Would You Wear It – Buttoned Up Plaid

Would You Wear It – Buttoned Up Plaid

Happy Saturday ladies. It’s no secret that women love to discuss outfits and fashion so grab a cup of your favorite tea or coffee and let’s get to would you wear it. Each week my friend Pam and I share a mannequin we have photographed and ask if you would wear what it’s modeling. Stores dress their mannequins to showcase their newest merchandise and hopefully give us styling ideas and we want to hear your thoughts.

I love to also have you share how you would style the outfit so please share your ideas so we can inspire each other!

mannequin wearing tweed blazer

So what do you think? Would you wear this look as it’s styled?

How could you style these pieces to work for your shape and lifestyle?

Fun plaid jackets for fall

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Now let’s go see what Pam’s mannequin is wearing at Over 50 Feeling 40

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


  1. Jan
    September 20, 2020 / 1:28 pm

    I avoid double-breasted jackets which look best buttoned, so I’d opt for the black/brown/white combo in the Aqua or Chelsea28 brands. Not a fan of “masculine” so I’d pretty it up with a paisley neck scarf or bold gold necklace & pumps or ballet flats & a saddle tan handbag. The jacket over a column of black makes for easy office dressimg as well. Thinking weekends, the jacket can top a pair of jeans and simple white or cream tee, minimalist jewelry & loafers or white Supergas. The cognac-color pants (I’d prefer ankle-length) are a versatile staple for pairing with a black or navy tee or sweater & tortoise accessories or rocking a red turtleneck or deep purple button-down The brown tee can do double-duty with cream or black pants & a few well-chose accessories These are three work-horse pieces that will do a lot with what we already have.

  2. Ann
    September 20, 2020 / 9:51 am

    I love jackets, especially some of those you have otherwise listed on the post, the longer ones. Plaid is fine for a jacket. For me, a big “no” to those pants with that jacket, they could be cute with a lightweight top but I would not wear them with any jacket; on me, the look would be unbalanced. And an even bigger “no” to those top buttons…
    Cute bag, though!

  3. Yvonne
    September 20, 2020 / 4:16 am

    I love wearing blazers, and still have a few single and double breasted. This outfit I would wear, but with a few modifications: the blazer would be in a black/grey/white plaid and the ankle pants in black. To me this feels more of a spring time of the year outfit, worn with loafers or a low heel. I would change the crew neck sweater to a v neck or bateau neck and add a red purse for a bit of colour.

  4. Beverly the Inspired
    September 19, 2020 / 5:38 pm

    Menswear styling has been around the block & back again since the early 1920s. This particular outfit reminds me of a 3-pc pantsuit Mother had in mid/late 1960s; mustard plaid jacket with matching & contrasting slacks. Worn with white go-go boots & white, slim structured handbag (not yet baguette style). Very MOD & fashionable.

    I admire menswear styling on others to this day. On me… no… just no. Looks as if I’m wearing hand-me-downs from an older brother I never had, TeeHee.

  5. Eve
    September 19, 2020 / 1:10 pm

    I’m fine with the top and pants but I’d rather have a Vee neck and longer pants. I could make them work. I just don’t like mannish looking Blazers. I like softer, looser jackets that flow over the body. A loosely constructed blazer is okay. I run from darts and dbl breasted. Plaid, I have some but usually reach for solids.

  6. Kay
    September 19, 2020 / 1:05 pm

    I like plaid. I do not like double-breasted blazers. This classic silhouette would not work with my boho-esque aesthetic. That purse, though, is so cute!

  7. Debbie Bell
    September 19, 2020 / 12:53 pm

    Love plaid & love olive green. A singke breasted or buttonless version of the jacket would get my vote.
    Although we love bare feet on Lake Huron beaches, LOL, I’d wear a loafer mule and agree about the necklace.
    I own that purse and seldom use it. Maybe I need to find an oldchain necklace ( I’ve used loved belts for this purpose before.) and make a shoulder strap.
    I’ve never done the bootie for no real reason!?!
    Thanks, everyone!

  8. Connie
    September 19, 2020 / 12:07 pm

    I love blazers. The hardest thing for me to quit buying when I retired was blazers and heels…so, I haven’t really stopped. I like the plaid, but would only wear it in black or navy since I often like to add red and cooler colors. If I’m wearing a blazer open, I avoid double breasted so the buttons don’t look so busy. Pants with a blazer I feel need to be at least ankle length. The purse is adorable. I’d probably wear loafers too.

