Fall/Winter Fashion

4 Ways to Wear Ankle Boots this Fall

Hello, friends! Happy Wednesday! Today Cyndi and I are teaming up with Deborah of Fabulous After 40 and Cathy of The Middle Page to bring you 4 ways to wear ankle boots.

I met Deborah and Cathy at the rewardStyle conference last January, and we all hit it off. I love what they’re doing on their blogs in the Fashion Over 40 space, and if you aren’t already following them, I know you’re going to love their style. Since ankle boots are one of the hottest fall trends this year, we thought it would be fun for us each to style a pair of ankle boots in our own way for your fall outfit inspiration.

If you’re visiting for the first time from one of their blogs, welcome! I’m a 44-year-old mom of three living in the suburbs of Philadelphia. I’ve been blogging for 10 years, and while fashion was a part of my blog for most of that time, I’ve only been focusing on fashion full-time since last September. It’s been a fun year and quite a learning process! Since I’m a stay at home mom, I mostly share casual looks with occasional going-out styles for events and date nights.

My favorite way to wear ankle boots is with skinny jeans, although I did show these same booties with a dress in Tuesday’s post, so if you missed that, you can check it out here.

1 of 4 Ways to Wear Ankle Boots this Fall: with a chunky side tie poncho and olive skinny jeans! Click through for 3 more ways to wear ankle boots!

These pants are the Sateen Five Pocket Leggings from LOFT. They come in three colors, and they’re incredibly soft and stretchy. I ordered my regular size 29, and I’d say they run fairly true to size, although they are the Marissa fit, and at LOFT, that means they’re designed for a more curvy figure. I find them to be a tad too snug in the waist for my comfort level, but they’ll probably stretch out with wear.

SALE ALERT >> LOFT is currently running a promotion with 30% off Fall Favorites + 40% off all Sale Styles.

1 of 4 Ways to Wear Ankle Boots this Fall: with a chunky side tie poncho and olive skinny jeans! Click through for 3 more ways to wear ankle boots!

I normally cuff my skinnies when I wear ankle boots, but these pants fit snug right down through the ankle so I just let them settle into my boots. I’m not wearing socks or anything to hold them in place; they just stayed put.

These are the Vince Camuto Feina Booties from the Nordstrom Anniversary Sale last month. I find them very comfortable, and I like the light taupe color because it’s versatile and goes with so much, but unfortunately sizes are very limited. (They do have most sizes available in the black, though!) If you’re in the market for new booties, check out my post, Booties Under $150 for some affordable recommendations.

1 of 4 Ways to Wear Ankle Boots this Fall: with a chunky side tie poncho and olive skinny jeans! Click through for 3 more ways to wear ankle boots!

My Side Tie Poncho is also from LOFT. It is very thick and heavy and will be fabulous for when it’s cold and damp outside. Unfortunately for me, we photographed this look last weekend when it was 90 degrees with high humidity! I was sweltering, and my hair frizzed out the second we walked outside. Ahhh, the things I do for this blog! Ha!

It really is a great poncho, though. I love the ties under the arms. They’re a cute detail, plus they help keep the poncho in place so it doesn’t slide around. I also like that the turtleneck is relaxed enough to pull it down some as you see here. I can’t stand a tight turtleneck — it makes me feel like I’m suffocating, and I also don’t think it’s as flattering. When you can pull it down some as I’ve done here, it shows more of your neck and makes you look more slender. Who doesn’t want that!?!

1 of 4 Ways to Wear Ankle Boots this Fall: with a chunky side tie poncho and olive skinny jeans! Click through for 3 more ways to wear ankle boots!

The pendant I’m wearing is no longer available in this color, but this one would also be pretty with this outfit, and this one as well. Or any substantial pendant necklace that you have in your closet would work. Since the sweater is chunky, I recommend not going with anything too delicate, though. You want something that won’t get lost in the bulkiness of the sweater.

The bracelets I’m wearing are sold as a set, and I love how the colors compliment these loden green pants.

1 of 4 Ways to Wear Ankle Boots this Fall: with a chunky side tie poncho and olive skinny jeans! Click through for 3 more ways to wear ankle boots!

Finally, I’m wearing a long sleeve layering tee from White House Black Market. I have this tee in three colors. It’s perfect for layering under ponchos and short sleeve sweaters in the fall and winter.

1 of 4 Ways to Wear Ankle Boots this Fall: with a chunky side tie poncho and olive skinny jeans! Click through for 3 more ways to wear ankle boots!

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Side Tie Poncho // Sateen Five Pocket Leggings // long sleeve layering tee // Vince Camuto Feina Booties (I also like these, and they’re 60% off!) // beaded cuffs // pendant (I also like this and this) // watch // sunnies

If this is your first time visiting, I hope you’ll stick around. Right now Cyndi and I are in the middle of our 26 Days of Fall Fashion style series, where we share a new outfit every day this month for your fall fashion inspiration!

And be sure to visit Deborah, Cathy, and Cyndi to see how they’re styling ankle boots for fall!

4 Over-40 Fashion Bloggers Style Ankle Boots for Fall

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20 thoughts on “4 Ways to Wear Ankle Boots this Fall

  1. Gorgeous!! Love the softer tones going on here. I can’t for the life of me pull off a poncho. I’ve tried so many, but even petites look weird. You and Cyndi definitely make me want to find one though, ha!

  2. you look adorable! love the poncho and those olive leggings are amazing! i have been looking for that color. so happy to have met you, and look forward to seeing you again! xx

  3. Wow, cute look JoLynne! I love ponchos this time of year. They’re so chic and cozy. I have a purple one similar to this that I wear all the time. And I see you’re featuring taupe suede booties, like I did! Taupe is such a fab color when you are in between summer and true fall. It works with everything in your wardrobe and always looks so rich. Can’t wait to collaborate again on some more great looks!

  4. I love the poncho! And it’s really a lot easier when you don’t have to worry about the cuff/don’t cuff issue. 🙂 I thought the Julie fit at LOFT was the curvy fit and Marisa was the straight fit? Is it the other way around?

    1. You are right. Julie is for women with smaller waists and curvier hips, and Marissa is for when your hips and waist are more proportionate, which is how I’m built – but these are a bit tight in my waist.

  5. Very cute booties. I have been wanting to try some. Really like the color of yours. Love your new fall nail
    Polish. Very pretty color.

  6. I read your blog from Cyndi’s as well. But, I was wondering where the comment section was. You look amazing in this outfit. I love everything from head to toe! 🙂

  7. Love everything about this outfit – the pants, poncho, shirt, shoes and accessories – all are so cute! It looks perfect on you. I’m tempted to buy the poncho; it is really cute and flattering, but it never seems to get cold in CA anymore! Is it really that heavy & warm??

  8. I visited with these sateen pants last week at Loft but didn’t try them on. I am thinking I should have and will head back in there to do so. Love that sage/olive green. And I wouldn’t have thought of tucking the pants legs into the booties but so glad you did! Great look. Best of all, I am thrilled to read we wear the same size. You always look so fit and trim. Your wear your size 29 better than I wear mine!

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