Using your Booties to Transition your Summer Skirts to Fall

Women over 50 wearing our booties to transition to fall

Using your Booties to Transition your Summer Skirts to Fall

Quote of the day: “Have no fear of perfection. You’ll never reach it.” Salvador Dali

Using our ankle booties to transition our summer skirts for the cooler weather is a smart idea. It’s a perfect way to cover up the bottom portion of your body somewhat, while still keeping your legs bare.

The three of us are going to experiment with these summer skirts in a couple of different ways for this theme! You’ll get a ton of different variety because it’ll also be the theme for our Ageless Style Group this week! So let me know in the comments how you tackle this change of season!!

Karen (blogette): Karen joined us in this challenge to wear one of her summer skirts with booties.

I think Karen’s skirt isn’t much different than my skirt, except hers has a tad of black in it! And the booties really pull out the black so nicely! Since we’ve learned it’s okay to wear white jeans in every season, then I think that the white print skirts can be worn all year also!

Booties to transition for Women over 50

Jodie’s (50+) Outfit: Ever since we wore booties with our dresses and skirts last year, I’ve become a huge fan of this look.

I’m not exactly sure why, except that it seems new and different from how I grew up! I’m of the age group that was told we always want to look leaner & need to make our legs look longer. And I realize that wearing ankle booties to transition our skirts for fall can break up the line of your leg. But I think once we get past that mental hurdle, then what’s stopping us from enjoying this style?

50+ Women wearing booties to transition summer skirts

I know the first time I had these peep toe booties, some members of the family thought the idea of having your toes exposed with booties was silly. And I can understand that thought….in the middle of winter! But they are quite perfect for these transition times!!

I rounded up a bunch of different ankle booties at the bottom of the post too! I realize most are not on sale at this time of year, but if you buy them now, then you have all season to wear them!

Summer skirts with booties to transition

While I was thinking of these categories, I wanted to try to keep the rest of our outfits relatively summeryish.

So I wore my one shoulder shirt! I have to admit, that I think I like this style of summer shirts even better than the off the shoulder trend. For one reason, because I tend to be drawn to asymmetrical items. But also because then I can at least wear one strap of my bra which makes it so much more comfortable.

If you want to browse some great deals for one of these shirts, then here is a great one, or this one is colorful! If you worry about the ruffles over your chest area, I will tell you that this could actually be a good thing!

The only part of these one shoulder shirts that I haven’t quite figured out is the accessories! I didn’t wear a necklace, because I couldn’t find the perfect one. And I even kept my earrings simple so you’d focus more on the outfit!

But I did decorate each wrist with bracelets instead!!

Peep toe booties to transition for fall

Skirt: Jamsworld–remade from a dress (similar here)~~Top: Old Navy (similar here)~~Boots: Indigo Rd. (similar here)~~Earrings: Slate from Rocksbox-Get a month free with the code JTouchofStylexoxo (here)~~Bracelet: (similar here)~~Purse: (similar here)~~Sunglasses: Nora NYC (here)

Nancy’s (60+) Outfit: The three of us also wore different lengths of skirts for this post.

Nancy’s skirt is a long midi skirt that she received from our visit to our local boutique, Trendz! She chose her light grey booties to transition this skirt for the fall look! I know since the skirt is darker, you could also pull out your black ankle boots too! But I really like the lighter color with this, because it almost looks like they are part of her leg!

Women over 60 wearing booties to transition for fall

This skirt has some lovely turquoise in the print, so Nancy chose her sleeveless blouse that has a neat cut out in the back! I always like these cut outs in the back of the shirt when they don’t dip below your bra line.

There are a variety of them that either come in prints or solids or even for your workout gear!

Booties to transition a summer skirt

The accessories are a mix of all of the colors in the outfit.

The necklace is one of Nancy’s favorites because it also has some great memories of her group of friends called the Lala’s! And although we always think of pairing these turquoise necklaces with turquoise pieces, they can also be a fantastic pop of color against bright pink or even yellow shirts!

