Fall Ankle Booties Styled 4 Ways

Hi Ladies!  I’m super excited to be collaborating with three fabulous blogger friends: Jo-Lynne from Jo-Lynne Shane, Cyndi from Grace + Beauty and Cathy from The Middle Page.

Ankle booties are such a key fall wardrobe staple that today we’re bringing you 4 different ways to wear them. Take a look at my outfit, and then pop over to their blogs to see more great bootie styling ideas.

If you are new to my blog, Welcome! I’m Deborah, and I’m here to help you Tweak Your Chic and Look Fabulous After 40, 50 and more!


This time of year I’m itching to wear booties, but it’s still quite warm out. So, when I spotted these suede cutout Booties, I thought they were the perfect solution. Why? They are a gorgeous, warm taupe shade which transitions really well from one season to the next.


I love the pretty peek-a-boo cutouts at the sides. They make these booties look really special. They’re also good for keeping my feet cool and stop my booties from looking too heavy, like they are weighing down my outfit.


I was out in Vancouver recently, dropping off my son at University, and it got quite chilly there. I didn’t have a coat with me, so I picked up this cute Utility Jacket from J.Crew that goes really well with my booties. I’ve never bought a utility jacket because they all seemed too dark and rugged for my taste. But then, I found this more feminine version, which is much more me.


I really like this jacket because it nips in a bit at the waist, giving me a nice shape. (So many utility jackets are super-boxy). It’s short and sassy like a blazer, and you can roll up the sleeves, creating a sporty, youthful vibe.


The color is perfect for me. It’s on the yellow side of taupe, and the pretty gold buttons and zipper give it a refined, upscale look. I just found out that this jacket is a best seller at J. Crew and I’m not surprised. It’s super practical too!


Here’s a great shot of my booties again. Aren’t they darling? They look more golden in the bright sun. And, see the gold zippers at the back? There are a lot of plain booties out there, but these have personality in a quiet, sophisticated way.


I paired my utility jacket with this classic, Vintage Cotton T-shirt from J.Crew. It’s that gorgeous new fall shade called Lush Meadow – so refreshing.

I’m wearing it with some jeans that you’ve seen here before on the blog. They’re High-rise, Ultra skinny Hoxton jeans from Paige, my favorite jean brand. Let me tell you; I love that high-rise. These jeans are very comfy, and the high, stretchy waist really helps hold in the extra bits. ( LOL)


You’ve probably been eyeing my bag? Isn’t it gorgeous? This is the new Brooklyn Crossbody Saddle Bag from Michael Kors. It comes in suede too.


Crossbody bags like this are a HUGE trend this fall, especially ones like mine with the thick guitar strap. It’s kind of funky, and a bit different for me. My Michael Kors Gold Watch and Kate Spade Knot Bracelet look great with the bag’s hardware.


So there’s a look at my new booties, and how I’m styling them for when I’m out and about, or walking the wooded path at my favorite park. Can you imagine how rich they’ll look once October arrives, and I’m walking through a beautiful blanket of colorful Autumn leaves? Here’s how you can..

Be sure to check out Jo-Lynne, Cathy and Cyndi’s  blog. They’re great! Click on the links below to read their posts and see how they’ve styled their fall booties!


Deborah // Jo-Lynne // Cathy // Cyndi


Join the Conversation

27 thoughts on “Fall Ankle Booties Styled 4 Ways

  1. I thought I would get some good ideas by signing up to your blog, but am very dismayed that every piece of clothing and every shoe and accessories is so highend for the “average” person! I’m not sure who could afford to spend over $400 on a pumpkin spice sweater, let alone shop at Nordstroms or Michael Kors? Although everything you show us is lovely, it is something that many of us could never afford.

  2. Deborah, You look fabulous! I noticed you tucked your jeans into your boots rather than cuff them. I’m curious as to why…Is there some rule about when to tuck and when to cuff?

    1. Hi Carolyn,
      I’m not wearing socks as it is hot here, but I will wear sockettes with them when the weather gets cooler. I like these better because your heel and toes are covered but you still get the cutout effect. You could wear a light sock too if you wanted. These are meant to be transitional booties. I wouldn’t wear them in heavy winter weather.

  3. I love the blue shirt and I was interested about your opinion about utility jackets – your reasons for not wearing them up to now are the same as mine! I love the jacket you are wearing – that colour would not work for me, but I think I will cast my eye around for somthing similar in a different colour. You have certainly inspired me and you look lovely in the pictures.

