The New Style Essentials for Women

Are there really style essentials every woman should have? I think so but mine are different than they were several years ago and likely different from yours. Having the “right” handbag was important at 31 – at 61, not so much.

Jennifer Connolly of A well Styled life wearing classic cashmere and hounds tooth from Ann Taylor
SWEATER | PANTS similar | SHOES similar /

Here are a few essentials that I believe are universal and help all women feel good about themselves.


It’s crucial to wear clothes that fit our bodies, well. Clothes that bunch, bind or dig in, aren’t doing you any favor. Only wear clothes that feel comfortable for the body you have today…not squeezed into something that fit 5 pounds ago. Put them away and wear what fits now. If you need to buy clothes that fit, do it. You deserve it!

Jennifer Connolly of A Well Styled Life wearing Everlane cashmere
This sweater is soft and loose so is perfect for lunch, laughter, and knitting with my peeps. I added the scarf because I didn’t want a necklace to catch on my project but feel undressed without an accessory.


It’s essential to wear clothes that make you feel good, emotionally. Many garments are utilitarian and serve as basics we build our outfits around. Whenever possible,  reach for things that make you happy. Whether it’s an accessory or pretty lipstick, choose things that make you feel good and as close to happy as you can get.

Jennifer Connolly of A well Styled Life wearing Ann Taylor pants
This knitting bag is getting shabby but it still makes me happy. I made it using handles and a French Grain Sack that I bought on a trip to Provence. There are great memories wrapped up in it.

Wear What Sends the Message You Want

Our clothes tell the world who we are so you need to choose ones that send the right message. If you’re not confident you’re outfit is sending the right message, step back and examine why. Is it more somber than you are? Sexier than you like to portray? Frumpier than you want to look? Check your image in a full-length mirror, from all sides, and ask what message it sends and how you can fix it.Jennifer Connolly of A Well Styled Life wearing Everlane Cashmere and Ann Taylor Hounds Tooth

We need to dress to please ourselves in our changing bodies. When I needed the larger size in these pants, I didn’t hesitate to go up a size. It’s only a label and I refuse to let a number on a garment tag define how I feel about myself.

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What are some of your style essentials? Please share below.

Thanks for reading and have a great day!


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  1. Jennifer, had a computer crash and cannot find the piece you wrote about purses: that is, carrying one large purse (but lightweight as possible!) like a mini tote but having a smaller purse on hand to put keys, lipstick, compact, etc., to use to run into the restaurant. If you could identify that post (perhaps by date or title by which is was “styled’), maybe I could retrieve it. I am in major need of a larger purse that is not heavy leather!! Thank you for help, and a Merry Christmas to you!

  2. I live in dresses (during summer) and wear flat sandals or shoes with them and somehow haven’t been accused of looking frumpy. It is far too hot (in Adelaide, South Australia where I live)for trousers/jeans and being short waisted find it tricky styling tops with skirts as the tops are generally too long or swamp my hour glass figure. Even though my arms aren’t great, I wear sleeveless dresses, because I feel that now I am 60 I can throw ‘caution to the wind’. My next confession will be probably shock some, but I also wear gym type clothes to the shops as I walk everywhere most days – up to 15 kms a day (when cool enough). I am afraid comfort and practicality win over style in this case. Good news is, my fitness level has improved and it is much easier to maintain my weight. Haing said all that, I do love your blog and fashion advice for the days I decide to smarten up my act.

    1. Good for you Susan!! I need more excercise and walking would be the simplest way. Hourglass figures are frequently overwhelmed by tunics because they don’t show your shape. A loose belt can help if you like them. I agree about the arms. If it’s hot, I throw caution out the door too. I am what I am and not ashamed to be comfy.

  3. Great read and you always reinforce what I’ve always believed – “if you look good you feel good”.
    My style essentials are:
    good undergarments,
    comfortable clothes,
    tops that flatter my hair and skin,
    tops and bottoms that can be mixed and matched,
    accessories that draw the eye to my top half and my face,
    light makeup and lipstick always when I go out.

  4. Thanks for the encouraging words about not letting the label (size) define how one feels about oneself! Needed to hear that as a certain medication has caused weight gain and now hate to shop for clothes that fit properly–not in the size I’ve always worn!

