Petite Challenges

Happy Tuesday, ladies. I am back today with another collaborative post with a few blogger friends. We decided it would be fun to challenge ourselves to style something we each thought we would never, ever wear.

Last month, Cindy Hattersley and I styled eyelet here …which was a first and last for me. As cute as some of the looks were, the eyelet is just not my style. I don’t feel confident wearing it, and that’s an important criteria for me.


This month, Cindy from Cindy Hattersley Design and I are joined by my friend Susan, who writes une femme d”uncertain age. I’m sure most of you follow Susan, but if you don’t, you are in for a treat. It was surprisingly easy for us to agree on which garment to style. We are all petite, and none of us wear caftans. I’ve long admired the look of caftans on other women, so game on!

jennifer connolly wearing emerson fry caftan

Caftans make great bathing suit coverups, but I seldom go to the beach or pool, so I bought mine to stay cool in the beastly heat we get during the summer. This one is from over 50 fashion blogger wearing enerson fry caftan

The challenge with a caftan is not having it make you look much larger than you really are. All three of us are petite so that posed an issue too. Most caftans are also made with printed fabric, which I seldom wear.

petite over 50 blogger jennifer connolly wearing blue caftan

When the temperatures go crazy here, nothing but loose cotton or linen will do. Even when I hide in the AC, I need loose, loose, and looser and took a chance on this one because I adored the color.

My husband is not used to seeing me in this shape so he kept saying, “couldn’t you belt it or something?”. I think that would defeat the whole airy and cool purpose so I just let it flow.Jennifer Connolly of A Well Styled Life wearing emerson fry caftan

Most caftans are made from very sheer or semi-sheer fabrics so you need a slip. I knew a polyester slip would defeat the whole purpose of wearing something cool so I ordered beautiful blue caftan on midlife blogger Jennifer Connolly

Was I able to prevent this caftan from making me look larger than I am? In a word, no. But when our temperatures are muggy and sweltering, there is nothing comfier than a light cotton caftan.

No one in my family thought this caftan was flattering on me, including me. But here’s the thing… I feel confident wearing it and it has a distinctive purpose so I will happily wear it all summer.
jennifer Connolly wearing emerson fry caftan

Now, let’s go over and see what Susan wears her caftan. I have a feeling she will knock it out of the park. Then come back so you go over to see how Cindy styles hers.

Do you love caftans? Do they evoke and stylish age when women dressed to impress and drama was the name of the game?

Be well, be kind, and wear what makes you feel confident.



  1. I think the caftan looks great on you! The color and print suit you well. I would wear this. Of course it looks best with the small heels. I have a linen dress I wear in hot humid conditions, such as while on vacation in Mexico; I have a great hat that goes with it. I don’t comment very often, but love your posts and everyone’s comments.

  2. Patti Fitzgerald says:

    I’m thinking that caftans prompt a love/hate relationship . . . love the billowing and cool breeziness of them, hate the way they add the illusion of about 30 pounds to my frame! I have a maxi dress that fits into this category, and I’m toying with the idea of a loose belt around my quickly disappearing waist. But I will say . . . when I’m going to be in a hot and humid environment, my personal comfort will win out, every time!

    1. I totally agree Patti! Beastly, humid heat calls for comfort.

  3. “Some one MUST find me a Cessna Citation IMMEDIATELY since there is NO WAY I’m getting on that wide body 767 !!! It makes my butt look HUGE !!
    Ladies, ladies… get a grip. Caftans are garments to cover your privates. What matters is how you feel. Nothing binding, nothing fussy, naked but decent.
    Jennifer, you look like a radiant, svelte woman who happens to be wearing a voluminous, airy, indulgently comfy garment. Please, let us not judge each other on apparent size. Why do women want to be small ?

  4. The only one I think I could wear is the black or navy lineny looking one that Cindy is wearing in the last two photos of today’s post. I couldn’t find any info on brand or where to buy. Can you tell me?

  5. Hey, Jennifer, you look just fab in that kaftan. So cool and comfortable and just as I would like to look in one myself. I am totally with you on this one, being a little lady myself and a similar age. Waft away and don’t you be put off by ANY comments that are not entirely complimentary! Very charming necklace too. X

    1. Thanks Rowena, no comments have deterred me from loving it for what I bought it for..100+ degree days and lounging at home. Xx

  6. Anne from the UK says:

    I’m sorry but I agree with your husband. A belt would have helped . However something that made me look huge would not get near my body no matter how cool it makes me feel .A beautiful women such as you Jenifer must never look frumpy!!

