How I Wear My: Booties

How I Wear My: Booties

Welcome to the 44th How I Wear My post!

Booties are such a wardrobe staple—we bet you have at least two pairs in your closet—that it seemed high time we featured them in a “How I Wear My” post. They look great with pants, skirts, dresses, even shorts, and can be dressy, casual or anything in between. They may be the hardest working shoe in your collection!

Let’s get How I Wear My: Booties started with my HIWM partner, Jill of Everything Just So!

Jill’s showing off her New York City street style in Calvin Klein wedge booties. Jill says they are perfect for winter and easy to walk in for long city blocks. Her coat is by J.Crew and she’s wearing a L’Wren Scott peony print scarf. Her bag is a YSL Tribute tote and she’s carrying Lord & Taylor red leather gloves.

As we all know, the east has been getting their fair share – and more – of cold weather this year. And although the sun may have been out, Jill said it was freezing when this picture was taken, around 25 degrees!


Linda of A Labour of Life looks modern and edgy in this bootie look and says, “Leggings and booties go hand in hand, one of those looks that make you still enjoy the cooler temperatures. I found this great tunic from Oakleigh Rose last year and added a pair of plaid leggings and a black moto jacket, so of course a black bootie from Forever 21 just seemed the perfect accessory.”


Malia of Style by Malia wears her booties elegantly. She tells us, “I love navy blue and leopard. When I saw this ASOS dress with the lace cap sleeves, I knew I had to pair this dress with my “Jetset” Nine West booties. I grabbed my Kate Spade Book Clutch and I am ready for a night out!”



Jane of Toronto Shopoholic is giving off a retro-chic vibe in this fur-collared cape, leopard clutch, skinny jeans and striped top. She says, “These are on the higher/mid-calf side but I still feel are more of a bootie than a full blown boot.”


Deborah of Fabulous After 40 is stylish and glowing in her bootie outfit. She says, “These are my Stuart Weitzman slouchy suede booties that I wear with just about everything. Here I’ve paired them with my favorite Eli Tahari leather pants and a creamy cable knit sweater by DVF.”

Rich Life Deborah Boland- Fabulous After 40

Nora of Jacket Society exemplifies California Chic in her cognac booties. She tells us, “I am wearing my favorite leather jacket that I bought in Italy with Gap white jeans and my Ralph Lauren booties, plus a couple of Jacket Society necklaces that are available for purchase on our web site.


Dianne Callahan, reader, shows us how to wear booties with a skirt. She says, “This is how I wear my favorite black suede booties that have a small ruffle. I love this outfit for transitioning from winter to spring in Southern California!”


Susan of Une Femme d’un Certain Age also wears her booties with a skirt in this sophisticated look. She says, “These heeled booties from Aquatalia by Marvin K. are not only waterproof, but comfortable. I danced in them all afternoon at a niece’s Bat Mitzvah.”


Debbie of Fashion Fairy Dust wears sassy red booties. So glam! She tells us, “These red booties are such an outfit maker. They add a fun pop of color to anything I pair them with.”


Cynthia of My Rose Colored Shades stays warm and fashion-forward in these buckled booties and plaid coat. She says, “This is one my current favorite booties. I’ve been wearing them everywhere!”


Yvonne of FunkyForty wears two-toned booties in this chic, casual look. She tell us, “I love wearing booties – mainly for casual or casual dressy. My most favourite ones are those with the pink inlay at the back. I bought these at the beginning of last year from Zadig et Voltaire but you can still buy them online. I love the fact that even though they are bright pink at the back they still go with almost anything. One of my mantras is the conviction that a white shirt, good fitting jeans and booties is a fab staple outfit that will keep you going through the years;-)”


Suzanne of Suzanne Carillo looks like a Hollywood movie star ( I just love this Vanity Fair-esque photo!) in her leather dress and metallic booties. She says, “I am a bit of a bootie and boot hoarder. I dare not count just how many I own. I often wear them year round. I find them much easier to wear than most high heeled shoes as my narrow heels don’t slip out of them.”


Pam of Over 50 Feeling 40 looks terrific in chocolaty brown Antelope Booties. She wears them with a beautiful cashmere cape from Catherine Robinson’s Cashmere.


Kimberly, owner of Dolce Vita Salon (my hair salon) always dresses so stylishly wherever she goes. Here she wears a beautiful gray Calvin Klein dress with Cynthia Rowley booties and tights.


