How I Wear My: Tall Boots

Happy 2017 and welcome to the first How I Wear My of the year, the 66th HIWM post in this long-running monthly fashion series!

Whether you wear them for function or fun (or both!), tall boots are such a popular item in January that Jill of Everything Just So and I wanted to dedicate this month’s roundup to them. We bet you are getting a lot of use out of yours right now and we wanted to see how everyone styles them! 

Let’s get right to it and see how January’s participants style their Tall Boots!

Jill of Everything Just So

Jill, my How I Wear My partner, starts things off and says this:

“I love a long lean look with tall boots so I kept the outfit on the dark side with Old Navy jeans, a black cardigan, a navy J. Crew T-shirt with a green lace insert, and black jewelry and accessories. I wear my tall boots as much as I can since they make getting dressed so easy!”

Malia of Style by Malia

Malia tells us:

“I love a boot and skirt and these eloquii over-the-knee boots were a first for me. The glitter heel sold me! I rocked it with a Society+tulle skirt and tee by fashion illustrator Nichole Kobi.”

Cheryl of Northwest Mountain Living & Style

Cheryl says this about her tall boots:

“I love OTK boots so much, I have three pairs. These caramel colored Dolce Vita boots are probably my favorites because of their color and casualness. I wore them with copper colored pants and a blanket scarf.”

Michelle of RetroChicMama

Michelle says:

“Tall boots can rescue me from an outfit crisis, lift a plain outfit to funky or sexy and work with 90% of my wardrobe! All year I wait patiently for the weather to cool enough so I can get them out to style over again”

Linda of Labour of Life

Linda tell us:

“Black and Burgundy can be such a striking combination and when that burgundy comes in OTK knock out boots well, I feel ready for anything! Some like to say we more mature types should stay away from OTK boots. I say, stay away? I dont think so!”

Catherine of Not Dressed as Lamb

Catherine says:

“This is my one pair of over-the-knee boots bought just over a year ago. For this outfit I thought the tan colour would work especially well with the charcoal grey of my sweater dress and the burgundy of my sleeveless coatigan – the ochre bag adds one more touch of warming colour to the whole palette! I’m loving all these deep, rich colours at the moment, and tan as an accent colour enhances where black would deaden them.”

Judith of Style Crone

Judith tells us:

“I discovered these tall suede heeled boots at a consignment store sale.  I wore them on New Year’s Eve with sequins and a statement necklace by blogger friend Carol Markel of Femme et Fleur.  They’re comfortable and perfect for dancing, which adds to their appeal.  I feel grounded in their classic elegance!”

Trina of Tea Time with Trina

Trina has this to say about her look:

“This is how I dress down a skirt – or actually a dress – for a cold snowy day. By pairing some OTK boots with a shorter skirt you accomplish two things, you make the skirt appear longer and you keep your legs warmer. Plus these babies have some nice treads on the bottom so no slipping on the ice.”

Nicole of High Latitude Style

Nicole tells us:

“In Interior Alaska, the cold season lasts about seven months. Thus, investing in nice boots is a must. Last summer, I was looking for a statement color, red or burgundy. When I saw these turquoise Jimmy Choo tall boots, I thought the color is an even better statement as I have many items in my closet that have turquoise accents.”

Ana of Mrs. American Made

Ana tells us this about her tall boot outfit:

“This photo was taken on a snowy but not too cold day so I didn’t need a big, heavy coat. Instead, I wore my #MadeinUSA tall brown leather boots tucked into skinny jeans and wore an American-made bright floral top by Splendid. The scarf and cardigan are good for layers of warmth and for picking up the lovely colors of the blouse. One of my favorite parts of this outfit is the belt. My husband made the buckle and gave it to me as a gift a few years ago.”

Greetje of No Fear of Fashion

Greetje says:

“This skirt is very hard to style for me. With this cropped top I needed a similar colour at the bottom to “book-end” the outfit. I had some really soft, very old boots in the closet. Bingo! Finding the belt with the studs to go with this outfit was something I was pretty proud of. I think it works really well.”

Julie of KayandStar

Julie tells us:

“These boots are not really tall – my legs don’t really work with tall boots. But they are fun! I love these boots from Artemis Boots in Carmel. I love all things embroidered and when I saw these boots, well let’s say I have my own collection – most are booties but a couple are taller boots.”

