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Weekly Outfit Inspiration for Women Over 40

Look who got her act together and started snapping daily outfit pictures!

We’re kicking off the new year with a very requested series, Weekly Outfit Inspiration for Women Over 40. Where I share the real life outfits I wore, featuring all the ts I recommend here on The Well Dressed Life.

Here’s what you need to know: I’m 5’10 and wear between a medium/large, 8 – 12 depending on the brand. I am married, with three kids, and a full time job. My style is cool, classic an casual.

Outfits Week of January 8th

Outfits Week of January 8th

Outfit Inspiration One

half-zip pullover with leggings
Half Zip /Leggings / Sneakers / Woven Bag / Hoops

Let’s start with my go-to uniform for days balancing work with running the kids around.

I’m wearing the Half-Zip sweatshirt from Amazon that I shared earlier this month. They call this “cropped,” but you can see it is not. It hits at my hips.

Featured is “coffee gray”; I also have it in white and blue. It’s a cotton/poly blend, under $40, in sizes XS-XL, and washes well. 

My leggings are from another Amazon brand, The Gym People. These are different from the CRZ YOGA leggings, which are incredibly similar to the Lululemon leggings.

The Gym People leggings are thicker (go up if you are between sizes), these will keep you warm so I use them for outfits, to walk outside, or stand on sidelines in the cold weather. For actual sweaty workouts, it’s either CRZ Yoga or Lululemon. 

For sneakers, I have another new pair that is SO GORGEOUS. The Nike Waffle Debut Running Shoe mixes black, white, and cream for a sophisticated look and pairs perfectly with all your neutral athleisure. Another under $100 comfortable sneaker option that runs true to size.

I ordered these from the Nike Store but found them at DSW here. 

I shared this woven bag from Amazon last week.

Here, you can see how it works as a crossbody. I’m carrying the largest size. It adds texture to the overall look, and I like the contrast of a polished bag against a casual outfit.

Finally, you can’t see in this picture, but I’m wearing these under $15 hoops. These are so lightweight I will work out with them.

Outfit Inspiration Two

Outfits Week of January 8th
Cable Knit Sweater, Mother Jeans, Veja Campo Sneaker, Badu Gold Bead Bracelets, Jenny Bird Earrings

I recently splurged on a pair of Mother Jeans. These are expensive.

If you are interested in giving them a try, the quality is great. And the fit, once you find the size that works for you, is awesome. But the challenge is finding a size because they are all over the place.

I‘m wearing the The Tomcat Frayed High Waist Ankle Straight Leg Jeans, in a size 30.

Other styles I tried on in a size 30 I couldn’t get them over my hips, and there was one pair in a 29 that slipped right on. So who knows.

It was a bit of an emotional roller coaters, but I’m trying to focus on what fits well and not my size or number on the scale anymore.

I recently hear a girl on TikTok say, in reference to her weight, “my relationship with gravity is none of my business” and I’m taking that into the new year.

I do really like these. Even with their button fly, they are super comfortable and easy to move in. I picked them up for warmer weather or mild days like we had last week.

Because these sit at the ankle, if you are wearing a sneaker you want them to be low profile, like the Veja Campo Sneakers I’m wearing above.

These are one of my most worn and loved shoes, and they sell out all the time. Right now, I found a full size range at Farfetch.

I layered this Gap Factory Cable Knit Sweater (featured at the end of last year) over an old J.Crew button down (sold out).

On my wrists are the Badu Gold Bead Bracelets from Amazon. I have a few sets of these. When you first get them, they feel tight, but they do loosen up quickly. And my earring are by Jenny Bird at Nordstrom.

Outfit Inspiration Three

Oversized Sweatshirt and jeans outfit over 40
Mother Jeans, Veja Campo Sneaker, Oversized Sweatshirt, Leather Bum Bag, Mejuri Long Boyfriend Chain

For this next look, I’m wearing the same base of Mother Jeans and  Veja Campo Sneakers.

I threw on this Oversized Sweatshirt from Amazon. It’s simple, very cozy, and has a slit on the side of the neck, giving it some interest. This is also under $40, in the color “coffee gray,” and I’m wearing a medium.

The necklace popping out is the Mejuri Long Boyfriend Chain, a bit of a splurge.

And my bag is a leather bum bag from Etsy with my initials embossed in gold.

Outfit Inspiration Four

Outfits Week of January 8th
Gap Factory Baby Boot Jeans, Ankle Boots Similar Here, Gap Factory Coat, Amazon Essentials Stripped Shirt, Belt , Lo & Sons Pearl

Finally, I adore the Gap Factory Baby Boot Jeans. They were our number one selling jeans of 2023 and for a good reason. Look how long and lean my legs look.

I’m wearing a size 29 in regular length. For under $ 60, you can choose short, regular, and long lengths in sizes 24 – 35. 

They are an ideal cut for wearing with ankle boots. Above, I’m wearing a popular pair from Sam Edelman (you might have them). Unfortunately, they are sold out, but this pair from Madewell are similar. 

You know I love a button-down, and this French blue stripe option is from Amazon’s Essentials line for under $20. I’ve seen similar styles for $200, which is so stupid. 

Also under $20 is this thin brown belt that looks designer without trying to fool anyone. 

This Long Topcoat from Gap Factory is on sale for $75 with an extra 60% off. I’m wearing the medium.

And my crossbody bag is The Pearl from Lo & Sons. 


Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


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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Tuesday 16th of January 2024

Love this feature !

Terri in Ohio

Tuesday 16th of January 2024

Thank you, Megan. It is so helpful to see your everyday, pulled together outfits—assembled from what I like to call “normal clothes.” Easy to copy.

Megan Kristel

Tuesday 16th of January 2024

Thanks Terri!!


Tuesday 16th of January 2024

Thank you for this kind of post. This is truly how I "get" to dress most of the time. :)

Megan Kristel

Tuesday 16th of January 2024

So happy this is helpful Stacey!


Tuesday 16th of January 2024

How comfortable are the Veja sneakers? Honestly, I looked at them at Nordstrom one time and it seems like there is not any good cushioning. Seemed like they might not be all that comfortable, especially if you are wearing them for most of the day. I love the looks, but would like a comfortable one.

Thank you for your feedback! Teri

Megan Kristel

Tuesday 16th of January 2024

I have three pairs and wear them frequently. I think they are very comfortable, not walking on clouds comfortable, but no issues wearing them all day long.


Tuesday 16th of January 2024

I am 5’9” with a 29 inch inseam. These “Mothers” are long enough for you ! Do you have the inseam handy ?

Megan Kristel

Tuesday 16th of January 2024

This pair is cropped and 27" so they hit right at my ankle. But if you go on the Mother website, under denim, you can sort styles by lengths. There is an entire "long" category. They have bootcut pair called The Insider Heel I want to try that has a 35 1/4" inseam. There are a lot of options.