Would You Wear It- Bermuda’s or High Low

Would You Wear It- Bermuda’s or High Low

Happy Saturday ladies and welcome to the weekend. It’s time for would you wear it. Each week my friend Pam and I share a mannequin we’ve found and ask our readers if you would wear what it’s wearing.

I love to hear your styling ideas and how you could make an outfit work for your lifestyle, coloring or body shape. Please keep your comments personal to you because other women will love what you hate and this is a no insult zone:)

My mannequins are from a window display this week so ignore the reflections that look like white paint splots:)

Since I have no links for these items, we can only go by what we see.

So tell me, ladies, would you wear all or part of these outfits?

Which pieces might work and how would you style them?


Here are the weekend sales to shop:

Nordstrom – their winter sale is on with up to 40% off.

Ann Taylor – 40% off with the code WEARIT.

J.Crew–  Up to 60% off sale styles, plus 30% off almost everything else with code WEEKEND.

Loft 40% off your full-price purchase, no code needed.

Talbots -Up to 70% off all mark-downs

Banana Republic – 40% off everything. Free 2-3 day shipping on $100 with the code BRSHIP

Chico’s – up to 50% off select styles

Bloomingdales – up to 70% off sale


Now let’s go over to Over 50 Feeling 40 and see what Pam’s mannequin is wearing.

Thanks for reading ladies and be sure you wear what makes you feel confident.



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


  1. Denise
    February 17, 2020 / 7:34 am

    When I first looked at the photo I thought “no way!” Then an interesting thing happened. I read all the comments which caused me to look again. Now I can say that the blue jacket would be really cute with the sleeves rolled up with a white tee underneath and a pair of faded jeans. Aaahhhhh, now I feel better!

  2. Susan
    February 16, 2020 / 7:23 pm

    Something about both of the outfits looked like clothing from late 1930’s or early 1940’s movies, especially the blouse. I usually like clothing styles from that era. I couldn’t wear them, but it is interesting to see fashion starting to change to some new ideas, inspired by past times.

    I am tired of seeing high low hems on blouses and skirts. I agree with you about seeing the inside of the back of the skirt. I think that the shorts outfit looks like something I have seen Katherine Hepburn wear in some movie, I don’t know which.

    I always enjoy seeing the styles on your Would You Wear This Posts.

  3. Theresa
    February 16, 2020 / 7:00 am

    My mom always said if you can’t say something nice…..

  4. Donna
    February 15, 2020 / 7:35 pm

    I love the white shirt and would wear it with high waisted skinny jeans or high waisted shinny black pants. I’d flip the cuffs and push them up and I’d wear a statement necklace in the low v neckline.

    I wouldn’t wear the orange skirt. The material is too clingy for me. Personally I find the mermaid style dated.

    I love the colour of the blazer. I would definitely wear it, I might even try it with the belt.

    The Bermuda shorts are a hard no for me. I don’t like the plaid. I usually avoid pattern on my bottom half. The length of the shorts is all wrong on my petite 5’2” frame. I’ll pass on this one.

  5. Jen
    February 15, 2020 / 3:16 pm

    Both would be a no for me. I like very classic cuts. This is a fun series.

  6. Susan McClelland
    February 15, 2020 / 2:34 pm

    I would try the blouse with the culottes/Bermuda’s. Coral is not a good colour on me so the skirt is out. The jacket is fine but not my favourite shade of blue. With the belt, I think it Iooks too severe with the long shorts.

  7. Michelle
    February 15, 2020 / 1:20 pm

    I think those are more of a slimmer culotte not a Bermuda short.

  8. Sharon Mulliken
    February 15, 2020 / 12:03 pm

    I would walk right by this window, admiring the trendi-ness of the outfits, thinking they would look great on tall models! I am 5 2 1/2″ and not real skinny, so I would be overwhelmed by these styles. Also, I am more classic and preppy minded, so again, I would just “walk on by”. Thanks for giving us the opportunity to think things through every week!

  9. Penny Jo
    February 15, 2020 / 11:14 am

    That would be no.

  10. Pamela Lutrell
    February 15, 2020 / 10:59 am

    I would have passed by the display because there is nothing here that appeals to me. I stopped to envision myself in the shorts outfit and just shook my head no. So I think these would not work for me, my style messages or my body shape.

  11. Cyndi
    February 15, 2020 / 10:35 am

    Blue blazer? Yes (but not belted) Bermuda Shorts? In general, yes, but these plaid ones with the wider legs don’t appeal. The blouse? No, wouldn’t be flattering for me (I’m a pear shape and those puffed sleeves would emphasize that). The skirt? Yes (but would prefer another color) BUT…I think these outfits would be super cute on someone taller and younger with a different lifestyle

  12. Elizabeth Day
    February 15, 2020 / 10:29 am

    No to everything in this window display except possibly the scarf. The blouse is much too white and poofy and shiny; the skirt isn’t for my body at all; no words for the plaid pedal-pushers (dating myself, I know); and I would not wear a blue jacket nor belt it. Sorry, I’m not being very constructive with this response.

