Seven outfits for my ordinary summer where I'm not vacationing in Italy

Who knew dressing for regular life could be fun too?

Liza Belmonte’s Seven Outfits of the Season pretty much changed the game for me when it comes to getting dressed.

Her take? If you want to make getting dressed easier, all you've got to do is figure out the 7 most common scenarios that pop up in your day to day life, then come up with a loose outfit formula you can apply to each scenario.

My summer isn’t looking glamorous. I’m not off to the Amalfi Coast. But I am hitting up the local pool, eating freezer pops, and doing a whole lot of nothing with the people who make it feel like something.

Not bad at all. 😌

So, here’s my list — the seven things I’m actually getting dressed for this summer:

1. Running errands

2. Rollerblading (you read that right)

3. Professional events

4. Hanging out at a friend’s house

5. Going to the pool (family friendly vibes)

6. Working from a coffee shop

7. The rare-but-it-does-happen fancy night out

Keep scrolling to see what I’m wearing for each one!

(This is my very first paid-subscriber post, and I’m so excited to share it with you! Free subscribers still get a solid little preview — and either way, I’m just really glad you’re here.)

1 | Running errands

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Once it starts getting hot, I prefer running errands in anything but jeans. Jeans are fine inside an air-conditioned coffee shop, but jeans while getting in and out of my oven car? Immediate swamp situation.

I would usually default to my Nike Tempo shorts here, but I’m trying to NOT wear them for everything this summer. (Wish me luck.)

Instead, I’m going for something that’s still sporty, but doing a little bit more style-wise. Like parachute pants! You cannot pry them away from me! I do not care that they are not trending anymore! I love them!

And they get five stars for always protecting my legs from searing hot car seats.

2 | Evening rollerblading

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I’ve wanted to start rollerblading for a long time. There’s this trail right near my house that’s perfect for it. And there is nothing that makes me feel kid-like glee more than rollerblading.

But y’all, I’ve been too scared to do it.

What if I fall? What if I break something? I’m not exactly a young’un!

But lately, as I’ve been slowly emerging from my post-divorce grief cave, I’ve been more scared of NOT living my life. Letting fear keep me from the things I want to do. Rationalizing myself out of my own delight.

Right now, I’m the youngest I’ll ever be again. So…here I go!

I’m so inspired by the fashion around rollerblading, too. The knee pads, the wrist guards — I mean, come on, when do you get a chance to wear things like this? They’re a total vibe.

3 | Professional events

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I practically never dress “business” — it just hasn’t been necessary in my work-from-home, suburban life. But recently, I’ve been more involved in civic stuff, so I’ve got things to go to.

When I dress for something outside my norm, it’s funny how fast I can lose my sense of self entirely. A quick Pinterest search for “professional outfits” offered lots of tailored Sezane-ish looks. This is not my style, but I thought, I guess that’s what you wear! as I threw a block-heel ballet pump into my cart.

But then I studied my cart and paused.

This is so not me. What would Caroline wear?

And then it came to me: