Cashmere, Flasks, and Second Acts
Designer Trish Wescoat Pound is building a universe — and TWP is the dress code.
TWP’s vibe lands somewhere between a Helmut Newton shoot and a Nancy Meyers movie. The clothes represent an idyllic version of the peripatetic woman’s life, one who exists equally in town and country.
Founder and Designer Trish Wescoat Pound has one of the better second-act stories in American fashion. She built Haute Hippie into a $40 million business, lost it in 2015, retreated to her pattern room, and came back a few years later selling shirts to friends at Miami trunk shows.
One of those friends ran into Andrew Rosen — co-founder of Theory, and as it happened, Trish’s first boss — who complimented the shirt. By the time that lunch ended, TWP had a business partner. That origin story matters because it explains everything about the clothes: they started as something a woman made for women she actually knew, and they have never stopped being exactly that.
TWP is almost five years old and already on the CFDA calendar. The line — made within a two-block radius in SoHo, cut from Italian fabrics — has developed the kind of fervor that produces scenes like the one I recently saw in Palm Beach, where women descended on her clothes in hordes. I sat down with Trish to talk about starting over, what she puts in her bag, and why thong underwear is, um.. behind her.
Jess Graves: You just introduced bags! Which are you reaching for most right now — and what’s actually inside it?
Trish Wescoat Pound: Right now, it’s our Howard Street Bag. I made one for myself in dark chocolate python - rich, understated, a little dangerous in the best way. It feels grounded but still indulgent. Very Paris.
JG: What’s in it at the moment?
TWP: Honestly? A hot mess. I organize it every morning with the best intentions, but by midday, it’s chaos again. I’m one of those people who has to set the entire bag on the ground and excavate it to find anything, no matter how carefully I’ve arranged it hours before. Inside right now, somewhere:
My Passport, airline tickets, and a baggage claim stub
The best pencils, some post-its, a leather notebook… plus a stack of linesheets
It’s a traveling office, vanity, and filing cabinet all at once.
JG: What’s the last thing you bought that solved a real problem in your day-to-day life?
TWP: A Topologie phone cord - the kind you can wear around your neck. Jorden Bickham introduced me to them. I was constantly losing my phone - in taxis, showrooms, and buried in my bag. It was becoming ridiculous. Now it just lives on me. Mine is bright green, which I love. It solved a very real, very daily problem. And I haven’t lost my phone since!
JG: Ooh, good for travel too. What’s one object you’ll never travel without, no matter how short the trip?
TWP: My Boy Crew sweater. I genuinely won’t go anywhere without it. Beaches, cities, flights - it’s always with me. There’s something about a great cashmere sweater that feels like armor and comfort at the same time. I love cashmere in general, but this one in particular has become a constant. It works everywhere — thrown over a slip dress, with denim, over a swimsuit, wrapped around my shoulders on a flight. The piece that makes wherever I am feel familiar!
JG: What’s the most beautiful functional object you own?
TWP: This question makes me want to buy more beautiful, functional things. I love a flask. For our Fall runway show, we made flasks designed to be worn around the neck. It’s practical, a little rebellious - definitely a conversation starter. Mine only has tequila in it. There’s something I’m always drawn to about objects that live in that space between utility and adornment. When something works hard but also makes a statement - that’s when it feels truly considered.
JG: I saw those flasks at the runway show and coveted them immediately. So decadent and cool! Where do you splurge without hesitation — and where are you surprisingly disciplined?
TWP: I splurge on travel - unapologetically. Travel, travel, travel. And food that truly feeds me. Experiences that expand me, inspire me, and change my perspective. I would spend my last dollar on a plane ticket or a meal that feels transporting. For me, those things are creative fuel. They inform how I see color, texture, people, and movement. Disciplined might not be the word I’d use to describe myself - not exactly my calling card. But I can be surprisingly restrained with the small, transactional things. Groceries, for example. The escalation of everyday costs feels outrageous to me, so I’ll question the little purchases. I’m thoughtful about the ordinary.
JG: What’s the most complimented item in your wardrobe?
TWP: My long reversible shearling coat. It never fails. I’m stopped constantly when I wear it. I’ve always believed outerwear makes the outfit. You can be in the simplest thing underneath - even sweats - but throw on the right coat and the entire look shifts. Sweats under shearling is actually one of my favorite combinations. It’s chic, but it’s also deeply functional - the balance I’m always chasing. (Our Long Aspen is unfortunately sold out, but we do have a shorter version available.)
JG: What’s a piece you’ve owned for years that still feels relevant every time you use it?
TWP: Vintage Levi’s just get better. A truly great pair is life-changing. The fit, the weight of the denim, and the way they soften over time. They work with everything, too: a button-down, a cashmere crew, a tailored coat, heels, or boots.
JG: God, good vintage denim just cannot be improved upon. What’s your non-negotiable when it comes to design — the thing you always notice first?
TWP: Fabrication. Always. It’s where we start. Andrew and I are truly fabric geeks. We work closely with our Italian mills and spend an enormous amount of time on development. The hand is the foundation. Something can look incredible on a hanger or in a photo, but if the hand isn’t right - if the fabric doesn’t feel as good as it looks - I won’t buy it. If the material doesn’t support the price point, it’s a no for me. The other non-negotiable is fit. You can have the most beautiful fabric in the world, but if the fit is off, it doesn’t matter.
JG: I agree. What’s the point if it doesn’t fit? I ruthlessly edit by those same standards. In that spirit, what’s one thing you’ve stopped buying altogether?
TWP: Thong underwear. At some point, I just decided: no more. Comfort wins, always.
JG: I cannot think of anything less cool than a thong. Discomfort is not luxurious. What does “luxury” actually mean to you, in practice?
TWP: Luxury is an intention. It’s time - time to develop something properly, to think it through, not to rush it. It’s ease - pieces that truly work in a woman’s life - ones she reaches for without thinking. And, ultimately, it’s quality and longevity. Something that stays relevant, that lives in your wardrobe for years. That, to me, is real luxury.
JG: Buy fewer, better things, take good care of them, wear them often! My ethos, too. It helps you edit mentally, as well. If someone wanted to understand your taste in five objects or fewer, what would you point them to?
TWP: Chunky cashmere. A substantial crew — especially at the end of cashmere season when it’s perfectly worn in.
Sneakers or worn-in Birks. Right now, I’m in the SFTM Adidas collaboration, but an old pair of Birkenstocks I’ve lived in says just as much. I like the contrast - polished but easy.
Vintage Levi’s. Denim on denim, always. I love my Levi’s.
Jewelry with meaning. A lab-grown diamond choker, or a stack of signet rings - with my daughter’s initials, mine. Pieces that are personal, worn for a reason.
A great bag or a piece of outerwear. One strong finishing piece. A great coat or bag can carry everything else. That combination - texture, ease, sentiment, and one defining statement - feels like me.
JG: Birkenstocks and denim, a perfect weekend uniform. Describe your perfect Sunday.
TWP: Home. In bed, watching a documentary or a great movie, with Jillian and my dog Theo. Simple. Or waking up in Paris together, heading straight to our favorite flea market, Paul Bert at Saint-Ouen. A sunny, full day spent walking around, inspired by all the objects of desire one can find there.
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