Plaid Blazer + Wearing Over the Knee Boots Over 40 - Elegantly Dressed and Stylish
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Plaid Blazer + Wearing Over the Knee Boots Over 40


Hello Ladies,

How was everyone’s weekend?  It has been bitter cold here in Charlotte, NC and Jess doesn’t do cold too well. However, being that I seem warm all of the time now ( midlife menopause) I told my hubby, where is the cold weather? So, I experienced the very cold in Harleysville, PA ( under 20 degrees) and i will take the “Southern Cold” instead! So, what is one to do besides cozy up near the fireplace and snuggle with the puppies? Wear layers! Today I am sharing a layered look in one of my favorite plaid Anthropologie blazers, jeans and OTK boots. I plan on writing a post on the importance of a investing in a good blazer, but today, I am talking about Over the knee boots.

I received these OTK boots last year from Santa, as I love the style, the 2.5 inch block heel was do-able and the rust suede would go with much in my closet. Some ladies have expressed the fact that they think one must be tall to wear OTK boots and it really is about proportion. I am 5 foot 9, but I believe if you want to wear them, you should! 😉 They have been a popular boot style each year, with more colors and styles available.

I find wearing a low block heel to be very comfortable and giving some length to the leg. Wearing a stilleto OTK boot can look a little, “Pretty Woman’ or “street lady’, so perhaps choose a wedge or block heel, which are on trend as well, so more styles are available.

Another thing to remember when wearing an OTK boot, is the style. Think of a bit of a heel for height, but wear with a pair of leather leggings and long sweater and you have a chic look! I love a white pair of jeans, OTK boots and a neutral sweater for a  pretty Fall-Winter look wearing white.

Try wearing OTK boots with a long duster and blouse. The long cardigan will give additional length to your look with the OTK boots.

Flat Over the Knee boot-

There are so many choices of this style of boot now, if you are interested in trying them and am not sure about a heel, there are lots of choices for a flat over the knee boot style. Try pairing them with a blazer and jeans for a put together look.

Mango- Flat over the knee boots

Sweater dresses-

I love to wear them with sweater dresses, which looks great on woman of any age, and is comfortable with a touch of sexiness. Want to wear a mini dress? Tights with a pair of OTK boots makes for a fun, feminine look. These pair are a pair of Vera Wang I bought and are flat OTK boots.

Here, I am wearing one of my favorite rust, navy, camel plaid ruffle blazer I bought on Poshmark from Anthropologie. Paring it with a rust cami, dark denim and my OTK, I added my cognac Rebecca Minkoff bag for a rich compliment.

I am always one who believes woman can wear what they love wearing, no matter the age. It really is a matter of feeling confident, no matter what you are wearing. If you are looking for a pair of these boots, it is the end of the season and the time to buy a pair. I have included some affiliate links for you, if you choose to do so!

Have you taken to the Over the Knee boot trend yet? 

I love to hear your comments. Thank you!

Have a great day!

Jess xo

Outfit details:

Jacket -Anthropologie from Poshmark,  Denim- William Rast designer, love these.

Boots ( last year Sole Society)

Handbag- Rebecca Minkoff -Ebay


Fake Fabulous

Glass Of Glam On Mondays We Link Up 

Visible Monday with Not Dead Yet Style

How I Fall with Pink Sole

Shoe & Tell with Style Nudge

Top Of The World Style  

A Labour of Fashion with A Labour of Life

Thursday Moda with Elegance and Mommy Hood

Thursday Fashion Files


  • Kimberly
    Posted at 07:36h, 21 February Reply

    I love your style! Thanks for sharing! I have a gorgeous pair of OTK boots, but struggle with styling them now, and haven’t worn them as much as I should. I like the idea of pairing them with a sweater dress or short stress, but wonder wear the hemline should hit. Mine have a slight curve otk so, not a flat silhouette at the top. Thanks! P.S. I wear flowy “Hollywood hair” too!

