Outfit Repeating Will Set You Free
On the endless joy of sticking to what works
In sixth grade, I had four pairs of pants that were long enough. It was the late 2000s. Longer inseams were usually the result of shopping the boys’ section or having my mom let out a seam. As a result, I meticulously planned my outfits for the week ahead, careful not to wear any pair of pants more than once per week (one day for chapel uniform) because I was that afraid of being caught outfit repeating.
In my first trimester of pregnancy, I had a growing waistline and a secret. Most days I was nauseous. And getting dressed—my beloved outfit creation!!—lost all its charm. Instead, I wore this sweater and a bigger than usual pair of Levis from eBay on repeat for days on end. Seventeen years later, I learned to find comfort in outfit repeating.
To begin to embrace outfit repeating, we need to shift the moment of celebration from acquisition to actual wearing. Finding a perfect piece for your closet is just the start. It’s thrilling, but it's what happens next that really matters.
It’s the worn-in rugby shirt your best friend monogrammed for you a decade ago. It’s the silk gown you wear to every other wedding, the hundreds of happy memories it holds. It’s the massive tshirt you tell yourself is only for bedtime, but secretly love pairing with Levis and boots for a late night dive bar run.
Fashion as we actually live it isn't about constant newness—it's about the relationship we build with what we already own. Personal style deepens with every repeat wear. Some people instinctively understand this. Others need to learn it. And that’s where these two reframes come in.
Intentional Favorites
As the saying goes, "Love it enough to wear it threadbare." We've all been conditioned to crave variety, to feel slightly embarrassed when someone notices we're wearing "that shirt again." But the most stylish people I know have signature pieces they wear relentlessly.
Jenna Lyons and her signature glasses is a great example—a reminder that the most confident style move is finding what works and sticking with it, rather than chasing every new eyewear trend that emerges each season.
When I look at what I've donated over the years versus what I've kept, there's a stark difference: the keepers have been worn dozens, sometimes hundreds of times. They've earned their place. The donations were often impulse purchases that promised variety but delivered only closet clutter.
Here are a few of my worn-a-thousand-times classic combos
This Lululemon tshirt + Modern Citizen shorts (on sale for $40) + Dorsey earrings
Vintage Eddie Bauer barn jacket + vintage floral rayon dress
A pair of Nike Tempo shorts in XL + a striped button down
Alex Mill jumpsuit + this cashmere striped sweater over the shoulders
The Echo Effect
Sticking to the eyewear example, Jackie Kennedy could have worn her oversized sunglasses occasionally. That would have been chic, certainly, and maybe those few photos would have been enough to cement their place in fashion history. But she wore them constantly, everywhere. She created not just a signature item but a signature silhouette that became synonymous with her entire persona.
Beyond sustainability, there's something deeply satisfying about wearing clothes often enough that they begin to hold memories. You start to get comfortable and creative, maybe the next time you add a necklace or tie a scarf at a slant. Soon you’re off to the races, relying on a tried and true combination when everything else in your life feels up for grabs. And that’s the freedom of outfit repeating.
Honorable Mentions
Mixing and matching bedding is an easy way for my bedroom to feel refreshed for summer. And just in time, Brooklinen's Memorial Day Sale is here! Save 25% off sitewide—and even more when you bundle! It's easy to build a bedding story that's uniquely your own with bundling. The best part? These sheets just get softer with every wash.
See you at 4p ET this afternoon for my chat with
!!Two boring recs: these sponges and this to carry iced drinks so they don’t sweat all over your hands on your walks.
Thank you for reading Long Live. It means so much to me. You can preorder my romance novel, Exit Lane, on Bookshop or Amazon. You can shop my favs here, follow along on Instagram + Tiktok, and shop my Notion template. You can book my Office Hours to talk shop here. Get matched at EV Salon. And if you want to partner on a future Long Live, email evan@communite.co x
My favorite thing to do is pick out a really good outfit for Saturday or Sunday (when I have more time to try things on and hem and haw over what's cutest) and then wear it again on Monday or Tuesday!! Copy/paste dressing!
MORE copy paste dressing!!! if it works and you feel comfortable WEAR IT AGAIN!! Great breakdown of the consequences of fast fashion on our long term wadrobes.