Would you Wear It? Dresses with Sleeves

Would you Wear It? Dresses with Sleeves

Happy Saturday ladies! With temps topping 90 last week I have been hunting for more casual dresses. The longer I look, the more I ask myself why designers make so few dresses with sleeves.

Welcome to this weeks Would You Wear It? Each Saturday Pam of Over 50 Feeling 40 and I share a mannequin we’ve spotted and asked if you would or would not wear it and most importantly…why.

Eileen Fisher dress with sleeves on A Well Styled Life

I ran across these two and wondered…would you wear it? Why or why not? Please share below.


With so few options in the stores, I hunted around online and found Soft Surroundings had a large selection.

Dresses with sleeves

Now let’s hop over to see Pam’s mannequin here.

Thanks for reading ladies and have a great day!


Affiliate links within this post may generate income for AWSL.



  1. Yvonne
    June 9, 2018 / 3:49 am

    I like both dresses, although I feel the one with stripes has a younger vibe and I would feel silly in it – I probably would have worn it in my early 50’s (I’m 64). The pink one looks like it would be really cool and comfortable, and at 5’7″ I could wear that length. I would wear with wedge sandals and an artsy necklace.

  2. Janet
    June 9, 2018 / 3:56 am

    I’m a huge fan of this shade of pink so that’s a bonus. The solid pink dress is unfortunately too shapeless for me. At least it has sleeves. The striped dress is better for my pear shape wirh short sleeves and a bottom half that falls away from the body. The colour is a bit boring for me but would work with colourful accessories.

  3. cindy
    June 9, 2018 / 3:56 am

    Well, the pink dress just looks like a plain sack so that would be a no. The black/white dress is cute, has a younger vibe but I would consider wearing it.

  4. Janet
    June 9, 2018 / 4:08 am

    I just saw the Soft Surroundings dresses. I really like them! They seem to understand what works with womens bodies!

  5. Dianne Clarke
    June 9, 2018 / 4:08 am

    I like them, but would have to try them on. I carry my weight through the middle so sometimes I just look pregnant in them! I think I could wear the pink colour, but the black and white dress might “wash me out” too much.

  6. beth byrd
    June 9, 2018 / 4:15 am

    I like the striped dress and I love it paired with the pink scarf. The pink dress is too unshapely and I don’t think it would be flattering unless you are tall.

    The striped dress looks cool and fun and very summery!

  7. Merri
    June 9, 2018 / 4:17 am

    My first thought was that yes I love a dress with a little sleeve – upper arms not a best feature at 61! These are too shapeless and at 5’2” it just looks too sack-like. I can’t say no to stripes and love the jewel tone pink. I would likely walk past & not try on.

  8. June 9, 2018 / 4:18 am

    I want everyone to know how random it is…such a coincidence that we took pictures in the same department! You in CA and me in TX! We did not plan this, ladies!!

  9. Diane
    June 9, 2018 / 4:23 am

    Would try both, love the stripes and the pink, and I’m not a pink person???

  10. June 9, 2018 / 4:29 am

    I do like sleeves. The pink one is too shapeless but the striped is cute. Even though I’m 65+ I’d wear it. A bright scarf or a nice long necklace would be great.

  11. Sondra Koons
    June 9, 2018 / 4:30 am

    Personally, I would not wear either one because the pink one simply has too much material for this old gal. I like the striped one better but too short for me. I wish designer’s would STOP making all of these sleeveless dresses that are too short for anyone over 20 yrs old to wear. WHY don’t they go back to the ‘just above or AT the knee’ instead of to the floor or WAY too short? Wouldn’t buy either of those for those reasons.

  12. Sandy Andry
    June 9, 2018 / 4:35 am

    I understand the upper arm issue. I’m 62 years old and started lifting weights several years ago. It’s given me definition in my upper arms. Just because we’re older doesn’t mean we have to accept what’s happening to our bodies. I wouldn’t wear the pink dress because it is too baggy. I love the striped dress. I’d buy it. I wear sleeveless dresses often in the summer and have cardigans I carry if I’m going to be in the A/C.

    • Cathy
      June 9, 2018 / 10:54 pm

      I so agree with you Sandy! ???????? I am 61 and also do weights. I wear sleeveless tops and dresses all summer.

  13. June 9, 2018 / 4:39 am

    I agree with the others, that the pink, while a fun color, is too shapeless. Being short, anything like that looks really awful on me.
    I wouldn’t wear the other one either–the waist is too high, and I like something a little more structured. I do like the cap sleeves on both–that top bit of shoulder gets sunburned and it’s hard to keep up with the sunblock.
    Of the other four dresses you show, I prefer the pale green one in the top left, but I know it’s the one in the top right that would look best on me.