The nice thing about turquoise jewelry is you can be a purist and stick with the Southwestern versions, or you can choose a modern look with it!

Booties to transition to fall for Women 60+

And even though this skirt is lightweight, I think we can get some great use out of it even in the winter months!! Putting on a pair of leggings or tights, and throwing a sweater on, will be exactly what she needs for the Denver winters!

What do you think? Should she look for a solid navy sweater like this or a striped one?

Booties to transition for Older Women

Skirt: Mad Style c/o Trendz (similar here)~~Top: Bellatrix (similar here)~~Boots: Baretraps (similar here)~~Necklace: (similar here)~~Earrings: (similar here)~~Bracelet: (similar here)

Charlotte’s (70+) Outfit: I had my mom wear her maxi skirt with her booties to transition the look for fall!

This skirt is one that my mom made, and even had enough left over material that I got a shorter skirt and Nancy got a scarf all out of the same fabric! Nancy’s scarf you’ll be able to see next month!

There was a time when I read that you should only wear sandals with maxi skirts! And yet, these ankle booties look fabulous with this skirt! Maybe that’s a good lesson to take everything with a grain of salt. Especially when it comes to “fashion rules”!

Booties to transition for fall on Women over 70

Mom’s booties are a beige color, and even if you don’t want beige or white, I do think the lighter colored ones are great! Almost like Nancy’s light grey pair above. Since we wear white and light jeans all year round, they can be exactly what you need!! I happen to think I’m going to need a pair of silver booties this fall! Anyone else like that idea?

Women 70+ with booties to transition to fall

The accessories for this outfit could really be quite varied!

Since my mom has almost every color of necklace under the sun, we could have shown about 10 different ways with this! In the end we went with the red and gold to brighten up the white shirt.

But since there are so many colors in the skirt, you really could wear black, grey, silver, orange, peach, yellow, or even green accessories with this skirt! Or you could just get a multi colored necklace that would work with it!

Booties to transition our Summer Skirts

The white shirt is always a classic, basic piece in your closet, I think. Even if your skirt doesn’t have white in it, it’s the perfect neutral for any outfit.

White shirts do need to be updated occasionally only because of stains and dinginess! If you haven’t bought one in awhile, there also are some that have fun details. The bell sleeves are always a fun detail, like I talked about in the fall trends post! Or there is the front tie look! Of course there’s a little lace that can add some interest to a white shirt, too!

Summer skirts with booties to transition

Skirt: Mom made it (similar here)~~Top: Express-thrifted (similar here)~~Boots: Hillard & Hanson (similar here)~~Necklace: (similar here)~~Earrings: (similar here)~~Bracelet: (similar here)

Summer skirts are usually so pretty, that you don’t want to put them away before you really have to. So adding in our ankle booties to transition them to the fall season is just one way to make sure you get tons more use out of them!

Thanks to one and all of you for your support. It means more than you know!

The Facts

Even if you wouldn’t consider purchasing your clothing online, it can be helpful to look through my links to see what is available! It certainly doesn’t hurt my feelings, if you click on them but don’t like them. Just so you know, one of the ways I make money from this blog is through these linked items.

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And if you’re new to the party, you can always see our outfits organized by categories, here! Don’t forget to check out the deals & discounts too, on this page!

I found a ton of different varieties of booties to transition your summer skirts to the fall season

  • Lovely look ladies! My favorite would be the one-shoulder orange top and that colorful skirt. Really looks fresh and lively outfit!

    Jessica |

  • Really fun looks! The booties really do a great job of pulling the look into the season! And such beautiful skirts! Love the prints!

    • Thanks so much Ronnie!!
      I love these skirts—funny how I have a ton of print skirts in my closet!!

  • Absolutely fabulous way to transition into fall. Jodie, I love your skirt!