Alice of Happiness at Mid-Life is dressed for the office or out on a date in these ankle booties. She tell us, “Growing up, it was a fashion rule not to wear these types of shoes for shorter girls because it cuts off your legs and makes you look even shorter. I have given up on fashion rules and wear my White House Black Market booties with skirts and dresses. I do love how it gives a bit of an edge to an otherwise feminine outfit.”


Heather of Chez Bliss wears low-heeled booties with her boyfriend jeans and orange Adora bag (we are Adora bag twins!) and says, “These are my new black Earth Origins. I like this brand for their great arch support–which I desperately need otherwise my back will pay. I am still learning the styling ropes of “boyfriend” jeans so this HIWM is a good excuse to experiment wearing booties with them.”


Nicole of High Latitude Style wears booties that serve two purposes…fashion and function! She tells us, “In Alaska, many people wear ducks. I always liked their funny look, but they where out of consideration because they had no heel. Thus, when I saw these heeled ducks, I had to have them. They are crazy, but I really love them. I never tie the laces. I think they are so much more stylish when worn open.”


Trina of Tea Time With Trina is giving off a modern Mad Men vibe in this classic and ladylike look. I love all the different patterns and textures! She says,”These booties help welcome in spring. I enjoy wearing them with cropped pants to dress them up a bit, but mostly find myself wearing them with skirts.”


Ana of Mrs. American Made looks ready for spring in her suede booties. She says, “This look is a nod to the very anticipated Spring weather here and a slightly fancier look for dinner with our Governor. I am wearing a cream-colored jacket with gold metallic threads by Nanette Lepore and #madeinUSA print top and colored jeans by Bullet Blues. These booties are sumptuous suede and made in California by Calleen Cordero.”


Teresa, wife of photographer, Denton Taylor, goes for high glamour in these fantastic booties. She says, “These are Cesere Paciotti booties with stiletto heels. I am wearing Armani leather pants, and an Escada silk blouse. You have to wear edgy stuff with these booties!”


Dawn Lucy of Fashion Should Be Fun wears a suede wedge in this casual and chic look. She tells us, “I’m wearing my favorite taupe suede booties. I love these little Vince Camutos! They go with so many things and the wedges make them super comfy.”


Cheryl of Northwest Mountain Living looks cozy and beautiful in her heeled taupe booties. She says, “I wear booties a lot and the booties in this picture get the most wear. They are comfortable enough to wear all day and look great with everything from jeans to maxi skirts. Here I am wearing them with an old pair of Lucky jeans, a cream turtleneck and a shearling vest.”


Catherine of Not Dressed as Lamb or Julie Christie in Dr. Zhivago (one of my favorites!)? It’s Catherine and she’s  wearing a neutral plaid wool coat with a feather cossack hat and suede heeled booties for an eye-catching and toasty warm look.


Libby of Libby Wilke Designs wears low-heeled black booties with a beautiful deep orange coat and colorful scarf. She tells us, “This is my first pair of booties! I recently had to start wearing orthotics and the doctor said to try Munro shoes. Well, they are fabulous. I bought these at Nordstrom and they are SO comfortable that I wear them every day. I’m still not convinced about the ‘bootie’ look, but for now, they do the trick!”


I have worn these Boden suede booties more than any other boots in my wardrobe, even more than my tall boots, which is saying a lot. The low heel fits my lifestyle and they are so comfortable. I could probably run in them if I wanted to!

I wore my booties with Hue faux leather leggings, my black Adora bag and a long, asymmetrical sweater from Stella Carakasi (from a couple of seasons ago but currently available on sale at their Stella Studio location).


Thank you, thank you to all the gorgeous and stylish participants. Jill and I very much appreciate your beautiful outfit photos!

Don’t forget to stop by Jill’s blog, Everything Just So, to see another 20+ bootie looks from our lovely participants!

How I Wear My Badge

For April, let’s focus on layers! If you start with a basic shirt or dress and begin piling on a sweater, a jacket, a scarf and jewelry until you have a beautiful and unique look we want to hear from you! Join us for “How I Wear My: Layers” by sending a photo to us at by March 30, 2015.

Don’t forget to include a few details of all the lovely layers you are wearing!


Thank you

Make it a rich day!




Disclosure: I was given the Stella Carakasi sweater and Adora bag in exchange for promotion. All opinions expressed here are, as always, my own. 