    • Jess Jannenga
      Posted at 12:00h, 21 February Reply

      Hi Kimberly! Thank you so glad you love my style and I would say if your OTK boots have a curved shape, the hemline could be a little shorter. are they Vince Camuto/ i have seen some pretty boots in that style. Yea for old hollywood hair! xx

  • terrigardner1
    Posted at 13:17h, 07 February Reply

    Jess, thank you for linking up. You find the most amazing things on Poshmark. The colors you’re wearing today are gorgeous on you and actually are some of my favorites. Look in’ stylish, as usual!

    • Jess Jannenga
      Posted at 09:58h, 08 February Reply

      Thank you Terri! I will have o share my circle bag with you soon.. bought on Posh of course! i need to check out some of the other shops too. xx

  • shelbeeontheedge1
    Posted at 14:26h, 21 January Reply

    Jess, I am loving this look! The plaid belted blazer is so marvelous! The colors are so great on you, too. Your OTK boots are fabulous. As always, you knocked it out of the park head to toe with this outfit!

    Thanks for linking up with me.


    • Jess Jannenga
      Posted at 12:35h, 22 January Reply

      Thank you Shelbee! They are 2 of my favorites in my fall wardrobe . xx

  • polishedwhimsy
    Posted at 02:36h, 19 January Reply

    Hi Jess! I’m coming over from Ada’s link up. The plaid Anthropologie blazer caught my eye. I am a long-time Anthropologie girl too so I get excited to meet someone with a similar love (or obsession :D). I am also loving your bag. The texture is just gorgeous!

    • Jess Jannenga
      Posted at 10:31h, 19 January Reply

      Thank you! I do love Anthro, they are unique and have such beautiful clothes. Thanks for popping by! xx

  • Laura || Walking in Memphis in High Heels
    Posted at 18:25h, 16 January Reply

    I love that plaid blazer, it matches perfectly with those boots! I love the colors in the plaid blazer, it’s so different!

    • Jess Jannenga
      Posted at 09:29h, 17 January Reply

      Thank you Laura! I love Anthropologie, and often find great deals thrifting online this brand. The ruffles and colors caught my eye! xx

  • thestylesplash
    Posted at 05:03h, 16 January Reply

    These colours look amazing on you Jess! I love your blazer and OTK boots. I bought a pair of stretchy black OTK boots in the sale recently but I’m still unsure about them – they are very long, coming up to mid thigh and have a heel. My intention was to wear them with a dress over tights as they are streamlined so don’t add bulk, but I’m now doubting whether I’d actually wear them very much. I’ll try them with a couple of different dresses and then decide whether to keep or return them.

    Emma xxx

    • Jess Jannenga
      Posted at 10:25h, 16 January Reply

      ooo, those boots sound sexy! i have seen the look with dresses both midi and maxi and loved it. i always shop on line too, so i just try things on at home, and like you said, you can always return if need be. Thanks Emma for your comment! xx

  • passion fruit, paws and peonies
    Posted at 03:22h, 16 January Reply

    Gosh you are so stylish! The boots are fab but I’m a bit too short to wear them. I have an eye on your jeans and that gorgeous jacket from Anthropologie! xx

    • Jess Jannenga
      Posted at 10:18h, 16 January Reply

      thank you Maria! I do try! I bet you could wear them if you are petite. So glad you like this outfit, the blazer’s colors caught my eye! xx

  • barrettadeb
    Posted at 22:04h, 15 January Reply

    Ooh Jess! Those colors are divine on you. I love when you wear rusts. The ruffled plaid blazer is so pretty. I should have known it was Anthroplogie. They have the BEST styles. I can’t wear OTK boots because I am a modest 5’1″. Lol! But that doesn’t stop me from wearing knee high boots. Love this post dear lady. 💋


    • Jess Jannenga
      Posted at 10:09h, 16 January Reply

      Thank you Debbie! I bought it on Poshmark, and often find great Antrhopologie deals there! I couldn’t pass up the color of these boots and they keep you warm in these cold temps! Glad to hear from you. xx

  • dhuckeba
    Posted at 18:20h, 15 January Reply

    Love that jacket!! Looks so good on you. The boots are pretty great too.