  9. Nancy Walden
    September 19, 2020 / 11:24 am

    I don’t like the way blazers fit my curvy body. I’m also not a fan of plaid, especially in “fall” colors. I look better in shorter jackets with more feminine lines. My favorite jackets for fall weather are denim with a curved front hem instead of a traditional banded hemline.

  10. Becky
    September 19, 2020 / 11:08 am

    I would wear this if the pants were full length. It is simple & classic which is what I like. I also like the taupe pants as a break from black. A nice fall look.

  11. beth byrd
    September 19, 2020 / 11:03 am

    I love plaid — and love the plaid on this jacket. But, I’d prefer a shorter jacket or a more fitted one. This one is too boxy — and those buttons are definitely misplaced.

    The cropped pants are so stylish, but not sure if I’d get my wear out of them being that I am in a cooler climate. The color is nice and I would also wear this jacket with black trousers.

    I’d wear this jacket with a black knit dress and boots for a fun look!

  12. Norma G
    September 19, 2020 / 10:35 am

    This outfit is very similar to items I have in my closet, so I would wear it with a few tweaks. A double breasted jacket is too boxy for me and my Glen Plaid jacket is single breasted. I have actually have 2 Glen plaid jackets, one in black and the other in brown. I cuff the sleeves to make them more casual looking and never button them. I think everyone has a black tee, I have a few. I’m not a fan of the shorter pants, but full length pants work better for me. I prefer a shoulder bag over a short handle bag. Of course, I would add a long necklace to help elongate the look.

  13. marilyn ackerman
    September 19, 2020 / 10:29 am

    I love jackets. They seem to be the finishing touch. Not plaid or hounds-tooth or any other geometric print though. Too sporty and in this case masculine for my taste. This jacket doesn’t appear to be constructed correctly. Maybe it is the shape of the manikin, or the fact that it is double breasted, but darts don’t seem to be in correct places. Pants are also too short with a jacket. At least for me. Sorry if I seem overly negative on this one, but just not for me.

  14. Lois
    September 19, 2020 / 9:54 am

    Honestly – I wore suits and jackets for so many years in my career that now that I’m happily retired, I can’t bring myself to put on a jacket. My attire is sporty and casual. I love the look of jackets on others, but I just can’t.

  15. Kate Granado
    September 19, 2020 / 9:51 am

    Hi Jennifer; love the idea of asking how we would change up the look. I like all the pieces. Double-breasted works for me if it is nipped in the waist a bit. But, anyway here goes with a couple of changes.
    I would wear a pair of booties with the pants. Since I can’t see the pant top and top-bottom, I think I would do a French tuck, keeping the blazer opened, a chunky gold linked necklace, a couple of chunky gold bracelets, push up the sleeves and go out and have fun. I would carry a tote or a tiny phone bag, over the sholder.

    • Jennifer
      September 19, 2020 / 5:59 pm

      That sounds really cute Kate, thanks!

  16. Cyndi
    September 19, 2020 / 9:42 am

    I never, ever choose patterns, stripes or plaids that don’t match or meet agreeably at seams or closures (this jacket looks good there) so they’re not abundant in my wardrobe. Double breasted isn’t a flattering look for me so this jacket with those buttons would be a no

  17. Mary
    September 19, 2020 / 8:58 am

    I have a plaid jacket in greens and blues (very soft colors) and a black checked jacket – now that I’m retired, I don’t know how to style them so I’ll use them – some here suggested with jeans. Any suggestions for me? I’m in Florida, so no wool please!

    • Jennifer
      September 19, 2020 / 9:25 am

      Try styling it with green or blue chinos. Toss over a simple tee and white jeans then wear dark slip on shoes

  18. Doxylover
    September 19, 2020 / 8:52 am

    Love this look! I’d roll the sleeves of the blazer a bit, add a statement necklace and cute ankle boots. Fall is my favorite time of year and fashions!

    • Jennifer
      September 19, 2020 / 9:23 am

      Fall is my favorite time too!!

  19. Jane
    September 19, 2020 / 8:22 am

    Love the whole look. I am so happy the fall colours are popular this year and wear all of them except the greenish yellow, they called it mustard, that was popular last year. The only thing I would change is the bag, cross body bags are more appropriate for me during COVID because I don’t have to put it down when I’m out and about! Add some flat loafer inspired shoes and it is a stunning outfit.