  1. March 4, 2015 / 5:59 am

    What a range of looks here, I love it! Everyone looks so good and I’m with you, I really love that photo of Suzanne (not to mention those golden booties). Another great HIWM roundup! XO, Jill

  2. March 4, 2015 / 6:11 am

    Love “rose colored shades” look and that of Theresa(?) Denton. All are great, but love their edge!

  3. Kathy
    March 4, 2015 / 6:33 am

    I love booties, and have worn them for years, almost daily. All great looks above, and especially loving Malia’s – those leopard boots are fabulous.

  4. March 4, 2015 / 6:45 am

    I love wearing booties and seeing everyone’s style! Thank you for putting this together.


    Hope to see you Thursday for TBT Fashion link up.

  5. March 4, 2015 / 7:34 am

    What an exciting array of boot wearing women. I’ve loved those leopard booties of Malia’s since the day she posted them on instagram, and those winter booties of Nicole’s, I mean who knew winter booties could be so stylish? And then we have Teresa’s dream booties and well, I could go on and on, each one of these ladies look stunning and so stylish in their booties.
    Your classic take on black leather with black booties is the perfect go to outfit in my book.
    Thank you, again, for this fun monthly party.

  6. March 4, 2015 / 8:16 am

    Thanks again for putting this together ladies : )

    Your style is very sleek and chic Adrienne.

    I really love Nora’s look with the mix of neutrals and textures.


  7. March 4, 2015 / 8:19 am

    I love lots of these boots and booties, so it feels unfair to comment on just one. I will do so anyway as she totally surprised me. “She” is Teresa. What awesome booties, what an awesome outfit.
    PS with my apologies to all the other ladies and to our hosts, for not mentioning them…

  8. March 4, 2015 / 9:11 am

    i have several pairs of booties and find that they are very versatile…as do these lovely ladies. Great to see such wonderful outfits all styled so differently…congratulations on post #44! That is quite amazing!
    The Adora bag is gorgeous….

  9. March 4, 2015 / 10:31 am

    Thank you so much for putting this together, another month of great looks from fabulous ladies. Looking forward to next month!

  10. March 4, 2015 / 11:21 am

    Another fun edition of HIWM! Nice to a see a few new faces too! Thanks so much for hosting this!
    Dawn Lucy

  11. March 4, 2015 / 12:16 pm

    I love all this inspiration in one place! Everyone looks fabulous!

  12. March 4, 2015 / 5:31 pm

    Thanks to Adrienne and Jill for another fantastic HIWM idea. Thanks to everyone who mentioned my wife Teresa, she loved reading the comments. Suzanne, you are looking quite the queen there and love those gold booties. One can never have too much leather either! Malia those are cute too!

  13. March 4, 2015 / 6:23 pm

    That was fun! Thank you so much for including me in my very first pair of booties!!! Having seen these great outfits and styling, I just may have to buy another pair…

  14. March 5, 2015 / 12:00 am

    Love all the booties in this post! 😉

    And your look is perfect Adrienne. I recently bought one of those sweaters with a slit like your’s and realized I needed to wear high-waisted pants or leggings. Styling it with the leather pants here like you did looks great.


  15. March 5, 2015 / 6:29 pm

    What a great collection of booties! Love Teresa’s sassy stiletto booties. And Nora always has great shoes and jackets. Love your monochrome outfit. That sweater has such a cool asymmetrical hemline. ~Cynthia

  16. March 7, 2015 / 6:18 am

    Adrienne thank you so much for including me – booties is a great theme as I think that it’s something just about everyone wears!! All the ladies look so great but Trina’s outfit is especially fabulous 🙂

    Must also say you look so good in faux leathers… nothing more to say other than er, HOT???!!!!

    Catherine x

  17. Juliet Russell
    March 9, 2015 / 1:06 pm

    Adrienne – Our mutual friend, Debra, led me to you years ago, but I lost track of you. Now, through Northern California Style I’ve found you again. Yay! Try as I might, I cannot subscribe to your blog – I enter my email address and click subscribe but nothing happens. I’ve logged in, logged out, restarted computer – nada. Help!

    • Adrienne Shubin
      March 9, 2015 / 1:12 pm

      Hi Juliet,

      I just added you to the mailing list manually. Hopefully you will get a notification. Let me know! Thank you for telling me.

  18. March 26, 2015 / 8:01 pm

    Wow, Adrienne that was a good one! Thanks for including me. I could really see everyone’s personality coming through with such a wide array of boots….. Oxford booties, who would have thought there was such a thing? Fashion is so fun and creative at the moment. Loving this regular feature. Cheers! Deb

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