Would You Wear It: Maxi Pencil Skirt

Would You Wear It: Maxi Pencil Skirt

Welcome to the weekend ladies! Although I have been on vacation for 5 weeks, I feel like I need a rest. #notcomplaining. Traveling in a small trailer is a different kind of holiday than most. No one is making your bed, doing your laundry, sweeping up or cooking most of your meals. You’re basically doing all the things you do at home but in a much smaller, cramped space. I work every day that I have internet so that keeps me busy too. We love doing it and will continue but possibly with shorter trips in the future.

I know I’ve been missing in action for most of last week, but it’s time again for Would You Wear It. Each Saturday Pam from Over 50 Feeling 40 and I share a mannequin we have spotted and ask if you would wear what she’s wearing.

I expect most of you know how I feel about this outfit, but I want to hear from you. So tell me, ladies, would you wear this and why or why not?

The sale edit is smaller than usual this weekend.

The Nordstrom sale is still going strong until August 6. I hope to get into the store downtown this weekend because I want to try on this jacket. The soft blush color may be just what it takes to allow me to wear a leather motorcycle jacket.

Eileen Fisher is giving an extra 20% off sale and $25 off regular with the code FUTURE, free standard shipping, and returns.

NET-A-PORTER is giving an additional 20% off items labeled Sale Must Have.

Ann Taylor is still having their semi-annual sale and giving 50% plus an extra 10% off sale merchandise.

J.Jill is giving an extra 40% off all sale styles.


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


Thanks for reading and have a great day!


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  1. Robi
    July 31, 2018 / 6:21 pm

    I’m 5’8″ and would definitely wear this! Love the colors and styling with the white shirt. That’s a perfect weekend look for me!

  2. July 30, 2018 / 12:04 pm

    I might wear this skirt depending on how the waist worked with my waist. I wear skirts all the time, but prefer cotton or linen – the poly fabrics make me very hot.

  3. Jody
    July 29, 2018 / 11:24 am

    I’m 5-11, so I would wear it! But I prefer pants or crops.

  4. Cathy Justice
    July 28, 2018 / 5:49 pm

    I don’t wear maxi skirts because I’m 5’3″ and always feel like little house on the prairie in them. But I love the outfit just not on me.

  5. Jill
    July 28, 2018 / 4:17 pm

    Yes, I would wear this skirt but with a plain knit top and sandals.

  6. Cynthia
    July 28, 2018 / 2:34 pm

    I LOVE this outfit, and would wear it in a minute. Gorgeous colors in the skirt, and the white shirt tied at the waist is such a nice contrast. I bet you like it too, Jennifer!

  7. Charlene Burroughs
    July 28, 2018 / 1:41 pm

    I would definitely wear the skirt! I am 5’6″ with long legs and a short waist. I would probably wear a t-shirt ot even a modest halter style top instead. My shoulders are wide and I have a small bust, so button down shirts are usually a no go for me. Love the pattern on the skirt and the necklace.

  8. Carol in Denver
    July 28, 2018 / 1:02 pm

    I like the outfit but would like it better if the skirt were solid black, in a luxurious 4-ply silk. Love the crisp effect of the blouse. Being somewhat fluffy myself, “crisp” looks more energetic and youthful than a knit top would, in my opinion. To me, the outfit as shown or as I would modify it is graceful and feminine.

  9. Diane
    July 28, 2018 / 11:34 am

    I have to agree with the majority of the shorter ladies that responded. This outfit would not be the best choice for me since I am 5″1′. I would feel chopped into threes. I would probably love it on someone else and secretly wish I could wear it! I do own a few maxi dresses in all one color and I feel the best in those as opposed to a skirt and blouse. As someone else stated the necklace is a bit too chunky for my small frame, but I do like it for someone else.

  10. Sue
    July 28, 2018 / 11:24 am

    I like the print and would wear it with a black top to extend the line.at 5’2” having a stark white top such as this with the black print skirt wold make 2 rectangles and not be flattering on me. Maybe a cute kitten heel in deep yellow?

  11. Becky HARTER
    July 28, 2018 / 11:18 am

    Definitely wouldn’t wear the skirt. I don’t have the right body for a pencil skirt & think I would find the length uncomfortable.

