Let’s Dress Up! Wearing Denim Overalls at My Age


The last time I wore denim overalls was about 20 years ago. I brought a pair to Australia when I went to visit my grandparents. It was the really loose fitting ones that were very faded. According to my brother, I looked like a farmer in them. Of course, I had to wear them with one side unhooked. I remember my grandma asking me what I was wearing…and then saying she wanted a pair.  I’m not sure if she was giving me a compliment or just trying to get me to take them off. But I ended up leaving those denim overalls with my grandma. She didn’t fit into them. And I don’t know really know what happened to them either.

At the time, I was glad that I got rid of them because I kind of felt ridiculous in them. That was the last time I swore to No. Denim. Overalls. Ever!! (insert tone from the no wired hanger line from the movie “Mommy Dearest”)

Most recently, I’ve been seeing them everywhere and told myself, “It’s a trend. Don’t buy into it!” The only people that would look good wearing them were babies, toddlers and super cool millennials. I changed my mind when I saw my friend Lauren wear a pair on her blog. She wore them so well and looked casually chic in them that she inspired me to reconsider my no denim overalls rule.


When Madewell asked me to host an event at their store at Old Orchard Mall, I started looking through their website and saw a pair of skinny overalls with a drop hem that caught my eye. As a “thank you” for hosting the party, Madewell gifted me a pair of jeans. Instead of picking a pair of jeans, I picked the overalls to try on just to see. I went into the fitting room, tried them on, and was surprised at what I saw. These updated denim overalls are fitted, high waisted, and have some stretch. Not only that, the length was not too long, although I think they’re supposed to be cropped on regular people. They seemed to fit my perfectly. I ended up taking the overalls instead and glad I did. It seems like so much in the denim industry has changed over the past 20 years!

It’s been 20 years since I have worn denim overalls. Maybe I will think they look ridiculous on me a year from now or maybe I will end up wearing for the next several years. We’ll see! But I guess the “Never Say Never” saying is true. And that fashion trends always seems to be cyclical. Some trends come back with better improvements from the last time they were around. For me, it’s the denim overalls.


I’m slowly trying to be open-minded about things and what I can wear. Maybe if I tried on another pair of overalls, I wouldn’t feel as good or they might not fit me as well.  What I’m trying to say is that I’m not going to let my age stop me from trying things (or clothes). I’m sure someone older than me can rock these overalls even better than I can. It’s just a matter of finding something that fits me well. So as a 41 year old, I’m here to tell you that denim overalls are also for women in their 40s!

Recap of Madewell Style Event




The Madewell event on Sunday was so fun to host and of course, I wore the overalls again. But this time, I wore an olive vest over it. I got a chance to invite friends and readers to the event and had the opportunity to style items from the store. Thanks to the team at Madewell – Old Orchard for giving me the opportunity to do something out of my comfort zone and to supply all the drinks and treats. And thanks to all my friends who showed up for the event. It was nerve wrecking and fun at the same time. Since this was my first time hosting event, there are so many things I’ve learned from the experience. There’s a lot of hard work and stress that goes into hosting. I know that next time (if I ever host again) that I will be more confident in myself and to really promote myself and the event. I’m just glad I got one event down under my belt. Thanks again Madewell – Old Orchard!!


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2 thoughts on “Let’s Dress Up! Wearing Denim Overalls at My Age

  1. laurenkahan says:

    OMG, thank you!!! So happy I had a part in swaying you to try them!! These look AMAZING on you! Never say never! 🙂

    And the pics of you and Luke dancing and jumping….LOVE!


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