Jean Skirt Outfit for Fall

Hello from the South Carolina Lowcountry! I’m being hosted by Mazda and spending a few days at the Montage at Palmetto Bluff. It is beyond gorgeous here.

I was surprised to discover that this is not just a resort; it’s actually a whole development comprising vacation homes, residential homes, a luxurious inn, a little town square, and lots of open space and wetlands that are being carefully and lovingly preserved. It’s still in development, and it’s really cool to experience the area and see how it’s coming along.

This is the Inn, and I’m staying in one of the guest houses along the lagoon.


I you’d like, you can follow my adventures on Instagram and Snapchat. I share a lot more on Snapchat so if you aren’t using it yet, you might want to try it out! It’s a lot of fun.

Meanwhile, back at the ranch… it’s Day 23 of 26 Days of Fall Fashion!

I picked up this denim skirt at the Nordstrom Anniversary Sale back in July, and for some reason, I haven’t worn it much. I always struggle with what shirts to pair with skirts because they always seem too long if left untucked, and tucking shirts in all the way around doesn’t really work for me.

I finally decided the only answer is the front tuck. I’m still not crazy about this trend because while it looks cute from the front, I don’t think it does much for the rear view. Still, it seems to be the best solution at this point.

Jean Skirt and Booties Outfit for Fall

Of course, a jean skirt is appropriate all year round, but there’s something I love about a jean skirt for fall. It’s so cute paired with ballet flats, tall boots, or booties. For this outfit, I decided to go with booties.

How to Wear a Jean Skirt and Booties

On top, I wore a navy and white striped V-neck tee. I absolutely love this linen one for the cut and quality and fabulous drape, but I’ll include some lower priced options below.

Jean Skirt Outfit for Fall

I kept my jewelry simple and just wore hoops and a mixed metal pendant.

Paige Stripe V-Neck Tee

This skirt is super comfortable. I wore it all day on Sunday, and I loved it. I can’t believe I haven’t worn it till now. It has just enough stretch that you can move, but it doesn’t stretch out. The length is perfect, and it has a nice wash with a little bit of distressing but not too much to deem it inappropriate for church and other similar venues.

Jean Skirt and Booties Outfit for Fall

I carried this R Minkoff saddle bag because I love how well it goes with the booties, and the casual style is perfect with this outfit.

Cute Jean Skirt Outfit for Fall

I added a leopard belt for interest, but you can hardly see it. Oh well!

This outfit is adorable on its own, and it’s perfect for those milder fall days when it still gets quite warm in the afternoons, but I also wanted to show some options for when it gets cooler.

Jean Skirt and Booties Outfit for Fall
One option is to throw a cardigan on with it. This is such a cute and cozy look. The cardigan I’m wearing is low inventory, but this one is very similar and is fully stocked.

Jean Skirt Outfit with a Long Cardigan

Jean Skirt Outfit for Fall with Long Cardi

Jean Skirt Outfit for Fall with Booties

Another option is a leather jacket. This is the variation of this outfit that I ended up wearing to church on Sunday.

This jacket came in my first Trunk Club last year, and I was excited to bring it out again this fall. I’ve always been a sucker for a leather jacket, and burgundy is a fun departure from the traditional black or brown. My jacket is no longer available, but I’ll link to several options below.

Jean Skirt Outfit for Fall with a Leather Jacket

Chic Jean Skirt Outfit for Fall with a Leather Jacket and Ankle Boots

Leather Jacket with Jean Skirt Outfit for Fall

This is by far my favorite of the three looks. I love the added interest of a top layer, and the jacket is more flattering than the cardigan, although they both work for different purposes. I can also see wearing this with tights and tall boots when it gets colder.

Jean Skirt Outfit for Fall with a Leather Jacket and Ankle Boots

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denim pencil skirts // stripe v-neck tees // taupe booties // crossbody // leather jackets // burgundy cardigans // sunnies c/o Maui Jim

I hope you’re having a good week so far! I’m off to test drive some Mazdas and then take a bike tour of Hilton Head. Fun, fun!!!

Be sure to visit Cyndi and see the fall outfit she’s styling today!

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30 thoughts on “Jean Skirt Outfit for Fall

  1. We only drove through South Carolina, but you could see how gorgeous the area was(when I wasn’t sleeping, of course!) Enjoy your time. I have always loved jean skirts, probably the only kind I would wear because I am the most comfortable in jeans! What a nice look that is simple to put together!

  2. Hi Jo-Lynne! Wow, what an awesome place to spend a few days. I agree that the jacket or the sweater really add that special touch to the outfit. What keeps the denim skirt from sticking to the tights when you walk?

    Have a great time!

  3. I love South Carolina and the place you’re staying sounds awesome! I wore a jean skirt to work yesterday with a light knit short sleeve gray sweater and brown wedges. The sweater worked because I didn’t have to worry about the tuck and it still looked polished.

  4. I love the booties with the short skirt! I’m trying to learn how to put my booties with something other than long pants and I’m beginning to think that neutral color booties are the key. Thanks so much for sharing, Jo-Lynne!

  5. What a great way to amp up an otherwise simple look with the booties and jacket. You’re making me regret sending those booties back!! You keep styling them in such cute outfits!

  6. You look great and what a beautiful area! I really enjoyed seeing the 3 different ways you came up with to style your skirt! That was fun to get an idea of how to wear something multiple ways. Thanks for sharing and enjoy your trip.

  7. Super cute! I have similar pieces to all of these. I just added your outfit to my Stylebook Closet App. I love the leopard belt with the striped tee – I would never have thought of that combination. Without the jacket its actually something I could wear now, while it’s still getting up to 90 everyday! Enjoy your trip!

  8. Do you mind sharing your body type? I assume you did AYW since you advertised for them. I’m doing it now and learning so much! You always look cute. I’m hoping you’re my body type so I can just copy you. 🙂

    1. Sure! I’m a #shortwaistedcurvy and my coloring is cool. I hope that helps. 🙂 I do want to also say that I don’t always follow the AYW rules so copying me isn’t always going to be spot on with AYW. I don’t have time to tailor things because I go through so many clothes so quickly (they’d sell out by the time I got them back from the tailor), and I simply don’t keep everything I feature on the blog. I do have a small pile of tops that I want to have taken in at the waist becasue I do plan to make them a part of my permanent wardrobe, but a lot of times I have to make do. Also, I know the drapey sweaters are against the “rules” but I just like them. I know I could look more curvy and thinner if I wore a fitted jacket, for instance, but for travel and casual days, I like these cardigans. All that to say, I don’t want to undermine what Kelly is teaching. I think she’s spot on, but I do make exceptions for certain trends I like or simply to have more variety to feature. I hope that makes sense.

      1. This helps a lot! I’m a short waisted pear. 🙂 I’ve already decided that there are some rules I will follow and others I won’t always follow. Some things I just feel good in. I totally understand where you’re coming from! Thanks so much for sharing with me.

  9. Jo Lynne, I just love your hair straight! It’s so cute on you that way. It frames your face just perfectly! These outfits are great, but it was your hair that struck me today!

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