How To Wear Plaid When You Are Over 50!

Plaid.  It’s my favorite color!   Just about any pattern will do.  Plaid is part of my heritage.  If your bloodlines are traced back to the UK or Emerald Isle, plaid is your culture.

I just cannot help it–plaid makes me happy. It makes me comfortable.  I just love plaid! And will never stop wearing it!

As a student, I wore a plaid jumper and as I advanced into the upper grades, wore a plaid skirt with a blazer.  A white shirt, knee socks and loafers completed the uniform.  And to this day, my sense of style is based on the uniform I wore for so many years to Catholic school.

Back in my day the uniform shirt was a crisp white blouse with a Peter Pan collar! This is basically the look that shaped my style.

Growing up, there was always a plaid wool blanket in the car or stashed away in a closet to come out and give me comfort as I sat on an easy chair reading during the coldest of days.  Our home is presently festooned with plaid ribbon draped upon the banisters as we get ready to welcome the most wonderful time of the year!

I kid you not.  This was my baby blanket.  Yes.  This blanket has been with me my entire life! Plaid and I go way back!

I’m surprised the label survived this long!

Oh…and there’s just something so enticing and attractive about a man in a plaid kilt.  Dontcha think?

THE Sean Connery!  In a kilt. What a man!!!!  I’m sorry but he is smokin’ hot in this kilt.  This is man candy for the mature woman!

But—sometimes Plaid can go bad.

Plaid gone VERY bad! This is an atrocious look!

There is sometimes a thin line between looking great and looking clownish.  Especially for the mature woman.

We do not want to look like clowns when we are donning our plaid attire!

And as much as I love Edina Monsoon, she is a fashion victim in this Burberry get up. At least lose the hat darling!

Sometimes less is better and with plaid, that rule is solid for me.  Look, I know and I realize that we can wear what we want.  We can wear the short skirts. We can wear the heels.  But—there’s a way to keep it classic, timeless, tasteful, and age-appropriate.

We CAN rock the plaid kilt shirt–the short ones! And we can rock them with heels.   But to give a long and lean look–stick to tights and shoes of the same color.

As much as I would still love to wear knee socks with my short kilt skirts.  It just won’t work anymore. It isn’t a sophisticated look–and has a tendency to give off the appearance that you are trying too hard to recapture youth!

So—come along with me as I show you some looks that just may make you “Mad About Plaid!”

Look Number One:  Plaid gone casual.  This yellow and black plaid kilt  is from Sport Kilt, where the motto is “A Man in a Kilt Is a Man and a Half”.  Well, a woman in a kilt is twice the woman!  Anyway, for an absolutely casual, I’m-going-to-run-errands, look,  This yellow and black plaid kilt is paired with a textured heavier turtleneck, black tights and loafers.

Now–I know I said that shoes and tights being the same color create a nice long line–exceptions to the rules for me are boots and loafers.  The cordovan color looks great with any color tight and its just a casual look.

Even with the Weejuns loafers, it is an absolute age-appropriate look!

Look one.  Plaid gone casual.  A turtleneck and Bass Weejuns  give this a easy vibe!

Look Number Two.  Same Skirt. Different sweater, some pearls and heels give this a more sophisticated office or date look.

Same skirt.  This time with a more fitted sweater. The sweater is a Tippi sweater from J. Crew.  Heels give this a sophisticated look and make the legs appear a lot longer.  Black Mary Jane heels from Paul Green (these are the ones I picked up for a heavy discount at Nordstrom Rack).  BTW, I’m wearing a bobbed wig today. I’m training the part to go to the left–what a challenge. Wig is BS609 from Brown Sugar.  The pearls give a classic look to an already classic look!

For yet another look that ties in, black over-the-knee boots also look great with a shorter plaid skirt!


What NOT To Do.  When you do wear plaid, don’t try to fight a dominant brighter color with that same colored top.  The yellow top in the photo below is a great top–but it doesn’t work with the yellow plaid.  Too much yellow.  Plaid looks best when everything else is toned down!

Ummm.  No.  The yellow top just doesn’t work with this skirt. It breaks the line up and cuts the body in half.  Stick with the black.

