It was 2010, and I was interning at an art gallery on the Bowery when a woman named Reese walked in with the best haircut I had ever seen in my life.
I knew I should have given her a moment to take in the art, but I couldn’t help myself, I walked up to her and started a conversation that quickly led to the story behind her haircut.
We talked about her hair for some time, and finally, she shared the talent behind her tresses. She uttered the following as I reached for the gallery price list on the counter, flipping it over to scribble on the back:
Teddi Cranford. Sally Hershberger. Meatpacking.
Not to be dramatic, but I slipped that piece of paper into my bag, having no idea that my life would change forever.
Before learning about Teddi— or Sally Hershberger for that matter— I got my hair cut at a salon in an outdoor shopping center in the town where I grew up in South Florida. The experience was always the same: they’d wash my hair, snip a few inches off while it was wet, and then blow it dry. The whole thing took about 40 minutes and maybe cost 60 bucks.
When I was young, my mom instilled a deep respect for caring for my hair— from regular brushing to weekly hair masks— but with most afternoons spent on the lacrosse field and weekends in a pool or at the beach, my hair was usually thrown up in a ponytail or moments away from needing another rinse.
Back then, social media didn’t exist in the way that it does today. I wasn’t scrolling through videos titled “What I Ask My Hairstylist When I Get A Haircut” or watching how-to videos on YouTube. I didn’t fully register that the right cut could elevate all the care I was putting into my hair, turning it into something that felt like me.
Growing up, there were the iconic haircuts that people would ask their stylists to recreate— Jennifer Aniston’s “The Rachel” being a top contender. As a Limited-Too-wearing kid of the 90s / early 2000s, I was more inspired by girl band hairstyles with choppy layers and high-maintenance highlights. I dreamed of stepping into the makeover scene at the John Frieda salon in Josie and the Pussycats, yes, the 2001 film—don’t get me started on how this is one of the most underrated movies and soundtracks of all time.
But here’s the thing I learned in time: there’s a reason why so many of us felt let down when we couldn’t recreate The Rachel days after leaving the salon. Or why those of us who chopped our hair into a punk rock prom queen pixie cut found ourselves frustrated when we realized it only looked good after heat styling and a cocktail of (often harsh, alcohol-filled) styling products.
For decades, we’ve been getting haircuts that don’t always match who we are or how we move through the world. But it’s not our fault—it’s how the industry has always worked. Stylists are artists, their focus is often on creating that perfect look in the moment (and I have immense respect for that skill). But a true collaboration that considers hair health, ease of maintenance, and how a cut will grow out over the next 60 to 90 days when you’re taking care of it at home?
That’s rarely been top of mind. Pun intended.
I vividly remember my first appointment with Teddi. Walking into Sally Hershberger at 25 West 26th Street felt like stepping into that classic New York movie makeover scene. And with that, I knew I was about to get the most expensive haircut of my life.
They led me to a chair by the windows overlooking the Meatpacking District. Teddi greeted me with her (then) signature red hair, a vintage tee, and her air of ease.
As one does when connecting over hair, we shared our stories. I learned that she grew up in Oregon and came to NYC to train at Bumble & Bumble, where she learned the fundamentals of styling and an excellent cut. But what stood out to me most was her approach: it wasn’t about chasing trends or replicating a look. Instead, she talked to me about crafting a cut that felt true to who you are.
It was a far cry from the over-styled looks that required hours of work to get right. I wanted something different—something that lived with me, instead of needing me to live up to it. Teddi understood that instinctively. With each careful snip, she was shaping something more personal, more thoughtful—something that would look as good (and usually better) on day 60 as it did on day one.
From my perspective, there were always limits to what she could do within the Sally environment. It was the kind of place where the cape, the cappuccino, and the scalp massage with the sulfate-filled shampoo were half of the experience. Don’t get me wrong, I love that kind of life, too. But often in salon spaces across the country, it can feel as though the experience takes precedence over the actual cut—especially if your stylist doesn’t have a long-term vision for your hair or a thoughtful approach that evolves with you over the years.
But once I found myself in Teddi’s chair, everything shifted. I knew we were on a journey together, and the cost of the haircut seemed like a small price to pay for feeling more like myself than I ever had before.
