Trish Wescoat Pound: How TWP Conquered the Hamptons

The counterintuitive thing about Trish Wescoat Pound and TWP is that the Hamptons did not discover her. Indeed, she had already been there. Haute Hippie — her first brand, the one she built to $40 million in sales and 300 specialty stores across 40 countries before she lost it in 2015 — had a store on Newtown Lane in East Hampton and another on Jobs Lane in Southampton. She knew the customer, the summer rhythms, the specific anxiety of dressing for a Saturday in August when the stakes are somehow both very low and very high. When TWP launched and went straight to Sag Harbor and Southampton, it was not a land grab. In fact, it was a return.

The Before

She grew up on the border of Kansas and Oklahoma in a very small town. Her mother was young when she had her. Moreover, resources were limited. She has said that her work ethic — the thing that is still, after thirty years, the only marketing strategy TWP has ever used — came from that time, from those particular constraints. Instead, she leaves the constraints where they are. Yet she discusses the work ethic.

Eventually, she arrived in New York and got a job as a receptionist at Calvin Klein. Not an internship. Not an assistant position requiring a design degree. A receptionist. She answered phones and filed things and watched how a fashion company operated from the room where the clothes came in and the calls went out. Watching was, it turned out, her greatest skill. Subsequently, she moved to Theory, then Michael Kors, then Liz Claiborne, where she became chief merchandising officer of the firm’s contemporary brands. When Claiborne reorganized, she received a severance payment. So she used it to start Haute Hippie in 2008. Indeed, she understood leverage before she had a word for it.

The Pivot Moment

It was 2015. Hilco had bought the intellectual property of Haute Hippie — the brand she had built from the severance check — after a group of employees allegedly ran up $700,000 to $800,000 on corporate credit cards and the operational damage proved unrecoverable. That said, she has described that period plainly: she lost her identity, her money, and her marriage inside the same window of time. Instead, another brand was not the next step. So she retreated to her pattern room.

For two years, she made shirts. Not the bohemian blouses that had defined Haute Hippie. Tailored shirts — men’s shirting architecturally reworked for a woman’s body. She sold them to friends at trunk shows in Miami. Not pitching. Not building. Just making the thing she wanted and handing it to people she trusted.

One of those friends ran into Andrew Rosen — co-founder of Theory, investor in contemporary brands, and, as it happened, the first boss Trish Wescoat Pound had ever had. Rosen complimented the shirt. The friend told him who made it. Eventually, Rosen called and invited her to lunch.

She showed up. The lunch was supposed to be a catch-up between two people who had worked together thirty years earlier. By the time the check arrived, it was a business proposition. Rosen would invest. She would keep creating. He would handle everything that was not her strength. After all, she had spent two years deciding she no longer needed to do this alone.

The Climb

TWP developed through the pandemic as trunk shows and officially launched for spring 2022 selling. The collection started with four core shirt styles — The Boyfriend, Soon to Be Ex, The Morning After, The Goodbye. Furthermore, everything is made within a two-block radius in Manhattan. Italian fabrics. No external marketing. Shirts retail from $310 to $495. Blazers from $695 to $995. Notably, Beth Buccini of Kirna Zabete called it a runaway hit with customers buying multiple units of the same style in different colors — the inventory behavior that tells a retailer a brand has moved from discovery to wardrobe foundation.

By 2023, TWP was on track to sell $15 million in clothes. The projection for 2024 was $30 million. Additionally, Puck called her the Goldilocks fashion star of 2023 — priced correctly, quality delivered, distribution disciplined. Her daughter Jillian, a stylist, became director of styling for the brand. Jillian had been in high school when she watched her mother lose everything. Now she is in the lookbooks.

The Hamptons Chapter: The East End Already Knew Her

Most emerging brands approach the Hamptons as a market to be unlocked. They run a summer pop-up, test the customer, and determine whether a permanent address is justified. Trish Wescoat Pound skipped that sequence because she had already done it once. Haute Hippie had permanent stores in East Hampton and Southampton during its run. She had spent multiple summers serving that customer, learning which towns read which way, understanding that Sag Harbor’s bohemian creative class and Southampton’s Main Street luxury corridor require different propositions from the same designer.

