Why It Matters If You Would Wear It

Happy Saturday ladies and welcome to your weekend. Grab another cup of your coffee or tea and let’s dive in. I have some thoughts to share so please bear with me.

Yesterday’s dressing room diary brought up lots of comments that got me thinking about how we feel in our clothes. Several of you liked the way I looked in a blouse that was not in my style wheelhouse. It was a pretty blouse, but just not me.

Most of us dress ourselves to look good…but our ultimate goal should be to wear what makes us feel confident. And while we’re at it, remember that looking good, much like frumpy, is in the eye of the beholder.   What feels good to you is a very personal decision often shaped by judgments we heard in our youth or off-hand comments made by others.

A reader commented that she doesn’t wear classic white shirts because she has an issue about feeling masculine. I found that fascinating because I have an issue about feeling masculine too and am very sensitive about my broad shoulders. And yet, I love to wear the very white shirts that she avoids.

Is that a fashion disconnect? Nope. We both know how a white shirt makes us feel and it’s not a pleasant one for her. Bravo! She wins because she knows her personal taste and is listening to how clothes make her feel.

Should we stretch ourselves and try new things? Absolutely! But this is where your gut instinct comes in. Listen to it. Experimentation leads to growth, but be sure to accept what just feels wrong.

Jennifer Connolly of A Well Styled Life


Now I’ve pontificated enough so let’s get to would you wear it!

If you’re new here, each week my friend Pam and I share a mannequin we have photographed and ask if you’d wear what it’s modeling. Stores dress their mannequins to showcase new merchandise and inspire us to shop. We want to hear from you.

I also love you to share how you might style these pieces, either together or separately.


Sweater dresses have been popular all winter and their popularity is continuing into spring.

So what do you think? Would you wear this outfit? How could you style this to fit your shape and lifestyle?

Please share your ideas in the comments and inspire us to think outside the box.

Here are a few highlights from the weekend sales:

J. Crew – 30% off your purchase with the code SPRING.

Ann Taylor – 40% off full-price styles with the code WEARNOW.

  • this leopard print top is pretty neutral and would be fun with a pair of white jeans.
  • this marled turtleneck looks super comfy. The pale colors make it a great transition piece for when you want Spring to arrive but the weather won’t cooperate.

Talbots – end of season clearance with an extra 70% off all markdowns and free shipping over $125.


Now let’s go see what Pam’s mannequin is wearing at Over 50 Feeling 40


This post may contain affiliate links which won’t change your price but will share some commission.


  1. Angela Pea
    February 24, 2021 / 7:21 am

    Yes for the JACKET on the left! I have a very similar one in a heavy weight chambray purchased a decade ago and I love love love it! It has aged delightfully and is now in that sweet spot of super softness that happens right before the material begins to thin at the stress points. I especially like to style it over a dress/skirt (but not a sweater dress…not my cup of tea!).

  2. Elizabeth
    February 17, 2021 / 4:39 am

    New to this blog – what a fun idea! I like sweater dresses but am very particular. So much can go wrong! The length on both of these would be way too long for me (5’ 5”). Wide horizontal stripes on the left – absolutely not on my curvy, size 16, over-50 body. I like the stripes on the right one. They add interest without taking over.

  3. Kathleen
    February 15, 2021 / 3:15 pm

    Nope and nope. Didn’t have to think about either one. Sweater dresses are not for me… not for many, I think. And I don’t like those color choices. On to other mannequins 🙂 I love your posts by the way. Great blog.

  4. Kay
    February 15, 2021 / 1:30 pm

    I have never liked sweater dresses. The idea of a “sweater skirt” makes me cringe. It’s just another one of those weird little fashion tics I have, and I just go with them.

  5. Jill
    February 14, 2021 / 9:46 pm

    I would not wear either dress. I don’t wear dresses as not sure about shoes or boots and don’t like to show legs. These are too clingy for my body shape. But I love the denim jacket. However does not look good with the dress. Jill

  6. Deirdre
    February 14, 2021 / 3:08 pm

    I actually bought a chambray denim jacket last week…. almost identical just paler.

    Never wear horizontal stripes… maybe under a blazer when I was younger.