  14. Also Jennifer
    June 9, 2018 / 4:45 am

    The pink is a nice color but needs a defined waistline of some type. The striped dress is cute but I wish it were about an inch longer (it might be knee length since I’m sure the mannequin is taller than I am).

  15. Susan
    June 9, 2018 / 4:57 am

    The pink is baggy and shapeless. The striped dress too young and the shorter sleeves draw more attention to less than perfect arms. I think a dress, even a looser style should still have some shape, which most of the Soft Styling dresses had. I particularly liked the striped dress (Soft Stylings) with the longer sleeves.

  16. Cathryn Gray
    June 9, 2018 / 5:19 am

    I would probably try both of them since they are dresses with sleeves, after all. I love stripes and black and

    white but this dress nay be a little too short for me. Love this shade of pink but doubt I would buy it because I look better in a dress that skims my figure a little closer.

  17. Roxanne
    June 9, 2018 / 5:20 am

    Love pink but not those dresses. If they look baggy and shapeless on the mannequins, that’s probably not a good sign. I’m a huge fan of Soft Surroundings because they style for women, not teens. They can be pricey, but the online outlet is awesome. I spied a gorgeous bathrobe in the catalog for $129 (way too expensive!), and later found it on the outlet for $19.99!!

  18. Heather
    June 9, 2018 / 5:22 am

    At 5’10” with narrow shoulders and broader hips, short sleeves and shoulder interest balance my figure, so yes to sleeves. However both these two dresses are too shapeless for my figure … I would feel large and boxy and need some waist definition. The Soft Surroundings examples would work better for me ????

  19. Lori
    June 9, 2018 / 5:30 am

    I personally loved the striped dress better of the two. I am 5’2” and 58 years old and think both dresses would be comfortable and age appropriate. I do have narrow shoulders and really struggle with tops/dresses with a wider neckline – usually falling off my shoulders, but wear sleeveless and dresses with sleeves throughout our warm South Dakota months. Cardigans and denim jackets help cut the cool AC indoors.

    This is a fun feature you and Pam have on Saturdays…thank you! Love reading all the comments, too!

  20. June 9, 2018 / 5:37 am

    Yes, I would wear either. I’m always looking for dresses with sleeves. I do not have attractive arms and they are flabby. I wish sleeves were more readily available.

  21. Linda
    June 9, 2018 / 5:46 am

    I agree that the dresses are too shapeless. I have found on my 60+ arms is not so much the muscles, but where my arm meets my torso seems to not be as toned. However, living in South Georgia requires cool clothing so I do wear sleeveless at times.

  22. Amy
    June 9, 2018 / 6:02 am

    I would wear the striped dress in a minute, adorable. It would be perfect for work. I have been seeking dresses with sleeves for 3 summers now, not just for the look, but also for office appropriate and warmth in air conditioning. The pink color is beautiful, but I don’t want to wear shapeless clothing. I work too hard to try to maintain some shape to wear that ????.

  23. Mary
    June 9, 2018 / 6:19 am

    Agree the pink dress is a bit too shapeless and big especially for shorter women, although in extreme heat it would be cool! Like the striped dress a lot and yes, even at almost 60, I would wear it.

  24. Pamela Mason
    June 9, 2018 / 6:22 am

    I woulda absolutely wear the striped dress. Love the shape and directions of the stripes, and it looks cool and comfortable. No to the pink, but if I were taller and willow-er i’d go for it.

  25. Linda
    June 9, 2018 / 6:36 am

    I would not for the following two reasons. Sleeves need to be a bit longer, say a three quarter that could be pushed up if needed and both dresses have no shape to them. They look rumpled and pulled out of shape.

  26. patval
    June 9, 2018 / 6:39 am

    Eileen Fisher is one of my go to designers I love her clothes and would wear them both, (the pink I would want is a softer color) I carry my weight on my upper half so these would work well for me. The thing about Eileen is they look classy on. They can be shaped with a denim blazer, her light and airy boxy jackets, a sweater, or one of her gorgeous scarves. Look at the Vivienne files for ideas. Eileen clothes usually make me feel fabulous. patval

  27. Barbara Montalbano
    June 9, 2018 / 6:48 am

    I wouldn’t wear either. I don’t like dresses that hang. I have a small middle but have hips – wear a size 14. I do like the sleeves. The way this looks on the mannequin would not even have me take a second glance.

  28. Barbara Montalbano
    June 9, 2018 / 6:50 am

    It looks like it would be good on a tall person. I wouldn’t wear either. I don’t like dresses that hang. I have a small middle but have hips – wear a size 14. I do like the sleeves. The way this looks on the mannequin would not even have me take a second glance.

