Shorts & Long Sleeve Sweater + Labor Day Sales

Welcome back to 26 Days of Fall Fashion — a stylish collaboration with Cyndi Spivey and me, where we each share a new fall outfit every day this month!

Styling shorts and a long sleeve sweater for those mild early fall days!

This time of year, I always enjoy outfits that create a juxtaposition between warm and cool weather clothing. Whether it’s shorts sleeves with jeans and ankle boots or long sleeves with shorts and sandals, I think it’s fun to mix it up. For today’s post, I’m pairing a cozy long-sleeve pullover with my favorite cut-off denim shorts.

Styling shorts and a long sleeve sweater for those mild early fall days!

I threw this outfit on one day last week and I liked it so much I had my husband snap some pictures before he went off to work. For one thing, this sweater is soooo soft. Unfortunately it is almost sold out, but this one is similar. In fact, I think I like it better than the one I’m wearing. And this one is cute and cropped, so that would work really well with shorts. I also ordered this one from the Gap this week. The medium was quite large on me so I’m sending it back for a small, but it would definitely be cute with shorts.

Styling shorts and a long sleeve sweater for those mild early fall days!

I carried a saddlebag in this rich Port color because I love the contrast it makes against the grey. If you like this Port color, the Brynn Hobo is on sale for 50% off. It’s actually a better size for an everyday bag. I like the saddlebag, but it’s pretty small for daily use. For a crossbody in Port, I love the Love Crossbody. These are all R Minkoff bags. She is one of my favorite handbag designers. She has a downtown style that appeals to me… classic but edgy.

For burgundy bags under $100, take a look at this Halogen Tassel Leather Crossbody and this Sole Society Faux Leather Tote. Both are great pieces that will go with so much this fall!

Love a pop of burgundy with grey and denim for fall fashion!

I almost wore sandals with this outfit, but then I decided to go ultra casual with my Converse Shoreline sneakers. I think they really work, and I like how the red stripe picks up the burgundy in the bag. It’s the little things that make me happy! Ha!

How to wear jean shorts with a long sleeve sweater

I’m wearing the Luna Pendant again. I love how it’s simple but different. Full disclosure: I’m a stylist for Stella & Dot and all links are to my online boutique. If you ever need help with an order, feel free to reach out! You can email me through the Contact link above, or just leave a comment on any post.

This is the kind of outfit I want to live in this time of year. In fact, I wore it again yesterday! We’re having some milder temps here in Philly this weekend, and it’s been a welcome reprieve from the heat and humidity we’ve endured for most of the summer.

How to wear jean shorts and a long sleeve sweater | Fall Fashion for Women Over 40

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similar grey v-neck pullover here and here // denim cut-offs (similar for less) // Chucks // similar bags in Port (or burgundy) here, here (50% off!), and here (under $100!) // Luna pendant // sunnies

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

So what are your plans for the weekend?? If you get my daily emails, you know we’ve had some sickies in the house. My daughter is doing better, but my son was still pretty sick yesterday so we’re laying low this weekend and taking it easy. I plan to bring last year’s fall clothes and shoes down from the attic and get organized.

Oh, I did get my Trunk Club unboxing on YouTube! You can view that HERE. I’m keeping the lace turtleneck and the white skinnies. I would have kept the black boots, but I realized that I have a pair almost just like that from last year! Thus, the plan to bring my fall stuff down from the attic this weekend. I need to know what I have so I can fill in.

SO much that I bought at the #NSale is sold out… which I sort of figured would happen, but it is still annoying. I don’t want to style stuff that isn’t available to you guys, so I’ll definitely need to take inventory and start placing some new orders.

This is a good weekend to do it because there are lots of Labor Day Sales going on right now. Speaking of which, the pink cold shoulder top I styled on Wednesday is 25% off! And so is that draped cardigan. Use the code WKND25.

Here are some more good sales you may want to check out:

Labor Day Sales

Nordstrom: Summer Clearance Sale, Save up to 40% off!


Splendid: 25% off EVERYTHING with code WKND25


LOFT: Buy one style, get the next 50% off new arrivals, and take an extra 50% off all sale styles


Grace and Lace: Labor Day Sale, take 20% off site wide + free shipping on all orders with code LABORDAY16

GAP: 40% off your purchase with code PARTY. That includes the V-neck cozy sweater I mentioned above as well as this Chunky Pointelle Sweater that came in the mail this week. I LOVE this sweater. It’s so feminine and soft and pretty. I got the pink, but I am tempted to order one in the Oatmeal Heather. You can see me wearing it HERE. For size reference, the medium in the pointelle sweater is roomy but I think it fits me the way it is supposed to, however, I sent the V-neck sweater back for a small.

Banana Republic: 40% off almost everything with code FALL40

Ann Taylor: Extra 50% off sale styles

J.Crew: (Online only) take 30% off your order of $200+ or 25% off your order of $125+ with code SHOPMORE.

White House Black Market: extra 50% off markdown styles.

Target: 25% off shoes, clothes, and accessories

Kohls: Save 20% off a purchase of $100 or more with code SAVENOW + $5 Kohl’s Cash for every $25 spent

Macy’s: Free shipping at $50 + extra 20% off most departments (some are 15% or 10%) and extra 25% off clearance

Happy Shopping!!!

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11 Responses

  1. I ordered this sweater in the rust color and you are right – it is SOOOOOO soft!!! Can not wait to wear it but it may be awhile till it cools off here in Texas. 🙁 Love it with shorts!!!

  2. This is really a fun, casual look! I’ve been seeing similar looks lately and love the look, but still struggle with it actually trying it myself. I’ll do a 3/4 sleeve with shorts, but it just feels strange to add more than that. I’m not one to boldly try something new, ha! Love the look though!

    I can’t imagine how frustrating it must be to have all those items from the nsale that you can’t link to because they’re sold out. I do hope you will still style some though. I’d love to see them and get more ideas. 😉

  3. I just watched your Utube video of the Trunk Club unboxing. What a great idea! Good job behind the camera Caroline!
    I love wearing comfy long sleeve tops when there’s a chill in the air. It’s in the upper 60’s here in South Central GA this morning with a slight breeze. Your outfit in the post is awesome on you! I would need longer shorts due to my age.

    I hope the family is feeling better! Make it a blessed day!

  4. Super cute! I have the Converse in a light gray which would be super cute with that sweater too. I can’t believe how much I wear them. They seem to go with everything and I love that they are slip ons.

  5. I was in Gap yesterday and I can vouch for this sweater, which comes in a lot of pretty colors. It’s soft and lightweight but not see-through. I bought Pink Heather, which is a coral pink IMO. I went down a size (to extra-small) as this sweater runs big, and it’s also long in the arms. It’s the Drop Shoulder Pullover Sweater. I may order Mint next, or dark blue.


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