8. Cheryl Ann
    January 10, 2018 / 6:31 am

    Good points, Jennifer. I enjoy fashion and don’t particularly look my best in jeans & T-shirt, so I’ve always “dressed up”. From the time I was in college or even high school, people have commented on my style. My mother and grandmother always “dressed up” too, so it’s how I’m most comfortable. Now that I’m retired, I still dress to please myself. You have been a great help in me finding a more casual, but still stylish look. Thanks for sharing your fashion sense with us!

    • Jennifer
      January 10, 2018 / 7:51 am

      My Granny was the same way. My
      Mom less so with clothes but always with hair and makeup. I just enjoy my day better if I put some effort into my appearance. Looking nice feels good and if it intimidates others, perhaps they’re in need of some personal sprucing up!

  9. Pat Noakes
    January 10, 2018 / 6:38 am

    I couldn’t agree more. Looking well put together makes such a difference in your life. You are looked at and treated as you appear. I have a little blog and I will share this today. I have added a Fashion section and is being well received. Thank you for your hard work. I never miss a day!

    • Jennifer
      January 10, 2018 / 7:52 am

      It does just feel better! Thanks for reading Pat!

    • January 10, 2018 / 10:50 am

      I’d love to read your blog, Pat. How can I find it? I added a fashion feature to my blog a couple of years ago. It appears every Friday.

  10. Laurel
    January 10, 2018 / 6:38 am

    Since I’ve retired, I don’t dress up every day, but I wear something I like that makes me feel good. And when I’m going out – even if only to the grocery store – I do my hair and a bit of makeup and dress in something that makes me look decent. And I don’t let anyone steal my thunder. Could not agree with you more!

    • Jennifer
      January 10, 2018 / 7:54 am

      Good for you Laurel. We can’t let others rain on our parade!!

  11. January 10, 2018 / 7:57 am

    Have fun on your trip. I look forward to reading of your new adventures.

    • Jennifer
      January 10, 2018 / 11:24 am

      Thanks Linda, I will be sharing from the road.

  12. Eileen
    January 10, 2018 / 8:03 am

    Funny world nowadays, looking good isn’t well received. I work in a gym in exercise clothes, and always use makeup, and yes, it makes people comment, I started saying, yes, I love makeup. My husband dared to wear chinos instead of baggie jeans, and the men asked, where are you going? One of my younger friends had a good idea, she wants to change casual Friday to “ fancy Friday “ ! She’s on to something! Let’s start !!!

    • Jennifer
      January 10, 2018 / 11:25 am

      She is on to something! Casual has gone too far for many people. I take pride in my appearance and find nothing wrong with that.

  13. Lee
    January 10, 2018 / 8:51 am

    Jennifer I am so glad you brought this up. I currently am struggling with this very issue. I am of the mindset that if you cannot compliment a person pleasantly then keep your damn mouth shut! I have been hurt recently by negativity with my attire. At this point I let it roll off my back. I decided just because they don’t like it, does not mean it doesn’t look good. I’m moving forward with what I like!

    • Jennifer
      January 10, 2018 / 11:29 am

      Good for you Lee! It’s their problem and rudeness, not yours. Dress to please yourself!

  14. Rita
    January 10, 2018 / 9:07 am

    So very true! I have had a friend say “why do you dress up to go to the store?” when I had on a t-shirt, jeans and a pretty scarf on! My idea of trying to look nice but not at all dressed up and it was said in a manner that made me feel I was dressing inappropriately! I shrugged it off though but it made me determined to make others feel good. I always try to comment on ladies I see with a “love your haircut, your blouse colors looks fantastic on you, or I love your style.” Whatever is applicable, and the smiles I receive are lovely! We should all be supportive of each other. Thanks for bringing this up Jennifer, wonderful post!

    • Jennifer
      January 10, 2018 / 11:32 am

      I’ve had readers tell me that family members say that to them too. It’s a subtle put-down and I love how you handle it. I prefer to compliment women and allow them to dress as they please. Who am I to judge another?

  15. Suzi
    January 10, 2018 / 9:08 am

    Jennifer, I too agree we should dress for ourselves and I love the uh huh comment, I will be implementing!
    Please tell me that fabulous white blouse is still for sale somewhere. It is gorgeous!