  • Gary Mathews

    I love booties on women. It’s a great look and really sets off the outfits!

    • Thanks Gary—it’s nice to hear a male perspective!!

  • I’m not a big fan of the peep toe look because what do I do if my toes actually get cold? Too much pressure. But I love the boots your step mom is wearing.

    • That is the reasoning my mother uses, Jennifer!! Maybe I wear them to rebel against her thinking that way??

  • Definitely agree with you about silver boots Jodie! I’ve spotted black ankle boots with a silver block heel (also available in grey with silver heel) that I’m tempted to buy … 😊

    • I’m actually going shoe shopping tonight, so we will see what I bring home….

  • Len Dela Peña Parent

    I love your look, Jodie. Perfect top and skirt! Could you be anymore perfect? Thanks for the inspiration!
    Much love, Len

    • Oh, Len!! It is you who are such an inspiration to me! Not only with your sense of style and fabulous photos, but your kind words and positive outlook!! I only hope to be more like you as I grow as a blogger!!

  • I like your boots Jodie. Perfect with the skirt. I’m loving the sunglasses you’re wearing too xx

  • This blog is great, thank you for sharing with us!

    Isn’t That Charming.

    • Thanks Emily!! I really appreciate you saying that!!
      I’m so glad you stopped by, and I hope you come by again!!

  • Jodie you are adorable in this flirty outfit!
    I LOVE an ankle boot with a skirt.
    So modern and chic.
    Nancy and your Mum are styled beautifully too….. three cheers all round for these looks!
    Thank you SO much for linking them up to my little linky!

    • Thanks Samantha!!
      This is one of my favorite ways to wear ankle boots lately!!

  • You look amazing dear.
    I love the outfit.

    Much Love,
    Zarrah | The Bandwagon Chic

  • amazing looks and amazing style…love the booties with skirts!
    kisses in the sandpit ❤︎

  • Man, I haven’t worn my booties for such a long time, kinda excited to dig them out now!

    • It is fun to change things up with the new seasons!!!

  • Judy Gramith

    Your skirt is such a beautiful mix of watercolor florals and your top and boots are very proportional to the length of the skirt. Fabulous outfit. It would be cute with a short earth tone jacket too!
    I also like Charlottes look. Her skirt is amazingly versatile in style, length and a bajillion great bright colors!!
    Nancy’s look is very pretty and her coloring is pretty with the blue but the proportion of the skirt length just isnt good with these boots. The boots might work with a straight skirt in that length but not a full one to my eye anyway…
    Fall seems to be comin on strong this week!

    • I did notice that proportion thing with Nancy’s outfit….of course not until after publishing the post, Jude. I do wonder why the proportions don’t call out to me right away when I’m looking at outfits?? Maybe I just need more practice?
      I wish I would have had her tuck in her shirt??

      • Judy Gramith

        I think we often judge proportions better on ourselves than on others. Tucking in the shirt or even belting over the shirt definitely would have improved Nancy’s look. I also think a navy boot might have been less abrupt and more elongating. Nancy’s more petite stature also makes proportion more critical I think

  • Terri Webster Schrandt

    Great ideas! it stays warm here, so boots have to wait a few more weeks. Love the looks!

    • Thanks Terri!!
      You’d be perfect for the perforated booties or peep toe ones!!

  • Such fun looks! I love your boots especially, Jodie!


    • Thanks Mary!! They have gotten quite a bit of wear, I admit!!

  • Lesley Wolman

    I love wearing booties with a skirt, and I agree that they are a wonderful way to transition fro summer to fall!

    • That’s because you are a wonderful fashionista!!
      ps…we need to get a photo of you as your avatar that shows us next to your name on comments!!! XOXO

  • Love the idea of this blog! Blessings on your site!

    • Thanks so much Betsy!! I appreciate those lovely words and hope you’ll stop by often!!

