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Maybe the next chapter isn’t about changing everyt Maybe the next chapter isn’t about changing everything.

Maybe it’s simply about staying curious, paying attention, and making room for what lights you up.

next chapter, midlife, over 40
What brings you joy these days? For me, it’s the What brings you joy these days? 

For me, it’s the little things: slow Saturday mornings, coffee, books, my plants, and piddling around the house with absolutely nowhere I need to be.

Nothing fancy. Nothing productive. Just things that make me happy.

Tell me one little thing that brings you joy lately. I’d love to hear it.
Who's heading to Country Calling in Ocean City thi Who's heading to Country Calling in Ocean City this weekend? 

I'm not, but if I were, I'd wear these outfits! 

Country festival outfits, Country Calling
What are you looking forward to in October? Octob What are you looking forward to in October?

October musing, October, poem,
Wait… are jean jackets really “out”? Because app Wait… are jean jackets really “out”? 

Because apparently someone decided they are, and I have one thing to say:

Nope

I’m 57. I’m not interested in keeping up with every trend or following a list of made-up rules about what I’m “supposed” to wear at my age.

If I like it, I’m wearing it.

The older I get, the more I realize that personal style has a lot less to do with what’s trending and a lot more to do with knowing what makes you feel like yourself.

So, jean jacket? ✔️
Wearing what you want? ✔️
Caring less about the rules? Absolutely.

What’s one fashion “rule” you’re happily ignoring? 

Wear What You Want,  Ageless Style, jean jackets
The latest issue of Lisa’s Letter, my midlife news The latest issue of Lisa’s Letter, my midlife newsletter, is out today! Subscribe through the link in my bio. 

weekly newsletter, midlife newsletter
Who’s ready to stop following made-up rules? Wear Who’s ready to stop following made-up rules?

Wear what you want.
Wear what makes you feel like yourself.
Your life is happening now. 

So wear the damn outfit.

Outfit confidence, over 50 style, wear what you want, fall fashion
Well, hello there. There are A LOT of new faces Well, hello there. 

There are A LOT of new faces around here, and I just want to say welcome and THANK YOU for being here!

Wear the Damn Boots has always been about this one simple idea:

Your life is happening now.

So if you’re here for the conversations about getting older, figuring out who you are in this chapter, personal style, confidence, beauty, empty nesting, or just the everyday stuff that makes life feel like yours, I’m glad you found me.

And since there are so many of you joining the conversation, I want to hear from you:

What do you want to see more of around here?

Tell me in the comments. I’m taking notes. 👢🥾

Welcome, thank you, Jen Hamilton, grateful

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Wear the Damn Boots
a mindset for living boldly at any age
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About WTDB

Wear the Damn Boots is a blog for the mid-life woman who is sick of second-guessing herself and trying to fit into society’s definition of beauty and aging. She’s not young but isn’t old yet. She wants to live authentically and not worry about what other people think. WTDB is a source of inspiration with a bit of personal style, fashion finds, book recommendations, wellness, and so much more. It should leave you feeling like you just had coffee with your best friend.

I created Wear the Damn Boots after standing in front of the mirror questioning my choice of outfits. After wasting so much time, I finally thought, wear the damn boots! I lay in bed that night thinking about why so many of us waste time doubting ourselves, feeling insecure, and giving in to negative self-talk. I reflected on all the missed opportunities because I was too worried about what others might think and say about me.

That evening was a pivotal moment because I finally learned that overthinking and second-guessing myself was sucking the joy out of my life, and I wanted to share that shift in mindset with women of all ages. I see Wear the Damn Boots as a mantra or affirmation to let go of whatever is holding you back from being the most authentic version of yourself. I hope you join me and Wear the Damn Boots.

recent posts

  • Books to Read This Fall
  • Fall Refresh: A Reset for the Woman You Are Now
  • The Day I Stopped Apologizing for My Face
  • How to Redefine Your Style in Midlife
  • Overthinking in Midlife: Why We Second-Guess Ourselves and How to Stop
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  • Beauty
    Beauty
  • Books
    Books
  • Confidence
    Confidence
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    Style

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