How to Dress for Fall When it Feels Like Summer

I just had this conversation with my best friend, Robin. We were discussing what an awkward time of year it is for those of us down south. All my yankee friends are busting out their boots and flannel, and we’re still suiting up and getting in the pool! I even facetimed with my son and daughter-in-love the other evening, and they were wearing jackets! Jackets y’all! In September! That’s just crazy talk right there. But I’m putting out my fall decor anyway, and pretending it’s fall, even if it doesn’t feel like it. So…getting to my original point, how do we dress for fall when it still feels like summer? Read on for style ideas and tips for the most awkward time of year!

(This is not a sponsored post, but this post contains affiliate links. I make a small commission each time someone clicks on those links and makes a purchase, which helps to support my blog.)

Five Pre-Fall Style Tips

  1. Think form over function: look for colors and patterns that evoke fall without being too heavy for early fall heat. Look for fall colors, florals and lightweight cardigans for layering.
  2. Invest in a pair of transitional shoes. Now is when you can bust out those cute slip-on mules, perforated booties and adorable sneakers.
  3. Put away the capri length jeans and pants, and opt for ankle pants and jeans. This longer length looks fantastic with those booties and mules and sneakers, oh my!
  4. Try a pair of bootcut jeans. This will be your go-to denim for date nights and ball games.The silhouette is perfect for pear shapes (like me) and will elongate your legs when worn with a bit of a heel.
  5. Time to put away that straw purse and update your handbag! Opt for a warmer hued tote or crossbody. You may be able to snag one on a summer sale if you stick to a basic color palette, like brown or black or even dusty pink, which works all year long.

Basic Black Dress | Floral Top | Topshop tote | Cole Haan Piper Mules |Superga Sneakers | Bootcut Jeans | Long Sweater | Denizen Jeans 

Let’s Talk Shoes!

Cole Haan Piper Mules: Funny story, I recently placed an Amazon Prime Wardrobe Order, and received these shoes. At first, I wasn’t too taken with them. I think the pointy toe threw me. I thought they were just a tiny bit out of my comfort zone, you know what I mean? I chose to send them back, thinking I wouldn’t get much wear out of them. And then I looked at the pictures I took for this post, and fell in love with them. So guess what? I re-ordered them! Because I’m crazy like that! As you can see by the photos below, I think I made the right decision! They’re going to be my new fall favorite, for sure. 

Cole Haan Piper Mules
Cole Haan Piper Mule
Denizen Jeans | Cole Haan Piper Mule
Denizen Jeans | Cole Haan Piper Mules

Superga Sneakers: The adorable sneakers were actually purchased from a friend, who wasn’t happy with the way they fit her. Hey, it happens y’all. Win-Win for me! They are so stinking cute, they stayed on my feet from the minute I tried them on! I wore them all day, and then to the KISS concert the next. The rose gold  is one of those neutral colors that will work with everything this fall.  I’m wearing them here with the Liverpool Jeans I received in my last Stitch Fix.

Pink Leopard Tunic | Superga Sneakers
Pink Animal Print Tunic | Liverpool Jeans | Superga Sneakers

Fall Sweater and Jeans to Wear Now!

As I mentioned, the shoes from Amazon were a definite keeper. I also kept this lightweight Lark & Ro long cardigan. It’s lightweight enough to wear to the office now, and the blush color is a perfect hue to transition  into winter. I’m styling it here with a basic gray tee, those fantastic Cole Haan Piper Mules, and the Denizen Jeans described next.

Lark & Ro Sweater | Denizen Jeans | Cole Haan Piper Mules
Lark & Ro Sweater | Denizen Jeans | Cole Haan Piper Mules

The Denizen jeans from Target are that ankle length I mentioned above. These jeans are amazing. I’ve gotten tons of compliments every time I’ve worn them. The lighter washed front of the jeans combined with a darker side seam work together to camouflage the hip and thigh area, while highlighting my curves. They have a slightly frayed hem, and aren’t overly distressed, which I like. And at $25 bucks they’re a steal! You need these jeans y’all. 

Denizen Jeans
Denizen Jeans from Target | Superga Sneakers

I’m hoping these ideas and tips help you if you’re in the same situation as we are down here! For more ideas, my daily style and more, please check out and follow me on Pinterest, Instagram and Facebook.

And now it’s your turn! How’s your weather right now? Are you still sweltering like we are? Do you have any tried and true tips for styling fall fashions in a warmer fall climate? Please share! I’d love to hear what you think!

9 thoughts on “How to Dress for Fall When it Feels Like Summer

  1. Hi Andy!
    I love your tips, and being from the South, I feel your pain! I know I really want to wear my sweaters and boots, but its a no go as long as its still in the high 80s here! I love dressing in Fall colors and taking out my leather bags. Those Denizen jeans look so good on you! I bought a pair last week after seeing them on a few bloggers and they are comfy! Love those snakeskin flats, the mix of pink and grey looks fab too!
    Happy Monday!
    jess xx

    1. Hi Jess! Those jeans are the bomb! I’m so hard to fit when it comes to jeans, but these are an absolute dream. And yes, I’m crazy obsessed with the mules. 😘 Thanks for commenting!

  2. Hi Andy…just found your blog and we are like style sisters! I love your look, ALL your picks and your positive fun energy just bounces off the page! Just followed you everywhere…look forward to “getting to know you” more. And FYI, I’m in the Boston area where it’s starting out below 50 and heading to low 70’s…if it can’t be summer, this is about as good as it gets! Cheers! Beth

    1. I’m so jealous of your cool temps, but I don’t envy your long winters. My brother lives just north of you, and his snow stories are epic! Thank you for your sweet compliments. You made my day!!

  3. You have such great style Andy, and I’m really enjoying your blog. My favorite pieces that you showed were the pink cardigan, and the pink animal print tunic. I even like the sneakers on you with the skinny jeans. I’m self-conscious of wearing skinny jeans with my sneakers. I think my feet are to big and they look silly. Anyway, thanks for a great post!

    1. Thanks so much! I’ll admit I don’t usually wear the sneakers and skinnies combo, so that’s a bit out of my comfort zone. But midlife is for stretching and learning and growing. Right?

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