Debbie of Fashion Fairy Dust

Debbie has this to say about her look:

​”I remember just a few years ago, being resistant to the idea of over the knee boots. Now they’ve become a Fall/Winter wardrobe staple for me. They work with so many things; skinny jeans, skirts, dresses, leggings. Not only do they look good, but they provide the added bonus of an additional layer of warmth, making dresses and skirts easier to wear when the temperature drops.”

Valerie of Now I’m Sixty Four

Valerie tells us:

“Although these aren’t the conventional ‘long boot’ they are knee high. They are Ralph Lauren wellies which I wore for my son’s wedding in France this October. We had to walk along the riverbank between the chateau and the watermill and back – a couple of miles each way.”

Suzanne of Suzanne Carillo 

Suzanne says:

“I’d been searching for a pair of tall lace-up boots for a long time before I came across these black ones at a vintage show. They are very high quality from Italy, probably from the early 1970’s. The dress came from an estate sale of a woman that sewed all of her own clothing. Each piece of vintage is an ever evolving narrative of owners and history. Wearing memories and saving brilliant pieces from landfills is why I opened Vintage by Suzanne Etsy store. Small choices in life create big changes for our world.”

Shelbee of Shelbee on the Edge

Shelbee tells us:

“I absolutely love tall boots! I probably have too many. Here I paired my over-the-knee brown boots with black leggings, a dark chambray tunic, and my favorite blanket scarf from Shelbee’s Shoppe. I love the autumnal colors in the scarf and how they tie together the black and brown. I used the dark chambray as the neutral that anchored the whole look.”

Glenda of So What to Twenty!

Glenda says:

“This outfit gives a wink into the statement – even in the midst of uncertainty – that there will always be opportunities to grow. Dressed in mysterious black, the ensemble is given pops of the unexpected with a skirt which reminds me of uncertainty with its fragmented pattern. To give hope, and newness into the coming year – a bright, Kelly green bag that definitely gives us a spark to embrace the many opportunities to grow. The items in this story have been with me for some time, but with new beginnings comes a fresh way of viewing things, so I have partnered the garments with each other to create a fashionable rebirth.”

Nancy of Nancy’s Fashion Style

Nancy tells us:

“I never chose shoes or boots by the way they fit, ony by the way they look. These boots are a good fit and easy to walk in.  And they are gorgeous too!”

Rena of It’s all Fine. Whatever tickles the fancy.

Rena has this to say about her look:

“This was the debut showing of my OTK boots, that I wore to a backyard get together with friends last fall. Since the weather was warmish, I was able to get away without wearing tights underneath the boots and yet my legs were nearly all covered.”

My Look

I have worn tall boots for decades. I wear them often in fall and winter with both dresses and jeans. I have only ever owned black boots until recently when I decided it was time to add some cognac boots to my wardrobe. I find cognac works well with so many of my outfits. I knew if I bought a pair in this rich shade, they would get a lot of use. So I went about searching for the ideal pair and found these tall cognac boots on sale for about $100.

They fit perfectly and are so comfortable, right out of the box. I wore them with my new beautiful sweater coat my mother sent me for Christmas. Isn’t the color pretty? Thank you, mom!

I styled my boots with jeans, winter white wrap top, a beaded necklace with a leather cognac tassel (similar) and my  much-loved Australian Outback hat from Montecristi Panama Hats in Napa Valley.

It’s a cozy, casual winter look I will wear again and again!

Thank you to all the participants this month!

We loved seeing how you wear your Tall Boots!

And now for February’s theme!

With Valentine’s Day in February it can seem like pink and red are THE colors for the month, but we want to show some love for one of our other favorites—Blue!

We have a feeling you 💙 this color as much as we do, so whether you prefer Cobalt, Turquoise, Royal, or Sky, style your most adored hue and join us for “How I Wear My: Blue.”

Photos are due by February 6, 2017. Send them to us at and be sure to include some text about your outfit, which we will use directly in our posts. Our color roundups make especially appealing posts so we hope you will join us!

How I Wear My Badge


Be sure to visit Jill’s to see even more stylish Tall Boot looks!

Make it a rich day!






  1. January 11, 2017 / 6:53 am

    It’s so fun to see how everyone wears the “same” thing yet it’s really so different!!
    I wonder if there is a woman out there that doesn’t own pair of tall boots? They seem like the most functional pair of footwear in the winter months!!
    I love your lilac sweater with the brown boots Adrienne!

