September always makes me want to pull out the boots, jackets, sweaters, and everything that says fall.
Then I step outside.
And September says, “Girl, not yet.”
Especially here in Dallas, September style can be tricky. The calendar says fall is coming, but the temperature may still feel very much like summer.
So instead of completely changing my wardrobe, I like to transition it.
For women over 50, this is also the perfect time to take a fresh look at our closets. Not because we need to follow every new trend, but because our wardrobes should work for the women we are today.
Here are a few simple ways I'm giving my wardrobe a September style reset.
1. Start Wearing Fall Colors in Summer Fabrics
This is probably the easiest September style trick.
You don't need a sweater to look like fall.
Instead, take the lightweight fabrics you've been wearing all summer and introduce them in deeper colors.
Think:
Chocolate brown
Camel
Burgundy
Olive
Navy
Black
Cream
Deep red
Plum
Charcoal gray
Imagine a lightweight black V-neck top with camel trousers. Or dark-wash jeans with a burgundy blouse. Even a simple chocolate brown dress can immediately make your wardrobe feel more seasonal.
Taylor-Made Tip: Change the color before you change the fabric.
2. Bring Back Your Dark-Wash Jeans
September is when I start reaching for darker denim again.
A great pair of dark-wash jeans can become one of the hardest-working pieces in your fall wardrobe.
For my petite plus-size ladies, pay attention to proportion. Straight-leg, trouser-style, ankle-length, and gently flared jeans can all be flattering depending on your shape and height.
Pair them with a V-neck blouse, lightweight knit, button-down shirt, or your favorite T-shirt and add a polished shoe.
Simple. Grown. Stylish.
3. Create a September Fashion Uniform
One thing I've learned from years of styling women is that getting dressed becomes much easier when you have a few outfit formulas you know work.
My September formula is simple:
Great top + flattering bottom + interesting shoe + accessories = DONE.
Try:
Black V-neck top + camel trousers + loafers + gold jewelry
White button-down + dark jeans + ballet flats + structured handbag
Lightweight knit + ankle trousers + slingbacks + statement earrings
Midi skirt + simple T-shirt + sneakers + denim jacket carried for later
You don't need 50 new outfits.
You need a handful of combinations you can repeat confidently.
4. Layer Lightly
September is not necessarily the month for heavy layering.
Instead, think about your third piece.
A lightweight blazer, denim jacket, cardigan, vest, or button-down shirt worn open can instantly make a basic outfit feel intentional.
And here's the key: you don't always have to wear it.
Carry your blazer. Drape your cardigan over your shoulders. Keep the denim jacket nearby for an aggressively air-conditioned restaurant.
You're creating the look of fall without overheating for fashion.
We are too grown for that.
5. Let Your Shoes Start the Transition
Before changing your entire wardrobe, change your shoes.
September is a great time to slowly put away some of the very summery sandals and bring back:
Loafers
Ballet flats
Sleek sneakers
Slingbacks
Mules
Closed-toe kitten heels
Lightweight ankle boots when the weather allows
Shoes can completely change the mood of an outfit.
A summer dress with sandals says July.
That same dress with loafers, a belt, and a structured bag suddenly says September.
That's what I call shopping your closet.
6. Don't Put Away Your Summer Dresses Yet
Speaking of dresses, please don't pack them away.
Some of your favorite summer dresses can easily transition into September.
Take a simple black midi dress and add loafers and gold jewelry.
Wear a sleeveless dress with a lightweight cardigan or blazer.
Add a belt and structured handbag.
Try a shirt dress with sneakers for daytime and slingbacks for dinner.
The secret isn't necessarily buying another dress.
It's styling the one you already own differently.
7. Invest in Transitional Pieces, Not an Entire New Wardrobe
Before you start filling up that online shopping cart, take inventory.
Ask yourself:
What am I actually missing?
Maybe you need a good pair of dark jeans.
Maybe it's finally time to replace your black trousers.
Perhaps you need a lightweight blazer that actually fits properly.
Maybe your wardrobe would benefit from a beautiful burgundy handbag or a pair of comfortable loafers.
Buy the piece that creates more outfits with what you already own.
That's a much better investment than buying something simply because it's trending.
8. Give Your Closet a September Edit
September is also a wonderful time for a mini closet cleanout.
Not the dramatic kind where everything ends up piled on the bed and three hours later you're wondering why you started.
Choose one category at a time.
Start with tops.
Then pants.
Then dresses.
Then shoes.
Ask yourself:
Does it fit?
Is it comfortable?
Would I buy it again today?
Can I create at least three outfits with it?
Does it represent my style now?
That last question matters.
Sometimes we're holding onto clothes that belonged to a previous version of ourselves.
Style After 50 Is About Knowing Yourself
Here's what I want us to remember as we head into another season:
We don't have to dress younger to look stylish.
And we certainly don't have to disappear into our clothes because we've reached a certain age or size.
We can wear the color.
We can try the trend.
We can show our shape.
We can change our style.
We can reinvent ourselves.
And yes, we can still have fun getting dressed.
The beautiful thing about style after 50 is that we've had enough life experience to finally understand something younger women are still figuring out:
Personal style isn't about wearing everything that's fashionable. It's about knowing what makes YOU feel fabulous.
So this September, don't rush to replace your wardrobe.
Edit it.
Restyle it.
Add a few beautiful pieces.
Try a new color.
Wear the outfit you've been saving.
And walk into fall looking like the woman you're becoming.
Because we're not trying to become younger versions of ourselves.
We're becoming more of who we already are.
The Taylor Made September Style Checklist
☐ Add one fall color to your wardrobe
☐ Pull out your dark-wash denim
☐ Create three go-to outfit formulas
☐ Add one lightweight layering piece
☐ Transition from summer sandals to loafers, flats or sneakers
☐ Restyle one summer dress for September
☐ Edit one section of your closet
☐ Make a list before buying anything new
☐ Wear something this month that makes you feel fabulous
Now tell me: What's the first piece you're pulling out of your closet for fall?
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