    The colors are interesting in that they are dusty sort of midwzy between pastels and darks…

  7. Sandra Matthews
    February 14, 2021 / 2:39 pm

    I think both these dresses are fun and would work beautifully on the right person. I prefer the pink dress on the right with stripes around the lower part, for me. I like the belt and would pair it with a jean jacket or leather Moto jacket and knee high boots for the winter, shooties or sandals for the spring.
    The dress on the left has a bit too much going on in the middle for me, but love the springlike colours. Again, I’d wear it with a jean jacket and shooties.

  8. MRSBEN2
    February 14, 2021 / 1:06 pm

    Though I do wear sweater dresses and like the colours in the one on the left; for my body type (slender) and height (close to 5’6″) I would pass on it. Reason; taking a cue from interior design the irregular horizontal stripes and marked vertical weave plus it’s length has a little too much going on for my personal taste. Whereas the dress on the right I would consider it but would prefer if it had a ‘V’ ( would add a long metal statement necklace) or even a ‘Cowl’ neckline (with a belt as an accessory). -Brenda-

  9. Sue H
    February 14, 2021 / 5:50 am

    Back in the day, when I was a size 0-2, I loved wearing sweater dresses. Now… umm…
    I don’t care for the colours or stripes in either dress. The jacket is too shapeless to really provide any sense of style.

    But I really wanted to comment on your musings. Confidence is always the most attractive thing we can wear. Size and shape don’t matter to a woman who steps out confident in knowing she’s rocking her style. And that’s all that really matters.

  10. Pink Azalea
    February 13, 2021 / 8:15 pm

    I like the dress on the left because of the colors. I wouldn’t wear either of them because it would require more shape wear than I would want to put on. I enjoy dressing, but when I am done I like to forget about myself. These dresses would probably make me feel self conscious about any lumps or undergarment lines.

  11. Lynette
    February 13, 2021 / 5:32 pm

    The dress with the stripes on the bottom I would pair with a brown leather short jacket and brown booties or boots. Each dress is not my colors but if I did wear it, that’s what I would do. The stripe dress is not for me. The color and horizontal stripes would be a disaster!

  12. Janey
    February 13, 2021 / 5:16 pm

    Nope I would never wear a sweater dress, I think you have to have the perfect figure (which I certainly don’t!) and wear the right underwear to look good in one.
    BTW – I love those pink earrings on your, they really suit your coloring.

  13. Jan2
    February 13, 2021 / 3:41 pm

    I wouldn’t wear either dress. I don’t care for the colors or the horizontal stripes, not to mention my days of feeling good in a sweater dress are long gone.

    A lot of our personal history goes into our comfort zone. I’m a redhead and an indentical twin, so I’ve gotten attention my entire life for the hair and the twin thing. I tend to stick with classics and add a personal twist (an unexpected color, a scarf, killer shoes or statement necklace, etc.). Like other reviewers here, when I do step out of my box, it’s usually short lived. Sometimes I’m resistant to trends that I call “not my generation.” I don’t wear ripped jeans (“deconstructed”), for example. Also, my generation didn’t wear clothing that outlined the cleave of our derriere. It was considered vulgar, so I can’t get my head around workout tights as pants. And having gone to Catholic school for many years, I’m still averse to wearing a pleated skirt with a 3-button blazer. But a moto jacket, wide-leg crops, a camo clutch, a pink trench coat … bring it on!

    • Jennifer
      February 13, 2021 / 7:58 pm

      Yay, Jan. I love your attitude.

  14. Nancy
    February 13, 2021 / 12:21 pm

    Sweater dresses do not look good on me, and I don’t care for the colors. They remind me of clothes from the 1970s-80s, which I don’t care for. Regarding wearing what makes you feel good, I agree. I feel best in classic, preppy clothes, while my sister wears flouncy, flowering clothes. On occasion I’ll let her talk me into trying her style, but I end up donating the item. Meanwhile, I know she’d look better in my style!

  15. Becky
    February 13, 2021 / 12:08 pm

    I appreciate your comments about wear what feels right for ourselves. Your clothes should give you confidence & make you feel attractive. Now, as to today’s dresses, they are a no for me. Neither would be flattering to my figure for several reasons.