    • Adrienne Shubin
      January 13, 2017 / 6:01 am

      Ha! I don’t think I know any women who don’t wear tall boots. They really are staple for a fall and winter wardrobe.
      Thank you for your submission – hope to see you next month for BLUE!

  2. January 11, 2017 / 6:55 am

    Everyone looks so great in this link up! It shows the amazing versatility of tall boots. I was on the fence when I first bought mine thinking, “how would I wear them?” Your post is proof that ways to wear tall boots are as varied as the individuals that style them. Peace! Cheryl

    • Adrienne Shubin
      January 13, 2017 / 6:00 am

      Love your OTK boots! I have been entertaining the idea of getting OTK myself but I think it would be a project, trying to find a pair long enough to go over my knee.
      I adore both looks you submitted….I think your style is spot on!

  3. January 11, 2017 / 7:30 am

    Oh what a lovely, inspirational bunch of women. So many styles/boots I really loved.
    As for your boots, they suit you (and I suppose your lifestyle) to a T. The coat your mother sent you is divine. I love bright colours in winter. Cheers you up so much.

    • Adrienne Shubin
      January 13, 2017 / 5:59 am

      I love my sweater coat too and think of my mom whenever I wear it, which is often! I like my cognac boots so much, I bought them in black too.
      I love your fun skirt look. I can see how that skirt would be hard to style. The cropped top was a perfect choice!
      Hope to see you next time for BLUE!

        • Adrienne Shubin
          January 31, 2017 / 5:45 pm

          Looking forward to seeing you for HIWM: Blue, Greetje!

  4. January 11, 2017 / 7:40 am

    Love tall boots and everyone looks fabulous! Thanks for another fun month of HIWM!

    Dawn Lucy

    • Adrienne Shubin
      January 13, 2017 / 5:58 am

      Thank you, Dawn Lucy. Hope to see you for BLUE next month! xo

  5. January 11, 2017 / 2:57 pm

    I am such a huge fanatic of tall boots! I wait all summer to bring them out. Once again, an amazing round up of fabulously fashionable ladies and I am honored to be part of this group! Thank you as always for all the work you and Jill put into this series!


  6. Vicky
    January 13, 2017 / 4:53 am

    Interesting how you call it a “sweater coat”. Here in the UK that’s a “coatigan”!

    • Adrienne Shubin
      January 13, 2017 / 5:57 am

      I have seen Catherine of Not Dressed as Lamb use that term but have never heard it here in California. I think calling it a Coatigan makes more sense than Sweater Coat!

  7. Jill
    January 14, 2017 / 9:11 am

    This is such a great post! I am especially crazy for Julie’s boots, which really seem like a work of art to me. Cheers to another month of fashion fun. You look so casually glamorous in your coatigan. That is definitely one of your colors! xx

    • Adrienne Shubin
      January 31, 2017 / 5:50 pm

      Julie introduced me to the boot shop in Carmel – I got a pair too but in black. Seeing Julie’s look, I wish I had gotten gray and blue!

  8. January 17, 2017 / 9:25 am

    Oooh Ahhh Sighhh all the way through this lovely lot! Honestly I don’t know whether to thank you or not Adrienne, this is deadly! So many gorgeous boots to covet & I really don’t need any more Arrrrgh!
    I’m biased of course but I think this is your best ever HIWM 😉

    • Adrienne Shubin
      January 31, 2017 / 5:46 pm

      Lots of great boot looks….I think I need to track down a pair of OTK! Thanks for joining us. Hope to see you for next month’s theme – BLUE!

  9. January 28, 2017 / 7:58 am

    I so enjoyed seeing all of these lovely ladies and their boots. I do visit all of them occasionally but it’s so nice to see all of them in one place. And I had popped over here to see images of California while I sit here in gray Michigan, so it was a nice surprise!

    • Adrienne Shubin
      January 31, 2017 / 5:45 pm

      I never really thought about that…you’re right! It is a nice way to see everyone at once. Thank you for stopping by. Hope you’re getting some sunshine in Michigan!

  10. January 28, 2017 / 6:12 pm

    so many great looks and then that coat/sweater of yours. It is gorgeous

    • Adrienne Shubin
      January 31, 2017 / 5:44 pm

      Thank you for joining us, Linda! I love my new coatigan (I hear that’s what they call it in the UK) is so pretty! My mom knows what I like. Hope to see you for HIWM next week – theme is Blue!

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