May Outfit Planner + a Big Announcement!
May’s outfits are live—and so is the next chapter.
May is here, and with it, a new lineup of outfits to carry you through the month with ease and creativity. Whether your schedule is packed or you’re simply ready for a style refresh, this planner is built to help you wear what you love—on your terms.
Each look can be reworked, repeated, or adapted to fit your style and your schedule. Use it as a guide, a starting point, or simply a source of inspiration when you need it!
This month’s post includes a Week 1 preview of May, a closer look at this week’s outfit lineup, and an exciting update I’ve been working toward. Paid subscribers can scroll to the bottom for the full calendar view.
A Look Behind the Outfits
Each outfit in this month’s planner started with a spark—something saved, remembered, or reimagined. Some came directly from images I’ve pinned or saved (labeled Pin to Planner). Others were loosely based on a mood or styling detail I loved—those are marked as Saved + Styled. If you see Revisit + Rework, it means the idea came from something I’ve worn before and updated with small tweaks.
These notes give a quick glimpse into the inspiration behind each look, but the goal is always the same: to help you explore your style with curiosity and creativity, using what you already own—and maybe seeing it in a new way.
Here’s a snapshot of what inspired many of the looks this month!
May 2025 Outfit Planner
This Week’s Lineup
Here’s a look at this week’s outfits, pulled straight from April and May’s planners. Each one was styled from saved inspiration and shaped into something wearable, flexible, and easy to make your own. All looks are linked1 if you want to explore the details or fill in any gaps.
Sunday: Revisit + Rework
I’ve always loved this sporty-meets-casual combo. This version feels a little fresher—same vibe, different dress, and a denim jacket to pull it all together.
Monday: Saved + Styled
A workwear-inspired look that’s polished but still easy. The cropped trench adds structure up top, while wide-leg pants and a striped tank keep it comfortable for the day.
Tuesday: Pin to Planner
I’ve always considered leopard a neutral, and this look is a good example of why. A black layer keeps it grounded, and the red loafers add just the right pop.
Wednesday: Pin to Planner
Saved this one the second I saw it—I’ve been so drawn to Parisian style lately, and the layering here captures everything I love about it. It’s one of those looks that’s more intentionally styled—something I’d pull from the planner on a day when I’ve got a little more space to be creative.
Thursday: Pin to Planner
Starting the month with a look that’s equal parts relaxed and pulled together. A chambray shirt over black basics keeps it simple, and the accessories add a little intention without overthinking it. An easy pick for errands, school drop-off, or whatever the day throws at you.
Friday: Saved + Styled
I saved the original for the easy, laid-back vibe—but styled it here with a casual date night in mind. The textured top adds a little something extra while still keeping it simple.
Saturday: Saved + Styled
Light, neutral, and easy to wear. The tie-front top adds just enough detail, and the sneakers keep it casual.
Sunday: Saved + Styled
Inspired by a saved look that had just the right mix of sporty and polished! This look is ideal for a casual day or even a few rounds of pickle-ball!
Monday: Pin to Planner
A polished mix of structure and contrast. The blazer and piped trousers do most of the work, while everything else stays simple and clean.
Tuesday: Saved + Styled
Still searching for the right satin trousers, but this look keeps them on my mind. Soft, structured, and easy to wear—exactly why they’re on my list.
Wednesday: Revisit + Rework
A fresh take on an older outfit. Swapped the blazer for a canvas jacket and sneakers for sandals—same base, lighter feel.
An Exciting Update
Next month marks seven years since I first started sharing style content—first through a blog, then on Instagram, and now here on Substack. What began as a creative outlet has grown into something much more: a way to connect, reflect, and help you feel more confident in what you wear.
To celebrate that milestone—and to continue building this space with care and intention—I’m opening up paid subscriptions!
To be honest, this decision didn’t come easily. I’ve wrestled with the idea of putting any part of my work behind a paywall: partly out of fear, partly because I wasn’t sure if I was “ready,” and partly because I never want to do something just because it’s what’s expected.
But over the past few months, I’ve come to see the value in what I create more clearly. I’ve seen how much time, care, and intention goes into these planners, these breakdowns, this space. And at some point, it just became clear: it’s time.
So—here we are.
Everything for May—including the full planner and weekly lineups—will be available to all subscribers through the end of the month.
Here’s how things will look starting in June:
If you're a free subscriber, you'll continue receiving:
A 7-day preview of each month’s Outfit Planner
Style Files, Style Guides, and the Monthly Edit
A weekly Sunday Spotlight that includes one outfit breakdown with styling notes
Paid subscribers will unlock:
The full 30-day Outfit Planner delivered each month
The complete Sunday Spotlight—including the one-outfit breakdown and the full weekly outfit lineup, with shoppable links to each styled look.
Access to the full Outfit Planner Archive
By subscribing now, you’ll receive access to the entire archive of 2025 outfit planners—including shoppable links—all in one easy-to-access place. When the June Outfit Planner goes out, it will land in your inbox in full.
A Thank You to the First 10
To celebrate this milestone and to say thank you for being here, I’m offering something special to the first 10 paid subscribers who subscribe in May: a personalized Styled by Sarah mini session.
You’ll receive five outfit ideas styled specifically for you. Whether you’re packing for a trip, planning a week of outfits for work or mom life, prepping for an event, or just looking for a reset, I’ll create five looks based on your lifestyle, needs, and preferences.
Once you're subscribed, I’ll reach out to learn more about what you’re looking for so we can tailor the styling together.
It’s something I’ve been wanting to offer for a while, and this felt like the right moment to try it. If anything, it’s a small thank-you—and a new way for me to offer deeper, more personal support as this space grows.
If this sounds like something you’d love, you can subscribe here and you’ll be counted in.
Whether you’re following along for the outfit ideas, the reflections, or something in between, thank you. I’m excited (and a little emotional) about what’s ahead, and I’m so glad you’re here for it.
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