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Fall dilemma: When is it acceptable to wear boots?

I’ve been ahead of the writing game this week, managing to crank out two pieces in just the past two days. And if I’m being honest, I’d love to write every single day.

There are so many moments where I have to reel myself in, stay focused on the tasks at hand, and remind myself that I’ll get my time to write more freely later.

Someday, I’ll set aside uninterrupted time to dive fully into my writing. I can already see it: a two-month retreat just outside Provincetown, right on the beach. The cool Atlantic breeze brushing my face and there I’d be, sitting with my oversized sweater, wrapped up in a soft blanket, laptop balanced on my knees.

The rhythmic sound of waves crashing in the distance would be my soundtrack — the perfect setting for the words to flow.

It’s peaceful and grounding, and I can almost feel the inspiration that place would offer, fueling each keystroke. One day, I’ll make it happen. But today, let’s talk about something that’s top of mind right now.

Boots.

I couldn’t be more excited about the chill in the air this weekend.

Don’t get me wrong, I love what each season brings. During my short time living in Scottsdale, Arizona, my friends used to tease me for being from Ohio.

I’d always reply with what they were missing out on — the variety of seasons!

Sure, Scottsdale offered different degrees of heat year-round, but here in Ohio? We get it all.

That said, fall is, without a doubt, my favorite season. I could go on and on about the crisp air, the brilliant colors of the leaves, the smell of a real wood-burning fireplace — and yes, the fact that oysters are back in season.

Oh, and we can’t forget boots. While cozy sweaters top my list, boots are a close second.

My husband and I have a date night planned tonight, and I’m already debating whether it’s too soon to bring out my stylish, snug boots.

Am I the only one who overthinks this? When is the “right” time to wear boots again? Is there some unspoken rule I’m missing, or is it just me? The sweater is an easy “yes.” Boots not so much.

It’s funny: we don’t bat an eye when people throw on a swimsuit and sunbathe on an unexpectedly warm day in September. We celebrate that!

No one scoffs at someone for wearing a hat on a sweltering day, even if it’s full shade. Yet, here we are, patiently watching the weather forecast, waiting for the signal to pull out the boots. It almost feels like there needs to be a streak of cool days before we’re all collectively allowed to wear them.

So, is there a designated “boot day” like there is for wearing white? Or do we just watch what everyone else is doing?

Maybe this is just my way of giving myself a little pep talk — because honestly, if I feel like wearing knee-high boots on the first weekend of September, why shouldn’t I?

Fashion is personal, after all. And for those who saw me last weekend … Well, they already know which way I leaned.

Here’s to fully embracing the changing seasons — boots, sweaters and all!

This is from me to you. I’d love to hear your thoughts. When do you think it’s the right time to break out those boots? Do you overthink it too?

Let’s embrace the small joys, whether it’s a cozy sweater, a favorite pair of boots, or simply the change in the air. Please share your stories, and let’s celebrate the little moments that make us feel most like ourselves.

Mother, author, entrepreneur and founder of Dandelion-Inc, Lisa Resnick wants to hear your story. Share memories with her by emailing lisa@dandelion-inc.com.

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