When TWP launched, it went to Sag Harbor and Southampton as early retail priorities — not as a validation experiment, but as a strategic continuation. Notably, the Hamptons fashion market does not warm up quickly to new names. TWP was not a new name there. Instead, it was a familiar designer in different clothes, which is the strongest possible introduction. The other founders who understood this — Rebecca Hessel Cohen of LoveShackFancy, who ran trunk shows on the East End for two years before she had a store, and Veronica Beard, which put its largest location in Southampton before Madison Avenue — all earned their address the same way: by being from here before it was useful to say so.

The Store That Doesn’t Perform Luxury — It Recognizes It

The Southampton store occupies a historic landmark building at the heart of Main Street. Seagrass flooring. Linen. Wood and rattan. The brand calls the aesthetic “lived-in residential charm,” which is accurate and also a description of the customer: a woman whose home looks like this, who does not want the store to look more aspirational than the life she already has. The interior does not perform luxury. It recognizes it.

The East End diagnosis is this: she does not arrive here to be seen. Previously, she had arrived the first time to build something, and it was taken from her. This time, she built it again differently — with a partner, a pattern room, and a daughter now styling the campaign. The Southampton store is the adult version of every summer she spent on Jobs Lane watching what that customer actually wore versus what she said she wanted.

What Trish Wescoat Pound Built — and What It Cost

TWP’s revenue trajectory — $15 million in 2023 with projections doubling annually — places it among the most commercially efficient contemporary launches of the decade. As reported by WWD, the brand reached 84 percent sell-through for spring, numbers that established wholesale players spend years trying to replicate. Notably, Andrew Rosen told the trade press they had done no marketing. The brand’s six standalone stores — SoHo, Sag Harbor, Southampton, West Hollywood, Dallas, and Aspen — are supported by 150 wholesale stockists across North America.

Subsequently, in November 2024, TWP launched at Selfridges London, the first international outpost, with plans for Charleston and Nantucket to follow. At the Selfridges dinner, Wescoat Pound gave a speech in front of 150 guests and said, of her thirty-year arc with Rosen as a through-line: “It’s interesting in life when things don’t work out the way exactly you think they’re going to but they do come full circle.” Then she sat down.

That said, she has mentioned in other contexts — only once — that when Haute Hippie ended she lost her identity, her money, and her marriage. She does not say it like a cautionary tale. Instead, she says it like a fact that has since been reclassified.

Where She Is Now

The Spring 2026 collection showed at the Radio Park rooftop above Rockefeller Plaza on a sunny Monday afternoon in September 2025, inspired by gardening — Wescoat Pound’s childhood hobby and current fixation, which she connects to fashion through seasonal planning, pruning, and the discipline of deciding what not to include. Reworked shirting, Japanese denim in reactive dyes, broken suits in clean slouchy trousers. Birkenstock collaborations. Lynn Yaeger wrote the show notes. Karen Elson walked. The woman who started in fashion answering phones at Calvin Klein is now the one whose initials are on the label and whose runway reviews appear in WWD the following morning.

In a recent trunk show at a retail partner’s store, TWP exceeded $200,000 in two days of selling. Wescoat Pound noted that multiple customers told her they used to buy luxury European brands and now buy TWP instead — not because it is cheaper, but because it works better and costs less apology. She told the story without triumph. The customer said it. She reported it.

The Same Radius. A Different Name on the Label.

The receptionist from the Kansas-Oklahoma border who once answered Calvin Klein’s phones is now the person Andrew Rosen calls when he wants to talk about the next collection. She designs everything in the same two-block radius in Midtown where she has worked for thirty years. Still, there is no marketing budget. Still, the work continues. Now the Hamptons stores are open year-round. Before, she had built something here and it was taken. This time, she built it so it belongs to itself. That is a different kind of store. The customer in Southampton knows the difference, even if she cannot say exactly why the jacket fits the way it does.

Explore more founders and figures shaping the Hamptons in the full archive at SocialLifeMagazine.com. If this story made you wonder whether Social Life could tell yours — that question is already worth a conversation.

Also in this series: Rebecca Hessel Cohen & LoveShackFancy · Zimmermann Net Worth · Veronica Beard Net Worth · Revolve & Jacquemus in the Hamptons · The Full Challenger Series