  • mummabstylish

    Nancy looks lovely in her outfit – great boot colour, however your boots kind of steal the show for me! I wasn’t a fan of peep toe boots for ages -couldn’t see the point in them, but that has all changed since blogging. I’m searching for some, but haven’t quite found the right ones for me!
    I’ll keep you informed Jodie. I hope you can stop by me blog, am sharing the 5 Over 50 challenge in LBD. x Jacqui

    • I really didn’t mean to steal the show, Jacqui..ha ha!!
      And I felt the exact same way about the peep toe booties at first. But it’s funny after seeing them over and over how fabulous they become, right?

  • Peep toe & light colored booties are so smart for this time of year since they fit well with end of summer outfits

    • Thanks Michelle!! I think I may have to go shopping to get some more now!!
      Ha ha!

  • Great pairings, Jodie! I love the idea of silver booties with fall and winter colors!

    • Thanks June!! I just found my $10 rewards for DSW, so I think I might need to go find them this weekend!!

  • Booties are so perfect for the transition! Amazing looks ladies and dying over your booties Jodie!

    • Thanks Kathrine!! I love these booties too—my husband was such a dear to drive all over town looking for them last spring!!

  • Nicole Mölders

    Interesting. Here in Alaska, everybody adds tights and keeps the sandals.

    • Well, you definitely have a totally different environment, right, Nicole??

  • Super cute, all four of you (I started to type three and not four). I’m so itching to get back into boots and I like how you’ve shown booties as a great way to transition into that style.


    • It’s funny how the changing seasons is so fun for different styles, right, Rena!!!

  • Wow, such beautiful outfits. You all three looks gorgeous in these colors. You ladies did a great job with these outfits <3

    • Thanks so much Rakhshanda!! I appreciate your positive words!!

  • OH wow I think you look so good in those colours J – in regards to booties I actually have a burgundy pair I am getting ready to wear for one last time… like my weather’s transitioning… yeah right !

    • How come you’ll only wear them one last time? You don’t like them anymore Lorena!!
      I think booties would be almost perfect for you…they aren’t as warm as tall boots??
      Thanks Lorena!!

      • Hey J! Actually the inside is peeling horribly, the laces are shedding and I feel odd in them. You’ll see them this week.

        • Ahhhh….I can relate!! I’ve had to get rid of shoes like that before. It’s almost sad, because I’ve loved them so much, but they only last so long!!

  • Rebecca Saffer

    Love that quote! You ladies did a wonderful job highlighting the look of booties with print skirts. The looks are polished but arty and fun. Your mom really rocks the red lipstick and looks stunning. I’d love to see Nancy’s skirt with a deeper and shorter top as well. Great job!

    • Isn’t that the best quote Rebecca?? I think finally I’m realizing it, and it makes life so much less stressful!! Especially when my desk is crazily messy!! ha ha!
      So you’ll have to see if you like Nancy’s skirt tomorrow better—it’s darker and shorter?? I always want to contrast the dark with a lighter color, but I’m trying to be more open to change!!

  • Always been a booties fan, one of my wardrobe staples…great post, loved it =)

    Fashion and Cookies – fashion & beauty blog

    • Thanks Vale!!! I’ve grown to love this look so much lately!!

  • Love booties! I need to get mine out. Love your colorful outfit Jodie, orange really suits you! I love those peep toe booties.. i would love a pair of cognac or brown myself.
    Have a great day!
    jess xx

    • Thanks Jess!! These are my first peep toe booties, but they probably won’t be my last pair—haha!!

  • Savvy Southern Chic

    Booties are great for fall with skirts. It’s all about proportions and textures to get the look right! Love your boots Jodie!

    • I think you’re exactly right Fonda!! And that means I need to experiment and see what works and doesn’t work!!