    • Jennifer
      January 10, 2018 / 11:34 am

      The same blouse is available here in white with black polka dots, which I really like too!

  16. Joanna
    January 10, 2018 / 9:17 am

    Why, oh why, do women feel the need to cut others? I think we have all experienced it.
    I’ve been told I’m too old to wear jeans at 61. I only wear properly fitting ones in a dark wash without tears. I love jeans! So, I decided to ignore these comments. And, any others that come my way. I’m afraid I don’t respond and because of that, those that are mean spirited feel that they can continue to criticize. I even have a good friend that told me I was too docile and then she bullies me. Ha! I tell my myself she is a good person and she is, but she also has a mean girl in her. I limit my time with her.
    My mother taught me “ If you can’t say anything good about a person, say nothing at all.” I wish others had been taught that.
    I hope you have not been receiving any mean comments on your blog. You always look chic. How do you respond to friends that criticize?

    • Jennifer
      January 10, 2018 / 11:43 am

      I think it’s wise to limit your time with her…she doesn’t sound supportive and that’s what friends are supposed to be! I get criticism occasionally on my blog but expect it goes with the territory. I wrote this in response to what readers have told me happens to them and things I have overheard. I don’t keep friends who criticise my appearance and if they happen to be family members I tell them off, and not nicely.

  17. January 10, 2018 / 10:12 am

    I love affirming women in the change room — if someone is trying on a garment that really looks amazing on them I will tell them. If they look terrible in a garment I keep my mouth shut. As my mother said, “If you can’t say something nice, say nothing.” Unless of course they ask me for my opinion and then I will kindly suggest why they might want to choose a different garment.

    • Jennifer
      January 10, 2018 / 11:44 am

      Me too Joan! Good for you. Constructive criticism is only constructive when it is asked for.

  18. Kathleen O'Brien
    January 10, 2018 / 10:27 am

    Oh my! This post hit a cord! I often don’t leave the house unless I’m “dressed”, and it’s often assumed because I’m a theatre costumer that’s it’s part of my gig. But then folks ask me if I’m sick or not feeling well if I don’t dress up! And then folks who don’t know me ask why so dressed up ?
    I remember my grandmother who wouldn’t even ride the bus downtown without always hat and gloves – she always looked so elegant to me. My mom often wore her nurses uniform coming and going and my dad was in the Navy and then in security with a uniform. So maybe it’s in the blood to dress nicely all the time. They never looked inappropriate or outta place to me.
    I worked at a shipyard in my past. I dressed appropriately for the office when I was there and changed into coveralls and hardtoes when I went to the drydock. It was just something I did, it felt right to me. Of course, there wasn’t too many women in my workplace then, but I saw that’s how the bosses did it, so I did too.
    I do think folks should dress appropriately for the task or job, but other than that I think we should be supportive and uplifting in our comments

    • Jennifer
      January 10, 2018 / 11:48 am

      That’s awesome Kathleen! I’d love to hear more about your job! I wish all women could be supportive but sadly, there’s a large group who are not and I simply wish would just remain quiet.

  19. January 10, 2018 / 11:13 am

    I have learned the best way to respond when insulted is to compliment the one giving their critique. That way I am at peace and find it easier to let go of what was said. Affirmation is powerful and we need more of it between women. Anyone who thinks their purpose in life is to criticize others leads a sad life.

    • Jennifer
      January 10, 2018 / 11:49 am

      I agree Pam! They’re just trying to spread insecurity around at other’s expense.

  20. Vicky Payne
    January 10, 2018 / 2:08 pm

    LOVE the hat!!! You look so cute!

  21. Janet
    January 10, 2018 / 3:31 pm

    Please respect my choices as I respect yours! I get great enjoyment out of dressing well and as an added bonus I get compliments frequently including from my appreciative husband. I believe we need to teach others what we need from them so I would directly address anyone who made a rude comment to me. As for family and friends, I expect their support or I don’t surround myself with them. That may sound harsh, but at 58 years of age I am confident in who I am and what I want and I am not going to settle for less. Thanks for touching on this subject Jennifer and by the way, I love this picture of you. That hat is stunning!

    • Jennifer
      January 10, 2018 / 6:59 pm

      Thanks Janet! I wanted us to discuss this so women who were being victimized in subtle ways would realize they needn’t put up with it.

