Skip to Content

StarFREE! Wardrobe Checklist Download + Weekly Newsletter DOWNLOAD

Outfits in Real Life: Chilly Morning Layers

Last week was Vivi’s Halloween parade at school, and there is nothing cuter than three-year-olds in costumes.

The morning started how it usually does, chaotic and over-scheduled, me thinking I had more time than I did.

One minute I had an hour to meet my deadline, and the next, I had to be out the door. So I threw on a comfy outfit and worked off my hotspot in the car as we drove to school.

I was just about to complain about how ridiculous are schedules are right now, how I can’t catch my breath, when I stopped and remembered I took a huge risk when I was 26 to have a chance at this kind of morning. 

Around this time, about sixteen years ago,  I was an assistant buyer at QVC and newly pregnant with our oldest, Maddie. 

One night in the office, well past when we should have left for the night, I walked past a colleague hunched over in her cubical, looking defeated.

She was a little older than me and had a few little kids.

It turns out it was her son’s birthday, and her whole family was celebrating at home, but she wasn’t allowed to leave. I didn’t understand why she didn’t just go, but she explained that her boss said she needed to stay. 

Until then, I had never once considered how I would work this stupid, demanding, over dramatic job and have a family. I hadn’t thought past having the baby. 

A few days later, I had to tell my boss I was pregnant because I was falling asleep standing up, and her response was, I swear to you, “That’s a problem.”

The toxicity of that environment stuns me to this day. 

I quit a few days later, and never looked back.

It was a pretty reckless decision. There were no savings, no strategy, just a mortgage, student loans, and a deep, burning instinct that I needed to get out.

By the time Maddie was born, I had started my first business and an entirely new and unexpected chapter in my life. 

And even though there were many lean years, times when we didn’t know how we were going to pay the bills, and a lot of uncertainty, I knew going out on my own was the only way to craft the life I wanted.

So it’s mornings like this when I sort of marvel with gratitude that everything worked out.

I tell you this not to boast, but because I know how lucky I am. The fact that I can work and not miss these moments with my kids is a huge privilege.

Outfits in Real Life: Chilly Morning Layers

Fleeced Lined Leggings: $30 | Plaid “Shaket”, $46 | Tank: $20 |  Bag Coach – Sold Out Similar Here | Boot: $259

Anyway, I digress, back to my outfit.

Honestly, I could have shown up in my typical bridge-troll attire, and no one would have flinched, but I’m glad I put in a little effort. 

And this outfit is made up affordable Amazon finds, anchored with a better bag and shoes.

The parade was outside, and it was a little chilly, so I grabbed these fleece-lined leggings.

I initially ordered them for mornings on the Schuylkill River, watching our now 15-year-old Maddie row.

They will keep you toasty warm if you are also freezing your tush off on a sideline somewhere. 

Available in XXS – 5X. I am 5’10, and a size 10 and ordered the large. 

To create a casual black column, I wore our favorite tank by The Drop, an exclusive Amazon brand.

I have at least three of these in black and white. The wear and wash well, fit true to size, all-round a 5 star find. 

Available in several colors, in also in XXS – 5X

And with a column of color comes a top layer that makes the outfit. 

This one I found on Tiktok, also from Amazon.

They are calling it a shacket, but as you can see, it’s really more of a lightweight coat. 

The shoulders have a slight drop, but other than that it has a slim fit, and three quarter length. So I don’t feel like I should be carrying an ax. 

I bought a neutral plaid pattern, but there are a lot of options to choose from, including some solid colors. I’m thinking of picking up the solid navy or maybe the pink. 

One of the reasons I encourage spending on a bag and shoes is because they will help elevate your look. And when I say spend, I mean buy the best quality you can afford, not go in debt for something designer. 


My new bag for the season is a Coach Crossbody, it’s sold out in the style above, but this one is similar in price and style

And then I’m really enjoying these Utility boots from Rothy’s. I ordered my regular size and wear no-show socks

Outfits in Real Life: Chilly Morning Layers

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.

Never Miss a Post

Enter your email address below to sign up for our newsletter and get your free copy of our Wardrobe Essentials Checklist sent to your inbox.

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.


Friday 4th of November 2022

First, I commend you on your decision to ditch the corporate life and spend your time with your kiddos, even though the situation was not ideal, financially. I must tell you, this is coming from a seventy something grandma, who wouldn't trade the years on one income, in order to stay home with my daughter, for anything. And congrats on sticking with it and building your business! Secondly, I just love seeing the outfits you put together without spending a fortune. I really like the casual "Shaket" in this post. Gotta say though it is very reminiscent of the Pendelton jacket my mom used to have. Just goes to show that what goes around comes around, and great style is never "out". Thanks for keeping me up to date with my granddaughters!


Wednesday 2nd of November 2022

Great outfit and great story. Thanks for sharing. I have been blessed to be home with my children and I have not regretted it.

Tracy Gray

Wednesday 2nd of November 2022

I love your outfit! And I can definitely relate to a toxic work environment. I’m going to order the Shacket. I had been debating on whether or k bill or I wanted and would wear it but I’m sold now! Thanks


Wednesday 2nd of November 2022

Love the outfit and love your attitude toward life and motherhood!

Tammy Stokan

Wednesday 2nd of November 2022

Your story is inspirational. You took a risk for all of the right reasons and the ROI will be immeasurable when you look back. Those chaotic and over-scheduled days will pale in comparison to memories of the moments where your kids knew their Mom showed up and was there for the big and small moments of their childhood.

Now for the outfit…love it! Those boots pair really well with colors on the jacket and you would never guess it all came from Amazon. This really demonstrates the “buy better shoes and bag” advice!