My relationship with Teddi has been one of the longest-running, consistent, close connections of my adult life. We’ve seen each other through so many phases and stages—she knew me back in college when I was still very much figuring out who I was, and she knew me as single Dianna, years before I met my husband (hi Bubs!). She’s been there through every job, every boss, every leap of faith. And perhaps most importantly, she’s been a constant grounding force, teaching me about something that’s become a major part of my life today: hair.
Teddi’s approach to hair inspired me to invest in what I was using at home— which was a relatively pricey investment for a then 20-year-old. I welcomed into my life the $250 Mason Pearson hairbrush, $70 Buly 1803 combs hand-carved in Switzerland, and $60 YS Park round brushes made in Japan. I upgraded my in-shower care and began to spend hundreds on Oribe and Christophe Robin. I suddenly knew that my hair was worth it. When it came to how I felt that day, hair was everything.
Teddi opened my eyes to a world where she was the artist and I was her DIY-at-home student.
Blame it on my art history degree, but one could argue that I’ve always been more of an art historian than an artist—someone, who observes, connects the dots, and appreciates the beauty of the craft and how the art makes us feel. And in this case, I found myself fascinated by the intricacies and players of the world of prestige hair.
It wasn’t until years later, when I graduated from NYU and was working in the consumer space that the disconnect became clear as day: the polished stories being told in salons and by salon brands felt completely disjointed from how we, as real people, actually talked about and cared for our hair in our own homes.
In 2015, Teddi opened a space that blended the lines between salon and home with Whiterose Collective. It would be in her chair, at Whiterose, where I would experience my first true dry haircut.
Cutting my hair dry, to my natural texture, would prove to be a game changer.
For background, the concept of cutting hair dry to suit its natural texture isn’t new—its origins date back to the early 1960s with Vidal Sassoon and the ‘wash-and-wear’ movement. Sassoon’s precision cutting techniques allowed for hair to fall into place naturally, without requiring intense styling.
What is a dry haircut, you ask? I’m glad you did.
A dry haircut is a technique where the stylist cuts your hair when it’s completely dry rather than wet or blown out straight. This approach allows the stylist to work with your hair’s natural texture, movement, and shape in its most authentic state. Instead of stretching out the hair and cutting it while wet, a dry cut gives a more accurate visual of how your hair naturally falls day-to-day.
What are the benefits of cutting hair dry?
Enhanced Precision: When hair is cut dry, the stylist can see exactly how your hair behaves—whether it’s curly, wavy, straight, or somewhere in between. This visibility allows for precise adjustments, so you can eliminate bulky areas, address uneven growth, and create a balanced shape that looks great in its natural state.
Customized to Your Texture: Hair texture can change dramatically when it’s wet. Curls may loosen, waves can disappear, and straight hair can lie differently, which can sometimes lead to surprises once the hair dries. Cutting hair dry ensures that the final result is tailored to how your hair looks and feels when it’s in its natural state.
Ideal for Shape and Movement: Dry cutting allows the stylist to take into account how your hair moves—how it springs, bends, and flows. This allows for the stylist to create shape and volume where it’s needed, or reduce weight where it’s not, resulting in a balanced, airy shape.
You can See the Results in Real Time: The stylist can assess and tweak your look as they go, making adjustments to ensure it suits your face shape and personal style. There’s no guesswork about how it will look once dried and styled, because you’re already there.
In the 1970s and 80s the Sassoon method was refined and adopted by stylists around the world, but the dry cut remained more experimental. It wasn’t until the 90s that the dry-cutting technique became widely recognized and celebrated with the rise of curl-focused salons like Devachan, founded in 1994 by Lorraine Massey and Denis Da Silva. They introduced the DevaCut, a dry-cutting technique specifically designed for curly hair, which they paired with their line DevaCurl. The concept was simple but revolutionary at the time: cut each curl individually when it’s dry to shape it according to how it naturally falls. This approach avoids the unpredictability that comes when curls are cut wet and then shrink up once dry.