  22. Linnie Z
    January 10, 2018 / 4:15 pm

    I never understood why some people (women) can be so mean. Most men are not. I agree that it is really nice when your spouse compliments you. My husband always tells me I am classy and beautiful. I do try to be classy. I always “dress up” as well. I have taken to wearing jeans more than I used to, but I think they can be very sharp. I try several different styles, depending on the occasion.
    Jennifer, I appreciate all the tips along with the sale advice. It is wonderful to have someone help with the legwork.
    My advice, to all women, dress as nicely as you want, whenever you want. Accept compliments. GIVE compliments. You just might make someone’s day.

    • Jennifer
      January 10, 2018 / 7:01 pm

      I so agree Linnie! Complimenting others is the good for everyone!

  23. Sandy
    January 10, 2018 / 7:42 pm

    I agree with you 100%. Wouldn’t it be rather boring if we all did the same thing! I enjoy seeing what some ladies put together because there are times I see things I was afraid to do but they look good.

    • Jennifer
      January 11, 2018 / 8:09 am

      I love getting inspired by how other women put themselves together!! It encourages me to try things

  24. Joanna
    January 10, 2018 / 9:56 pm

    On a different note, I love your hat. Is it still available?

    • Jennifer
      January 11, 2018 / 8:13 am

      It is several years old from a company called Coolibar. They easy care and pack well. I’ll look for a similar one for you. This prices appear to have gone up;)

      • Joanna
        January 11, 2018 / 4:05 pm

        That would be great!

  25. Julie from Melbourne,Australia
    January 11, 2018 / 2:08 am

    Jennifer people can be nasty because they don’t take the same care as you and they also might be envious of your outfits.I always try to complement other women and friends and like it when they reciprocate.It doesn’t cost anything to be nice.
    I always like to dress well too when I go out anywhere:it makes me feel good and that I have self-respect.I was brought up by a mother who always looked after her appearance and my sister and I have followed in her footsteps.
    Hold your head up and do what is best for you.

    • Jennifer
      January 11, 2018 / 8:17 am

      I agree. It’s sad when husbands criticize their wives efforts. I’ve have readers tell me it’s not uncommon!

  26. Michaela
    January 11, 2018 / 3:56 am

    You wouldn’t believe how nasty people can be. My daughter lost her hair after chemo and strangers in supermarkets make hurtful comments. (Always females.)
    The other daughter has put on a few pounds and looks a bit chubby and again females on the beach make rude comments.
    I tell my daughters that these people obviously have problems and have no lives of their own. Who thinks it’s great to go around being rude at random?
    As for the “frenemy” – who needs them?

    • Jennifer
      January 11, 2018 / 8:20 am

      I’m so sorry and hope your daughter is doing better Michaela. I have zero tolerance for that type of behavior. Rude insensitive people think it’s ok and it’s not.

  27. Joan
    January 12, 2018 / 3:23 am

    In “Dressing with Condident style”, you are holding a striking red purse. Where can I find one?

  28. Donna O.
    January 17, 2018 / 10:48 am

    Aargh! This is why I looked for a blog for “older stylish women”! Most of the slacks in my closet are now skinny, and I wear them with longer tops. Last week I saw a lady who looked a little older (than I think I do until I see myself in a photo) in skinnies, and thought, “Do I look like I’m dressing too young?” She did have on a short jacket and top that didn’t cover her bum and thighs, but she was thin. I’m going to have a heart to heart with my very stylish 28 year old daughter the next time we’re together. It’s so tough to dress confidently when you feel like you’re in your early 40’s but are finishing out your 60’s!

    • Jennifer
      January 17, 2018 / 1:33 pm

      The trick is to listen to your gut instinct…she knows if you are confident wearing something. Don’t be afraid to experiment and try new things. None of us want to look like mutton dressed as lamb so check in with yourself and use a 3 way mirror. The older we get, the more freedom we should be feeling with our wardrobe. Rather than limiting us it should be making us happy.

Leave a Reply

Your email address will not be published. Required fields are marked *

Unauthorized use and/or duplication of any images or written material is strictly prohibited without express and written permission from this blog's author and owner. A Well Styled Life® a registered trademark.
powered by chloédigital