    • Jennifer
      September 19, 2020 / 9:23 am

      Great point about the handbags these days. Me too or I’m wearing belt bags

  20. Joanna
    September 19, 2020 / 8:04 am

    Ummm The top two buttons look like nipple buttons. So for that reason alone, it would be a no for me. Also, I don’t wear brown and am not a fan of plaid blazers. The purse is cute but I prefer a hands free over the shoulder type.

  21. Cathy
    September 19, 2020 / 7:50 am

    I love the colors but not the double breasted for me. The pants might actually be longer on me. I love the purse but I don’t really carry on any more. I’ve been on the look out for a black and tan small plaid jacket to pair with jeans. I have a very casual lifestyle for either workouts, gardening or jeans.

  22. Theresa
    September 19, 2020 / 7:49 am

    Looks nice, the jackets buttons are all wrong. Love the pants which I would wear. I am not a plaid person, so I would not wear the jacket.

  23. Linda
    September 19, 2020 / 7:48 am

    Seeing that the majority of women hate the two top buttons, I would just go to a tailor and have them removed! That is a pretty simple solution!

    Or just remove them myself. It’s really not a big deal!

    • Jennifer
      September 19, 2020 / 9:21 am

      I often remove buttons too;). A no brainer

  24. Sarah
    September 19, 2020 / 7:48 am

    The placement of those top buttons gives “double-breasted” a whole new meaning! Ugh! I agree as well that these colors are drab, although I realize that’s very subjective. This is a pass for me.

  25. Linda
    September 19, 2020 / 7:40 am

    I LOVE this outfit! The tank under the jacket, the jacket and the color of this entire outfit. The ONLY thing I wold change is the length of the slacks. I would want them traditional length , which is breaking over my shoe. I am still in athletic shoes and would like my shoes hidden just slightly.

    I would wear this outfit so many places! So a huge YES even that purse ROCKS! Send it to me! LOL!

    • Jennifer
      September 19, 2020 / 9:20 am

      Consider it on it’s way to you Linda:)

  26. Virginia Loftin
    September 19, 2020 / 7:31 am

    Classic, even with the slim pants silhouette. I think it’s great-looking, and since brown tones are a fall 2020 trend, it feels current. I don’t wear double-breasted jackets, so would look for a similar jacket in a different cut. But yes — this is modern workwear. And a classic plaid jacket would also work with dark wash jeans for every day. (Even people who don’t work outside the home can take things up a notch or two. During these long months of working remotely, I’ve gotten dressed every single day. I’m not me if I’m not put together.)

    • Jennifer
      September 19, 2020 / 9:18 am

      I agree, Virginia. I have to put myself together or I’m not me. I love a plaid jacket with jeans.

  27. Deb
    September 19, 2020 / 7:10 am

    To me it is a very bad remake of the 80’s look when women wanted to look like men in a corporate setting – none of it is for me – the double breasted buttons, the drab plaid, the brown colors . Nope – not even the little sad bag

  28. Marcia
    September 19, 2020 / 7:09 am

    This look has me written all over it. Perfect for early fall here in Canada. I love the colours and shapes and would wear this outfit often. The pieces would mix with other wardrobe items easily. Top marks for this one.

  29. Elaine @ Following Augustine
    September 19, 2020 / 7:07 am

    No, the jacket is too structured and businesslike for my retired lifestyle and the pants are too short for fall/winter in Canada. If I was to wear the jacket, which I might have in my younger working days, I would wear it over a warmer colour, not black, and I’d remove the “nipple” buttons before I ever wore it!

  30. Rhonda Ragain
    September 19, 2020 / 7:03 am

    I have to agree with most of the posts above. I am now retired, so this is too formal for my lifestyle. Even when I was a manager, I preferred single buttoned jackets and seldom if ever in brown tones with my coloring. The pants are too short for this jacket and not a flattering look for most. I’d love a blue or green plaid jacket with a single button and straight or skinny jeans! That would flatter my body and lifestyle much better.

  31. Linda L
    September 19, 2020 / 6:48 am

    Too structured for my SoCal retirement lifestyle. I can’t wear browns with my all white hair anymore. Double breasted blazers need to be buttoned for the style to work and then when you sit down you have to unbutton or else get that big bulky excess fabric bunching. Years ago I would love a plaid blazer with a denim shirt and either jeans or khakis.