  7. Sandra Sallin - Apart from My art says:

    OK, you convinced me. I’ll buy one for wearing around the house. Not in public. Of course, no one sees me anyway these days. But I can see it being cool for the hot weather.Let’s face it La Contessa is the only one who looks fabulous in a caftan. But then again we all need to be 5’11!

    1. Lol, you’re so right. I didn’t know she was that tall!!

  8. Elizabeth says:

    The colours, smaller print of the caftan suit you well. Love that necklace!
    But (sorry), the boxy cut is not flattering. You have a nice trim figure & I’d suggest shortening this caftan to slightly above the knees and wear it with very slim white leggings, capris, and/or cropped pants and casual sandals.

  9. Love the caftans. I bought two in Sri Lanka last year which fit perfectly. I’m 5’0″ so that is challenging. I guess the women in Sri Lanka are generally shorter, so I was happy to find these comfy dresses. I usually wear them only at home lounging on the deck, but I can see them making their way into public on a hot day. Mine are a bit wider, but sewn most of the way down the sides about three inches from the edge, adding to the flowy look, and giving a sense of sleeve. They also have a drawstring just under the bust which draws the garment in, but since it doesn’t carry on all the way around the dress, as part of the drawstring goes inside the dress. Hard to describe I find as I try to do it.

    You look cool and fresh Jennifer. I love the cat heel sandals too – where are those from?

    1. Linda Root says:

      The drawstring on mine helps the silhouette a bit, too. I do appreciate the drawstring is partially hidden. I want another caftan because the colors are so fun! I look for vertical lines within a print.

    2. These sandals are about 15 years old. I seldom wear them so they’ve lasted a long time.

  10. I have several caftans I bought recently. They are perfect for wearing around the house, much cooler than pants and a top. I like prints, and the choices are endless.

    1. They’re a great alternative to leggings and a tee when you’re hanging out at home.

  11. Elaine @ Following Augustine says:

    The colour and the pattern look good on you and the caftan looks very comfortable, but I agree that it’s not the most flattering shape for you. Great for relaxing in on a hot summer day though. I haven’t worn a caftan in about 40 years, but this morning you three have me thinking that maybe I should be looking for one or two!

  12. I have issues with caftans too. The one shown here is a bit big on you but the neckline and shoulders fit well so this is a good look for a very hot day. It also helps that the color +print are flattering.

  13. I had a caftan once. It was very long, almost touching the floor. I really liked it for wearing around the house. The blue color looks good on you but the way it is cut makes it look too big! I think if the top was more of a butterfly wing instead of short sleeves, it would appear as more slimming.

    I loved the bright colors of the second lady but hers was so short it appeared as a large top, not a caftan. Still I loved it on her with the pants.

    Caftans are to me, a very important part of any gals wardrobe! They never go out of style either!

  14. I think you look great in that color of blue print plus that necklace is just right. This was an interesting topic especially for petites. Thank you. I haven’t felt comfortable in caftans since I felt they overwhelmed me.

    1. I think this overwhelms me but for very hot weather, I’m ok with it.

      1. Jenn you look great. All the accessories perfect. By the looks of how it looked on you, I think all you need is to go smaller size or have it altered to fit your body frame I’m only 5.2. I loved it & think you for posting it. I live on the coast just south of Galveston where caftans are a must 👏

      2. Thanks Kathy. I love Galveston. Such a special place and the water is beautiful. But humid!!

  15. Seems we all agree those long voluminous ones do not work on our frames. You look so great in blue. You picked a doozy this time my dear! And Gail try Anthro and J Crew they often carry talls.
    I have a caftan that I wear as a swim cover-up that I love but it is more tailored and probably not a true caftan either. This was fun!

  16. Karen Mathewson says:

    I really love this caftan on you, but it looks big on you. I was wondering if you could have a seamstress take in the sides for a slimmer look. The blue pattern looks so stylish on you!!

  17. I think you look cool, comfortable, and confident…..and I love the color and pattern on you!

  18. LA CONTESSA says:

    IT will definitely work in the HEAT of the SUMMER!

  19. I lived in caftans in the 60’s, but I’m really dating myself!My favorite was from Bobbie Brooks and was a monet like print! I remember magazine spreads of ” the beautiful people ” all lounging around.

