How to Nail Your Personal Style Over 50

It’s an often-repeated and common belief that we’re either born with great style or we’re not. That’s like thinking you’re either born with good manners or you’re not, which we all know is nonsense. I’m updating this post from last year with some new thoughts on how to develop your personal style over 50.

over 50 fashion blogger showing how she nails her personal style in white blazer and red jumpsuit

Style is a skill we can learn and like anything else, the more we practice, the more confident we become. If you’re lucky enough to be exposed to style and stylish people early on, your sartorial choices may feel easier. But what if you’re not? How do you develop your personal style and is it too late to develop it after 50?

row of pink blouses on closet rod

By the time we’re over 50, 60, 70, we’ve done a lot of living and want our personal style to reflect our confidence. Our clothes need to tell the world who we are now and allow us to step out in confidence.

Fashion advice for older women is everywhere but not all of it is relevant so here are a few ideas that may help you nail your personal style in midlife.


Jennifer Connolly wearing black victoria emerson bracelets

“If a woman has a closet full of clothes but nothing to wear, she doesn’t know herself very well.” – Bill Blass

  • Everything starts with self-knowledge. Who are you now and how do you want to been seen?
  • What’s your lifestyle? There’s no point in building a wardrobe for a sophisticated urbanite if you live in a rural area and need clothes for your casual activities.
  • Your wardrobe needs to be functional for your climate. If you live in Florida year-round, you don’t want a wardrobe of suede boots and faux fur jackets for winter.
  • Understand your body shape and dress to accentuate your best features and downplay the ones you’re not crazy about.
  • Buy what you love, and wear what fits your current shape. Wearing clothes that are too loose or too tight doesn’t give your body the respect it deserves.


Pay attention to the women around you. Are there certain looks you gravitate to over and over? Be aware of the colors you’re attracted to and the shapes you like.

styling a popped collar under a sweater

Start a Pinterest board and save images that appeal to you. After you have a large collection, go back through them and look for similarities. Are the colors similar? Do most of them have classic elements or are they more creative? Are the details feminine or dramatic? This helps train your eye to see what aspects of an outfit you admire.

AVOID RUTSpainting on hair color

We’ve all been there and no one wants to look like they’ve gotten stuck in a time warp. If you’ve always loved classic style be sure to keep it fresh and modern by styling pieces in new ways. Pop your collar. Half tuck your shirt. Stay abreast of trends but don’t be a slave to them or you risk looking tragic.


BE BRAVEshowing personal style combining leopard print with denim and multiple bracelets

Try new combinations and see what feels right. Take selfies in the mirror because they give you a totally different perspective on how things look on you. Do you recognize that woman in the mirror? Does she look the way you want to look? There are no wrong answers with fashion so don’t let fear stop you from trying.


ACCESSORIES MAKE THE WOMANwoamn walking down sgtrett in white shirt and jeans carrying bronze handbag

Personal Style is all about taking fashion and making it your own with personal touches only you can add. Be inspired by another womens style but give it your own twist to make it personal. Accessories are the game-changer here and will give your outfits personality. Collect ones that spark joy, then mix and match them to create your signature look.

And finally, know that great style can be found at every price point, so don’t feel limited by your budget.

How would you define your personal style?










  1. I have a closet full of clothes, but tend to grab the same few favorites regularly. While I’m in my late 50’s I still feel like I’m 30, and struggle to find a style to suite my chronological age as well as my psychological age, lol. It is a work in progress, which I hope to master soon.

  2. Jennifer, thank you for all you do and all the great ideas can you bring our way! I find myself in a bit of a quandary about how long to keep my clothes. I know there is no one right answer but I wonder if there are any guidelines or advice? I have always been interested in fashion, and skew a bit bohemian/romantic/artsy. I find my clothes don’t particularly go out of style, yet I like to purchase a few new things each season and so my wardrobe grows too big to be efficient.
    I am also guilty of dressing, or rather buying, for my fantasy life. I would have many choices for attending a Moroccan wedding but would be hard pressed to dress for the rare business meeting or funeral.

