What to Wear Between Seasons:
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7 Summer-to-Fall Outfit Formulas for Women Over 40
Stilettos & Mascara | The Hollow Quill
There comes a point every August when getting dressed feels unnecessarily complicated.
It’s too warm for chunky knits, too cold for linen head-to-toe, and somehow the weather changes three times before lunch. One morning you’re reaching for sandals, by dinner you’re wishing you had on your Uggs.
If you’ve ever stood in front of your closet thinking, I have nothing that works right now, you’re certainly not alone.
The good news?
You don’t need an entirely new wardrobe every time the season shifts.
The secret to transitional dressing isn’t buying more—it’s learning how to layer the pieces you already love while introducing a few timeless fall staples that work just as well in September as they do in November.
For women over 40, the goal isn’t chasing every trend. It’s creating polished outfits that feel effortless, flattering, and versatile enough for workdays, weekends, dinner dates, and everything in between.
This season, fashion is embracing classic silhouettes with rich autumn colors, elevated basics, and comfortable tailoring.
Think soft olive greens, deep burgundy, chocolate brown, charcoal gray, creamy neutrals, and touches of leopard print that never truly go it of style.
Today I’m sharing seven foolproof outfit formulas that make getting dressed during that awkward in-between season incredibly easy—plus shopping collections to help you recreate each look without spending a fortune.
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Hi, I'm E. Lynn Jimenez, founder of The Hollow Quill and the voice behind Stilettos & Mascara. I believe great style should be effortless, comfortable, and confidence-boosting—especially for women over 40. Here, you'll find wearable fashion, timeless wardrobe inspiration, and practical style ideas that help you look polished without sacrificing comfort.
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Why Transitional Dressing Works
Rather than packing away you summer wardrobe overnight, think of late summer and early fall as an opportunity to mix seasons together.
Pair breathable fabrics with structure layers.
Keep lighter colors but ground them with richer accessories.
Swap sandals for loafers before reaching for boots.
Instead of dressing for the temperature at 8 a.m., dress for the entire day by choosing layers that can easily be added or removed.
The result is a wardrobe that feels intentional instead of seasonal.
1. Linen Trousers + Fitted Tee + Lightweight Blazer
This is the outfit that quietly says, I have my life together.
Linen trousers remain comfortable during warm afternoons while a fitted cotton tee keeps the silhouette streamlined.
Throw on a lightweight blazer in olive, camel, or chocolate brown, and suddenly the entire look feels autumn-ready.
Complete it with:
Leather loafers
Delicate gold jewelry
Structured tote
Brown belt
Perfect for: Office days, lunch meetings, travel, or casual Fridays.
Linen Trousers + Fitted Tee + Lightweight Blazer
✨ Shop This Look on LTK
Love this timeless transitional outfit? I've linked every piece (plus affordable alternatives) in my LTK shop so you can recreate the look in just a few clicks.
2. MIDI Dress + Cropped Denim Jacket
Don’t retire your favorite summer dresses just because the calendar says September.
Adding a cropped denim jacket instantly transforms floral or solid midi dresses into transitional outfits.
Choose white sneakers during the day or block heels for dinner.
Swap straw bags for leather crossbody bags to make the look feel more seasonal.
Perfect for: Brunch, wine tasting, farmers markets, and weekend outings.
Midi Dress + Cropped Denim Jacket
✨ Shop This Look on LTK
One dress. Endless possibilities. I've rounded up this entire outfit—including jackets, sneakers, bags, and accessories—in my LTK collection.
3.Wide-Leg Jeans + Sleeveless Blouse + Loafers
Wide-leg denim continues to dominate this season because it’s equal parts comfortable and sophisticated.
Pair dark-wash denim with a sleeveless satin or crepe blouse and finish with classic loafers.
If temperature cool off later in the evening, simply add a cardigan over your shoulders.
Color combinations to love:
Ivory + Olive
Burgundy + Cream
Chocolate + White
Navy + Camel
✨ Shop This Look on LTK
Classic pieces never go out of style. Browse every item from this outfit, along with similar editor-approved favorites, in my LTK shop.
4. Tailored Shorts + Tissue-Thin Sweater
Late summer is the perfect excuse to wear shorts a little longer.
Choose tailored shorts instead of denim cutoffs and pair them with ultra-lightweight knit sweater.
Half-tuck the sweater into the waistband and finish with ballet flats or loafers.
The outfit feels polished without trying too hard.
Perfect for: Casual office days, coffee dates, and sightseeing.
✨ Shop This Look on LTK
Late summer layering has never looked so effortless. I've linked every piece so you can recreate this look from head to toe.
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5. Little Black Dress + Suede Accessories
The little black dress never takes a season off.
Instead of styling it with raffia accessories, introduce suede textures.
Think:
Cognac suede handbag
Chocolate slingback heels
Suede belt
Gold jewelry
Lightweight trench if needed
These simple changes instantly move the outfit into fall without feeling heavy.
✨ Shop This Look on LTK
The little black dress is a forever staple. Find this outfit and more timeless wardrobe essentials waiting in my LTK collection.
6. Straight-Leg Denim + Crisp White Shirt + Animal Print Sneakers
If there were one outfit I’d recommend every woman over 40 own, this would be it.
It’s timeless.
It’s flattering.
And it works almost anywhere.
Roll the sleeves on an oversized white button-down, front tuck it into straight-leg denim, and finish with leopard-print sneakers.
The subtle animal print acts like a neutral while adding personality.
Layer with:
Camel blazer
Crossbody bags
Simple hoops
Classic watch
This is one of those outfits you'll wear on repeat. I've gathered every piece—including affordable alternatives—in my LTK shop.
7. Satin Skirt +Tank + Lightweight Cardigan
Few combinations feel as effortlessly elegant as satin paired with soft knits.
Start with a satin midi skirt, add a simple fitted tank, and finished with a lightweight cardigan worn open or draped over your shoulders.
Choose rich jewel tones like burgundy, forest green, charcoal, or espresso for a more seasonal feel.
This outfit easily transitions from office hours to date night with nothing more than a shoe change.
✨ Shop This Look on LTK
Elegant enough for date night and comfortable enough for everyday wear. Browse every piece from this look, plus similar finds, in my LTK collection.
The Colors Defining This Season
If you’re adding only a handful of new pieces to your wardrobe, make them in colors you’ll wear all season long.
Look for:
Olive green
Chocolate brown
Burgundy
Charcoal gray
Cream
Camel
Espresso
Deep navy
These shade mix beautifully with the whites, tans, and denim already handing in your closet.
A fall palette that transition right into winter.
My Favorite Style Rule
One of the biggest style lessons I’ve learned is that getting dressed becomes much easier when every new piece works with at least three outfits already in your closet.
Instead of asking, “is this trendy?” ask:
“Can I wear this five different ways?”
That’s how you build a wardrobe that feels timeless rather than temporary—and one that works beautifully through every season.
Pour yourself another cup of coffee, browse the collections, and start building outfits that will carry you beautifully from the last days of summer straight into sweater weather.
Because great style isn’t about keeping up with every trend—it’s about feeling confident in every season.
Until Next Time…
Summer is hot enough without your hormones turning up the temperature. If you're navigating perimenopause, you know the struggle of unexpected hot flashes, sleepless nights, and trying to stay comfortable when the heat feels relentless. In this guide, I'm sharing the cooling products, breathable wardrobe staples, hydration essentials, and simple daily habits that have helped me survive the hottest days of summer—so you can feel a little more like yourself, one cool breeze at a time. 🌿☀️