Everything I Wore This Week Volume 18.0
From outfit moods to life updates—plus the Lilly Pulitzer dress I didn’t know I needed (thanks, Sirens).
WE’RE OFFICIALLY ON SCHEDULE, BABY.
Turns out all I needed was to start doing this full-time—and now the newsletter is (finally!) going out on time.
It’s been an exciting week. I officially announced that I’m working on The Kiley Edit full-time: outfits, writing, my book (The Mother My Husband Knew), and—coming soon—an app I’m building with my husband, Chris.
Everything I said in I’m 36 & I’m Starting Over (Sort Of) still holds true. Starting something on your own is equal parts scary, exhilarating, and hard. But your support has made it all feel a little less terrifying—so thank you.
As for this week’s version of “research,” I binged Sirens start to finish. Yes, I rewatched the scene where Meghann Fahy screams “F*** Michaela” more times than I care to admit. While casually cruising ThredUp, I stumbled on a Lilly Pulitzer dress that screamed Devon/Simone energy—so obviously, it had to be mine. A little method acting. A little main character energy. Expect some Lilly looks this summer.
Everything I Wore This Week
This week’s looks are a bit lighter than usual, but I’m still sharing daily outfits on Instagram—so be sure to follow along. And as always, let me know if there’s anything specific you’d love to see in future posts!
Quick note: Items with affiliate links may earn me a small commission (at no cost to you). "Similar" items are listed in place of pieces that are no longer available or come from brands that don’t align with my values. If you spot something that feels off, I always appreciate the heads-up.
☕ Monday
Mood: Memorial Day Monday
Wearing: Abercrombie & Fitch Short-Sleeve Crochet-Style Polo, Black Mid-Rise Barrel Jeans, Missoma Ripple Oversized Stud Earrings, Missoma Ridge Heart Necklace, Missoma Filia Double Chain Necklace, Red Mesh Flats
We hosted friends and family for a day that was both joyful and reflective. My husband cooked an incredible meal—pulled pork, corn on the cob, and the creamiest smoked gouda mac & cheese. I wanted my outfit to feel festive but still respectful. Also, shoutout to this amazing Elderflower Gin Fizz I made (with the help of ChatGPT. You can find the recipe in one of my latest posts: I <3 AI: 5 Ways I Actually Used It This Week)—I’ve made it multiple times since. It’s a keeper.
Outfit Details
🌧️ Tuesday
Mood: Happy Hour Hue
Wearing: Abercrombie & Fitch Denim Column Midi Dress, Charlotte Stone Lenu Kortman, Olga Berg Kimmi Hotfix Top Handle, Missoma Ripple Oversized Stud Earrings, Missoma Ridge Heart Necklace, Missoma Women’s Peace and Love Jelly Heart Necklace
I grabbed this denim dress from Abercrombie & Fitch a few seasons ago, and it’s still one of my favorite versatile pieces. It’s one of those “easy win” dresses—you can throw a jacket over it, layer a tee underneath, or just let it stand on its own like I did here.
For happy hour, I kept the base simple and let the accessories do the talking: statement heels, a top-handle purse, and a few playful jewelry pieces that brought in just the right amount of fun.
The pinks don’t match perfectly, and honestly? That makes me love it even more. These Charlotte Stone heels have become one of my most-worn pairs—you’ve probably noticed them popping up everywhere. I can’t help it. They’re just so fun. They remind me of something Carrie Bradshaw might wear… if she ever gave in to a sensible block heel.
Outfit Details
✨ Wednesday
Mood: Red Blazer Love
Wearing: Abercrombie & Fitch High Rise Wide Leg Jeans, Abercrombie & Fitch Short Sleeve Martini & Fries Graphic Tee, Red Mesh Flats, Red Oversized Blazer, Coral Bucket Bag, Julunar Silk Scarf, Betsey Johnson Heart Earrings, Missoma Link Double Chain Necklace
This look is what happens when you mix power dressing with a side of fries—literally. I’m obsessed with this graphic tee featuring martinis, fries, and a cheeky nod to girl dinner. And I do love girl dinner. Cinnamon Life cereal? A go-to. That frozen TGI Fridays Spinach Artichoke Cheese Dip? Elite. So, pairing it with a bold red blazer and wide-leg jeans felt perfectly on-brand. The accessories are giving “effortlessly extra”—heart earrings, a coral bucket bag, and a silk scarf that basically begged to be part of the party (and now might never come off). Playful, a little polished, and totally my kind of balance.
Outfit Details
🌼 Thursday
Mood: Confetti Collision
Wearing: Lucy & Yak Ragan Cotton Jumpsuit Memphis Print, Yellow Open Toed Mules, Studded Leather Belt, Yellow Crossbody Purse, Missoma Square Pearl Earrings, Missoma Filia Double Chain Necklace
We all know I love a Lucy & Yak moment, and this jumpsuit is no exception. I wasn’t dressing for anything in particular—just a random Thursday—but the print made it feel like a celebration anyway.
The vibe? A little retro, a little chaotic, a lot of color. Add a studded belt, sunny accessories, and my go-to Missoma jewelry, and suddenly my "just throwing something on" turned into a whole look.
Outfit Details
🔋 Friday
Mood: Citrus + Cobalt
Wearing: Vintage The Body Co Blue Pants, Orange Muscle Tank, Blue Alligator Print Top Handle Purse, Snakeskin Mules, Chunky Silver Necklace, Missoma Hera Dome Double Ridge Medium Hoop Earrings
These vintage pants from The Body Co were a total thrift score I picked up in Iowa—and I’ve been obsessed ever since. The texture, the electric blue, the perfect high waist? Yes, yes, and yes. I wanted a bold contrast, so I threw on this orange muscle tank and let the color-blocking do the work.
Finished it off with snakeskin mules (obviously), and wore it to a working happy hour where I got a compliment from… a brand manager? A publicist? Either way, someone stylish and important. So, I’m counting it as a win. Just ignore the fact that my foot is a little cut off…you get the idea :D.
Outfit Details
✨ Wrap-Up
With everything going on behind the scenes, this weekly ritual has been one of the most grounding parts of my routine. It feels so good to focus on what’s next—and even better to be building it with Chris by my side. We’ve worked together before and chose to keep going... and yes, I’m saying “we,” because he’s a big part of this journey. He likely won’t make a newsletter appearance—but never say never. The man has taste.
I also rewatched Emily in Paris this week—so if you sense more drama and dopamine in next week’s outfits, that’s why.
🖤 Which look was your favorite?
🧠 Want to see a week of outfits built around just one piece?
More looks, links, and real-life style right this way:
Until next time, may your loafers be metallic and your coffee be strong,
Kiley
Read More
I <3 AI: 5 Ways I Actually Used It This Week
I love, love, love using an AI assistant—like, can’t-live-without-it love. It makes my life easier in ways I didn’t even realize I needed. And honestly? If you’re not using one yet, you’re missing out.