  12. Renee
    July 28, 2018 / 11:07 am

    I’d definitely wear it and at my height of 5’7″ this totally works for me. Love the entire outfit!

  13. Jacie Bond
    July 28, 2018 / 11:02 am

    So great to have you back, Jennifer. Camping is not for me! As a Canadian, I really appreciate your perspectives on how to achieve a variety of looks with minimal clothing. I recognize even BC weather can be a challenge in the summer it is here in Alberta. I LOVE the maxi outfit!. At 5’7” I can wear it and feel quite elegant yet also casual. At 74, I would prefer to wear that look all the time – covers up my knee replacements. Just last week purchased a very similar white shirt which has been on my radar for months due to the multi uses you have shown us. Lastly, a big thanks for the idea of tying our tops for providing shape. What a huge difference that makes.

    • July 28, 2018 / 12:21 pm

      Thanks, Jacie! I am thrilled to be back. I am wearing a white shirt tied at my waist today as a matter of fact. It helps camouflage my larger muffin top that’s courtesy of my fish and chip addiction.

  14. Bea
    July 28, 2018 / 10:44 am

    OH how I love this, However, since I sm on the shorter side, I would pair the skirt with a solid dark top to give it a more vertical visual, creating a taller look. I am a fan of white shirts, but the colour block would cut me in half, making me appear shorter and wider, especially when the shirt is knotted at the waist. I’d propably accessorize with a longer neclace or a bold cuff .

  15. Darla
    July 28, 2018 / 10:42 am

    I would definitely wear this outfit. I am only 5’2″ tall, but I always get complimented when I wear my maxi pencil skirts. The border print of the skirt is fun, and I love how the chunky necklace ties in to this. The white blouse makes the outfit look timeless. This inspired me to search my personal closet and put together a similar outfit, using items that I already own. Thanks for the inspiration!

  16. Pat
    July 28, 2018 / 10:23 am

    Definitely would wear this outfit! The skirt is the center of attention. The white blouse makes it look crisp. Flat sandals in a neutral or in metallic would be perfect! Glad you are home safe and sound.

  17. Susan S
    July 28, 2018 / 10:09 am

    I love this outfit and would wear it if I could. Pencil skirts don’t look good on my pear body type , do I probably wouldn’t even try it on … but I do love the whole outfit !

  18. beth byrd
    July 28, 2018 / 9:59 am

    I really like this outfit! I love maxi skirts and dresses — I’m 5’4″ and find them slimming.

    I think the print of the skirt looks fabulous with that white blouse! And that necklace is the perfect accessory!

  19. Joanna
    July 28, 2018 / 9:03 am

    What a gorgeous print! I’m 5’8″ and can wear longer skirts. A crisp white shirt. You bet! I don’t wear big necklaces. I find on my thin frame they overwhelm, so I would leave that behind and wear a smaller necklace in the vee.
    On your longer trips, why not stay in a hotel part of the time. That would give you a nice break with a pool to relax around. You could even wear that pretty skirt over your bathing suit as you walk around. Or, even eat out more often. I told my hubby that I’m on vacation too and dining out is a must.

  20. Cindy
    July 28, 2018 / 8:52 am

    I wouldn’t because I don’t care for maxi’s, but I would if it were knee length or even midi. Love the blouse and necklace though!

  21. July 28, 2018 / 8:50 am

    Though I’m tall and thin and could probably pull off this look, I don’t care for the length of the skirt. I would prefer something shorter.

  22. Cindi
    July 28, 2018 / 8:49 am

    I don’t wear maxi skirts unless it/s a special occasion. I don’t think they are flattering on me for everyday wear and I’m not sure they are appropriate for a work environment. But, I would wear this as a midi or knee length skirt. I like the pencil skirt shape. The other outfit is a definite yes! My style exactly! I like the skinny jeans and the shape of the top for casual wear.

  23. July 28, 2018 / 8:45 am

    I love knee length pencil skirts and when I “dressed” more, I had several. I’m tall and slender but don’t think they’d work unless I was. The skirt you’ve pictured is a print. Too busy, so no. I wouldn’t wear it.

  24. Linda
    July 28, 2018 / 8:40 am

    I WOULD wear BOTH outfits! I loved them both! If I wasn’t stuck in athletic shoes due to foot problems, if I had a pair of invisible shoes, both of them would be in my closet! I love the geometric prints as they are slimming and would look great on my 5’ 6” frame! The necklace on the one you have Jennufer really brings out the colors on the skirt and that simple white blouse is perfect with it! Both are a hit with me!

