What to Wear in October: A Guide to Getting Dressed This Month

What to Wear in October: A Guide to Getting Dressed This Month

October is when fall starts to feel real—but that doesn’t necessarily mean sweater weather has arrived where you live.

Fall photo collage.

Depending on where you are, you could be waking up to chilly mornings and shedding a layer by lunchtime, still experiencing temperatures in the 80s, or finally reaching for the sweaters and jackets that have been waiting in your closet.

And what you need from your wardrobe starts changing too. You may be spending more evenings at home, swapping sandals for closed-toe shoes, adding layers to outfits you were wearing a few weeks ago, or simply wanting what you wear to finally look like October.

So rather than thinking about October as a reason to start shopping again, take a look at what this month actually calls for—and the fall outfits you already have that can take you through it.

When It's October, But It's Still Warm Outside

One of the hardest parts about getting dressed in October is when the calendar says fall and the temperature says otherwise.

You want to move on from the clothes you've been wearing all summer, but a heavy sweater, jacket, and boots still don't make sense when it's 80 degrees outside.

This is where your wardrobe needs to look like it has moved into fall without necessarily getting heavier.

Think less about dressing for a traditional idea of fall and more about transitioning what you're wearing. The right colors, fabrics, shoes, and seasonal elements can change the overall feel of an outfit without leaving you dressed for weather that hasn't arrived yet.

If this is your October, the Fall for Warm Weather eBook is the one you'll probably use most right now. Instead of waiting for cooler weather to start dressing for the season, use the outfits inside to make the transition while temperatures are still warm.

GET THIS EBOOK


Prepare for the Temperature to Change Throughout the Day

October is also the month of checking the weather in the morning and realizing that one temperature doesn't tell you much.

A cool morning can turn into a warm afternoon. A comfortable afternoon can become a chilly evening. And an outfit that worked perfectly when you left the house may feel completely wrong a few hours later.

This is when layers become useful—not just because they make an outfit look more like fall, but because they let your outfit change with the day.

Before getting dressed, think about where you'll be, how long you'll be gone, and what the temperature will be later. You may not need to start with a heavier outfit. Choose one that lets you add or remove something without the rest of the look falling apart.

Depending on your climate, you'll find outfits that work for these in-between October days in the Fall for Warm Weather and Classic Fall Capsule Wardrobe eBooks, or Fall Over 70.

When Fall Weather Finally Arrives


Then there is that point in October when you walk outside, and it actually feels like fall.

This is when more of your fall wardrobe can finally come into rotation.

Woman in her 50s wearing a classic casual fall outfit.

Sweaters make more sense. Jackets aren't something you're carrying around just in case. Closed-toe shoes become an everyday choice. Your outfits naturally start incorporating more texture and layers.

The Classic Fall Capsule Wardrobe eBook gives you the outfits to turn to as temperatures cool, and you're ready to fully transition into your fall wardrobe.

Instead of standing in your closet trying to figure out what goes with what, use the outfits you've already been given and start noticing which pieces are doing the most work in your wardrobe.

GET THIS EBOOK

Don't Forget About What You're Wearing at Home

As temperatures drop, we're naturally spending more time inside.

October weekends might mean watching football, catching up on a book, baking on a Sunday afternoon, having family over, or simply lounging around the house a little more.

And suddenly, what you wear at home matters a lot more than it did when you were constantly heading out the door during summer.

Woman in her 60s wearing leggings and denim button up shirt lounging at home in fall.

That doesn't mean you need to be dressed up around the house. It means comfortable doesn't have to automatically turn into whatever old leggings, sweatshirt, or T-shirt happens to be within reach.

Leggings, joggers and sweatpants can absolutely be part of a stylish fall wardrobe. And the shoes you wear with them—from slippers to flats—can make even a simple at-home outfit feel more intentional.

The Fall At Home Capsule Wardrobe eBook gives you 60+ outfits for exactly these kinds of days, so your fall wardrobe doesn't stop working simply because you're staying home.

GET THIS EBOOK

Start Paying Attention to Your Fall Shoes

October is also when shoes begin doing a lot more work in an outfit.

The sandals you've been wearing are disappearing from rotation, but you may not be ready for heavy winter shoes either.

This middle ground is where your fall shoes can completely change how your clothes feel for the season.

Instead of thinking you need an entirely different outfit, look at the outfit you're already wearing and consider whether changing the shoes is enough to make it feel more appropriate for October.

And remember that this applies at home too. A stylish flat, clog, loafer, mule, or slipper can make leggings, joggers, and sweatpants feel like an actual outfit rather than clothes you happened to throw on.

Bring More of Your Layers Into Rotation

Early fall can be light. October is when layering starts becoming much more useful.

But layering doesn't have to mean piling clothes on.

The best layers give you flexibility. They let you start with a simple outfit, adjust for changing temperatures, and make better use of clothes already hanging in your closet.

This is also a good time to look at your fall wardrobe and ask a simple question:

Can the pieces I bought actually be worn together?

A closet can be full of perfectly good fall clothes and still leave you feeling like you have nothing to wear if only certain pieces work together.

As you use your fall eBooks throughout October, don't only look at the finished outfits. Pay attention to how often the same pieces appear in different ways. That's where you'll begin seeing how much—or how little—your wardrobe is actually working for you.

If You're Over 70, You Should Be Able to See the Clothes on Women Your Age

Fall style doesn't stop at a certain age, and neither should the inspiration you have available to you.

If you're in your 70s or beyond, October brings the same questions: What do I wear as temperatures change? How do I make my clothes feel current? What shoes work with these pants? What can I layer over this? And how do I put together outfits that still feel like me?

Woman in her 70s showing how to wear a sweater dress with sneakers in fall.

The difference is that it helps you actually see the clothes modeled and styled on women closer to your age.

The Fall Over 70 Capsule Wardrobe eBook was created with that in mind, giving you fall outfits and wardrobe inspiration specifically represented on women in their 70s and beyond.

GET THIS EBOOK

Fall photo collage.

Let October Tell You What to Wear

You don't need to wear every fall piece you own simply because it's October.

If it's still hot, work with the weather you have. If mornings are cool and afternoons are warm, build an outfit that can adjust. When temperatures finally drop, bring more of your sweaters, jackets, and layers into rotation. And when you're spending the day at home, don't treat getting dressed like it doesn't count.

Your fall wardrobe should move through all of it.

That's where your fall eBooks come in. Instead of searching for another outfit every morning, use the one that fits where you are in the season:

Fall for Warm Weather for those October days that haven't quite gotten the message that summer is over.

Classic Fall Capsule Wardrobe when cooler weather arrives, and you're ready to fully lean into fall dressing.

Fall At Home Capsule Wardrobe for the increasingly cozy days you're spending at home, without settling for clothes that feel thrown together.

Fall Over 70 Capsule Wardrobe for fall outfit inspiration represented on women in their 70s and beyond.

October doesn't require a new wardrobe. It requires knowing which part of the fall wardrobe you've already built makes sense right now.

It’s not about spending more money. Build intentionally, and you’ll find yourself in more outfits than shopping for new pieces can ever do.

Not sure which fall style suits you? Start here.

 
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