    1. I love your comment, Penelope. Try retiring items for a season or two, then bring them out and see if you still love them as much. You’re right, there is no hard and fast rule, but I use these… does it fit, is it faded, do I own a newer version that I prefer, would I be happy if I reached for it and find I’d donated it?

  3. I enjoyed your post, Jennifer, once again. I am a victim of living in a beach destination area where casual, and laid back is the required dress code. If you’re wearing shoes you’re overdressed! I like to dress casual and comfortable without overthinking what to wear! I’ll always choose “pearls with jeans” and smile, as the family matriarch… because I’ve earned it!

  4. This was a wonderful post. Unfortunately, I am the woman with the closet full of clothes and nothing to wear. This helped me to realize I need to make a plan, and become a better shopper. There seems to be a serious disconnect between what I own and what I’m aiming for.

  5. Just spent couple of weeks ordering and returning dresses for wedding shower. Ended up wearing dress in closet that is more classic and fitted than many of current styles. Realized that is where I fit the best. No need to follow trends if they dont work.

    Also, miss in store shopping. Limited places in this area. Nothing like it. Online can be so frustrating.

    Great post

  6. Great post today, Jennifer. I’ve always been more “buttoned up” and am trying to relax my style more. Still staying classic, tailored but not so rigid. Your posts are so helpful. Thank you for your great inspiration and ideas.

  7. Wonderful ideas, thank you. I have a Pinterest board and found most of my saves are jean outfits. That’s what I gravitate to for my lifestyle.

  8. Your posts are always so inspirational. I am guilty of having too many clothes that are unseasonal for the climate I live in, as they suit the times I vacation in a warmer climate. I have recently retired and given away most of my work suits and more formal clothes, and I need to redefine what is going to be best for me now.

  9. This was such a helpful post.
    My Mom was a seamstress and made my clothes and hers.
    She could put fabric and style together in an amazing way.
    She taught me to sew but I did not love it like she did.
    She always dressed stylish and I did receive some of her gift.
    She always said “feathers make the bird”. So I try to dress in a way that fits who I am. Kind of sporty with a bit of flair. I feel good about me and try to dress that way also.
    Again thank you for your wisdom.

  10. Jennifer I enjoy your blog so much. Your frequent reminders to wear what makes you feel confident get me every time! If an article of clothing doesn’t translate as “me” I feel like the clothes are wearing me, and not the other way around. I feel best when my clothes *almost* fade into the background, and let me shine.

    I agree so much with Bea’s comments: Understand your body shape and work to accentuate your best features while downplaying those that are not so great. Finding comfortable clothing.

    The inspiration from you and your blogger friends related to style identity and colors also helps!

  11. I can think of two reasons that make it difficult to find your style, #1 manufacturers limited styles, and the lack of sizing, petite/ plus/ tall. And I agree with anon, your shape dictates what you can wear( unless you make your own clothes). And I agree it’s easier to try to be fashionable if you fit the norm of the times, in body shape and coloring. Interesting subject.

  12. Great ideas and insights. Socrates was right: This above all, to thine own self be true. Some of us take a longer road to learning about style while to others it’s iseemingly nnate.

  13. Hello
    Great post. My style has evolved over each and every decade. I’m very comfortable with my style at age 65. I will say that I dress very differently season to season. Summer is my favorite. I wear fashionable work out attire and tons of sun dresses. I have a pool so I have a large bathing suit collection.
    In winter I wear a lot of black, grey, white and pink. I work part time in aftercare school program. Can’t be afraid to get dirty. In summer I wear pink ,orange , blue, white and prints. I’m not a fan of shorts unless the are bermuda. I also don’t wear jeans, I don’t like how I look in them.
    I get tons of compliments. So I must be doing something right.

  14. I am so guilty of wearing clothing that is too large on me for the past 7 years.

    I don’t know why but I just developed an aversion to wearing fitted tops.

    I will try to pay more attention to this and try to slowly stop it.

