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How to Style One Dress Eight Ways

I am joining my pal Jennifer from a Well Styled Life for our Monthly Over 50 Style Edit. Let’s chat about how to style one dress eight ways.

I ordered this fabulous Vince 3/4 sleeve Dress. I chose this dress because the reviews were great and I loved the cut. I was not disappointed. One reviewer commented that she pulled it out of the box and said this is going back until she tried it on. I completely agree. I am in love with this dress and it could easily be a season spanner. I am wearing a small , and it fits perfectly. It is nearly a maxi on me and I am 5’4. I might have it hemmed if it bothers me. Here I styled it simply with a simple scarf, a Gigi Pip hat, and my combat boots. It would be great with the H&M jacket that I featured in my post on How to Nail High and Low Fashion. I am wearing it over my shoulder so you can see the cut of the dress


Here I am wearing the beautiful Pendleton scarf that I featured in my Outfit of the Week a few weeks back. I am wearing my inherited treasure necklace, other native American accessories, and my Bedstu boots with my Wren Gigi Pip hat.

cindy hattersley wearing pendleton scaf and native american accessories


Another “outside the box” way to style it would be adding a sweater vest for a casual everyday look. I purchased my vest locally at Andbe Boutique, but I have linked a similar extended-size version from Asos, and one from Madewell. I layered two necklaces (one from my pal Mary Ann), and old coin accessories. All or similar are linked below photo.

cindy hattersley in vince dress and vest


I am styling the Vince black dress here with the Lysse Charlotte Sweater Wrap. If you use the link and code Cindy20 you can get 20%off. I am wearing it with a fun hat from Andbe from Kooringal, and my Bedstu boots. You can see the same wrap styled in this post How to Pair Black and Brown.

cindy hattersley in vince dress and Lysee Charlotte Wrap


I love this silver moto jacket from Chicos (found on ebay), (there are several on ebay here ) with the Vince dress for a different look. The hat is from Janessa Leone which I found on Poshmark. I am wearing a necklace from Paula Carvalho.

cindy hattersley in vince dress janessa leone hat


I am loving the Vince dress with this great jacket from Lysee. If you use my link you can receive 20% off your order with code Cindy20. I am wearing it with a great leopard scarf from BR (no longer available but similar linked below the graphic). You can find this coat styled differently in y post Travel-Friendly Pieces you will Love.

cindy hattersley in vince black dress with Lysee jacket


I am wearing the Vince Dress here with one of my favorite Johnny Was pieces (the Jenny Kimono (on sale)). You can see this kimono styled independently in my post Easy Tips to a Collected Look in your Wardrobe. I am wearing it with an inherited native American turquoise necklace, earrings that were a gift from my husband, and Native American bracelets (also a gift from my husband). He has gifted me most of my collection over the years for birthdays, anniversaries etc.

cindy hattersley in johnny was kimono


Lastly, I am styling the Vince dress with a great leather blazer from Sundance (a gift from my daughter a few years ago), a leopard belt, my comfy gentle souls Emma suede boots (on sale), and an older J Crew crossbody found on eBay. You can find several of the bags on eBay here.

cindy hattersley in sundance leather jacket with vince dress-one dress eight ways


Whew! That was a long post. Do you have a favorite look? I would love to hear about it. I can’t wait to see what Jennifer is styling for us today. As always, thank you so much for being here. Let’s pop over and visit Jennifer to see what she has for us.


Reader Interactions


  1. Beth says

    Today’s post was exactly what I have been looking for, Last year I purchased a black faux suede dress and your post has showed me some great and more casual ways to style it. I also feel that some of these looks can translate to black slacks and a black roll neck. Thank you, Tomorrow I will Shop my Closet and find some new looks,

    • Cindy Hattersley says

      Hi Beth

      I am so happy to hear that! You are absolutely right many could easily transition to an all black pant look underneath.

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  2. Nancy Brantley says

    Again, you are so chic in everything you put together!! But…I’m not sure the sweater vest is your style?? Dress and vest looks too straight instead of showing waist sillioutte. If you have nice figure at our age I think straight looks are not for us.

    • Cindy Hattersley says

      Hi Nancy

      You are right. I rarely wear anything straight up and down because the biggest part of my body is the bum!

  3. Barb L says

    Love each look. What a great piece the dress is, and thanks for all the variations in styling it! I’m drooling over your turquoise pieces and the Johnny Was kimono. Great post Cindy!

    • Cindy Hattersley says

      Hi Barb

      Both of those necklaces I inherited from my mother-in-law. Her hobby was buying dinnerware and turquoise jewelry. I also have a very heavy concho belt that was hers. There was also plenty to pass on to the girls in the family as well.