  20. It looks cool and comfortable but I would not wear it in public. The color is very nice.

  21. I honestly cannot wear caftans! I am just too large and they make me look even larger! I also have that problem with linen tunics , but I do wear them.

  22. I think the caftans on you two look great. I’ve always wondered about them but have never tried one on. At 5’1 I would try a shorter one with slim pants but I still don’t know if I could pull it off. I’m short waisted and even the loose tops everyone wears are sometimes just too wide.

  23. Susan Blakey says:

    I really think it looks smashing on you, Jennifer! What works is that the print is small and repetitive so it doesn’t overwhelm you. And I to be honest, I don’t think it makes you look bigger either, because you’re not completely covered up.

    Thanks so much for inviting me to participate. I had such fun and found a way to wear a style I’ve been wanting to try forever.

  24. You addressed a lot of the same concerns that I ponder when dressing a more petite frame on hot, humid days. Yes, to loose cotton or linen fabrics that allow air flow. The shorter the body, the more risk there is of creating a blocker look. The hot weather will not embolden me to throw all sense of modesty out the window. That being said, you look very cool and confident in your choice of hot weather clothing! The color is beautiful and your accessories are spot on. Even the small detail of wearing a slip adds to your entire look of confidence.
    I find it a real challenge to maintain my personal confidence while dressing for comfort during the summer months. You offered me a new option to consider!

  25. Hmmmm no. I have tried them and always feel they are wearing me instead of the other way around. You look beautiful in that color and I think you pull it off but I’ll bet a cute loose sundress would be better and just as cool. I like it that you give us different looks to consider. It’s fun.

  26. You really spoke to me on today’s blog. I have a flowy caftan from 20 years ago that I wear over jammies when I want my coffee on the patio. I don’t care how it looks on me because I enjoy it, but I would never wear it in public. At 68 I’m 5’3” and not slim. I don’t wear long skirts or maxi dresses for that reason. They always look like I’m in my nightgown.

  27. Great post Susan! At 5’ 4” I don’t think a caftan would be my most flattering look. However, you did look comfortable, fun and confident. I think I would try one in a fun summer print. And, a caftan would be great in our Florida heat. I also think loose clothing for heat.

  28. This was an interesting blog and reinforced my belief that at 5’1”, craftans are not for me! (So much fabric, so much volume.)

    I do think that the shorter ones with slim pants or the closer to the body ones are more flattering, though, so I might try one of those craftans. Thanks, Jennifer. That was fun.

    1. I agree, the shorter ones are much more flattering. I also prefer straight ones to full ones. I may need to see one to get just what I want.

  29. Christine Smith says:

    Hello Jennifer, I think that the caftan looks great on you. I now that it is not the usual shapes that you wear, but, as you said it is loose and comfortable in the sweltering heat. The colour is beautiful on you! BTW, the eyelet shirt looks fabulous! Like you, I am not much of an eyelet girl, but I think that the reason that you do not feel good in it may be because in my opinion, eyelet fabrics tend to be scratchy as opposed to soft to the touch. Love your blog!

    1. I think the eyelet may also be too feminine looking for me.

  30. I love your blog and always enjoy the things you post, but do you have any suggestions for fashion bloggers for older, tall ladies?? I am 5’10” and thin – and in my 60s. Items from Ann Taylor, Talbots and Chico’s are often too short and “square” for me.

    1. I know this blog is about petites, but to Gail, yes I am 6’ and 61. Try J Jill and Gap. They carry tall. WHBM also cut nice and long!

      1. Don’t forget Old Navy. I ordered some tshirts recently and accidentally ordered one of them in a Tall. I had never ordered Tall before but was pleasantly surprised that it’s a nice tunic length (I’m 5’ 8”).

    2. Banana Republic and J Crew also have tall clothing. Ann Taylor and Loft carry a few as well.

    3. I’ll hunt around but do know Loft and JJill also carry Talls.

    4. LA CONTESSA says:

      I have TALL sources for YOU if you want to use the link on Cindy’s Blog to me…………send me an email!

    5. Gail, I Have the same issues, 5’ 9”, slender and 67 yo. I would love to find a blogger who addresses this demographic.

    6. Gail, I am also on the tall side at 5’9” and am curvy. Land’s End is another great source for tall sizes, especially swim wear and sun protection clothing.

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