  • booties are a great option for an autumnal vibe when it’s still warm out, and when it gets colder I love to pair my over the knee boots with dresses and skirts.
    Chic on the Cheap

    • That’s such a great idea, Lydia!!
      I’m definitely going to have to use that for a future post. My mom (the 70+ model) just received some OTK boots, and now I need to get some for Nancy (the 60+ model)!!
      We could collaborate and join forces??

      • Yes I would love to!

        • That’s fabulous Lydia!! We are going shopping on tomorrow night with Nancy, so hopefully we can schedule it for the end of October or beginning of November. Does that sound good??

  • I don’t know when I’ll be able to start transitioning my wardrobe to Fall… These 100+ temps every single day are killing me! Loved the colors of everyone’s skirts!

    • I can see how the longer summers would be a good thing…and a bad thing!! It’s fun to change out the clothing, but at least you’re not freezing your booty off!!

  • donnanance

    Booties look great with all the outfits! All your stylings are different and a perfect way to show the versatility of booties. xoxo

    • Thanks so much Donna!! I love to hear that other women like this look as much as I do!!

  • Love all the pairings especially your look Jodie. Gemma x

  • Jodie your outfit is just so beautiful! I love how you all styled your booties and I agree it is a great way to transition to fall! Love it!

    • Thanks Cheryl!!!
      I’ve been wearing them tons lately!!

  • Pauline Starsmore

    You all look very nice, I have bootees very similar to Nancy’s is she small, because I am only about 5′ 1″ or so. A style adviser did tell me not to wear skirts any longer than knees, but as I am not really slim I feel they make me look a bit dumpy,perhaps I should try your style as Nancy’s looks nice.

    • Thanks so much for saying this Pauline!!
      I do understand what the stylist is saying, but I’ve come to learn that all “rules” or advice can be different depending on the situation, cut of the item and many other factors. And as much as I hope we look our best, sometimes I think we get too caught up in having outfits look “flattering”. Does that make sense??
      I sent this wonderful comment to Nancy too, so she could smile at your words! She’s only 5’0″!!

    • Pauline Starsmore

      Thank you so much for your reply, It looks as if you are all quite short, so it just shows you don’ have to be really tall to look fabulous.

      • You are exactly right Pauline!! In fact, I’m only 5’2″ and my mom (the 70+ model) is only 5’4″!!

  • Bev @ Walking Well With God

    I love this one…booties and skirts to transition into fall. I always think of booties with jeans. Thank you for taking me outside my comfort zone. My challenge right now is, post surgery, finding any closed toed shoes or boots that will fit AND be comfortable. Will have to work on this one as fall is on it’s way.
    Bev xo

    • I’m so impressed that you are open to trying new styles Bev!! I truly think that keeps us young at heart. But you certainly do have a challenge with the post surgery detail. I’d probably visit the thrift store to see if a different size would fit??

  • Oh this is a very hard one if you normally wear knee length skits and have “stout” legs! You can totally get away with it, but I would only ever wear ankle boots with a skirt if I had the buffer of black opaque tights!

    • I know what you mean, Gail….but I also think you are being too hard on yourself. You have fabulous legs and there’s no reason not to show them off!! We really are the most critical of ourselves, because I could tell you that my legs have quite the veins and sun spots on them!!!
      But tights are fabulous for the winter—I know I’ll be wearing them tons!!

  • You all look so fashion forward with your footwear game….I’m not sure why I have yet to try this look…but if I ever needed convincing this post should do it!!!

    • That’s so cute to hear, Em!!
      I know it’s not always our first thought to pair ankle boots with skirts (and bare legs) but for some strange reason it really floats my boat!! Maybe because I see all the younger girls do it, so it makes me feel young at heart?? Is that silly??

  • Mireille

    Beautiful looks! I bought a new pair of tan booties during the Nordstrom sale that I have already worn twice with dresses. Very versatile! Can’t wait for fall to really be here but at least our mornings are getting cooler!

    • You are such a fashionista Mireille!! I love that you love this look too!!

  • Great styling as always ! Love your picks !
    Have a great start to your week ! !