    • Cindy Hattersley says

      Hi Maeve

      Thank yu so much. As I said both of those necklaces I inherited from Steve’s mother. I rarely wear anything big like that. Everything needs to be kept to a minimum for me to pull it off. Steve’s mother was more like the Contessa when it came to jewelry more was more!!

  4. Katherine says

    Hi Cindy,

    You look fab-u-lous in everything, but you always rock all your looks. I can see you modeling for Sundance in your spare time.

    • Cindy Hattersley says

      Hi Katherine

      Thank you so much. I do love Sundance but they definitely have not “come a calling” ha!!

  5. ~ Mrs. M. ~ says

    ~ Cindy H.: In photo 7, I love the turquoise earrings you’re wearing. Are they by Oscar Betz? ~

    • Cindy Hattersley says

      Hi Mrs. M

      They certainly are. I own the pin that matches the earrings as well. Love his work and boy has it gotten expensive!

  6. ~ Mrs. M. ~ says

    ~ Cindy H. I forgot to add that I’m referring to the Pendleton Womens Oversized Featherweight Wool Scarf you’re wearing in the first photo. I’m also glad to know that you love hats just as I do. Living in the WV mountains this time of year, wearing a hat is a must. My preference is a cowgirl hat, which I wear year round. It’s also the perfect accessory to compliment all my outfits. ~

    • Cindy Hattersley says

      Hi again

      I love that scarf too, it is beautifully made. I am a convert to hats. I never used to wear them but now do year round!

  7. ~ Mrs. M. ~ says

    ~ Howdy Cindy H. I admire your personal style. Here you are again, rockin’ one dress many ways; with the “backdrop” in red, my favourite colour. Talk about longevity and CPW (cost per wear)! And that infectious smile of yours makes all your outfits shine. Cheers! ~

  8. Mary Ann Pickett says

    Wow…I am going to order this dress! I will of course have to hem it. Thanks for all the creativity~

    • Cindy Hattersley says

      Hi Mary Ann

      That dress would be adorable on you and it would be a great weight for Florida.

  9. Jennifer says

    What a fabulous dress! It’s such a great chameleon in your wardrobe. I love all your outfits but with the kimono is my favorite!! Bravo, you knocked it out if the park this month.

    • Cindy Hattersley says

      Hi Jennifer

      That dress is a winner! You never know, but I think it would be flattering on so many different shapes.

  10. Annie Diamond says

    WOW! Cindy, you have just proven that with the right accessories, you only need one dress! Every look is completely different, but equally as gorgeous. The vest over it is so unique and with your combat boots…you rock these looks!
    Love the hat too!

    • Cindy Hattersley says


      I was channeling you with the vest over the dress. I was trying to think what would Annie do? How did I do…a bit of the Annie look?

  11. Dianne says

    OMG you look stunning intuit dress. I especially los the last outfit with the belt and leather jacket – super cute! You can totally rock to maxi – I WISH i could.
    thank you for the inspiration

    • Cindy Hattersley says

      Hi Dianne

      Thank you so much. I love that jacket because my daughter gave it to me for Christmas the year Summer was born for taking care of Summer. I will always treasure it as it was such a thoughtful gift.

  12. Karen Wisn says

    I completely see why you love this dress …. I’d love to get one just like it but alas, it only comes in black. I’m an autumn in my color wave and am drained of all color wearing black. 😕 I’ve vowed not to add anything black to my closet. So many of you wonderful women with posts show black so consistently. I try to think brown when I see black! Sarah London helps me here. Thanks for your creative posts.

    • Sarah says

      I’m with you, Karen. It’s the perfect dress, but as a “spring” I look terrible in black. Still, wonderful to have Cindy give us all these great styling ideas! I’ll keep looking for something similar in navy or camel that I can adapt.

      • Cindy Hattersley says

        Hi Sarah

        I totally understand about black. I try not to “always” wear black. I can imagine how hard it is to find some of your best colors this time of year!!

        • Sarah says

          Your ideas are always inspiring and can be adapted to any pallet. It would be helpful if designers and retailers would offer an item in both warm and cool colors. That would solve a lot!

    • Cindy Hattersley says

      Hi Karen

      You know it is funny that you mention brown. I just did a post recently on black and brown. I look terrible in brown for the most part, but try to wear it for you ladies because I know not everyone looks great in the same colors! So sorry that the dress does not come in other colors. It is a wonderful dress that can span the seasons.

  13. La Contessa says

    Good job!I just pulled a Maxi black dress out of my closet to see if I can wear it!
    Hope to pull off a festive look this weekend,
    I shall play today and see what happens,

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