    • Maggie
      September 19, 2020 / 8:30 am

      Nothing about this outfit would work for me. I didnt wear plaid in the 70’s and I wouldn’t wear it now. Too boxy, too brown, too masculine for me.

  32. Bea
    September 19, 2020 / 6:03 am

    Oh my…those extra buttons at the top look like they’re trying to be nipples. And what’s happening with the darts? I don’t know if it’s my screen, but it appears that the darts are also trying to impersonate nipples. Very poor construction, if that’s the case.
    That being said, I’d pass on this outfit. Colours are wrong for me, double breasted doesn’t flatter my body shape and I’d need the pants to be at least ankle length.
    The purse is cute though!
    Thanks Jennifer, love these Saturday posts!

    • mary jo tesch
      September 19, 2020 / 7:22 am

      I agree!!!

    • jmp
      September 19, 2020 / 7:30 am

      I also agree. Oh those buttons!!!

  33. Diane B
    September 19, 2020 / 6:03 am

    This look for myself is a no due to the colour firstly, then the length of the pants for fall just makes me feel cold. I have never been a plaid person and the double breasted plaid is just too much. Also as mentioned, the buttons on the top at the breasts….who would put them there, there is no function and they just draw attention. However, I have a friend who would wear this really well. She is a slim autumn and would pair this with a pumpkin or golden turtle neck and look stunning. Add a pair of congnac boots and a short statement necklace and good to go.

  34. Deanne
    September 19, 2020 / 6:01 am

    I wouldn’t wear this, don’t care for double breasted jackets and I don’t care for that taupe pant with it. I scoured the market last fall for just the right plaid blazer, and finally found on I like at JCrew, black, ivory and a dash of yellow. I like it dressed down with black jeans and either a black tee or an off white plain sweater. It’s a nice third piece that could be dressed up with black pants.

  35. MP
    September 19, 2020 / 5:51 am

    The plaid jacket is so dreary. I like plaid but with better colors – navy, shades of blue, maybe a dark background would help. I would pass on the pants — dull color and bad length. The purse is cute but the handles would drive me crazy. I need a shoulder strap or a crossbody. Nothing here for me. Happy Saturday.

  36. Rose
    September 19, 2020 / 5:51 am

    I really love plaid but probably not a double breasted one. Since my hair is silver now those colors don’t look great on me and in the northwest the pants would have t be regular length. The purse is cute though!

  37. MRSBEN2
    September 19, 2020 / 5:40 am

    Though do like the slimmer cut of the pants, their length is not appropriate for our FALL climate so would prefer them at least ankle or full length that in turn would dictate my style of footwear. However with that said; I would pair them ‘as is’ with a slip on loafer in a suede or soft leather or maybe a closed-in ‘n heeled peep-toe shoe. As for the blazer; I do like it (as they are my go-to outerwear for Fall though normally are that of a wool blend) but would definitely remove the two buttons located at the breast point and pair it with a light-weight turtle or v-neck sweater which I prefer over crew necks. In respect to the purse, though cute would prefer a cross-body or wristlet bag or even a large tote with longer handles that could be slipped over the shoulder. For jewelry, would keep it simple but with no necklace and would inject a pop of color either by means of the sweater, shoes or purse. (i.e.: In deeper tones of the red family.)

    Question for you Jennifer: I notice that you wear Mules and am wondering do you find them difficult to keep on your feet with their open backs regardless they are flats?

    • Jennifer
      September 19, 2020 / 9:15 am

      I wear mules often and love them. They need to come high on my foot to stay on well. The tiny ones are just annoying so I pass on those ones, no matter how comfy I think they are, I do t want to have to “work” to keep my shoes on 🙂

      • MRSBEN2
        September 19, 2020 / 11:19 am

        Thank you Jennifer! I don’t currently own a pair and as they do look comfortable, am tempted to try them so your tip that ‘they come high on the foot’ is much appreciated.

  38. Karen Needler
    September 19, 2020 / 5:30 am

    I love a good plaid blazer, but these days as a high school teacher in Vermont, I wouldn’t wear it much. Back in my corporate days, sure. However, I don’t care for double breasted blazers because they look best, to me, buttoned up, and I prefer to leave blazers open while indoors. Instead, I’m eyeing a gorgeous purple herringbone wool J.Crew blazer (single breasted)!!! Watching for the price to drop. Jeans or solid pants on the bottom – I snagged black, navy and grey high-waisted Pixies at Old Navy this summer!

