Wednesday, January 11, 2017

How I Wear My: Tall Boots

Happy 2017 and welcome to the first “How I Wear My” of the year! Whether you wear them for function or fun (or both!), Tall Boots are such a popular item in January that Adrienne of The Rich Life in Wine Country 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!

I do believe we have checked off all the boot categories in this roundup: over-the-knee boots, riding boots, high heels boots, even sitting boots (look for Nancy). You are going to want to add several more pairs of this wardrobe staple to your closet after seeing this post. Enjoy!

Adrienne of The Rich Life in Wine Country.

Adrienne of The Rich Life in Wine Country, my lovely “How I Wear My” partner, writes, “I have loved tall boots for a very long time yet I have only ever owned black tall boots until recently. I finally decided to buy a pair in a color that works as well as black does with my wardrobe: cognac. I find this color looks great with just about everything from grey to black to navy and even non-neutrals like pastels. These boots were reasonably priced (around $100 on sale at Macy’s) and they are super comfortable...right out of the box, even! I wore my boots with jeans, a creamy white top, and a Peruvian alpaca wrap I have had for years. I am a hat lover so I added my favorite Australian outback hat which I can wear in light rain.”

Greetje of No Fear of Fashion.

Greetje of No Fear of Fashion writes, “I bought these over-the-knee boots to go with a rather short dress. Mistake. Made it a bit slutty. But with jeans and a beautiful top, I think they are heaven.”

[Editor’s Note: Greetje never fails to make me laugh with the way she puts things. Also, I want to add her to my Bob Hall of Fame. Membership is ongoing!]

Suzanne of Suzanne Carillo.

Suzanne of Suzanne Carillo says, “This outfit features beige Miu Miu boots and a beige hat, both are 100% secondhand. The boots and hat were bought at estate sales. The jacket skirt and blouse were all thrifted. The hat, jacket and blouse are all vintage. I adore how this outfit came together to create a cohesive look that is contemporary with a nod to vintage styling.”

Linda of A Labour of Life.

Linda of A Labour of Life says, “50 Shades of Grey. I used to think it was such a blah colour ‘til I realized how many variations there were. Wearing a knit skirt and cardigan with some fun tall boots helps me get winter ready.”

Michelle of Retro Chic Mama.

Michelle of Retro Chic Mama looks so elegant-yet-edgy in her AllSaints knit dress and boots, with a vintage mini Chanel bag worn cross-body. I love this look on her!

Tamera of Tamera Beardsley.

Tamera of Tamera Beardsley says, “These tall vintage cowboy boots were a passed to me from a friend. They inspired not only my outfit, but a fabulous road trip to the desert!”

Dawn Lucy of Fashion Should Be Fun.

Dawn Lucy of Fashion Should Be Fun writes, “Loving the OTK boot trend, though I get a bit disappointed when they only come up to the knee on me. And I’m only 5’7! Anyone else have this issue? Still love these burgundy boots I found on sale at Nordstrom Rack and wearing them with my Karina dress and new Kate Spade satchel.”

Jodie of Jodie’s Touch of Style.

Jodie of Jodie’s Touch of Style says, “Living in Denver, Colorado, it would be just plain silly not to have a couple pairs of tall boots in your closet. Needless to say I have more than a couple pairs—ha ha! This is a pair I picked up at a consignment shop last year. I love how they are lighter than the normal black & brown boots! I recently wore this pair of boots with this colorblock dress for our “Animal Prints as an Accessory” post. My talented mother, Charlotte (the 70s model on my blog), actually made both the dress and the purse! Isn’t she amazing?”

[Editor’s Note: Charlotte is indeed quite the amazing lady. I love that she made Jodie’s dress and bag.]

Catherine of Not Dressed As Lamb.

Catherine of Not Dressed As Lamb writes, “These are my oldest, oldest pair of knee high boots (about 7 or 8 years old?) and they’re still going strong. I’ve always loved the studs on them - even now they get so many compliments and I reckon their cost per wear is almost in the minus figures for them by now. They always look good with an A-line midi skirt as here... There are a lot of colours and textures in this outfit but as many people know I’m rarely a minimalist!”

Nancy of Nancy’s Fashion Style.