Look Number Four.  Stick to a uniform look.  Ugh. First of all, I want you to know that I went to FOUR stores yesterday to look for GREEN tights to go with this outfit. Macy’s, Nordstrom, Marshalls and Walmart.  Not one store had green tights in their inventory.  So pretend that I’m wearing green tights in this photo.

Here’s a kilt with a lot of colors interwoven.  The red stands out–but green, black and navy are also in the mix.  This is where a bit of color looks great.  A navy blazer worn over a forest green lightweight sweater gives this a polished look.  Green tights would be the finishing touch–or a fake tan. (Geez, I really need to tan my legs! Again, pearls worn with a darker sweater just bring more light to the face.

Look Number Five.  The plaid pants.

Same green sweater.  Same plaid.  But this time. PANTS!  Ankle length pants give an updated look to plaid pants and heels give a longer look to the legs.  Fit is key here.  The pants are a slim cut but fit the curves.  They are also lined so they aren’t itchy.  This is a great mature look.  It is sophisticated and classic.   This is a perfect office look but also a more upscale and dressier casual look and the plaid works without looking clownish or like a costume!

Look Number Six.  The plaid blazer

This photo was taken last winter with my old phone. But I have to tell you–I received a ridiculous amount of compliments whenever I wore this–and from strangers no less!  I think it is simply because plaid blazers are not very common.  Add to that, I paired the blazer with distressed straight jeans (horrors–they aren’t skinny jeans!) and loafers.  Shocking that I have this plaid in a blazer, and pants, and a skirt.  But, I  wear each item separately!

What NOT To Do.  Don’t overdo the plaid with one outfit.  The look on the left–it just looks silly.  The plaid blazer with the plaid skirt is just overkill. It’s different with solids–solid colors give off a suiting look.  With plaid and prints it borders on the clownish and fashion victim look.

Plaid with plaid.  No.  Just no.  It needs to be broken up a bit!  

Look Number Seven.  A pop of color!

First of all, thank God I tried these on.  I gained weight because these are a bit tight around the bum.  What a time of year to start watching points!!  Anyway,  Since black is the dominant color in these pants, a red sweater brings a bit of  brightness–which is fun for the Holiday season.  A light buttery yellow sweater or black would work just as well, if not better!

Look Number Eight.  More pants!

Black Watch Plaid.  One of the most popular and more understated plaids around.  And also the most classic look.   This is a safe bet to go with if you are a bit hesitant about wearing plaid.  The dark colors in the plaid blend so well together.  Again–length is key.  This pair hits at the ankle and looks neat and clean.  Worn with navy heels and a navy sweater, it’s a timeless, elegant and serious look.  Green or black shoes and tops look just as good as the navy.  This is one of my favorite plaids.

Look Number Nine.  The plaid pencil skirt.

Where a kilt is fun and kicky–the pencil skirt is more serious.  It brings forth a no-nonsense look to office attire and is that look when you want to attend a country club luncheon.  (Hey, don’t look at me–I don’t get invites)

Navy shoes, navy tights and a navy sweater give this a no-nonsense and a tasteful and stylized look.  Personally, if my legs were tanned, I would forego the tights–even in winter.  But–that’s just me!

This hits all the notes for  how to wear plaid for the mature woman. I love this look–even with the tights!

I was getting tired.  Being your own photographer is quite challenging–especially when you aren’t that good at it!

Look Number Ten.   Another festive look!

You know when you just can’t get the photo quite right?  I thought perhaps I could get a decent shot if I laid down on the floor.  I didn’t.

Instead, I opted for just sitting down.  This skirt–Glen plaid, is the simplest plaid ever.  But, with a bright red sweater, it says “Holiday Time!”   And the great thing about Glen plaid is that the only colors are black and white–and some of the pattern is so closely knit that it looks gray. Really–any bright color would look great with this skirt!

Look Number Eleven.  The plaid shirt.

Who doesn’t love a plaid shirt.  Usually worn with jeans, the plaid shirt is one item of clothing that we’ve all had since childhood.  Now it’s grown up.  Pairing plaids with different textures and patterns is both tricky and difficult.  Here, with a tweed skirt, the shirt works.  A black sweater to tie it in with black tights and boots gives this a fun and flirty look. And YES–mature women CAN wear short skirts.  This is proof.  In fact, I liked this look so much that I wore it out to run errands earlier this afternoon!