  • Maureen
    Posted at 17:42h, 15 January Reply

    Your OTK boots are beautiful but I really want your plaid blazer! I am seriously swooning so hard over them and I am not the blazer kind of a gal. The color, the style and everything about it is just gorgeous. I think I’ll stare at them for a bit longer. 💕💕💕

    Maureen |

    • Jess Jannenga
      Posted at 10:13h, 16 January Reply

      Thank you Maureen! I saw this and loved the rust and navy plaid, and have a few pair of OTK boots , these are my favorite. xx

  • thisblondesshoppingbag
    Posted at 13:28h, 15 January Reply

    Oh, I’d love to be 5’9″! I think you’re the perfect height for OTK boots. Sometimes when I wear mine I feel like I’m all boot and no leg, ha! These colors are all so pretty and look fantastic on you! Stay warm Jess, I’m with you, there’s a huge difference between “Southern cold” and rest of the country cold, I’ll keep ours!

  • Mother Daughter (@MnDchitchat)
    Posted at 11:28h, 15 January Reply

    We are in Fl and it has been in the twenties a few mornings and the wind is cutting, but the sun is shining and I will take that over snow any day. lol Great look, I wouldn’t wear otk boots but they are a good look on you. I should say I can’t wear the boots because of wide calves and knees. lol

  • Suzanne Smith
    Posted at 10:29h, 15 January Reply

    Hi Jess! I so agree with you that the Southern cold is better! My daughter is in Boston and she has been miserable…especially after leaving Savannah GA!
    Your jacket is so beautiful! I love the ruffled front and the boots and bag and just the whole thing! By the way, not many people can pull off a sweater dress, but you are definitely one that can! Have a great day!

    • Jess Jannenga
      Posted at 10:34h, 15 January Reply

      Oh boy, Boston would be cold, and i love Savannah! Thank you for your lovely compliment. This is the first ive worn the OTK boots with jeans, but like this style as well. Oh, sweater dresses are among my favorite dresses to wear. thank you! xx

  • Jodie
    Posted at 10:01h, 15 January Reply

    It’s such a modern and fabulous look Jess!!
    I love that any aged woman can wear these boots—and they certainly are warmer!!

    • Jess Jannenga
      Posted at 10:10h, 15 January Reply

      Thank you Jodie! Absolutely! I think all ladies can wear these and they are fun to style with anything from long dresses to sweater dresses, and jeans. xx

  • Roxanne
    Posted at 09:51h, 15 January Reply

    Rust is definitely your color, Jess! My otk boots have definitely been getting some use in Chicago this winter! They are the first thing I reach for to keep my legs warm! I love the outfit with the sweater dress, too.

    • Jess Jannenga
      Posted at 09:54h, 15 January Reply

      Thank you Roxanne! I know, they do keep your legs warm and I always love the look. I wear them more with dresses, but had to try em with jeans. xx

  • Patti
    Posted at 09:27h, 15 January Reply

    Yes, we’re having Southern Cold now, which does not compare to Northern Cold, but we still bundle up! You really rock the OTK boots, and this blazer is stunning. thanks for linking up, xo


    • Jess Jannenga
      Posted at 09:55h, 15 January Reply

      Yes we do Patti! It is going to get warmer after this week. Glad you like the look! xx

  • Jess Jannenga
    Posted at 08:52h, 15 January Reply

    Hi Debbie! I bet! I suppose I shouldn’t complain too much! I am a believer than everyone can wear this style of boot, if you love them.. but it has to be something you love and want to wear. There are so many styles out there as well. I will make a note on writing a post on accessories! Thank you Debbie! Enjoy your day as well. xx

  • Debbie Hull
    Posted at 08:32h, 15 January Reply

    Hi jess ! I live in Michigan and we are cold ! Brr ! I can’t wear otk boots due to the fact that I am a plus size but I do love the rest of your outfit. I like the brown necklace. Can you consider doing something on accessorizing with jewelry ? I know it’s not clothing but it’s still apart of our look. Thanks and have a nice day !

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