Style Rules to Live By

Style rules. Fashion do’s and don’ts. What not to wear. How do those make you feel? I run across more than  I care to these days and most are directed at women over 50. They’re designed to help women get dressed by ruling out unflattering options and narrowing our choices but they can also stifle creativity and limit our fun. I tend to ignore most but there are 4 that I swear by.Jennifer Connolly of A Well Styled Life showing why a long sweater makes you look taller and slimmer

Dress the body you have now

Not buying something you love because you want to lose that last 5, 10 or 25 pounds is tragic. That type of thinking sabotages your confidence and appreciation of self which has nothing but negative consequences. Dress the woman you are right now with respect and delight.

Own and wear what you love

Mediocrity and average get old fast! Yes, we need basics in our wardrobe but an entire closet full of basic pieces can be boring and feel dull. Before you invest in another pair of black pants, consider if it might be more fun to add a red or patterned pair to your look. Do you love black pants that much?Jennifer Connolly of A well Styled Life

Wear the best you have

Don’t save things for a special occasion. Leaving your favorite things unworn because they may get a stain or mark on them is counterproductive. Wear them at every opportunity. Clothes left to languish in our closet for that perfect occasion are frequently forgotten and therefore wasted. That fabulous skirt you adore? Toss it on with a tee shirt and comfy sandals. That sparkly scarf you wear once a year? Wear it with a classic white shirt and jeans.

Don’t wear uncomfortable clothes

If it binds or tugs, pinches, pulls, gaps or needs constant readjustment, you’re torturing yourself. Wear clothes you can put on and forget. That strapless bra you’re constantly hiking up isn’t worth the effort and doesn’t improve your look. High maintenance clothes have their place, but only when the care is needed in their cleaning. And even then…


Fashion rules provide some women security but they shouldn’t prevent you from enjoying the process of getting dressed. Our clothes do send a message we need to manage but they’re also meant to be enjoyable. Life’s too short to not take a few risks. And fashion risks seldom prove fatal.

What style rules do you follow?

Thanks for reading and have a great day.


  1. Barbara Sullivan says:

    I do have a question about fashion rules. I have a handbag with bamboo handles. Does that make it a summer-only purse?

    1. A bamboo handle is a classic that’s popular year round. Gucci made the look popular and it’s not tied to a season.

  2. I love a crisp white button down, but I’ve always thought I look larger in a white top as I’m well endowed. thoughts? maybe add a silk scarf?

    can you recommend a good brand of white button down?

    love your site and suggestions!

    1. Talbots and Chico’s make very nice white shirts. Maybe a brooch or some fun earrings to draw the eye up from your bustline to your face.

  3. One thing I have learned during CoVid is that I love leggings. Only wore them fir exercises until quarantine. Throw on a long shirt and some sassy hells, ready for dinner. Colorful scarf? Sure. Funny jewelry. Go ahead. Thanks for the encouragement

  4. When I decide to paint our home my husband would say “why don’t you go put on some clothes you don’t like or don’t mind getting ruined?”
    My daughter would reply “mom doesn’t have any clothes she doesn’t like and why would she?”

  5. Great words to live by–I am guilty of saving things for a better occasion. No more–each day is a good day to celebrate! Plan to step it up often!!

  6. Love this! These are the rules I will now follow.

  7. How true, wise words I just love the comments, wear what you’re comfortable with!!!

  8. “Dress the woman you are now with respect and delight”. That is the best fashion rule that I have ever read. Thank you for that wisdom.

  9. Yours are wonderful and empowering! I take great offense to those who prescribe restrictive rules about what 50+ women should wear. You might as well throw a black shawl over me and park me in a corner rocking chair! I remember reading an article years ago saying women over 40 shouldn’t wear blue jeans. Seriously?! You can see this touched a nerve for me! Love it, wear it, embrace it! Life’s short, buy the shoes!

    1. Absolutely Janet. Can you tell I read a few “rules” lately that seriously annoyed me? We’re too smart for that garbage, unless we want them, which some women do.

  10. Absolutely agree with using and enjoying all the “good stuff” while we can. I have a beautiful gold locket that belonged to my great grandmother which I enjoy wearing very much. My mother was horrified that I regularly wear it to work! Why not? It has sparked many a conversation with people who have commented on it. I own cashmere sweaters which again I wear regularly, not saving them for the moths!! The only ‘rule’ I personally follow is to purchase the best quality and most comfortable footwear I can afford. Doesn’t matter how elegant the kit a face that is reflecting sore feet is never pretty…

    1. I love this Allison! The moths have consumed too many goodies I was saving. That one special coat they ate still haunts me!!! No more. I wear them now.

  11. I do not like style rules! In fact, when I saw your title, I cringed. Your rules, however, are packed with wisdom! How can we go wrong if we wear what we love, what fits well and what makes us feel beautiful and confident? I would simply add, above all, wear a smile!

