How to Break Free from a Style Rut and Find the Joy in Getting Dressed Again

One humbling shared human experience is that, sooner or later, we all end up standing naked in front of our closet, paralyzed by the feeling of having nothing to wear. But this isn’t the moment to just throw on some workout clothes and call it a day, cautions Miami-based stylist Kelly Klein.

“Putting effort into how you dress is such an act of self-love,” says Klein, who, in addition to working one-on-one with clients, also writes an eponymous Substack that I’ve recently discovered and become not-so-secretly obsessed with. Part of my obsession is rooted in the recognition of a kindred spirit: Klein, here, expresses what I’ve long believed to be true, which is that fashion can absolutely be a form of wellness. “It's a mood stabilizer,” she says. “It's good for your mental health. It is so intense, the way I feel it. If I don’t properly get dressed, I feel sluggish, I feel less creative. I feel so much less like myself.”

Klein’s gift is that she’s able to help people break out of this universal rut—not by buying or acquiring more but by teaching them how to see the clothes they own in a new light. Below, she shares her go-to strategy for getting your creative juices flowing again, the one piece you’re probably underusing (and how to change that), two of her favorite small styling hacks that make a big difference, and more.

A Conversation with Kelly Klein

What are some of the most common reasons that people end up in a style rut?

A lot of clients come to me postpartum, when their bodies have changed and they want to figure out how to dress themselves. Or maybe their bodies haven't changed, but they’re just in this new phase of life when they want to look cute but also comfortable.

The other big reason is that people get stuck in patterns—reaching for the same things over and over again, not taking risks, and maybe saving the pieces that they love for something special as opposed to actually wearing them. I always say our clothes are much more versatile than we give them credit for. There are ways to dress things down, so nothing is really worth “saving.” You should wear the beautiful thing to the grocery store, you know?

What’s one easy strategy for getting unstuck?

Play with color. I like to feel excited by an outfit, and I think color is such an easy way to do that. My biggest tip is when you have one pop of color, whether it's in the top half of your outfit or the bottom, you should add another color on the opposite half to balance things out. It could be small—maybe an interesting-color shoe or a colorful beaded necklace. And it doesn't have to match. But having two those touchpoints really makes the outfit feel more harmonious.

What are your favorite color combinations right now, and where do you find inspiration?

I get the spark by f*cking around in my closet and truly playing with my clothes. And when clients ask me for my number one tip for looking good, it's always the same: Plan your outfit the night before. Because when you're rushing and you're dealing with your kids or you're just stretched for time, you're not going to be making as good decisions as if you just planned the night before. So give yourself time to play around with the clothes that you have. By doing so, you're going to find the combinations that make you tick.

Right now, my favorite color combination is pink and red. I’m really inspired by the stylist Danielle Goldberg, who dressed one of her celebrity clients in a pink-and-red dress for a red carpet, and something about it just clicked for me. So I've been playing around with pink and red—which may sound cutesy but actually feels kind of bold and interesting when you ground it with a good shoe and add some edge with accessories.

Other good combinations are colors that sit next to each other on the color wheel. I love green and blue together, or red and orange, or purple and blue—colors that have similar undertones. Bonus points if one of those shades is more of an earthy tone. At my Still Here styling event, they had this really cool burnt-orange jean, which I loved pairing with a red T-shirt. Mixing a brighter color with a dirtier earth tone is a helpful trick when playing with more than one color.

What is the most overlooked or underutilized piece in people’s closets?

I would say a button-down. Oh my god, it can do everything. I’m serious. You can wear it as a light jacket, which I'm kind of doing today. You can wear it as a sexy top, just by the way that you tuck it and manipulate it. You can cuff or roll the sleeves to elongate your arms. You can wear it as a cover-up if you keep it open and tie it around your waist. Even just tying it around your waist, with pants and a jacket on top, adds such interesting proportion. There's nothing a button-down can’t do. You can wear a button-down on a red carpet (and people are), or you can wear it to the beach.

Speaking of button-downs, you once wrote an entire Substack dedicated to a concept called “the sandwich.” Can you break that down?

Oh, I love the sandwich. I didn't even mention the sandwich in all my examples just now because I got too excited. A sandwich is a way to maximize a button-down, so instead of wearing it on its own, you "sandwich” it between two layers—let’s say a white T-shirt and jacket, or an oversize cardigan. Think of it like the meat or cheese between two slices of bread. It’s just a great way to add texture to your outfits. That little sliver of lapel that peeks out at the neckline adds so much dimension.

I love that. It’s so simple but also kind of genius?

It's hard to have an original idea nowadays. I try not to consume too much content because then I get really in my head, thinking, Whose idea was this? Was it mine? It's like that Paul McCartney lore about the song “Yesterday”—apparently, he waited many, many months before putting it to paper because the melody came so easily to him that he swore that it was out there already. Sometimes when an idea is really great, it just comes to you without much effort.

You’re a pro at using accessories to uplevel your outfits. What’s your favorite way to wear a scarf right now?

This was definitely inspired by the runway and something I'm so excited by. I love an unexpected element in an outfit, so I will take a scarf and drape it around my neck, letting one side hang longer and tucking in the shorter side. Then I’ll layer a jacket on top and wear it closed so that you’re only seeing that hint of fabric stick out underneath. The asymmetry is what makes it interesting—you can't quite tell where the extra fabric is coming from, and that uncertainty is part of the appeal. It's sort of doing what this GWYN camisole, which I love, is doing.

Good outfits are about creating contrast on purpose. The contrast can be obvious, like wearing an all-white outfit with a black belt. But it could also be pairing a really casual element with something really polished—like in that amazing picture of Alexa Chung wearing a full suit with a straw tote.

What are some small-but-impactful styling hacks that can make an outfit you might have worn a million times feel fresh?

Hint at the waist, either through a half-tuck or by folding your sweater underneath itself to let whatever you’re wearing underneath peek out. It could be a little sliver, like we talked about, or a few inches that just draw the eye upward and give the outfit more shape. That’s a big one, in terms of manipulating your clothes.

Rolling your cuffs or pushing your sleeves above the elbow always makes an outfit feel more relaxed and intentional. And it really does elongate the arm. As we're getting into warmer months, I would say knowing how to roll your sleeves is really important. I think it’s as important as knowing how to layer a white T-shirt underneath a sweater—it sort of signals that you know what you're doing.

Do you have tips for making those manipulations—i.e., a hiked hem or a pushed-up sleeve—stay all day?

Yes. So, if you have a sweater that is really oversize, of course just folding the hem underneath won't work. But oftentimes there's ribbing at the hem, and if you roll that underneath, it will stay because of the tension of the rib. If it doesn't, I like to just add a hair clip, like we did here. The hair clip is great because a) it’s functional, and b) there's an unbotheredness to it. It's like putting a pencil in your bun.

I learned how to cuff a shirt from my mom. But you basically just pull the sleeve all the way up, above your elbow, and then you're rolling on top of that and letting some of the cuff stick out. Letting it be messy. I think there's something interesting about seeing the underside of the fabric. It's not something I want you to overthink at all—it should take no more than five seconds. (Editor’s note: Klein demos this here.)