Nancy of Nancy’s Fashion Style says of her boots, “These are…Sitting Boots. They walk awful! But they are so beautiful. I never chosen shoes or boots by the way they fit, only by the way they looked.”

[Editor’s Note: You have no idea how much I love the idea of an entire category of shoes made for sitting in. I think I own a few pairs of Sitting High Heels, ha ha! Thank you Nancy for your honesty!]

Shelbee of Shelbee On the Edge.

Shelbee of Shelbee On the Edge writes, “I styled my navy blue knee-high boots with my retro-inspired patchwork swing dress from Shelbee’s Shoppe. I layered an ivory swing cardigan over the sleeveless dress to keep my shoulders warm. I was hesitant about purchasing tall boots in navy blue, thinking I wouldn’t get much wear out of them. But it turns out they are so versatile and I have definitely gotten my money’s worth out of these super comfortable boots!”

Ana of Mrs. American Made.

Ana of Mrs. American Made says, “This is a fun look for work featuring a festive floral print dress by Nanette Lepore with a wide leather belt and worn with my vintage American-made Laundry off-white wool coat. The boots are tall brown leather and made by Frye quite a few years back. I take them every year to the cobbler to be spruced up so they have lasted a long time. And I am wearing the tassel necklace that I made from some beads that came from a piece of my grandmother’s jewelry.”

[Editor’s Note: Ana brings up a great point that a well-made pair of boots can last for years if cared for properly. Get to know your local cobbler or shoe repair shop!]

Rena of Fine, Whatever.

Rena of Fine, Whatever writes, “I’ve challenged myself to wear my OTK boots to work and this is the first outfit I styled with them. With a skirt, the boots are neatly tucked up under my hemline which tones down the edginess of the OTK style and yet adds a little extra flare to the standard pairing of a skirt and cardigan.”

Malia of Style by Malia.

Malia of Style by Malia says, “This midi dress called for tall boots. The dress is from Gwynnie Bee. The cardigan is one of my favorites from Eloquii and my tall boots are Nine West.”

Valerie of Now I’m Sixty-Four.

Valerie of Now I’m Sixty-Four pairs her tall boots with a horizontal stripe dress for a feminine yet cozy look. And that is one serious oven she stands next to.

Nicole of High Latitude Style.

Nicole of High Latitude Style says, “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 that this color is even a better statement, as I have many items in my closet that have turquoise accents.”

Claudia of Happyface313.

Claudia of Happyface313 writes, “I don’t wear boots very often, only if I really have to. And while I was still wondering on how to stage a pair of boots, it began to snow. Quite heavily. So the decision was basically made for me. Here I’m wearing my black boots with a black wool dress, a purple long sleeved T and matching purple tights. To give this wintery outfit a bit of glam, I added my Kachinas shawl in various shades of purple.”

Trina of Tea Time with Trina.

Trina of Tea Time with Trina says, “This is a casual everyday look with skinny jeans, an oversize white button-down and blanket scarf. This look can and does fit almost any occasion for one who is on the go, it’s casual yet stylish and just a tiny bit edgy due to the OTK boots.”

Colette of Styled Comfort.

Colette of Styled Comfort writes, “I love wearing my tall boots with my favorite pair of jeans and a statement piece like this faux fur vest. The boots by Ecco are super comfortable and I love the rich brown color, soft leather, and double zippers. The faux fur vest from the cabi Fall 2016 collection keeps me nice and warm during these chilly winter months.”

Cheryl of Northwest Mountain Living.

Cheryl of Northwest Mountain Living says, “These Michael Kors boots are so versatile and elevate any outfit I put them with. I loved them with this fun faux fur vest and leggings.”

I like a monochrome look when I am wearing tall boots so I pulled out my trusty Old Navy skinny jeans, a long black cardigan, and a great new T-shirt I recently got from J. Crew.

So crazy about this green lace insert on a very casual T-shirt.

I love the emerald green lace panel against navy blue. I probably should have bought more than one of these shirts since it’s so easy to wear. I love it with black jewelry, including a floating bead necklace from Macy’s, my Hermès Hapi 3mm bracelet, and my new Fitbit Flex (I am obsessed with this thing, forget how many steps I get in a day, I finally know for sure how bad I am sleeping at night!).