I’m Obsessive About– Tights and shoes matching.   I’m not one to be incredibly “matchy-matchy”.  However, when it comes to wearing skirts in the winter–especially short skirts, the tights have to match the shoes.  It makes the legs appear longer and gives a lean look-I can’t stress this enough.  I’m a HUGE fan of bare legs, but they need to be tanned. And if you cannot get those legs tanned during the colder months, the tights work wonders.

No Plaid Overkill.  Save the plaid scarfs for when you are wearing solids.  Seriously.  Or stick to the same plaid as the skirt or pants.  Mismatched plaids do not look good!

Keeping it toasty and tasteful.  I wear plaid scarfs with solids.

He’s got the right idea!!!

Seriously. It is.  This plaid Lady Jacket that I bought last winter at a great discount from J. Crew is one of my favorites.  And it is a great jacket for the mature woman who can’t afford the famous designer Chanel jacket.  Dressed up or down. Doesn’t matter!

OMG. This plaid jacket is such a fun one. And very age appropriate!

Look what I found this afternoon!  GREEN TIGHTS!!  At Primark.  I went back to the mall on a mission.  My goal was to go to every store until I could find green tights!  I’m so happy!

The green tights from Primark.  Four bucks a pair.  Life is good!

So yeah.  With a few pointers and tips, you certainly can wear plaid while remaining classic, elegant, fun and tasteful.  And mature women wear it best!

How could I write about plaid and not include these guys–who are now in the mature bracket!  Bay City Rollers!

Plaid gone bad.  Way bad!  But I still love the song….

Saturday Night!

About Catherine

Far from perfect, but enjoying life as a non-perfect and flawed individual at 60 years young. I'm still wondering what I'll be when I grow up! The characters in my life's screenplay include my better half. He is a refined Frenchman who grew up in Paris and summered in St. Tropez. I grew up in Long Island and summered in Long Island. I am not refined. My three grown children are also a big part of my life. For their sake, they happily live where their careers have taken them! But I can still mother them from a distance! I write about the mundane. I write about deeply shallow issues. But whatever I write or muse about--it'll always be a bit on the humorous and positive side! It's all good!
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40 Responses to How To Wear Plaid When You Are Over 50!

  1. Sharon Daly says:

    My favorite outfit of my pre-teen years: black watch plaid ankle pants with a navy roll neck sweater. Wish I could find pants like that today. Yours are terrific.

    • Catherine says:

      Hi Sharon!! I replied via my phone but it never showed up. Ugh! Technology! Anyway, Those black watch pants are from a few years back –I purchased them at Loft and boy, they have been worn so much. They will never go out of style. I would suggest going online and googling ankle length black watch plaid pants. I’ll bet you can find something!!! The roll neck sweater. I bought a navy one at j. crew last year. They took their roll neck sweater out of retirement. We have the same taste!!!! XOXOXOXO!!!!

    • Paul says:

      I think You will like Kilt from Kilt Master

  2. Molly says:

    Hi Catherine–I really enjoy your blog! Your bubbly spirit is uplifting and you give great tips. Thank you!

  3. Linda Seymour says:

    I am in my 60’s and feel very uncomfortable dressing for an event wearing a nice dress but no stockings! I love tights but they are sometimes too casual. I like to wear light black stockings but I keep hearing that is definitely out now! What is your opinion on this?

    • Catherine says:

      Hi Linda. OK. You are going to think that I’m a total lunatic when you read my answer but there is a reason that I don’t wear panty hose (but I love tights in the winter). I equate panty hose with carpeting. You know how carpeting is full of mites and never really gets clean? Ugh. Well, to me, panty hose is just a petri dish for yeast infections. I can’t stand the “feel” of them either. The feel of panty hose is like nails on a chalkboard to me. That’s why I love to fake tan my legs. And I know that there are different schools of thought whether or not panty hose/stockings are out our in–I say wear what you are comfortable in!!! XOXOXOXOXOXO!!!!

