Transitional dressing doesn’t have to be confusing. Here’s how to layer with style and intention.

If you’ve ever stood in front of your closet during that weird in-between season—too warm for sweaters, too cool for sundresses, wondering what on earth to wear, welcome. You’re in exactly the right place.

Every year around mid-August, I hear from my clients:

“Tina, it’s chilly in the morning, blazing by lunchtime, and I have no idea how to dress for any of it.”

And I get it. The seasonal shift from summer to fall is one of the trickiest times to get dressed—especially when you’re over 40 and want to feel put together, not like you’re grasping at layers that don’t belong together.

That’s why I’ve pulled together five of my favorite transitional outfit formulas—looks that flex with your lifestyle, your changing body, and the weather. They’re stylish, intentional, and best of all? You likely already have most of these pieces in your wardrobe.

1. Lightweight Sweater + Jeans + Cropped Jacket + Sunnies + Statement Bag

This is your go-to when the breeze kicks up but it’s not quite fall yet.

• Think breathable knits in olive, taupe, or camel

• Soft or stretchy jeans for comfort

• A cropped jacket adds structure and warmth

• Add a great pair of sunnies and a textured bag to pull it all together

Pro tip: Swap in ankle boots as the temps start to dip.

SHOP THE LOOK

2. White Button-Up + Jeans + Textured Mules + Oversized Coat + Polished Jewelry

This one is all about mixing classics with cozy.

• Start with a crisp white shirt and wide-leg jeans

• Add texture with boucle mules or tweed slides

• When the weather flips, layer on an oversized plaid coat

• Keep accessories structured and polished—think pearls and a leather tote

This formula always earns compliments. Always.

SHOP THE LOOK

3. Midi Skirt + White Shirt + Striped Sweater (over the shoulders) + Sandals or Sneakers

This is what I call “Ciao Bella meets Parlez Vous Français!”

• Floaty midi skirt + clean white shirt = instant ease

• Tie a striped sweatshirt or knit over your shoulders for interest

• When it cools off, layer with a denim jacket and add sneakers or ankle boots

Jewelry tip: Add pearl drops or a delicate chain to keep it elevated, not fussy.

SHOP THE LOOK

4. Shirt Dress + Corset Top (Optional) + Denim Duster + Boots

If you love a little earthiness in your look, this one’s for you.

• Wear your shirtdress solo now, or layer with a corset top for shape

• As fall rolls in, throw on a denim duster or longline jacket

• Slide into tan or brown boots, and don’t forget the gold hoops

Bonus: This combo works beautifully on curves and gives you that “I just effortlessly threw this on” vibe.

SHOP THE LOOK

5. Vibrant Maxi Dress + Trench Coat + Statement Accessories

Don’t pack away those bold summer dresses just yet.

• Keep the fun going by layering your favorite maxi with a classic trench

• Add a heel or boot to ground the look

• A colorful mini bag and bold earrings keep the outfit playful and modern

This formula transitions beautifully from vacation mode to dinner date with ease.

SHOP THE LOOK

The Key to Transitional Dressing in Midlife?

🧥 Layer with purpose.
👚 Use what you already own.
👗 Build outfits around pieces that feel like you.

You don’t need a massive closet overhaul—you just need a few well-thought-out combinations that work with your body, your lifestyle, and your climate.

Ready to Fall Back in Love with Getting Dressed?

If you want even more style formulas and real-life outfit inspiration, make sure to watch this week’s YouTube video here—I show you exactly how to wear each of these looks (and why they work).

 Click to watch below! ⬇️

And if you’re craving more clarity and confidence in your style, grab my Quick Start Style Guide. It's a free download, and it's packed with simple tips to help you start dressing with ease again.

Let’s make this your most stylish season yet.

💛 Tina Faye Schwahn
Personal Stylist & Founder, Real Style | Real Life