    1. Thank you for sharing what I forgot to mention, Elaine. It’s all about our joy.

  12. Appreciate your comments. Way too much advice out there is always wear one color. Always cover your arms. Don’t wear prints. Well, I am in my 60s and no one is going to mistake me for someone in my 20s. So there are some wrinkles on my arms. There are a few things that are definitely not for 60 year olds, like no booty shorts or tube tops, but it would be a very boring life if I used all of that advice and looked at all times like I was going to a work meeting clad in black pants and a conservative solid jacket or sweater…

    1. All that advice serves some of us, but not most of us. If I listened to all the rules I couldn’t leave the house! I wear sleeveless tops all the time and don’t give a hoot who it offends. At 100+ degrees all bets are off.

  13. Kathleen O'Brien says:

    Oh my goodness! Yes, yes, yes, to all of it! The saddest thing about getting some of grandmother’s things was that they were pristine – I mean that she made them or got them and NEVER used them, she was saving them for “special”. So some amazing lace, dishes, and jewelry was never enjoyed by her or anyone else. Languishing in a drawer and boxes stored away. Wear those shoes, wear the jewelry, or pass it on in some way so it can have a life and you can too!

    1. I have similar things from my Granny. My goal is to pass them on to my daughter well used and partially worn out 🙂

  14. I totally agree with you, Jennifer! If not now, when? One rule I’m trying hard to follow is dressing to look my best everyday, not just on days when I’m doing something important or special. Even if I’m doing nothing more interesting than running errands, just catching sight of myself in a mirror or shop window has an effect. If I look good, it’s a big mental uplift. And if not, it’s a downer.

    1. I hear you Cathy. I think it’s easy to struggle with this one. It’s so much easier to grab something you don’t have to think about because it gets tossed in the washer and dryer. Going that extra mile adding accessories can make all the difference.

  15. Yes! Wear the best…eat on the fine china…drink from the crystal…enjoy each moment…completely agree! I do follow some rules which have served me well to dress the body I have…like a great fitted jacket with properly placed seams can make me look 10 pounds thinner! I loved What Not Wear…and it taught me a lot. Now, I properly apply some “rules” to my dressing along with my creative fun pieces…it works for me. I am one who needs guidelines to send the messages with my style I want to send and to portray confidence!

  16. I recently adopted the wear the best you have philosophy for even everyday errands. I’ve been surprised by the unexpected compliments I’ve received – and not from a well trained saleswomen. The positive remarks lift my spirits that I still have a stylish look in retirement. Love your blog and your ongoing transition into your next chapter with your husband.

    1. Bravo Chris! Wearing our best shines through and is a form of self respect that gets noticed. Thank you for sharing with us.

  17. Hi Jennifer,
    Style rules I follow are….
    Complimentary colours and using the guidelines I pick up thru blogs. The guidlines I personally like! 😉
    The blogs have made me think! Break out of my rut. I look at clothes differently and try new things.
    I’ve also come to accept my “middle roll” and dress accordingly. Hence, I’m happier!
    When I broke the jean mode this spring & summer, I wore looser, flowing cotton pants, I found them really comfortabl and so stylish. I’m curious to see if they follow into fall and winter.
    Regards…Robin T

    1. Way to go Robin! It’s all about using guidelines we like. Being dictated to, is old school, and frankly, I’m too old to tolerate that.

  18. Terrific advice, Jennifer! Over the past few years I’ve gained some weight. And while I’m in the process of trying to slim down some, I’ve learned that it’s just not worth it to try and fit into too-snug garments. I’ve come to terms with the size I am now — not the size I want to be — and purchase accordingly. Why be uncomfortable.

    1. Way to go Beth!! Uncomfortable is torture and we deserve better.

  19. I recently bought a black and white striped, sequin top and plan to wear it everywhere! Such great advice Jennifer! Brenda

  20. Wear the best you have…I have a habit of buying something nice and then not wearing it because I’m afraid of a stain. So true! I’m getting better at putting on that special top and even shoes!

    Goid points!

    1. I’ve been guilty of that too Pauline! Then I either outgrow the item or forget I have it!! No more! Wear it now.

  21. Julie Peachey says:

    Oh Jennifer! I just love you xxx you speak such words of wisdom. No pretence,I feel a genuine sense of sharing.

  22. Deborah wiltshire Whaley says:

    You are absolutely spot on Jennifer. Especially about wearing favorite clothes now not saving them for later. I feel that way about Crystal and China too. Oh not to forget let’s wear our goood jewelry too. I dislike the idea of age rules too. My motto is if it looks good and feels good and makes you happy then wear it. That goes for all ages. I know a few women of a certain age who can still rock skinny jeans and a leather jacket. Thank you for these reminders and as always you look stunning!

    1. Julie Peachey says:

      Love your comments and totally agree. Why save it? Any of it! Wear the things you love, wear the jewellery you love. Begat good will in Di hiding in your safe or drawer? And here’s a to…you think your kids might like it when you’re gone? Unlikely. They will either store it in a drawer, reset it or sell it! Sane goes for China and crystal you love. Enjoy. NOW????

      1. Julie Peachey says:

        Sorry, atrocious spelling and autocorrect ????

      2. Spelling and AutoCorrect are my enemies too Julie! Life is to be enjoyed now, not postponed for later.

    2. I know those women too and love to see them strutting their style! Life’s way to short to save anything! I’ve been going through the same process with my china and silver as well, use it or toss it is my new motto.

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