  25. Ann
    July 28, 2018 / 8:33 am

    Not for me … I’m short so the decorative bottom would only make me look shorter.

  26. Gloria A Randle
    July 28, 2018 / 8:02 am

    I would definitely wear the skirt! You could put together a great outfit with it. Thank you.

  27. July 28, 2018 / 7:56 am

    No I would not wear the skirt. Not a fan of maxi skirts and the pattern is too bright. Love the white shirt not the necklace though. It looks clumsy at the neck. Hope you enjoyed your visit in Canada but I am sure it is great to be home.

    • July 28, 2018 / 8:47 pm

      We had a fabulous time and it’s great to be home.

  28. Lori Stewart
    July 28, 2018 / 7:53 am

    I love it. I am 5’8’ with long legs and a short waist, so this would be perfect for me. I like the vertical print with the big border at the bottom. I also like the colors in the print and border. It give a great pop of color.

  29. Scarlett
    July 28, 2018 / 7:50 am

    Yes, I would wear it. Looks polished and comfortable at the same time.

  30. Mary
    July 28, 2018 / 7:24 am

    I love this skirt and would absolutely wear it. I would not wear the blouse tied in front like that thought – maybe a knit tee or tank with a jean jacket.

  31. Eileen
    July 28, 2018 / 7:15 am

    No, I’m 5’5” and pear shaped, so a line styles work better, plus, walking is difficult in a long pencil shape. I agree this would “cut you off” horizontally in too many places, so better on a tall gal.

  32. Anon
    July 28, 2018 / 6:48 am

    This outfit would work for my height, frame and coloring. So yes, I’d wear it…and I didn’t think I’d say that.

  33. Charlotte
    July 28, 2018 / 6:34 am

    Yes, I’m petite too and I think I look taller in outfits like this. I like it a lot.

  34. Debbie Davis
    July 28, 2018 / 6:19 am

    Love the skirt – but on someone else – tall and thin. Love the tie front blouse and chunky necklace! I would wear that in a heartbeat. Glad you’re back from your vacation!

    • July 28, 2018 / 8:46 pm

      Thanks Debbie! It’s great to be back.

  35. Sue Kempe
    July 28, 2018 / 6:16 am

    I’m 5’9” and definitely would wear it, not because of my height, but because I love it. But I wouldn’t buy it’s because it’s a one and done outfit. The skirt is too memorable. I know I would tire of it before I had my money’s worth from it.

    • July 28, 2018 / 8:45 pm

      Excellent point about it’s memorability! I find that true of most prints.

  36. Diana
    July 28, 2018 / 6:15 am

    I’m not a maxi length fan. Too many times the longer length skirts and dresses make the wearer look like they’re wearing a bolt of fabric. If this skirt was knee length, I would try it on. The white dress shirt is classic and can be paired with many different combinations.

  37. Susan
    July 28, 2018 / 6:15 am

    I love it- I’m 5’9, so have straight skirts already. I’d probably do a knit top though…

  38. L H Carter
    July 28, 2018 / 5:59 am

    The vertical lines at the top of the skirt might be broadening. I like the colors and the bottom border print. I’d switch out the top to less tailored tee and keep the necklace since turquoise is my favorite color.

  39. Sue Michel
    July 28, 2018 / 5:55 am

    I wouldn’t. Although I like pencil skirts and maxis, long straight skirts I feel look matronly. The print is nice though.

  40. Catherine
    July 28, 2018 / 5:46 am

    I am 5’9″ tall so I don’t think I would have trouble wearing this. Love the colors and the crisp shirt. I have teal sandals so I would wear those with this outfit too.

  41. Sophia Montgomery
    July 28, 2018 / 5:33 am

    I like a maxi if it is slim for my 5-3 frame. Love the look and the piled necklace tucked inside the collar gives a white shirt pizzazz!

  42. Susan
    July 28, 2018 / 5:26 am

    There seems to be too much of the lower print, cutting the skirt in half. I too, am 5’ tall (on a good day!) so anything that chops me up is a big (haha) no-no. But I do wear long skirts. They have to be full length or midi’s with boots in the winter. This skirt should be used in a post on “How to look shorter.”
    Welcome home, Jennifer! You’ve been missed!

