Fall Ankle Booties Styled 4 Ways

Hi Ladies!  I’m super excited to collaborate 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 an essential fall wardrobe staple that today we’re bringing you four different ways to wear them. Take a look at my outfit, and then pop over to their blogs to see more excellent bootie styling ideas.

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


I’m itching to wear booties this time of year, 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 that 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 special. They’re also good for keeping my feet cool and stopping my booties from looking too heavy like they weigh down my outfit.


I was out in Vancouver recently, dropping off my son at University, and it got pretty chilly there. I didn’t have a coat with me, so I picked up this cute Utility Jacket from J.Crew that goes 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 like this jacket because it nips in at the waist, giving me an excellent 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 the taupe, and the pretty gold buttons and zipper give it a refined, upscale look. I found out 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 bare 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 helps hold in the extra bits. ( LOL)


Have you 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 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 here’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


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27 thoughts on “Fall Ankle Booties Styled 4 Ways

  1. I thought I would get some good ideas by signing up for your blog, but I am shocked that every piece of clothing, shoe, and accessory is so high-end 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 fold and when to cuff?

    1. Hi Carolyn,
      I’m not wearing socks as it is hot here, but I will wear sockets 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 was interested in your opinion about utility jackets – your reasons for not wearing them are the same as mine! I love the jacket you are wearing – that color would not work for me, but I think I will cast my eye around for something similar in a different color. You have certainly inspired me, and you look lovely in the pictures.

    1. Thanks, Fiona, for your lovely compliment. This is an excellent 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 more refined version, more me.. and if 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 and 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 a very stylish, trendy, and maintains classy look; I Ran right over to the J. Crew site and ordered the utility jacket, which was on sale! Also, have my eye on those booties; hum, I might need to add those to my fall list.

    1. Hi Sheryl, Yes!! I 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 humming and awing about buying something.. “Get it, Get it!! It’s important always to 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 much more fun—all the best to you, Sheryl. I’m happy you dropped into chat. Have a great weekend! Cheers, Deborah

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

  5. I like this outfit; actually, I love it!!! I 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 evil in these types of clothes! Mountain Equipment Co-op is not a place I choose to buy clothes for every day :):). !! 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. This is key when doing 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 unfathomable beauty!

    1. Yes, Vancouver was breathtaking. Next time, I’ll have to do some photo shoots for the blog! You’re right. This outfit is great for running around in. It’s practical and chic, 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 usually 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 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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