Since the 2010s through today, dry cutting has become more mainstream as people want cuts that look good without requiring extensive styling and a cut that celebrates the way hair naturally falls, curls, or waves without the need for excessive heat or harsh styling products.
You’re probably wondering then…
Why do most salons in this country still offer wet cuts?
Historical Technique and Training: Most stylists are trained to cut hair wet during their education, as it’s considered the foundational technique in the industry. This method originated as a way to handle all hair types more uniformly, making it easier for stylists to learn precise cutting angles and techniques without the added complexity of texture or varying lengths that might occur when hair is dry.
Uniform Tension: Cutting wet hair provides uniform tension, which helps stylists create more even results, especially for straight or fine hair types. With wet hair, there’s less risk of cutting one section shorter than another due to varying tensions in dry hair, where the stylist has to navigate natural texture, movement, and volume.
Client Preference and Experience: As noted above, many clients enjoy the whole experience of having their hair washed, cut, and styled at a salon. The shampoo and conditioning process can be a relaxing part of the service, and blowouts give clients that finished, salon-fresh look that many find satisfying.
Getting your hair cut wet and then blown dry can still result in an excellent cut—it just depends on your stylist’s ability to truly understand your natural texture and factor that into the wet haircut. Not all stylists are trained at that level, which is why, when you do your wash day routine at home, the result doesn’t look quite the same.
If you're curious about a dry cut that caters to your natural texture but this is new for you, have an open conversation with your stylist about this approach. It’s a bit of a mindset shift—walking into the salon with freshly washed and air-dried hair, ready to be cut as is, and skipping the usual shampoo, conditioner, and scalp massage ritual is a different experience.
That said, you can always have them wash and blow-dry your hair after the dry cut to leave the salon feeling extra fabulous. I’ve done this with Teddi a handful of times. She cuts it to my air-dry, and then we finish with the cut, she’ll wash and blowout so I walk out with that fresh, polished look if I have something that evening I want a blowout for.
The thing about achieving the hair you’ve always dreamed of is that it takes time. It often takes a few cuts to get it exactly where you want it, and consistent care at home to bring your hair to its healthiest state. That way, when you show up to your stylist, you’re bringing your most hydrated, nourished, air-dried hair. This relationship becomes a partnership—one where you and your stylist grow together over time.
It’s similar to working with a facialist healing your skin or a chiropractor adjusting your spine. One session is helpful, but true transformation comes from the ongoing work and commitment to the process, together.
This newsletter is already quite lengthy, so I’m going to try and wrap things up and hope that this journey inspired you to try a dry cut (and invest in excellent products and a daily haircare ritual that give you the best air dry of your life :).
One of the things I’d love to hear from you, Dear Reader, is about your haircut!
I’d love to know:
Do you get your hair cut wet or dry? If dry, do they cut into your natural texture or do they blow it out first?
Do you have a hairstylist you love? Any type of cut. Share in the comments.
I adore Teddi in NYC, and I’m always looking for more dry haircut recommendations all over the world. Are you in another city with a great dry-cut stylist? Share!
Questions, thoughts, any of it— the comments are yours and I can’t wait to answer. If you have questions for Teddi I’ll share them with her to help reply too :)
And now, for our usual outro—
3 things I Love and A Haircare Tip
Oura Ring. ($299, +$5.99/month) I’ve been wearing it for two weeks now, and so far, I’m into it. If I’m being honest I’m a little bit salty because days after mine arrived (after a year of debating if I should order it) they launched the newest one, the Gen 4. I asked their customer service about exchanging it and their team replied with a pretty complex process, and with that, I realized I didn’t care that much. I chose the silver finish— after doing my usual pre-purchase ecomm image sleuthing, I realized there was not one marketing material from the brand where a gold ring was shown on a paler person, with freckles, who had a pinker undertone (hi, it’s me!). So I went with the silver, plateau design versus the fully rounded. The fully rounded version looked too much like a literal ring, and ironically, the plateau Heritage style was more affordable. Style (or there lack of) aside, it’s been helpful to track my sleep score, introduce a readiness score into my life (I’m drinking less!), and also have activity tracking to make sure I hit my daily step goal (oh, the joys of mostly WFH). Improving your life is very approved by me. But the main reason I got it? Cycle tracking. I’m getting off birth control for the first time in 14 years. I finally read Woman Code by Alissa Vitti and I’m ready to not have the extra hormones in my body. I’ll share all about in another Substack about my functional health journey over the last year and a half. I’m excited to track my cycles and be more in sync. Stay tuned.
