AYR (All Year Round)

AYR (pronounced “air”), shorthand for All Year Round, did not arrive with a celebrity launch party or splashy runway show. It was incubated inside Bonobos and launched online in 2014 by a small founding team—Maggie Winter (co‑founder/CEO), Jac Cameron (co‑founder/creative), and Max Bonbrest (co‑founder/COO)—with an explicit, pragmatic brief: build seasonless wardrobe staples that customers wore repeatedly rather than chasing seasonal trend cycles. The brand’s origin as a Bonobos‑backed womenswear incubator is documented in contemporary reporting and by the company itself. ([forbes.com](^[1]), [en.wikipedia.org](^[2]))

The commercial logic for AYR was straightforward. In its first year the business sold fast: the founders reported roughly $2 million in gross sales in AYR’s first year of operations, a sign that a tightly edited product assortment—an indigo skinny jean, a chambray shirt, an oversized poplin popover and a wool 'robe' coat—resonated with a millennial urban shopper looking for timeless basics rather than disposable trend pieces. The Bonobos relationship gave AYR a launch platform and operational infrastructure at a moment when direct‑to‑consumer brands were still proving the model. ([sandbridgecap.com](^[3]), [forbes.com](^[1]))

Contrary to the roster supplied with this brief, public records and business reporting do not show Molly Howard or influencer Ali Pew as founders or co‑owners of AYR. Molly Howard is publicly associated with La Ligne and other ventures, and Ali Pew is a noted editorial and creative director at outlets such as Goop and Cultured—but neither appears on AYR’s incorporation or founding coverage. The verifiable founders and early executive roster remain Maggie Winter, Jac Cameron and Max Bonbrest, with Zandy Reich later serving in an executive capacity. That distinction matters: AYR’s trajectory is the product of fashion‑industry operators, not a celebrity licensing play. ([en.wikipedia.org](^[2]), [worldretailcongress.com](^[4]), [goop.com](^[5]))

From a business model standpoint AYR stuck to a disciplined playbook: direct‑to‑consumer e‑commerce as the engine, small production runs to create scarcity, a tightly curated core collection of 'hero' items and a surprisingly old‑school catalog that the founders—particularly Maggie Winter and Max Bonbrest—used as a high‑engagement marketing channel. By the end of the 2010s AYR had extended distribution into wholesale partners including Nordstrom (pilot into a few doors in March 2015) and selected online retailers, but the brand remained predominantly digital. ([sandbridgecap.com](^[3]), [forbes.com](^[6]))

The AYR story is also a study in surgical growth. Reporting in 2022 described AYR as having tripled its business in 2021, becoming profitable that year and growing a small, high‑productivity team (the founders cited an unusually high 'revenue per head' metric). Repeat customers multiplied, and by the metrics reported publicly were responsible for more than half of transactions—a sign that the product philosophy (buy a few well‑made pieces, wear them all year) produced high loyalty. That growth came without pursuing broad assortment expansion; AYR remained focused on staples and controlled cadence. ([forbes.com](^[6]))

AYR’s path has not been without turbulence. The brand’s early shelter under Bonobos became a mixed blessing when Bonobos itself was sold to Walmart in June 2017 for $310 million, and later changed hands again in 2023—events that reshaped strategic options for incubated brands and minority investors. The retail sector’s shakeouts in 2023–2024 (including the chapter 11 of Express, a buyer of Bonobos assets) created an unstable wholesale landscape and underscored why AYR’s digital first posture was a hedge against brick‑and‑mortar volatility. ([vox.com](^[7]), [en.wikipedia.org](^[8]))

Operationally AYR leaned into scarcity and small runs—an intentional supply strategy that created sellouts and waitlists but also exposed the business to inventory risk and the classic DTC problem of balancing customer demand with limited SKU depth. The company also weathered the supply‑chain and production shocks of the late 2010s and pandemic period, electing to remain 'small to get big' rather than chase rapid scale, a decision the founders have described as both defensive and strategic. ([forbes.com](^[6]))

Where AYR has punched above its size is in brand craft and distribution discipline. The company’s core jeans (nicknamed by insiders as one of the 'hero' pieces), the catalog strategy, and a founder‑forward content voice produced strong repeat demand. By 2025 third‑party e‑commerce monitoring data flagged AYR generating multi‑million monthly revenues (Particl reported approximately $3.8 million in Apr 2025 and about $23 million in the preceding six months), which—if accurate—would position the company as a mid‑sized DTC apparel player with meaningful unit volumes. Those numbers are consistent with AYR’s historical pattern of high conversion on a compact assortment. ([particl.com](^[9]), [forbes.com](^[6]))

For celebrity entrepreneurs the AYR case is instructive because it highlights two distinct roads into fashion. Some celebrity‑fronted brands are licensing and marketing vehicles; AYR presents a counterexample of founder‑operator credibility. Its founders came from traditional retail and product roles (J.Crew, Madewell, H&M, Theory), which gave AYR product rigor and the operational chops to make a lean business work. That operational authenticity—rather than simply a celebrity name—helped AYR earn durable customer loyalty in a crowded landscape. ([forbes.com](^[1]))

As of mid‑2025 AYR reads as a quietly successful independent label: product‑led, digitally native, and cautious about expansion. There is no public record of an acquisition or IPO, and no authoritative public valuation; the most concrete public financial signals remain revenue patterns and press statements about profitability and repeat purchasing. That performance, combined with a tight inventory model and a loyal customer base, suggests AYR’s future options include continued DTC expansion, selective wholesale partnerships, or a strategic sale to a larger fashion player—each route carrying tradeoffs between scale and the product discipline that made the brand valuable in the first place. ([forbes.com](^[6]), [particl.com](^[9]))

• February 2014: AYR launches online as a Bonobos‑incubated womenswear label.
• March 11, 2015: Wholesale pilot in Nordstrom begins.
• Late 2015 – 2016: AYR spins out of Bonobos and incorporates as an independent company; Series A led by Dutch, LLC.
• April 4, 2018: SoHo flagship opens on Lafayette Street.
• August 2018: AYR opens second store on Abbot Kinney Boulevard in Venice, Los Angeles.
• 2021 (calendar year): Revenue triples and AYR becomes profitable.
• April 2025 (reported): Third‑party e‑commerce monitoring reports multi‑million monthly sales.