  13. beth byrd
    February 15, 2020 / 10:25 am

    The color palette is very appealing to me. I am always drawn to softer and more muted colors, so these colors are something I’d wear.

    I know I wouldn’t be able to pull off either of these outfits. However, I would wear the belted blazer with long plaid pants. It has a classic look and would be a great outfit for this transitional weather.
    Like Michele above, I have spider veins on my legs and don’t wear anything but long pants these days.

  14. Pat
    February 15, 2020 / 9:40 am

    I would not wear any of it as none would flatter me or my body. The skirt is pretty but seems too fussy, and the blouse is too full. The shorts are too full and long and look shapeless and frumpy. The blue jacket is nice but not my color. I do wear scarves tied like that.

  15. Deb
    February 15, 2020 / 9:37 am

    Actually well designed window. I just would not wear the items. Too young for me . Do like the color palette they chose.

    • Jennifer
      February 15, 2020 / 7:51 pm

      I agree, it’s a very pretty color palette.

  16. Mollie M.
    February 15, 2020 / 9:34 am

    Sorry, but neither outfits appeal to me. Whoever puts them together does not have any style

  17. Tina
    February 15, 2020 / 9:16 am

    I would wear the Bermuda’s and the jacket, but not together. Maybe a soft sweater of shirt, tucked in. The skirt is a big NO, but love the white shirt that it is paired with, would add a scarf with more color.

  18. Cindy
    February 15, 2020 / 9:07 am

    If I wore skirts, I’d try the high-low.
    Pass on everything else.

  19. Jan
    February 15, 2020 / 8:55 am

    Even on these tall, slim models, they still looked overwhelmed by yards of extra fabric. Transfer that to my 70’s model 5 ft 5 in frame and I would look like I grabbed a large sheet off my bed and tried to create an outfit! But, I do love the colors. You always tell us Jennifer, wear the style and size that best suits the shape you are today. I accept that I can not pull off the same clothes, makeup or hair styles that I did even 10 years ago. Life is all about constant change and how we react.
    This was another fun blog and so much fun to read everyone’s response! Thankyou!

  20. Elaine @ Following Augustine
    February 15, 2020 / 8:26 am

    I like the idea of the Bermuda short suits that are on trend for this spring and if I was still teaching, I would likely invest in one. If the trend didn’t last, I could continue to wear the pieces individually. I like the shorts shown here, but not the jacket. I would prefer them with a darker more fitted blazer (perhaps navy or charcoal) and no belt.

  21. Bab
    February 15, 2020 / 8:19 am

    Interesting styling but it’s a heck no for me.

  22. Diane B
    February 15, 2020 / 8:13 am

    I really like the outfit on the left. The skirt is something I already have style wise, and the top is very interesting. The right is too structured for me, like a more feminine look. I have to wear “shorts” that cover my kneecaps but these are too loose and masculine looking.

  23. Jane
    February 15, 2020 / 8:10 am

    Love the shorts! Would be happy to wear them with chunky sandals or flats. Would wear the blazer without the belt, open with a T-shirt. The skirt would be a try on, I think it would make my tummy even rounder, but it is so pretty and would flatter a flatter body.

  24. Eileen
    February 15, 2020 / 7:55 am

    As a pear , love the blouse and skirt shapes. Though the items may be too oversized for me. Bermuda shorts… no.

  25. Susan
    February 15, 2020 / 7:54 am

    I love the bermuda’s because they almost give the illusion of a skirt. I work in a professional office and would definitely wear that outfit with the blazer and a mid heel pump. The belt around the blazer looks good on the manikin, but not sure about how it would look in real life on my body. I almost think the belt might make the outfit a little uncomfortable. I’m a petite 5’3″, 110lb, 62 year old woman who loves finding new outfits! Thanks for sharing – now I’ve got another picture to add to my file!

  26. Linda
    February 15, 2020 / 7:48 am

    I would not wear either. I have a dislike of the color orange, maybe if it was a different color? The jacket doesn’t look very happy with that belt. To me, the jacket doesn’t need a belt. But if it had to have it, perhaps the color of the belt could be changed to match the jacket. I am not fond of the color contrast.

    Sorry I have been absent as medical issues with my husband have overwhelmed me but we have nurses and therapists to help me with him now.

    • Jennifer
      February 15, 2020 / 7:47 pm

      Welcome back Linda. I’m glad you’ve got some help now.

  27. Janet
    February 15, 2020 / 7:42 am

    On first glance, I thought, “No way!” I still don’t like the shorts outfit but I would try on the other one. I like the fullness of the blouse with the definition at the waist that the skirt gives. I’m not tall but I do have a waist, and I think I could scrounge up some low heels to give me a bit more height. I have never worn orange but I maybe it would be ok if it’s far away from my face. This would be good for spring and summer air-conditioned office wear.

  28. Dawn
    February 15, 2020 / 7:19 am

    No, I would not wear anything pictured. The blouse has too much volume, the skirt is a beautiful color, but I no longer wear high low since my legs aren’t what they used to be. For the same reason I don’t wear Bermuda’s, and I prefer fitted, shorter blazers.