Leveled Up Closet Organization. ($9 - 40 for organization items, on the organizing front, it’s range here but I was quoted ~$150 - 200 /hr) Who knew that labeling sections would help keep me sane and keep everything in its right place? As much as I’d like to thank this list of stuff, the real shoutout goes to Organized By Danielle. She was a thought partner in helping me edit my closet and organize it in a way that made sense for my life. We did it over the course of three days. It wasn’t an easy task, but she made it so. She also taught me how to properly fold my clothing and I feel like I have a new adult skill (Bubs the Virgo organizer in our home). If you’re reading this and feel weighed down or overwhelmed by the stuff you have, I recommend reaching out and getting quotes from organizers in your city. Since the reorg, I feel much lighter and more connected to my style. I’m also even more mindful of what I welcome into my space — with everything in a place (with not a ton much room to welcome more), I’m shopping with even more intention. Hiring an organizer for any part of your life won’t be inexpensive, but, for me, it’s some of the best money I’ve spent this year. Bonus that I was able to let go of a ton with The Real Real. They made it insanely easy, too.
Emme Parsons Susan Sandals. ($395) I wanted to share these because they’re my most understated yet hardest-working shoes in Miami (and on every vacation, too). During my closet clean-out with Danielle, I also did a few virtual styling sessions with Allison Bornstein to define my personal style through her Three Word Method™. As we went through my outfits, Allison would always ask, “What shoe would you wear with this?” and I kept coming back to these babies. She helped me realize that while I love shopping for a fabulous, statement-making shoe, what I actually wear—what I always reach for—is something minimal. I gravitate toward whimsical and / or structured elements in my clothing, so I need a minimal shoe to balance everything out. I own five pairs of these Emme Parsons flat: two in black, two in nude, and one in chocolate brown. I’ve worn three of the five pairs to the ground, so it’s time for a refrehs.
A Haircare Tip
Since this whole newsletter is essentially a haircare tip, I wanted to share a semi-traumatizing haircut story—because let’s be honest, don’t we all have one? Hair is everything!
Just before I left for the fall semester to study abroad, I had an appointment with Teddi at Sally Hershberger. But when I arrived, the receptionist informed me that Teddi had to call out sick. [Enter tylist’s name here], a very cool dude—former drummer, no less—who had just cut Karlie Kloss’ hair into a bob. The salon assured me he could give me a great cut, for Teddi’s usual price. I was young, naive, and far too excited to be in such great hands, so of course, I said yes.
He had a vision for me—a fresh bob, à la Karlie. But here’s the thing: I’m not a supermodel, and I definitely couldn’t carry the cut the same way. I walked out of the salon with the shortest hair I’d ever had, and no clue how to recreate that sleek, polished look on my own. Every day, my hand was glued to my blow dryer, just trying to make it look half as good as it did that day. Don’t get me wrong, I left the salon feeling fabulous. But a few days later, staring in the mirror at home, I couldn’t help but ask myself, What did I just do?
Thankfully, I was heading out of New York for the semester and had time to grow it all out—bangs included. For the next few months, headbands and bobby pins became my best friends. By the time I returned to Teddi’s chair in the new year six months, I had moved through the worst part of the growout. Thankfully, there’s very little non-archived evidence of this awkward growth phase as Instagram had launched that fall (I downloaded it while studying in Florence). Oh, the best, early fun days of social media.
I know this isn’t the wildest haircut story (trust me, some of you have shared epic tales), but it was a reminder that, while hair is just hair and it grows, it does matter. It changes how we feel and move through the world. And you’re allowed to feel however you want about your hair—we’re on this journey together, figuring out how to take care of it and feel our best.
Take your time, and take care, always.
Dianna
Would love to find a stylist in LA that does dry cuts!
Best haircut I've ever had was from Teddi!