WGN Segment: One Outfit, Two Seasons

Watch the segment on the WGN-TV website

Let’s talk about one outfit, two seasons. There’s always that awkward time of year when you’re ready to start dressing for fall, but the weather hasn’t gotten the memo. You’re tired of your summer clothes, but it’s still way too warm to pull out the sweaters and boots.

The good news is that you don’t have to completely change what you’re wearing. Sometimes, you just need to change the seasonal message of your outfit.

One of the easiest ways to do that is with color. Instead of putting away the lighter and brighter colors you wore all summer, try pairing them with colors we traditionally associate with fall: think chocolate brown, burgundy, olive and rust. You might be surprised by how different that summer color suddenly feels.

Then you can take it a step further. Change the handbag or shoes. Add a scarf or different jewelry. And when the temperatures finally cooperate, add a jacket, wrap or other third piece.

For this segment, I styled three models—and myself—to show you how the same basic outfit can make the switch from summer to fall. We’ll start with just a few simple changes and work our way up to a more complete fall transition.

Because you don’t need a whole new outfit for a new season. Sometimes, you just need to change what you wear with it.

**This post contains affiliate links. I only recommend products and services I genuinely believe can help during this stage of your journey. If you purchase through these links, I may earn a small commission at no additional cost to you.

One Outfit, Two Seasons: Start With Color

When we think about transitioning an outfit to fall, our first instinct is often to change the clothes. But before you reach for a sweater or jacket, try changing the color combination instead.

I call this my “desert sunset” look, a rust skirt paired with turquoise.

Rust is a color we naturally associate with fall. I could have paired this skirt with ivory , navy or black, and any of those combinations would work. But the turquoise gives me the best of both worlds. It keeps the outfit feeling fresh and bright enough for those warmer early-fall days, while the rust brings in the richness we associate with the new season.

And that’s really the first lesson of the summer-to-fall switch: you don’t have to stop wearing your summer colors when September arrives. You may just need to pair them differently.

Shop My Look:

I actually wrote an entire blog post on “The Best Colors to Wear with Rust” if you are interested in tryin g even more oolors with rust this fall. The post was just updated with all new shopping links.

🎨 COLOR THEORY: Why Rust + Turquoise Works

Rust gets its warmth from orange, while turquoise falls into the blue-green family. These colors come from opposing areas of the color wheel, which creates contrast and helps each color stand out.

It’s a complementary-inspired combination that gives you the energy of contrasting colors without feeling too harsh. And because the rust has depth and earthiness, the overall combination can still feel rich and sophisticated for fall.

If you are interested in learning more about color theory, check out my blog post on color theory and color analysis

Same Clothes, Different Season: Olive + Butter Yellow

Erica’s look is the perfect example of how you don’t always have to change your clothes to change the season.

Her late-summer outfit starts with a butter yellow sleeveless sweater and olive cargo skirt. Olive is already a color we associate with fall, but paired with a butter-yellow necklace, flat sandals and a straw lemon tote, the overall outfit still says summer.

So instead of changing the clothes, we changed the seasonal cues.

The straw tote becomes an olive quilted bag. The sandals become olive sneakers. And the yellow necklace is replaced with an olive necklace.

Same sweater. Same skirt. Completely different seasonal message.

This is also a great trick for those early fall days when the temperature still feels like summer. Let your accessories say fall even when the weather says otherwise.

Shop The Look:

🎨 COLOR THEORY: Why Olive + Butter Yellow Works

Olive and butter yellow are both warm, earthy colors that sit relatively close to one another on the color wheel. That creates a sense of harmony rather than strong contrast.

The yellow brings lightness and energy to the summer version, while repeating the deeper olive in the accessories makes the second look feel richer and more grounded for fall.

Let One Piece Bridge Both Seasons: Burgundy + Pink

Natalie’s look starts with a color combination I love for this time of year: burgundy and soft pink. The burgundy immediately brings fall into the outfit, while the lighter pink keeps it from feeling too heavy when the temperatures are still warm.

For the late-summer version, I paired the burgundy blouse and pink pants with an ivory handbag. The lighter bag keeps the look fresh and also prevents everything from feeling too matchy-matchy.

But here’s the fun part: the shoes don’t change.

The two-tone slingbacks incorporate both burgundy and pink, which means they work beautifully with both versions of the outfit. If you’re lucky enough to find a shoe, or any accessory, that connects the colors in your outfit and can take you through more than one season, take advantage of it!

Not everything needs to change.

