workwear
(5)
Anthony DiPaolo and the second life of a work boot
He bought Work 'N Gear in 2002, expanded its ways of reaching customers, and helped turn used boots into donations. Anthony DiPaolo's retail career comes into focus through the things people keep wearing.
Emily Sly
Emily Sly is a Denver-based marketing executive who became Chief Marketing Officer of TRUEWERK, the performance workwear brand, in late 2025. She spent 13 years at Crocs, rising from a regional account services rep to VP of Global Marketing during the brand's global comeback, then led brand and marketing at Funko and headed marketing at PopSockets before joining TRUEWERK. She is known for helping consumer brands articulate why they matter and for translating brand purpose into consistent experiences across every customer touchpoint.
Heather Gruccio
Heather Salvatore Gruccio is Executive Vice President and Chief Merchandising Officer for Ann Taylor and Ann Taylor Factory, the KnitWell Group brands headquartered at 7 Times Square in New York. A Wake Forest communications graduate, she built her merchandising career over nine years at Coach, sharpened it in mid-luxury at Tory Burch, and joined Ann Taylor in 2016 as Senior Director of Merchandising for non-apparel. She moved up to Vice President of Merchandising in 2017, SVP and GMM in 2020, and was elevated to EVP and Chief Merchandising Officer in 2025 after leading a product-and-perception reset that turned a 70-year-old mall brand into a name fashion press started writing about again. Her thesis is unfussy: women still want to look pulled together, they just want to be comfortable while doing it, and heritage is an asset rather than a liability if you actually know how to cut a jacket.
Larry Nusbaum
Larry Nusbaum is a consumer-products and retail turnaround executive who serves as President and Chief Marketing Officer of Work 'N Gear, the Mid-Atlantic and New England workwear, footwear and healthcare-apparel chain, and as an operating partner at Dark Alpha Capital. Over two decades he has run companies as CEO, CMO and COO across housewares, electronics, personal care, apparel and fitness, most visibly at Ronco, the Ron Popeil gadget brand he bought out of bankruptcy with Marlin Equity Partners in 2007 and steered from a reported $7.5 million annual loss to roughly $4 million in profit on about $30 million of 2009 sales. He has also led Midwest Trading Group, where he acquired the phone-accessory brand TYLT in December 2023, and restructured the artisan-goods company GlobeIn into a subscription model. At Work 'N Gear he took a 25-year-old, roughly $40 million retailer through a 2025 Chapter 11 filing, a DIP financing, a shrink from 38 stores to 26, and a April 2026 asset sale to a family-office-backed operator that repaid the lender in full and set up a relaunch of the e-commerce platform and up to ten stores.
Sarah Miyazawa LaFleur
Sarah Miyazawa LaFleur is the founder and CEO of M.M.LaFleur, the New York workwear brand she named after her mother and built to take the guesswork out of getting dressed for professional women. A Harvard graduate who walked away from a private equity job after four months, she launched the company in 2013 with designer Miyako Nakamura and Narie Foster, popularized the curated Bento Box, and later coined the post-pandemic dress code she calls Power Casual.