    • July 28, 2018 / 8:44 pm

      Lol! Thank you Susan! It’s great to be back

  43. Deborah
    July 28, 2018 / 5:21 am

    I am 5′ 6 & 1/2 and I would wear this . I often get the petit maxi so the proportion is better. I do not like the full gathered maxi styles. I think the outfit looks very chic, love the necklace and the way it makes that color pop!

  44. July 28, 2018 / 5:20 am

    I would not wear the skirt. I am on the short side at 5 ft. 5 in. with shorter legs, and not being able to wear any kind of heel, I think it would look terrible on me. I would wear the blouse.

  45. Mary
    July 28, 2018 / 5:16 am

    I like the skirt and shirt. I would wear the skirt with a solid color t shirt. The necklace color is good, but the beads are too big so no to that. I prefer bracelets to necklaces.

  46. Susan Clark
    July 28, 2018 / 5:05 am

    Happy you enjoyed your trip and that you have the opportunity to travel. I love a maxi skirt. I am 5′ 6″ so I would definitely give the maxi outfit a try. I purchased a black and white bold print maxi this summer and I wear it with a bright knit 3/4 sleeve top or t shirt. I purchased the skirt in petite because I don’t like a too long skirt and that feeling of too much material. That was the fix for me. I would swap out the white button-down shirt for a knit top as I am full-busted. I love that chunky necklace- reminds me of beach glass.

    • July 28, 2018 / 8:42 pm

      Beach glass is on my “want to own” list. It’s so pretty and has a history.

  47. Maria Barrera
    July 28, 2018 / 4:49 am

    Glad to have you back! I love the outfit but I am too short to wear a long skirt. Though, I would wear a full dress. I am only 5’ tall!

  48. C Cartwright
    July 28, 2018 / 4:49 am

    I love the outfit! And would wear a petite version of it, and yes, I am only 5’2”.

  49. Margot
    July 28, 2018 / 4:44 am

    I’m 5’4” and would totally wear this outfit. I have something like this in my closet already but did go with a petite in the skirt to get the proper length/proportion.

  50. Lynn
    July 28, 2018 / 4:32 am

    I would wear it! Maybe a bit taller at 5-6, but I just purchased a solid black skirt last week. I like seeing this with a white blouse and chunky necklace.

    • Carol Daily
      July 28, 2018 / 9:09 am

      Yes I would wear it except the shirt looks hot. I like maxi skirts in the summer because they are cooler than pants for me and I need to hide my legs.

  51. Cindy
    July 28, 2018 / 4:28 am

    Great to have you back! I’m not a fan of pencil skirts or maxi length (I’m short) so I wouldn’t wear the skirt. I do like the necklace & would wear it.

    • July 28, 2018 / 8:40 pm

      Thanks Cindy, it’s great to be back

  52. Sondra Koons
    July 28, 2018 / 4:26 am

    I wouldn’t wear the maxi skirt (or a maxi dress either) because I’m barely 5’2 1/2” tall. It’s a beautiful skirt though and the necklace is my favorite color. But….I wouldn’t be able to pull off wearing that either as I feel it would overwhelm my body. The woe’s of being petite!!!

  53. Sandy
    July 28, 2018 / 4:12 am

    I would not wear this b/c I’m only 5′ tall and I think long skirts/dresses overwhelm my petite frame. My legs still look good at 62 years old, so why would I cover up the best part of me? If I saw this on someone else, I’d like it – especially someone taller. I like the neutral top with the print skirt and especially like the necklace. Glad you’re home, Jennifer. Welcome back!

    • July 28, 2018 / 8:39 pm

      Thank you Sandy!! I’m happy to be back.

  54. July 28, 2018 / 4:11 am

    So great to have you back from vacation, Jennifer, to make WOULD YOU WEAR IT twice the fun. I do not personally feel confident in maxi skirts, but if this print was in a knee length pencil skirt, I would wear it in a heartbeat!

  55. Sussan
    July 28, 2018 / 4:08 am

    No, I would not wear it. The skirt conjures up memories of when I lived in Saudi Arabia (for over a decade) and it reminds me too much of ‘modest’ clothing.

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