I hope your 2017 is off to a stylish start and you are wearing your tall boots everywhere!

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 heart 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!

Please stop by Adrienne’s to see even more terrific looks featuring tall boots.

And THANK YOU to all the fine foxes who joined us this month!


jodie filogomo said...

What a fabulous roundup Jill!!
I have to think almost every woman has a pair of taller boots---especially if you live in an area that gets cold!
The variety that we've all shown is quite amazing!
And I think that lace detail on your shirt is perfect! I may even try that as a DIY project!!

Unknown said...

Everyone looks so gorgeous! I have been participating in your link up for years and I think this may be my favorite one so far! Well done! Peace!

PS I dont' have a google account so it looks like I an anonymous. But it's me, Cheryl Tucker of

No Fear of Fashion said...

And another great round of inspirational outfits/boots.
You always look so chic. Have you ever thought of moving to Paris? You'd fit right in. Being a bit stuck-up would help. Hmm.. no, you better stay where you are.
Thank you for the compliments on my hair. It never fails to make me laugh (see my comment in the post Bob Hall of Fame.
And as a matter of fact the comment of "looking a bit slutty" was my husband's. He doesn't believe in sugar coating. But of course, he could have been wrong.

Dawn Lucy - Fashion Should Be Fun said...

Another fun HIWM! Thanks so much, Jill!

Dawn Lucy

nancy baten said...

Thank you very much! I think a lot of women own,, sitting shoes or boots,,! I've got several! :-) :-) :-) awful isn't it. Lol.

Adrienne Shubin said...

Love this month's posts! I think I need to get on the OTK bandwagon - so many great over the knee boot looks.
Looking forward to BLUE in February!
xo, A

Coulda shoulda woulda said...

Everyone as usual looks fabulous. I don't wear boots anymore but I feel I just need the right pair and there has to be a pair out there for me!!

Shelbee On The Edge said...

So many fabulous looks once again, Jill! And as always, I am quite honored to be in the company of it all! And yes, Nancy's "Sitting boots" category has definitely caught on. I recently wrote a blog post referencing Nancy's shoe category when I styled the most adorable pair of open toe lace up booties that are most definitely "sitting shoes"! I couldn't even stand them long enough for photos. Ha. But whether they are sitting boots, walking boots, running boots, or posing boots....all of the boots styled here are magnificent! Thank you again for all the hard work that you and Adrienne put into this series. Looking forward to the next one!


Suzanne Carillo said...

Lots of participants this month!

Thanks for the great round-up ladies!


Jill said...

Hi Jodie! Oh please post if you do a DIY lace panel on a shirt. I would love to read that! xx

Jill said...

Hi Cheryl, I thought you had a Google account! Sorry about the hassle re comments I have had some annoying (and X-rated!) messages when I leave it open to anonymous commenters. I loved your look this month. I think I will share it on the FB page. xx

Jill said...

Hi Greetje, you and your husband are so funny! I will see what you had to say re Bobs. I think yours looks perfect! As for moving to Paris, oh I can do Parisian reticence, no problem. I have heard about this from French friends and read about it too ha ha. Guess I will stay in Brooklyn for the moment. Your looks was one of my favorites this month. xx

Jill said...

Hi Dawn Lucy, you looked great for this roundup and so true to yourself. xx

Jill said...

Hi Nancy, your lines about sitting boots cracked me up so much, I just loved it. I know I have several pairs of high heels that I can only sit around in so they are in pretty perfect condition, ha ha. Loved your look this month, thank you for joining us! xx

Jill said...

Hi Adrienne, oh girl, you are so tall, you NEED a pair of OTK boots, you will have legs that go on forever! I don't own any either but part of me wants to try a pair! xx

Jill said...

Hi Naomi, no boots for you? I would love to hear why. Not even riding boots? They are so comfortable! xx

Jill said...

Hi Shelbee, I hope you join us for Blue. With your coloring and amazing eye-makeup I'm thinking you could knock it out of the park no matter what shade you picked! xx

Jill said...

Hi Suzanne, I loved that outfit you put together. It belongs in a magazine! I hope you will join us for blue. xx