  29. Lezlie Davis
    June 9, 2018 / 6:55 am

    I want a longer sleeve (above elbow) but they are hard to find!

  30. Debb
    June 9, 2018 / 7:27 am

    I have to go with the majority here – the pink is too much dress and rather shapeless…more MuMu (or MooMoo) than dress. The shorter one is a consideration, but again the length is an issue for me as my legs are not my best feature! Truly enjoy the “would you wear it” segments! Thanks!

  31. Susan Ledford
    June 9, 2018 / 7:38 am

    I am 58 and purchased the striped dress week ago. I have wanted a dress but have hesitated because I have a tummy now. The higher waist and the central seam with contrasting stripes was perfect for my body type. I am thrilled with my dress. It hits at knee level for me. I wear nude Jockey slip shorts underneath. I tried on the pick dress which hung on me and accented my tummy so it was a no go.

  32. Jo
    June 9, 2018 / 7:41 am

    JJill has lots of dresses this summer. I like this one with sleeves, although in TX summer one is better off with sleeveless and a light weight jacket or sweater for indoors

  33. June 9, 2018 / 7:46 am

    I would walk passed both of these dresses. They are shapeless and would not flatter any women. The scarf is way too long and and does not do anything for the dress. I like dresses with sleeves, at least elbow length.
    Sorry, I would give the a no!

  34. June 9, 2018 / 7:47 am

    I would walk pass both of these dresses. They are shapeless and would not flatter any women. The scarf is way too long and and does not do anything for the dress. I like dresses with sleeves, at least elbow length.
    Sorry, I would give the a no!

  35. Ann Griffin
    June 9, 2018 / 7:51 am

    I own that striped dress and can’t stop wearing it! I love the pockets. The fabric is not shear, and it’s easy to wash. Very flattering and comfortable. Great to throw over a swimsuit. Perfect summer dress.

  36. Linlee
    June 9, 2018 / 7:59 am

    I look and feel horrible in garments that are shapeless/have too much material…so no to the pink dress. I like the striped dress a little better and the Nordstrom website shows the dress as longer than here on the mannequin. I might try it on. I do like the Kendra Scott necklace on the pink dress. I have several of these in different colors.

  37. Eileen
    June 9, 2018 / 8:08 am

    I would not wear either dress, mostly because I like a elbow or three quarter length sleeve. Why? I can use the same dress most of the year by adding tights, boots, etc. if it has sleeves. I would buy, or at least try on the checked top with sleeves in the other blog, If it was a DRESS! It could be season spanning and very versatile. As a side note, my friends and I have mentioned to the sales clerks at Nordstrom to tell the buyers, we want sleeves! We started asking 15 years ago. I guess manufacturers and buyers are allergic to sleeves.

  38. Bonna Nichols
    June 9, 2018 / 8:25 am

    Pink no, just too much of everything!
    Like the little stripe number, fun easy to wear.

  39. Kathleen O'Brien
    June 9, 2018 / 8:55 am

    I’m always stuggling to find to dresses and even tops with a sleeve – even in the heat, I will NOT go sleeve-less. I might try both of these dresses. However, the lenght of the sleeve might be a factor, why is most “short sleeves” hit right at the part of the arm that almost makes them look worse?!? A little bit long please.

  40. Debbie
    June 9, 2018 / 9:07 am

    Would wear either one. All about the accessories to dress them up or down. They are both pretty versatile and scarves or a jacket would work to spice them both up if needed. Work or casual options for each.

  41. Anon
    June 9, 2018 / 9:10 am

    I’m with Sondra on this one, but I like hemlinrs just below the knee. I swear sleeveless and short hems are just for the manufactuerers. A couple of dollars saved per item maximizes profits.

  42. June 9, 2018 / 9:23 am

    I love the black and white dress. I like the reverse direction of the stripes that give it interest. The looser fit would make it a little cooler – a must in the 100 degree plus of the valley. I don’t think it is too young, as some have said. I wear sleeveless all summer – even though my arms are starting to go (I’m 67).

  43. Ann Stevens
    June 9, 2018 / 9:41 am

    I’d look like an elephant in the pink one — too long and too baggy — so that one is out. I like the striped one and it might be a good length for me since I’m only 5’4″. If it’s above the knee it wouldn’t work for me at 71 with chubby knees. I look better with something at knee length.

  44. Cheryl Ann
    June 9, 2018 / 9:46 am

    I actually bought one like the pink shapeless dress in a beautiful cotton knit fabric. It is very loose; I love the softness! Now I’ve ended up wearing it to stay cool around the house and even have slept in it. It’s really better than a robe!

