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The end of summer can feel a little bittersweet. The days get shorter, the kids head back to school, and those carefree summer evenings slowly give way to busier fall routines. But here’s the good news: you don’t have to pack away all of your favorite summer clothes just yet. In fact, some of the best pieces in your summer wardrobe can transition beautifully into the new season with just a few styling tweaks.
At Love Olive, Co., we know how important it is for your clothes to be versatile, practical, and timeless—especially for moms and busy women who don’t have time for a complete closet overhaul every season. That’s why we’re sharing five of our favorite end-of-summer staples that are still going strong for fall 2025. These are pieces you probably already own (or need to snag now before they sell out!) and will keep you looking polished all season long.
Nothing says summer like a breezy dress—but don’t retire yours just yet. Midi and maxi dresses are the ultimate transitional piece. They keep you cool on those lingering warm afternoons but can easily be styled up for cooler evenings.
Why they work:
Longer hemlines give just enough coverage for fall.
Easy to layer with jackets, cardigans, or even sweaters thrown over the top.
They work with sandals now and ankle boots later.
How to style for fall:
Try layering your favorite midi dress with a denim jacket and booties. For a cozier vibe, slip a chunky knit sweater over your dress, add a belt to define your waist, and let the hem peek out for that effortless layered look.
👉 Love Olive, Co. favorite: Our Catherine Dress-French Blue is one of those pieces you’ll wear now with sandals and again in October with boots and a cardigan.
If there’s one piece that every woman should own for late summer and fall, it’s a cardigan. They’re the kind of staple you’ll grab again and again, whether you’re running errands, sitting at a football game, or cozying up at home.
Why they work:
Perfect for chilly summer nights and crisp fall mornings.
Neutral tones pair well with just about everything.
Easy to dress up or down.
How to style for fall:
Wear your cardigan open over a dress for a relaxed vibe or button it up and tuck the front into jeans for a more polished look. A belt around the waist can instantly elevate a cardigan, making it look more like a structured top.
👉 Love Olive Co favorite: Our Raleigh Cardigan-Latte is lightweight enough for now but has that cozy feel you’ll want later.
Once upon a time, people said you shouldn’t wear white after Labor Day—but thankfully, those rules are long gone. White and light-wash denim look chic year-round and add brightness to your fall wardrobe.
Why they work:
A fresh, clean alternative to darker fall shades.
Instantly modernizes sweaters and jackets.
Works with both sandals and boots.
How to style for fall:
Pair light-wash jeans with a camel sweater and loafers for a timeless look, or tuck a blouse into white denim and layer on a leather jacket. Don’t be afraid to mix lighter bottoms with deep, rich fall tones like burgundy, olive, or rust—it creates the perfect balance.
👉 Love Olive Co favorite: Our Tandy Denim-White is the pair you’ll reach for again and again.
Yes, sandals can live past summer—especially when they’re neutral, simple, and easy to style. Mules, especially, are a great transitional shoe since they’re closed-toe but still light enough for warmer days.
Why they work:
Comfortable for everyday wear.
Pair well with cropped denim, dresses, or skirts.
Easy to slip on for moms on the go.
How to style for fall:
Try wearing your sandals with jeans and a chunky knit on those early fall days when boots still feel too heavy. Neutral mules are also perfect with dresses or trousers for a polished but effortless vibe.
👉 Love Olive Co favorite: We love our Murray Mary Janes-Black because it works now with sundresses and later with denim.
The best tops are the ones that can handle a little bit of everything—school drop-offs, casual Fridays at work, weekend errands, or a night out. Flowy blouses and tops are perfect because they’re breathable in the heat but also layer beautifully in the cooler months.
Why they work:
Lightweight fabrics feel comfortable now.
Easy to layer under blazers, denim jackets, or cardigans later.
Flattering for all body types.
How to style for fall:
Tuck a blouse into dark denim and add ankle boots for a polished but easy look. Or, layer a structured blazer over a flowy top for church, date night, or even a meeting.
👉 Love Olive Co favorite: The Eisley Top-Cream/Blue transitions perfectly from summer days to fall layers.
Transitioning from summer to fall doesn’t mean starting from scratch. With just a few styling tricks, the pieces you already love can carry you well into the new season. Midi dresses, cardigans, light-wash denim, neutral shoes, and flowy tops are wardrobe staples you’ll thank yourself for investing in.
At Love Olive, Co., we believe fashion should make you feel confident and comfortable no matter what season of life you’re in. Whether you’re chasing kids, heading to work, or enjoying a fall date night, we’ve got the pieces to help you look and feel your best.
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