    You always look so “put together ” and so appropriately and prettily dressed; I especially like the outfit you have on in these photos! Love your blog and all the great advice!

  5. Totally agree with you on fit–wearing clothes that flatter my figure is key. Also, wearing clothes that are harmonious with my coloring is the biggest game-changer for me–ensures that people see me first and then the outfit! And equally key are clothes that match my energy/seasonal style. I look best when I am my most authentic!

  6. Hi Jennifer! I wrote something my iPad decided to gobble up, so I apologize if my comments appears twice. First, I wanted to say I was very happy and relieved to see a post from you and to know you are safe from the terrible fires.

    I totally agree with Kathleen above who spoke about wanting to appear youthful and not young. To me, it seems a bit sad to see a 60 year old trying desperately to hold onto the look of a 25 year old. At this point in my life (65) I want to come across as timeless, classic, and elegant. Think Audrey Hepburn or Princess Grace. I have 2 dilemmas at the moment. First, because of my broken heel and now the other broken leg, heels will never be an option. I’ve given up wearing dresses for the most part because I just feel frumpy wearing flats with them. Second, if you or your dear readers have any suggestions for bras with lift, I would love to know about them. Even though I am not terribly well endowed, gravity gets us all! I think that contributes to an aged look.

    PS I have never thought anything you wrote sounded dumb! And I love your knitting bag and the story behind it!!

    1. I agree with Kathleen too. I’m so sorry to hear of your challenges. I’m also the most comfortable wearing flats and admit I avoid wearing dresses with them. I am determined to do away with frumpy so will try to find some looks to share here that make them wearable. Stay tuned! Xx

  7. My essentials have changed so much in the last five years. I agree with you that it can change over time and when we enter into different stage of our lives. I guess there are some things…like great fitting jeans which will always be an essential for me.

  8. My style essentials are pretty much what you described, comfortable is key these days. I’m not exactly the size I want to be, but I dress the size I am. As I’ve gotten older, I’m way more particular about fit, not too tight or even too loose, nothing poking or prodding me. I’ve also found I’m become more modest, I don’t want to show too much or having anything creeping out of necklines or hemlines. I like things to look clean and modern and youthful without being too young and “mutton dressed as lamb”. I also like to look well put together and appropriate for the activity.

  9. Jennifer, I have never commented before but have followed you for some time. Thanks for these useful tips. I never had any sense of style as a young woman but as I got older I realized how important it is to feel confident about my appearance. You have helped me more than you could imagine as I am a very minimalist, throw-on-something-and-run-out-the-door person!

    1. I’m so happy to hear you’re getting some inspiration, Janet. It’s easy for many of us to just toss on and go, but that little extra effort goes a long way to make us feel better and in turn be treated better by others. Thanks for reading!

  10. I feel a lot more comfortable wearing clothes that fit. I wear petite sized clothes, especially on the top, I’m a pear shape, size 4P, 5’ 5” small shoulders, chest and back with short arms, and over 60. Finding coats is getting more difficult, as the stores are carrying less petite clothing, and I can’t try them on. The merry go round of ordering, trying, returning, is getting tiresome. Could you , or your readers, recommend any brands? That would be SO helpful! Thanks so much for your blog, love it!

      1. Have you tried Talbots? They have a large section in the store I visit and carry petite sizes on line and in their catalogs.

  11. I totally agree with everything you said here Jennifer!!
    It always amazes me how many of my friends say they aren’t going to buy any clothes until they lose weight. But that doesn’t make you feel good about yourself and seems silly to me!!

  12. Comfort
    No cleavage
    Lady parts covered by tunic or top
    No tights without a tunic
    No gym clothes on the street
    A scarf to keep my neck warm and add colour
    Coordinated colours
    No designer labels showing if possible
    Keep it simple
    Good foundation garments/bra and panties
    Few patterns/ prefer plain/checks, stripes,polka dots
    Look to overall silhouette to creat long line
    Cross body bag to leave hands free
    Hat that covers my ears in winter

  13. Hi: I loved today’s post especially not letting a label and number define how you feel about yourself. I know I forget that every company’s size 10 is not the same. I’m taping this to the full length mirror in my bedroom as a daily reality check for myself. Thanks.

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