  15. I have always loved clothes and stylish dressing – thanks to my mother’s influence. She dressed stylishly to the day she died at 85 years old. So I have had years of practice. Yet I continue to learn new things and really enjoy your blog, Jennifer. One of your suggestions today means the most to me: understand your body shape and work to accentuate your best features while downplaying those that are not so great. Finding comfortable clothing that minimizes my bust and, at the same time, makes me look taller & thinner is the ultimate goal. Color is another important requirement. I find that as I age, colorful clothing helps me feel upbeat and stylish. So my new shopping guidelines include color, comfort, fit, and illusion.

  16. I had started to get excited about getting out of my leisure wear after being cooped up , going places , dressing casual chic, going out to dinner and lunches again, buying new clothes, etc. I thought by having my vaccines I had an assured sense of freedom. Now we are back wearing masks due to rising covid cases. Somehow wearing a mask just does not motivate me to care about what I want to look like or to shop. The mask wearing just ruins it all with getting the look I want. I have bought all kinds of masks to coordinate with outfits , but still looks weird with masks . Masks really just don’t do for the look we are trying to achieve.

    Is anyone else going through this ?

    1. Hi, Donna. Masks are definitely a downer, but I think we are going to be wearing them for some months to come. I don’t bother coordinating the masks to clothing – just try to ignore the whole thing and wear the best quality protective mask I can find.

      Somehow this does not stop me from having fun with my outfits, though. (I still love shopping and putting together neat outfits.) Stay well and happy.

      1. I have to wear mask at work. I just wear the paper ones and throw away each day. I play around with makeup to make my eyes pop when wearing a mask. Also been fooling around with dangle earrings. Maybe that would help? Have fun.

  17. I decided to purge my closet of things I don’t wear. I was amazed to find the reason I didn’t wear so many was because they were too big. I haven’t lost weight so I guess I didn’t notice until now they were too big. I’m getting more critical about fit and sticking to just a few colors. This time I hope my closet works for me and not my sister in law who looks great in my one size up clothes. She’s thrilled.

  18. Love this post. With the change of seasons, I’m always evaluating my wardrobe. I’m one of those who has a ton of clothes, but nothing to wear.
    There are some things that excite me, but if I cut my wardrobe down to just those things I might only have 10 outfits. I’m always struggling with what’s the right color, what’s the right size and constant weight fluctuation. It’s frustrating! Also, I tend to buy the same things over and over again because I have so much. So…this year I vow to “do different!” Working on it, and posts like this really help!

    1. I think we all buy the same things over and over, I know I do. If an item is one you buy too many multiples of, try spending a bit more on one and get the best one you can find. Then wear that pair over and over and over.

  19. Thank you for such great advise. I struggle finding my personal style. I definitely need to be brave. Going to start my Pinterest board.

  20. I think that old saying came from the idea that some women are born with the right proportions for mass-produced clothing, and many more are not. The people “born with style” simply inherited the “right” body shape seen by manufacturers as their average customer.

    Designers used to produce clothing for whatever body type was in fashion at the moment. As we all know, it is not possible to change one’s shape when their body is no longer “in”.

    The right fit for our individual bodies is not easy, but this goes a long way toward having personal style. We need choices, like high-waisted pants for a long torso when low-rise pants are au courant, Call it fashion democracy. Nobody looks stylish in ill-fitting, uncomfortable clothing meant for a body they don’t have.

  21. Thank you for the great advice. I particularly find it hard to be brave. Sometimes being brave works but I worry about looking silly. And now that I rarely go into stores due to concerns about COVID, finding adventurous items that work is even harder. You have a great style that looks wonderful on you. I’ll keep trying!

  22. Like this “ try it you might like it attitude”.
    I stick with the same traditional style so my closet looks pretty much the same.
    I love the idea of taking selfies when changing it up. I will try this to add a bit of flair.

