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October Try-On Edit: New Pieces Worth Trying for Women Over 40

Welcome to the first installment of our monthly Try-On Edit, where I share new pieces worth adding to your wardrobe, what’s working, what’s not, and how to style them in real life.

My goal with this series is simple: to help you build a wardrobe that feels effortless and current without wasting money on pieces that don’t fit, flatter, or function.

This month’s edit focuses on three pairs of bottoms in a range of silhouettes (aka, not skinny jeans), each one versatile enough to wear now and straight through the season. Together with a few coordinating tops and layers, there are nine total pieces that can be mixed and matched to create easy, polished outfits all season long.

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For reference, I’m 5’10” and my weight typically sits between 145 and 150 pounds. I wear anywhere from a small to a large depending on the brand and cut, and I’ll include fit and sizing details in each outfit description below.

All of these are brand new pieces that I haven’t shared before, and I’m excited to show you how they work in real life outfits.

Let’s get into the looks.

Outfit 1: Relaxed and Polished in Jeans and a Tee

SPANXshape™ Authentic 360 90s Straight Leg Jeans, $158 | SPANX®
Cotton Cropped Tee
, $48 | Margaux The Phoebe, $355 | Monica Vinader Signature Link Bangle, $450

For the first outfit, I’m wearing the SPANX® shape™ Authentic 360 90s Straight Leg Jeans in the wash Elysian. For whatever reason, maybe my terrible lighting, these look a lot darker in photos than they really are. In person, they match the product image perfectly.

They do fit wider in the leg than they appear online. I’d say they feel more like a girlfriend jean than a traditional 90s straight, which usually leans slimmer. That said, I really like them. They’re incredibly comfortable, and I love where they hit at my ankle.

I’m wearing the medium in regular length, but note that I find SPANX pants run very long.

My top is also from SPANX — the Cotton Cropped Tee in white. This is a great example of two things. First, “cropped” these days often just means short, not midriff-baring. Second, the proportions are great. The tee hits exactly where you want it to — you never want your waistline to be directly centered visually, if that makes sense.

Because the jeans hit right at my ankle, a ballet flat or low-profile sneaker works best. Here I’m wearing The Phoebe from Margaux. They’re a splurge, but I love them.

This is a cute look to wear as is with your favorite everyday jewelry, or use it as a base and layer a sweater or cardigan on top.

Outfit 2: When in Doubt, Wear All Black

SPANXshape™ Authentic 360 Corduroy Micro Flare Jeans, $158 | Ripley Rader Black Turtleneck, $128 | J.Crew New Stevie Ankle Boots in Stretch Leather, $298 | The Favorite Belt, $108 | Monica Vinader Signature Link Bangle, $450

I love an all-black look, and every single piece here is a winner.

Let’s start with the pants, the SPANXshape™ Authentic 360 Corduroy Micro Flare Jeans. You can’t tell in the photo, but these are made from a soft, fine-wale corduroy with just enough stretch to stay comfortable while still looking tailored. The micro flare is exactly how I like a flare to be, with just enough volume to sit nicely over your boots. I’m wearing the medium in regular length, and as you can see, they hit perfectly. The long length would be too long, and hemming them would take away the flare. (Sizes range from XS – 3X with regular, petite and tall options.)

Now, the boots, the New Stevie Ankle Boots in Stretch Leather from J.Crew, with a very manageable 2¼-inch heel. These get a 10/10 from me.

The turtleneck is from a new-to-me brand, Ripley Rader, an LA-based label that manufactures everything in their own factory in the city. It’s made from a super-stretchy fabric. I’m wearing the medium, and I’d guess the large isn’t much bigger. Their sizing goes up to 4X, which is great to see.

Finally, I added a belt for a little visual interest, the Favorite Belt by Favorite Daughter. It’s excellent quality and well priced at $108. You can choose your hardware. I went with goldtone, but it also comes in silver.

To finish, I’d throw on a long camel coat and carry a big, fabulous black bag and be on my way.

Outfit 3: Stepping Outside My Comfort Zone

Paige Stevie Straight Jean, $259 | SPANXsmooth™ Jersey Crewneck Long Sleeve Top, $68 | J.Crew New Stevie Ankle Boots in Stretch Leather, $298 | Monica Vinader Signature Link Bangle, $450

Finally, I’m way outside my comfort zone here, and I’m okay with it.

My jeans are the Paige Stevie Straight Jean. This is another instance where they look slimmer on the model than they do in real life. They definitely feel and look more like a wide leg, but if I went for an actual wide leg, they would probably be too wide. So I like that these are a little baggy. I actually feel kind of cool in them.

Because they are fuller at the bottom, a fitted top works best. I took the 29s, and honestly, who even knows what size we are anymore. The 28s might have given me a slightly slimmer leg.

Here I’m wearing the SPANX® smooth™ Jersey Crewneck Long Sleeve Top in a medium. This is such a great piece. You can wear it on its own like I am here or use it as a layering base under a blazer. It’s simple, versatile, and very comfortable. (Sizes range from a XS – 3X)

For shoes, you need a heel with these. I tried a platform sneaker first and looked like a skater boy from the early 2000s, way too baggy. The heel on the J.Crew boots gives just enough height to let the leg fall nicely and balance out the proportions.

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MEET THE AUTHOR

Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Mrs. Todd

Thursday 30th of October 2025

That third outfit is definitely my comfort zone, and you look fabulous in it!

Jan

Thursday 30th of October 2025

Can’t thank you enough for this excellent post! It’s wonderful to see what these different options look like on a real, live human being, especially with the shoes and length both described and shown. You win the Internet for today, girlfriend. Keep up the good work!