  29. Crystal
    February 15, 2020 / 7:14 am

    I don’t care for the high low skirt as it is would accentuate my bumps and bulges. However I really like the shorts. It does remind me of cullots. I think they would look good with boots in cool weather.

  30. Jo in Chicago
    February 15, 2020 / 7:12 am

    The blue jacket is nice, but I would not wish to wear any of the other pieces.

  31. Dianne??
    February 15, 2020 / 6:35 am

    I’m with Ellen……I can’t say something nice!

  32. Kay
    February 15, 2020 / 6:32 am

    Not for me ~ colors, style, proportion, etc. are all wrong for me at my height (5’4″) and age. The skirt style in a shorter version I might have worn in younger days but not the color. What else can I say but that I don’t like either of these ensembles!

  33. Linda Barnes
    February 15, 2020 / 6:29 am

    I would wear them all but without the belt on the jacket and with the blouse over the skirt.

  34. Sandy
    February 15, 2020 / 6:24 am

    It’s a no for me.

  35. Linda GR
    February 15, 2020 / 6:03 am

    I’d wear the scarf and the blazer, without the belt, but nothing else appeals to me. The colors are nice though.

  36. Ellen
    February 15, 2020 / 6:00 am

    If you can’t say something nice…

    • Jennifer
      February 15, 2020 / 7:17 am

      Lol, thanks Ellen. Happy Saturday

  37. RoseAG
    February 15, 2020 / 5:41 am

    The definition I get of a Bermuda short has them an inch above, not below the knee. I think these are more culotts. Semantics aside, it’s a No for me on the dressy Bermudas. If I do stepped-up Bermudas I go preppy not drapey, and would wear the cotton Drifter sweater or twill blazer to ward off a too cold movie theater or sea breeze.

    I do like the blouse and skirt but would put a belt below the high-waist of the skirt. The blouse is really cool.

  38. Cj
    February 15, 2020 / 5:41 am

    Love the style of the skirt but would only wear at natural waist. I also like the blazer and Bermuda shorts but without the belt.

  39. Susan
    February 15, 2020 / 5:35 am

    I love the orange skirt and top but I couldn’t wear the top. The other outfit I would wear the bottoms but not the jacket it’s too tailored for me if it were a looser and shorter I would wear it

  40. Susan K Wilson
    February 15, 2020 / 5:32 am

    I would wear the skirt but not the top. I like the top but it just wouldn’t work on me.
    I would wear the bottom of the next outfit, but not the jacket. If the jacket was shorter and not tailored I would probably wear it.

  41. Norma
    February 15, 2020 / 5:20 am

    Yes ,I like the Bermuda’s,no belt for me. The dress no,I don’t think I would look good in it.

  42. Gail Schwartz
    February 15, 2020 / 5:04 am

    I really like the Bermudas but I would have them shortened above my knee.

  43. Gaye
    February 15, 2020 / 4:55 am

    Would wear shorts but maybe lose the belt-perhaps a cardigan or jacket alone. Do not particularly care for skirt. Love your site

  44. Linda Gaertner
    February 15, 2020 / 4:54 am

    I would never wear the Bermuda’s. I’m too short and they would do nothing for me.

  45. Michele
    February 15, 2020 / 4:46 am

    I personally would not wear either of these outfits. Unfortunately my legs are covered with spider veins, so year round I wear full length or ankle pants. Once in a great while I will wear cropped pants. These Bermuda shorts are too full for my taste and the jacket is out of proportion. The skirt style isn’t bad if you have the figure to pull it off but the blouse paired with it is way too big.

  46. Karen Burns
    February 15, 2020 / 4:41 am

    I love the outfit on the right but would not wear it with a belt. I would probably add a little shell under the jacket.

  47. MP
    February 15, 2020 / 4:40 am

    I like straight, tailored Bermuda shorts but these are too full for me. I would walk past this window without stopping. Nothing appeals to me.

  48. Linda V
    February 15, 2020 / 4:40 am

    I must say NO to everything. I hate plaids. The outfit on the left would only look good on a very skinny person. The blue jacket is nice but too long for my body.

  49. Paulette Levy
    February 15, 2020 / 4:38 am

    Neither of these outfits are me, at all. Here is what doesn’t work for my body type (and age really). I’m smallish, 5 ft 4 maybe! Shrinking lol. The puff sleeves and longish skirt will drown me! Love the skirt color! But, would not purchase either piece. I never liked the fuller long Bermudas or shirt pants as shown. Not me! I want my Bermudas to hit just above my knee cap, and be a more snug tapered fit. The jacket with belt is okay, but I prefer no belt. I just feel neither of these outfits would help me look nor feel my best?

  50. sheryl
    February 15, 2020 / 3:57 am

    i would have loved the skirt in my younger days…the bermudas…nope. on me that would never have worked. although i do love capris jean shorts. but thats a different fit.

  51. Kristy
    February 15, 2020 / 3:16 am

    No. Maybe the scarf 😉

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