  16. Penelope
    February 13, 2021 / 12:00 pm

    I think a very straight figured woman could wear either one and look attractive. But I have too many curves and I don’t like to emphasize them. In fact I find it hard to dress my petite, somewhat hourglass figure in the classic /casual styles that feel right for my personality and lifestyle but not my body type. Just as the woman in the comments who doesn’t like wearing clothes that make her feel masculine, I don’t like clothes that are ultra feminine… and accentuate all these curves. I don’t like the attention it creates. Getting back to the featured outfits today, they would make me feel too visible and very uncomfortable.

  17. Janis
    February 13, 2021 / 12:00 pm

    You make such a good point about wearing what makes us feel confident. I can’t tell you how often I’ve really, really tried to like something that I think I “should” wear, but it never felt right. If you don’t feel confident in what you are wearing, it shows… even in the way you walk.

    Oh, and I love your hair in the picture of you with the coffee mug. I have taken pictures of you to my hair dresser (back when I visited salons) and said, “I want THAT!”

  18. Francesca B.
    February 13, 2021 / 11:55 am

    I really resonate Jennifer about your thoughts on listening to your gut instinct. A couple of days ago I found a Badgley Mischka Sleeveless Floral Shirt Dress in the blue colorway in my size in the clearence section of Nordstrom Rack for $67.00 and i quickly pounced. So it has arrived and I am just not sure i can wear such a stong pattern and being 57 whether the dress is for a younger woman? So I am listening to my gut instinct but equally I know its a real bargain and with the right accessories it could be a winner for the warmer months. This is going outside the box of my usual look. So I am thinking….
    I quite like the striped dress on the right:) Thanks for the fun!
    Happy weekend!

    • Jennifer
      February 13, 2021 / 8:02 pm

      If the pattern feels too strong, work your way into it by adding a solid cardigan. It sounds like a pretty new look.

      • Francesca B
        February 13, 2021 / 9:09 pm

        Thank you for the suggestion. It is growing on me now and l am going to keep it. Everyone likes it and this is the year for re invention and living!

  19. Linda Todd
    February 13, 2021 / 10:37 am

    I would wear the dress on the right if it was in a different colour. This pinky mushroom cour would never suit my coloring, and just as importantly I really dislike this color. The dress on the left with its all over stripes and ribbed effect would highlight mystery broad shoulders and straight hips and of course the ribbed style would highlight any tiny lumps and bumps made by my underwear. I could go knickerless and bra less but no maybe NOT.

  20. Patricia
    February 13, 2021 / 10:28 am

    I wear dresses much more than I wear slacks…..both summer and winter. I like how they feel and how I feel when I wear them. I’m 77. I’m 5’1” and weigh 95 lbs. but even though I am small, age has left me with a few lumps and bumps…..mainly in the tummy area! I love these sweater dresses but the wide stripes on the first model would look fine on me if they were vertical instead of horizontal. The second dress would only shorten me with the stripes at the bottom. I have several sweater dresses. They are in plain colours and are not skin tight. I usually size up when I buy them so they look stylish but skim my figure rather than hugging it. As well, I like them above my knee. The jacket doesn’t flatter as it is too long and rather boxy. I think a short Jean jacket would look better.

  21. Joanna
    February 13, 2021 / 10:26 am

    I don’t like either sweater dress. The stripes are what bothers me. I much prefer a solid sweater dress and one that skims the body, not hugs.

    I have to say you look radiant in your picture today. I think the pink earrings add instant blush. You have a wonderful smile, Jennifer.

  22. beth byrd
    February 13, 2021 / 10:07 am

    I wish the dress on the left were paired with a shorter more fitted jean jacket. Although the jacket shown is nice, to me it doesn’t do anything for the outfit except make it look a bit sloppy.

    As for both sweater dresses, I might wear either one if they were shorter. I’d pair them with tights or leggings. I’m by no means tall or thin, but the look might work for me in a shorter length.

  23. Lin
    February 13, 2021 / 10:07 am

    I love the “Manikin Day”.
    Back in my 20’s I owned a striped sweater dress that look wonderful. Today It would not.
    I would try the barn jacket. That is my style today. Comfort and hides a multitude of sins.

  24. Dianne
    February 13, 2021 / 10:05 am

    I would have to say a big No to both dresses. Not attractive to me at al, the blue Jean jacket is really not suited, I think, to that dress. Wish these stores would find clothes more appropriate for women our age snd not for a much younger woman. Just my opinion Jennifer. Have a great weekend!!

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