Iconic outfit repeaters & what we can learn from them

I’ve talked at length about my love of outfit repeating, and a need to normalize it romanticize it, but today I want to go one step further and study some of the people I consider iconic outfit repeaters. To put them and their style under the microscope, dissect the lessons they offer, and consider how we can apply the findings to our own closets.

Fran Lebowitz

First up, my spirit animal in so many ways - Fran Lebowitz. After doing a no buy 365 wardrobe challenge, I feel pretty confident I could easily live out of Fran’s closet. It’s the ease and simplicity for me. Fran is someone who openly preaches buy less stuff, but buy better quality. It’s so refreshing to see someone who walks the walk on her own advice. She doesn’t stray far from her comfort zone, but I see someone who always looks relaxed, even though you could argue a tailored jacket is the opposite of relaxed. She offers a great reminder to take care of your things, and wear the hell out of them. While heavily documented across numerous occasions and time spans, her blazers always appear pressed, her boots polished and everything she wears look really well taken care of. Take pride in your pieces, store them with care and attention, and get things repaired as and when they need it.

Her repetition shows an air of confidence and knowing that I want to replicate in my own wardrobe. Frans approach to outfit repeating proves the same outfit works no matter the occasion, whether she’s walking around the city, at an awards ceremony or a gallery opening, she wears the same thing and it works. One great quality wool blazer, coat or jacket will work hard in your wardrobe throughout your life. I get 90% of my wool blazers second hand or thrifted. I’m also, surprisingly, feeling the cowboy boots. Watch this space!

Kate Moss

I feel like in the early naughts, there was a very specific Kate Moss look. I’d describe the uniform as skinny jeans, black rayban wayfarers, black boots, a blazer or leather jacket, and always, always, a scarf of some kind. She also often wore a lot of black but used texture and the scarf as a way to break things up, a reminder that all black looks are indeed eternally chic. Trends come and go, but wear what you want, when you want. Yes, even if Tik Tok is telling you it’s not cool anymore to wear skinny jeans!

Kate Moss has always set trends because she doesn’t wait for permission to wear what she wants to wear. Seeing articles that say ‘Kate Moss is making skinny jeans cool again’ makes me roll my eyes so hard. If you like it, wear it! And no the goal of personal style isn’t to set trends, but to embody what make you feel good right now.

Abisola Omole

I cannot say enough good things about Abi’s personal style, especially the way she incorporates lime green shoes into so many of her looks! I’ve seen Abi wear this dress or a very similar variation so many times and what always strikes me is how she always leans into elegance. I mean this with no malice, but it is refreshing in a world of ‘undone’ and ‘effortless’ looks to see someone make an effort. As a self confessed oversized clothes lover, I’ve also been experimenting recently with a few more fitted pieces, inspired by Abi.

Owning one great dress you love and feel great in (if you’re not a dress person maybe a jumpsuit?) offers an incredible blank canvas. Abi’s looks remind me to use a focal point when i’m working with what I consider a ‘blank canvas’ item like a t-shirt dress, or a dress that’s a block color. When she pairs her dress with the lime green pointy shoe it adds immediate impact. The color is fun, and yet the sharp toe feels a little more serious. It offers a nice contrast against the fluidity of the fabric the dress is made out of. In the middle look, the neck scarf draws your eye towards the neck which instantly changes the entire feel of the dress. I’ve been leaning into playing more with my neck scarves again at the moment, and I do love how much it adds something to a plain tshirt, a plain shirt or even a dress. Abi is a reminder you don’t have to have a reason to get dressed up/you don’t need an occasion to dress elegantly. You are the occasion!

Chloe Sevigny

One thing I love so much about Chloe, in addition to her incredible style, is the fact that when I look at her red carpet looks, there’s often repetition of a piece or pieces from her past sprinkled in to what a stylist may or may not of picked out for her. If you look at any decade of her being in the public eye, she has always worn socks with a loafer, or socks with a shoe in general. We all have our own interpretations of what timeless means, and it should be personalized to us and our tastes. What I’ve learnt from Chloe is how to add an unexpected element to my outfits alongside the consistency. For instance, the patent black rain mac she always wears plays with shine and light, while the crinkle texture let’s it lead the outfit. The moment she adds that patent coat the outfit arrives somewhere, it becomes a Chloe Sevigny outfit.

When I wear one of my go to outfits, I always think: what would Chloe add to create something unexpected? I look for something that leads the outfit, sometimes that’s created via contrast, and sometimes it’s adding in a really old piece from my wardrobe I haven’t picked up in a while.

Adam Sandler

There is a photo of Adam Sandler wandering around New York City in an old wool coat eating pickles out of a jar, and that’s the level of IDGAF energy I want in my life. As such, I consider him an icon. Adam’s not afraid to outfit repeat, especially with bright colors. Even if he always wears the same (or similar) red sports shorts, tennis socks and black trainers, he mixes things up with a graphic tee, sunglasses or a baseball hat to make the same outfit feel new and fresh.

Living in LA it makes sense for me to own a few different pairs of sunglasses and i’m always surprised how much they make outfits I repeat feel a little new, or different. It’s the little twists and tweaks that can have a big impact. I’ve been trying to make a more concerted effort to change up my sunglasses daily, and this alone makes a huge difference in how I see and experience the same outfit.

Laura Harrier

I haven’t seen an outfit of laura’s I don’t like. When I look at her off duty looks it’s always her most casual fits I love the most, especially her approach to jeans and a white tee. It’s classic sure, but again, the use of a claw hair clip, the considered toe of a shoe add some personality. What I love about these outfit repeats is that you could pretty much put her in any era and it still works, it would be hard to pinpoint exactly which era the photos were taken from if we didn’t know.

If you always wear jeans and a white t-shirt consider experimenting with different tucks, or maybe you can roll up the sleeves of the tee? Maybe you try turning up your jeans? In the second image, I like that while her jewelry is minimal it still adds something to the look, and that watch! Experiment with mixing metals with your accessories as a subtle way to add some interest.

Princess Diana

When I look back at photos of Princess Diana’s casual looks, she was never without her Harvard sweaters, a pair of tennis socks, white trainers and usually a white cycling short. I appreciate these looks in particular have seen a lot of discourse in the fashion space, but I think that’s with good reason. She was iconic! There are very specific additions that make this feel a little more put together, more intentional. For example the minimal gold hoops, the tortoise shell sunglasses and a structured leather tote bag. Something about the tortoise shell sunglasses with the polished bag makes this still feel serious, and not quite as playful. It’s still grown up is what I think i’m trying to say?

It’s also a nice juxtaposition of mixing casual items with more formal pieces, something I love to do myself. When I think about why it works, it’s not just what she added but how she wore it. For instance, the sleeves rolled up on the sweater to show more skin and give some shape to the sweater. Playing with the proportion of the sock and how much is exposed.

I’m not gonna lie, this was a hard edit to narrow down, I thought of so many other people after i’d written this, I may need a part two.

When it comes to iconic outfit repeaters, i’m curious, who is your favorite?

Thanks for reading

Harry x