  23. Great information.I worked as a personal shopper and image consultant for many years.It was. so easy to dress others but I found it more of a challenge to look objectively at myself. Now I am way over 60 and discovering new ways to put outfits together that suit my age and lifestyle.
    I lived in the San Francisco Bay Area but now find myself living in tropical Queensland Australia. No Nordstrom JJill Old Navy or Chico’s !!!..just to name a few. I am a redhead with naturally curley hair very fair skin and a curvey petite body. Being retired and on a very tight budget is also a challenge here. There are some high end clothing stores and items do go on sale but finding “warm toned colours” can be difficult. If I could wear black white or any cool toned colours it would be easy here. This seems to be a very “cool to toned” country.Crisp white shirt? no problem…cream one? not going to happen. At times I findi myself in a ” personal style dilemma” I now feel I know what would work for me but finding it is the problem. I will continue to try to stick to basics and use accessories creatively to add interest. The cooler months may not be such a challenge. In our hot humid Summer I wear wrinkled linen and count the days until Fall arrives! Having a sense of humour is sometimes the key to having or knowing our personal style!

  24. I think for the most part, I am a classic dresser. I love a crisp white shirt with the collar popped. I only buy jeans in a dark indigo or black wash. A LBD is a must! I love scarves as they add colour and texture to an outfit.
    I tend to wear black in my outerwear no matter the season. I’m trying to get out of that and have bought a red winter jacket. I wouldn’t be surprised if it gets returned though. The tags are still on with the receipt in a pocket. 🤔
    I love shoes & booties. Too much so! My hubby counted them one day and I was surprised that I have 40 pairs. How much is too many? Please tell me you have at least as many pairs.

    1. Just found this. If it makes you feel better I donated 70 pairs of shoes, booties, plus 3 dozen handbags and I still have over 200 pairs 😉

      1. I just saw this , too. I have so many shoes, at least 75 pairs in my closet, and more stashed in another closet. I think it’s because I have difficult to fit feet, so when I find them, I hang onto them. Yesterday, I saw a new physical therapist for an initial visit. He wanted to examine my shoes for wear pattern. I could see him looking closely at them, a pair I’ve been wearing all summer, but interspersed with sandals. He finally said, “next time would you bring another pair you’ve worn more?” I just examined a pair of Ecco7s I’ve had for two years, and which I think I wear frequently during fall, winter, and spring. I don’t see any wear on the soles, but that’s what I’ll take–unless I just take a bag of a bunch.

      2. That’s so funny and familiar-sounding, Mary. I think we all have a lot of shoes because our feet are tricky.

      3. Oh THANK GOODNESS!! I have never counted my shoes or purses but fear I am close to the Imelda Marcos category. Good to know I’m not alone!

  25. Great post today! I’ve lost weight recently and struggle to see my “new body” as I decide my new style. Your suggestions are helpful!

  26. I love your ideas. You have helped me be a little bolder with my style. I’ve always been classic and a little sporty, similar to my mom. She always looked and dressed beautifully. As did my sister. As I’ve gotten older I’ve realized you are just more overlooked so trying a little harder helps with self esteem.

  27. i wore a uniform of some kind most of my life and find myself now at 67 trying to figure out what my style is…

    1. Join the club. I have worn a uniform since I started school aged 5, until I retired aged 55. I have always struggled trying to find a stylish, casual look, gravitating between a relaxed boho look (which generally swamped my figure) to a more tailored look which always felt a bit too ‘stitched” up and at aged 63, can be a bit ageing. I always check out what Jennifer is wearing as I think she has really nailed polished, casual dressing which has given me some great style ideas.

  28. My personal style has developed from years of observation and years of trial and error. Today, I may see someone who has a clothing or hair style that I may admire but I know it does not fit my personal style. For me, my personal confidence is the bottom line. When I look in my closet today, it can be sorted into a 90% group of basic, classic items and a 10% group of trendy items. I tend to add a few trendy pieces of clothing in the summer months. More often than not, they might only survive one season. My goal now is to enhance my personal clothing, hair or makeup style. I loved the style and confidence that my mother and her sisters had developed. Maybe, they sprinkled a bit of that magic dust on me.
    I watch very closely the style and details that you are showing us Jennifer. It really works to keep me current.

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