    1. Thanks Fiona for your lovely compliment. This is a good example of not just jumping at something because it is in style. Utility jackets have been popular for about three years, but it’s not until now that I’ve bought one. I was waiting for a version that was more refined, more me.. and it this never came along, I would have passed on the trend altogether. Did you know this jacket comes in other colors and so does the t-shirt? Click through the shop links to see the other choices. Thanks for taking the time to write in. Cheers, Deborah

  4. I’m on the “more” side of the 40, 50 and love this look. I find it challenging to say the least to find outfits that do not “age” me or with trends that are more geared for the younger group which are more times not, run on a more relaxed look, which is just not my thing. So to find you on G & B blog was a delight. This is a look for me, which includes the very stylish, trendy, and maintains a classy look, Have run right over to the J. Crew site and ordered the utility jacket and it was on sale! Also have my eye on those booties, hum, think I just might need to add those to my fall list also.

    1. Hi Sheryl, Yes!! Just noticed it went on sale the day I posted. Lucky you!! As for the booties, as my mom used to say when I was uhmming and awing about buying something.. “Get it, Get it!! It’s important to always keep yourself looking nice.” And you know what?… she was right. I’ve found that when you look good, you feel good and life is so much more fun. All the best to you Sheryl. I’m so glad you dropped into chat. Have a great weekend! Cheers, Deborah

    1. You know, I wore these all day yesterday and I felt pretty darn good. People underestimate how something new and stylish can really give them a lift. These are both cute and super practical.
      Thanks for popping in to take a look Jaymie! Cheers, Deborah

    1. Glad you liked them! Cyndi you looked adorable in your outfit. I was just over at your site. Ladies, be sure to check out Cyndi’s cool 70’s inspired outfit and cool booties! Cheers, Deborah

  5. I really like this outfit; actually I love it!!! I really struggle to find age appropriate, flattering, run around casual clothes that don’t make me look frumpy!!! This outfit fits the bill! Since you were in Vancouver, I’m sure you saw lots of mountaineering wear on the city streets…… I look beyond bad in these types clothes! Mountain Equipment Co-op is not a place I choose to buy clothes for everyday:):). !! Now back to your outfit, I love that it’s casual, but still a little glamourous! You don’t look like you are trying too hard or overdressed, either. This is key when you are out doing normal everyday things like groceries, errands and hockey games….. Bonus, the heels are low enough to be safe when climbing down those sky high bleachers with no railings:):)…… Thanks for posting some chic Canuck wear!! Isn’t Vancouver beautiful? Nice outfit to wear while soaking up the city’s unfathonable beauty!

    1. Yes, Vancouver was breathtaking. Next time, I ‘ll have to do some photo shoots three for the blog! You’re right this outfit is great for running around in. It’s practical and chic which is just what I need for my lifestyle. Thanks for dropping by Lynn! Cheers, Deborah

  6. Love the look! I have never tried this brand of jeans. Do they run true to size. I normally wear a size 6 Not Your Daughter Jeans and a size 8 in other brands. Utility jackets are a nice weight and pack well. I have a mustardy colored one that I have really enjoyed over the past two years and will bring it out again, in late October or if I travel. Living in Florida is a crap shoot for fall outfits. Layers are great…..

    1. Hi Jill,
      Jeans are a funny thing aren’t they? I wish they would universalize the sizes. I am normally a size 6 in pants. When I wear NYDJ I find I can downsize to a 4. Paige jeans go by waist size. I’m a 28. So I would say, yes, Paige fits true to size. Love Florida. I’m a bit of a snowbird. I’m down there usually twice a year!

  7. Hi Deborah,
    I just found your blog, through Cyndi ( Grace and Beauty) I love this Autumn look, the little Bootees
    Look fabulous and I like what you did getting a nipped in waist military jacket. I have a
    Military jacket which has a drawstring waist which I keep pulled up to add shape. I see you
    still wear a straight/skinny jean which I also love, I’m going to try the boot cut but will reserve
    judgement until I see how they look. It takes me back to the 7Os when I was a teenager and
    Everything was flared, with platform soles.
    I’m going to subscribe to your blog as it’s just my style, I’m 52 and live here in the UK, where
    we are having a fabulously warm Autumn. I love Canada and have family there.
    Have a good day
    Nicky ?

    1. Hi Nicky, So great to meet you and welcome to the community! I love having readers from the UK. Glad you enjoyed the post and feel free to email any suggestions for things you’d like to see on the blog.Cheers, Deborah

  8. Love the color combo you pulled together here. I have been eyeing up those booties, and now I may have to pull the trigger. I like the lower shaft – it doesn’t cut off the leg line so drastically as the higher ones that I have. And I WAS dying to get details on that purse. I love it. Sophisticated yet trendy. So fun teaming up today! Looking forward to future style collabs!

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