  39. - Vicki Mikola Dack
    September 19, 2020 / 5:20 am

    Agreed, would wear the outfit if the trousers were longer — ankle length at least and 2″ heels Cropped pants seemed to be my daily home clothes these days.

  40. Jan
    September 19, 2020 / 5:19 am

    Who thought it was a good idea to place those two buttons on the front darts of this jacket?! I am not a fan of a double breasted jacket anyway but this just solidifies my big “no” for this one. You pair the large plaid with the double breasted feature and it becomes a very boxy look on my shorter frame. But ultimately, my social life offers no need for me to wear this jacket. A big “no” to the pants also. My fall/winter wardrobe only includes longer pants or jeans. I’m doing some research on the new, soft cords that are showing up this fall. Love all the colors that are available and can see them mixing with several of my favorite sweaters.

  41. Susan McClelland
    September 19, 2020 / 5:03 am

    I wouldn’t wear this outfit, primarily because brown isn’t a great colour on me. The proportions of the blazer and the pants also wouldn’t look great on me – I’m 5’7″ and wear a size 2 so crop pants usually end up being short on me.

  42. Cynthia B
    September 19, 2020 / 5:00 am

    Gotta admit, when I saw the plaid blazer, my heart sort of went pitty-pat. I’m a sucker for a nice plaid and have always loved the dressed look of a blazer. However, because I’m working from home for the foreseeable future, and getting ready to retire soon (hopefully), I’m finding that I wear my blazer type jackets less and less. As for the outfit at hand, I agree with the others on the length of the pants….they hit the leg at the worst spot for most of us….mid calf. Yuk. I would agree also that if I bought it, I’d pair it with skinny denim…..might consider it after all 😉

    • Jennifer
      September 19, 2020 / 9:09 am

      I’d wear it with skinny jeans too 🙂

  43. Linda
    September 19, 2020 / 4:57 am

    I have never liked the double-breasted look. The short pants look odd, especially since this outfit would be for cooler weather. The colors in the jacket are all wrong for me, but I would wear the black top.

  44. Cathy Cunningham
    September 19, 2020 / 4:45 am

    I would wear this outfit but with full length pants. Perfect for Fall today in London Ontario as we have frost this am.

    • Jennifer
      September 19, 2020 / 9:08 am

      Frost already! Wow

  45. Tina
    September 19, 2020 / 4:37 am

    I’m 5’1” and would feel overwhelmed in the plaid blazer and the oversized look. I prefer more structured jackets. I like the look and it wouldn’t be my look. The plaid is versatile and could be worn with many colors or over a dress.

  46. Paulette Levy
    September 19, 2020 / 4:27 am

    The pants here just don’t work for me! I think I’d pair this great jacket with a black Jean or even deep indigo Jean. I might add a pop of color in the tee or turtleneck. I’m thinking for me – an ivory mock turtleneck or a pretty new deep blue tee or lightweight sweater. Nothing too heavy.
    The pant color just doesn’t work for me, at all. And the top worn under the jacket could be lighter or brighter.

    • Jennifer
      September 19, 2020 / 9:08 am

      I love the idea of wearing the jacket with dark denim. Thanks Paulette

  47. Cindy
    September 19, 2020 / 4:21 am

    If I was still in the corporate world, I’d wear a similar outfit. I don’t like cropped pants for a “business-y” look, so the pants would need to be full length. Double-breasted jackets have never been my preference, so I’d probably opt for a simpler jacket.

  48. Patti Shannon
    September 19, 2020 / 3:24 am

    I just don’t like pants that short, especially as we enter fall. I wouldn’t spend that much on the blazer since I’m retired and have no need for it but I like the look. The handbag is cute but I really do better with a crossbody so I don’t put it down in the grocery cart in these days of Covid (and for security). If I dressed in that manner and the price point was better, I’d wear a longer pants version of it with ankle boots and a long statement necklace.

  49. sheryl
    September 19, 2020 / 3:14 am

    i think it needs a little pizazz, so i would change the pants to black first. then i would try either cognac or black shoe boots..oh and the pants have to be longer too…the purse is kinda cute, but really, i have to have a shoulder bag, the one pictured you always have to just hold in your hand, and if you are a person who just needs the sunglasses and credit cards it might work, but most of us need a bigger bag. also either a long pendant necklace or maybe an eye catching broach.

    • Jennifer
      September 19, 2020 / 9:06 am

      Great ideas! Thanks for sharing Sheryl

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