  45. Susan
    June 9, 2018 / 10:15 am

    I love the black and white dress, but feel it is too short. I’m tall with a big bust, so the pink one would look matronly and dowdy on me. I just can’t love EF clothes– when I try them on, they don’t make me feel confident at all, just shapeless…I do think they look good on other folks, but not me.

  46. Rosalyn
    June 9, 2018 / 11:30 am

    I tried on the stripped dress in green and black and liked all but the short length. I think it would have been elegant if longer and I was imagining jade jewelry with it. I’m over 70, but tall and thin enough to try for elegance. I wouldn’t want all that bare leg.

  47. June 9, 2018 / 11:55 am

    The bright pink dress is too shapeless for me and the colour is not one that suits me well. I would probably try the striped one on. I like its cool, casual look. I wouldn’t choose to wear the pink scarf with it, but I can visualize several other ways to accessorize it. Depending on how long it was on me, I could also see wearing it over leggings.

  48. Cathy
    June 9, 2018 / 1:15 pm

    Sorry, I don’t like either they look sloppy to me. The striped one might be ok as a swimsuit coverup. It might be the fabric.

  49. Kathy Carter
    June 9, 2018 / 1:38 pm

    I am small boned and the pink dress would be slipping off my shoulders – besides being huge, it is shapeless. The striped dress is cute and I might wear it IF it were a little longer in length. Things that are too shapeless are not generally flattering with my petite build. I live in hot Arizona, and I, too, have been frustrated with the lack of cool, attractive, comfortable shirts and dresses with a cap sleeve or short sleeve – which are typically more flattering to women above a certain age and/or fitness level.

  50. Diana
    June 9, 2018 / 3:40 pm

    I would have to say no to both dresses. I DO like that they have sleeves, I won’t wear anything without them! These dresses are too much for me, …too shapeless, too much material, making them look hot to wear. I have an apple shape and need A-line cut tops and dresses to make my no waste, look like it does have a waste. All that extra fabric, also makes them look like they would be hotter to wear, I’d wear them if there was less volume and an A-line cut.

  51. Joanna
    June 9, 2018 / 3:46 pm

    No to both! The pink one has far too much volume for me. I would look swamped in it. And, the striped with capped sleeves is far too young a look for my age (64).
    However, Soft Surroundings has some very nice ones designed with mature but stylish women in mind. I would definitely shop ar a Soft Surroundings if there was one close.

  52. Becky
    June 9, 2018 / 4:15 pm

    I like the color of the pink dress, but it looks like lounge wear to me. I might wear it to drink my morning tea on the patio but not in public. I’m not sure about the striped dress. I think I would have to try it on to decide.

  53. Julia H
    June 9, 2018 / 4:35 pm

    The pink dress is very shapeless and looks like a pillowcase with sleeves. I would not wear it and can’t imagine that it would look good on many body types. The black and white would be cute on someone petite. Is it shorter in front or does it appear that way on the mannequin?

  54. Bette
    June 9, 2018 / 6:34 pm

    I actually have the pink dress. I’m only 5’2 and had the dress cut off and hemmed to a more appropriate length. My sleeves must come to below the elbow. I had the tailor take the extra cut off material and extend the sleeves.
    Wa la, perfect. I do this often if I love the item and it needs to be hemmed (providing extra material) but the sleeves are too short

  55. Christie Thomas
    June 9, 2018 / 8:30 pm

    Both dresses are cute, but a bit out of my price range! I’ve found some very nice dresses this summer at Loft, with both regular and plus sizes. I prefer short sleeves but also purchased some sleeveless dresses and wear them with very light sweaters.

  56. Joan
    June 10, 2018 / 9:16 am

    At first I didn’t like either dress… but the thought the shorter one could be used with leggings in cooler seasons and the pink one looked more like something I would wear at home. I wonder if a soft belt would look good with it. Such as a scarf loosely tied around to give it a bit more shape and contrast of color

  57. sandra
    June 22, 2018 / 6:58 am

    I would not eat either dress. The pink one maybe if in a neutral linen fabric. The shorter one if a tad bit longer. Imo they are way over priced. I prefer a classic sleeveless shift dress or a maxi dress. I live in Georgia and being cool and comfortable is a priority. As I age, I have to put so much more time into looking nice and presentable. Im 57 so EVERY outfit must have proper shapers underneath. Getting dressed now takes forever!

  58. Kelli
    April 7, 2019 / 1:52 pm

    An emphatic YES to both dresses! I’m at my boldest, most dynamic in styles without a waist (these, other chemises and t-shirt/tank dresses, and narrower shifts) as well as in wrap dresses. These colors are also among MY colors!!!

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