  4. fiona says:

    Thanks so much Catherine, I’ve been wondering what on earth I was going to wear to an afternoon party this weekend, you’ve reminded me that I can wear my red tartan skirt with black roll neck, tights and boots. I have quite a few tartan and check pieces in my wardrobe, I must be fond of it because I wore a tartan uniform for eleven years when I was a flight attendant with Caledonian Airways.
    I really like those cigarette pants of yours and the pencil skirt is lovely too. Primani is great for coloured tights, glad you found some. What a blast from the past to hear Les McKeown & co, took me right back to 1973. xxx

    • Catherine says:

      Hi Fiona! OMG. Yes!!! Take out your Tartans and rock them. You are living in Tartan country!! I would be plaiding every day!! I’m so glad that you will now be wearing them again! LOL. Bay City Rollers remind me of a bar that I used to frequent in NYC during my single days. My girlfriends and I would play BCR “Saturday Night” constantly!!!! XOXOXOXO!!!

  5. Barbara says:

    What an excellent Blogpost, One of your best and absolutely my favourite.
    You look great.

  6. Cindylou says:

    What a great post. One of my favorites. I too went to Catholic school. We wore a stitched down pleated Black Watch skirt, Peter Pan collar blouse and a forest green Eton blazer or navy cardigan. And of course loafers and navy knee high socks. I used to rock a pair of red tartan plaid pants at parties in high school! I just love plaid but don’t have much in my current wardrobe. I’ll have to fix that following your great tutorial. No wonder I love your style-our fashion sense has the same genesis. Well done.

    • Catherine says:

      OMG. Cindylou. I attended St. Patrick’s grammar school. Our uniform blazer was, like yours, a forest greet Eton blazer with white piping and the St. Patrick’s emblem. Our uniform skirt was green with red and similar to the skirt that I’m wearing in the don’t and do photo. We were allowed only to wear either white or green knee socks or white or green tights. I will never forget the day that Sylvia Hashagen came into school with red tights. Sr. Mary Isabel, the principal made her walk home and change. I can’t make this up.
      Still, that uniform look shaped my style!! Very glad that you enjoyed the post!!! XOXOXOXO!!!!

  7. I love the plaid with the dark stockings and dark shoes. Cool look.

  8. LA CONTESSA says:

    FORGIVE ME………….as I do not think you should show your knees anymore!Tights or NO TIGHTS!I would like to see you in a long MAXI PLAID SKIRT for the HOLIDAYS!I think its an EAST COAST~ West Coast thing as women our age on the WEST COAST DONOT WEAR SHORT SKIRTS!!!!!!Except for TENNIS!AND thats a TOPIC in itself!
    IT is just NOT FLATTERING in my opinion!Knees show age……………

    • Catherine says:

      Hi Elizabeth!!! Of course I forgive you!!! Yeah. I wear what I want. I don’t care about my knees giving away my age because I don’t give a hoot who knows how old I am. LOL. Those short skirts–they are my comfort zone. I go topless on the beach when I’m in France–I’m sure my girls give my age away but –whatever. Long skirt. Short skirt. East Coast. West Coast. We should all wear what we feel comfy in and support each other!! XOXOXOXO!!!!

  9. vavashagwell says:

    Love your tips on plaid! I guess J. Crew is coming out with a red plaid jacket AND matching pants in the near future. Wouldn’t ever wear them together, that’s for sure!

  10. eveange33 says:

    Oh great post Catherine. My Catholic school uniform was navy blue pleated skirt with white shirt, white socks and black shoes so, of course, I can’t stand navy blue or even blue anymore. But plaid, that is another story. I love plaid as well but that is not so easy to find in France where people are afraid of colours (that is apart from black, navy, grey and taupe, all that is so … dull and sad in my opinion, is life and Nature with those colours? NO) and prints. You have to go vintage … and vintage is not very common in France either.
    You’ve got great legs Catherine and you are right to to show them off with nice tights which enhance them, not to hide them, nothing to be ashamed of here.
    I love plaid, yes, and especially glen plaid (ou imprimé Prince de Galles) since a lot of years: this season, glen plaid is again in and I rejoice and wish I could stock some very good quality garments for when the trend will fade again but, alas, nothing that fit me or my credit card. Anyway, with my new flat bought, I need to be very careful with my spendings and clothes are just superfluous, I already have plenty.
    I do not own that much plaid but a jacket, a pair of trousers and, of course, 2 glen plaid skirts. Short skirts: I agree with you, women can wear short skirts whenever they want, the years do not mean anything to it but your free will do!
    I wear thighs and stocking nearly all year long, black mostly, often fancy, but also light grey, orange, purple … I only have bare legs when it is hot enough and I wear sandals or open shoes or flats. Actually, I do not know how you can bear the cold with bare legs, how you can walk in the streets in the cold weather. But, I admit, I do not like cold.
    The short bob wig really suits you, you look very elegant: can I be like you when I “grow up” (as if I wasn’t already grown up)? Of course, I would not look like you: for starter, I am under 5″ so It is going to be difficult and well, better let you being you and I being me after all. I hope one day we’ll be able to meet, probably in France as I am not going to set foot in the US any time soon.

    • Catherine says:

      Hi MB!!! You know, I just realized that I’ve never seen any plaid skirts or pants on anyone when I’m in France!! A plaid scarf but that’s it–and you explained it all! Even your school uniform was without plaid!!! I love it because it’s colorful and fun. ANd I will wear my short skirts and heels until I’m in my 80’s!!!
      I’m glad that you like that bobbed wig. Surprisingly bobbed wigs are better to wear in the winter when wearing a textured heavy sweater because the fibers won’t hit against the synthetic hair and cause tangling!!!! XOXOXOXO!!!!

  11. Sue says:

    I love, love, love that short wig on you!!! Enjoy your blog everyday

    • Catherine says:

      Wow! Thank you so much Sue!!! I’m digging that bob too! When my bio hair was shorter, I could never get it straight enough to bob like the wig!!! LOL!! XOXOXOXO!!!

  12. hipchick66 says:

    Great article! Love all the plaid (former Catholic schoolgirl as well) and you wear it all so well!

  13. cgcopy says:

    What a fun blog — and what terrific style you have, Catherine, plaid or otherwise!

  14. Karen says:

    I loved this post. AND you did an excellent jog photographing yourself. I was just sitting here thinking to myself if I even owned anything plaid anymore. I think I got it in my head that because I am plus size that it made me look even larger—but I know I’ve had some plaid in my lifetime…and you will think I am crazy…but I always wanted to be a catholic school girl. LOL. XOXO

    PS. I especially love how you wear pearls!

  15. Juliet says:

    Oh shades of primary school uniform! We had a red mcpherson tartan kilt and royal blue cardigan – my mother made our kilts as the shop versions were “sloppy” and mother thought she could do better (oh man she absolutely could and did), she used to make my sisters highland dancing costume too – except the socks, she decided to let herself off that detail. I totally agree with tartan, plaid or other checks – go simple and go restrained colour palette. You’d love Glasgow there are some big hairy/leery bagpipers in kilts that busk, think braveheart with pipes, they always draw a big crowd when they appear. You look fantastic

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  17. Seriously, Cathe! All the plaid in this post has me in a heavenly place! I want all the plaid and I just keep adding more and more to my wardrobe! You are fabulous in every way, my friend. Thanks for linking up!


  18. Lise says:

    Previously I thought plaid was dowdy but this post has totally inspired me to get some! I love the pencil skirt, blazers and pants. Your figure and your legs are great btw. and I was thinking this before I read the comments.

    • Catherine says:

      Hi Lise!! Oh no–plaid is fun!! I get what you mean though about dowdy but I think it also depends on the cut and style of the clothing! Go and get some plaid!! Now!! Hurry!!! XOXOXOXOXO!!!!

  19. Pingback: How To Wear Plaid When You Are Over 50! | By the Mighty Mumford

  20. Terri Meadows says:

    I love this article! I have always loved the schoolgirl look especially if the skirt is plaid and as I’ve gotten older (Im 45) I’ve been feeling more and more like my favorite look is no longer age appropriate but after having read this article I feel hopeful and happy about it again, thanks so much!

  21. Pingback: Plaid – To Wear; Not To Wear? | KUEL LIFE

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