To move the outfit further into fall, we simply swap the ivory bag for a more dramatic burgundy floral bag and add a burgundy wrap. Now the deeper color has a stronger presence, and the whole outfit feels richer and more fall-like—without changing the blouse, pants, belt or shoes.

Shop The Look:

🎨 COLOR THEORY: Why Burgundy + Pink Works

Here’s something you might not expect: burgundy and pink can create a monochromatic color scheme.

Monochromatic doesn’t mean everything has to be exactly the same shade. Pink and burgundy both belong to the red color family; we’re simply using different values of that color—pink is lighter, while burgundy is deeper and darker.

Using different values is one of the easiest ways to make a monochromatic outfit more interesting. You get the harmony of one color family without looking like you’re dressed head-to-toe in exactly the same color.

Take It All the Way to Fall: Chocolate Brown + Light Blue

Jennifer’s look takes our summer-to-fall switch one step further. And it features one of my favorite color combinations: chocolate brown and light blue.

For the late-summer version, the light blue takes the lead. Her striped top already introduces chocolate brown, but paired with light blue pants, light blue sandals and a light blue handbag, the overall effect still feels fresh and summery.

So how do we make it feel more like fall?

You can start with the easiest switch of all: simply repeat the fall color.

A solid chocolate brown neckerchief brings more brown into the outfit and immediately changes the balance of the two colors. And don’t overlook solid scarves! A scarf doesn’t have to add a print or another color to be useful—it can simply reinforce a color that’s already in your outfit.

Then we can take it further.

First, swap the light blue handbag for chocolate brown. I deliberately chose the exact same bag in two different colors because it shows just how much impact color alone can have. The style of the bag hasn’t changed—only the color has.

Next, trade the light blue sandals for chocolate brown booties. Now we’re not only changing color; we’re introducing a shoe that sends a much stronger fall message.

And finally, when the weather is cool enough, add the chocolate brown jacket. We’ve taken the same light blue pants and striped top from a warm late-summer day all the way into fall.

Shop the Look:

🎨 COLOR THEORY: Why Chocolate Brown + Light Blue Works

Chocolate brown and light blue give us another example of warm and cool colors working together.

Brown gets much of its warmth from orange, while blue sits opposite orange on the color wheel. That relationship creates contrast, but the softer light blue and rich chocolate brown keep the combination from feeling too bold.

It’s one of the reasons I love this pairing: the light blue keeps chocolate brown from feeling too heavy, while the chocolate makes light blue feel completely at home in fall.

Your Summer-to-Fall Switch Checklist

Before you put away a summer outfit you still love, take another look at it. You may be able to keep wearing it longer than you think.

Ask yourself:

Can I pair a summer color with a traditional fall color?
Think light blue with chocolate brown, pink with burgundy, butter yellow with olive or turquoise with rust.
Can I change the handbag?
Straw, raffia and lighter colors tend to send a summer message. Try a richer color or a bag with a little more structure or texture for fall.
What happens if I change the shoes?
You don’t have to jump straight from sandals to boots. Sneakers, ballet flats, slingbacks and other closed-toe shoes can be great in-between options.
Can I repeat the fall color somewhere else?
Jewelry, a belt or even a simple solid scarf can bring more of that fall color into the outfit without adding another layer of clothing.
Can I add a third piece when the weather gets cooler?
A jacket, wrap or lightweight layer may be the final step that takes the outfit completely into fall.

And remember: you don’t have to do all five. Sometimes changing just one or two things is enough.

One Outfit, Two Seasons Can Really Work

Transitioning your wardrobe from summer to fall doesn’t have to mean putting one wardrobe away and bringing out another one.

Start with what you already have. Look at the colors differently. Pay attention to the seasonal message your shoes and accessories are sending. And then add layers as the weather—not the calendar—calls for them.

Most importantly, don’t assume a color or a favorite piece has to disappear simply because you associate it with summer.

Sometimes the piece isn’t the problem. It just needs a new partner.

That’s the real summer-to-fall switch: same wardrobe, new combinations—and a lot more ways to wear what you already own.

Ready to Get Your Own Closet Ready for Fall?

Before you start shopping for the new season, take a look at what you already own.

I created my Fall Closet Checklist to help you do exactly that. It will walk you through what you actually need for the way you live, what in your closet is still working, and where there may be a few gaps worth filling.

Get the Free Fall Checklist

And if you’d like more practical ideas for wearing what you love in a way that feels current, polished and like you, come join me on Instagram or Facebook. I’m always sharing outfit ideas, styling tips and real-life answers to the style questions women over 50 are actually asking.

Instagram: @dianne_instyle

Facebook: @dianneinstyle