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Caitlin Covington · Aug 12, 2026

Looking Ahead at the Month

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Caitlin Covington · Caitlin Covington

I’ve always loved August, for so many reasons - even though it’s still hot outside, it feels like the start of a new season. Our kids are going back to school, which means fresh routines for everyone, and we start prepping for fall (fall fashion, fall trips, fall content!). I’ve already started incorporating some fall coziness into my everyday routine. Here’s a peek at what I’m looking forward to this month:

While cool weather hasn’t officially arrived, fall fashion has! I’ve been slowly transitioning over my wardrobe from bright summer hues to autumnal colors like chocolate brown and olive green. This cardigan is one of my latest purchases (I’m wearing it here), as well as these matching woven flats, which I’ve already worn with everything from dresses to jeans. Another favorite transitional purchase has been these lace shorts (seen here) - they’re right on trend and easy to style, which really counts for something! I love wearing them with a tee for summer, but can also see them styled with an oversized sweater and boots in the fall. I’ve also been really loving funnel neck jackets - I just got this one in the mail and although it doesn’t look like much online, IT IS SO CUTE IN PERSON. I’m kind of crazy about it!

At the end of August, our two big girls are off to school - and yes, one of them is officially a Kindergartner (excuse me while I wipe my tears). While I’ve absolutely loved having them home for the summer and it will certainly be an emotional send-off, I’m also really excited about the structure and routine that back-to-school brings to our lives. Since Chris and I both work from home, summertime can feel quite chaotic for us - no alarm clocks and no strict routines (which is truly what summertime is about!), but I think we’re all feeling ready for some structure again. I have big plans for the hours that the girls are in school, including trying some new fitness classes and achieving some work goals I’ve set for myself. I already purchased a new, chic planner and notebook to kickstart my productivity (hello adult school supplies! haha).

I’m so ready for fall travel, we went ahead and booked a mini fall trip to the mountains next week! It’s a beautiful house in the countryside, and it should be cooler since the elevation is a lot higher. The girls are going with us, of course - I ordered these monogrammed bags for them that will make perfect packing cubes. And since we are bringing Eleanor (her first trip EVER!), we will be packing our baby travel accessories, like a portable crib and this absolute must-have. Since this is our first trip with all three kids, we don’t have huge plans or expectations - we mainly want to sit on the porch swing and sip coffee in the mornings, play outside all afternoon, and enjoy the cooler weather! (And maybe wear some cute fall outfits.) It will be a good test-run before our annual trip to Vermont this October!

While I’m not looking forward to this day, I couldn’t write this post without mentioning that my dad’s birthday is in August - a date that was once celebrated, but now makes this month feel extra heavy. We should be throwing him a party for his 67th birthday - he should be on the floor playing with his grandkids, holding his new granddaughter, he should be laughing as my kids blow out the candles on his cake before he can. He was the most selfless person I have ever known and spent every other day of the year celebrating everyone else - his birthday was the one day we got to celebrate him. If I’m honest with myself, most days I push my grief down and avoid truly “feeling” it - but this month feels impossible to do so. On the inside, I’m still a little girl who really, really needs her dad.

Sorry to end this post on a sad note, but I think that’s part of what makes this August feel so different for me. It’s a month that holds so much anticipation and excitement, but also a reminder of what - and who - we’re missing.

I’m trying to remind myself that both things can exist at the same time: I can be excited for a new school year, fall fashion, cooler weather and family adventures, while also missing my dad. Maybe that’s what I’m looking ahead to most this month - not just a new season, but learning to embrace all of the feelings that come with it.

Here’s to a new month, a fresh start, and hopefully a little more fall weather. 🤎

xoxo

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