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  1. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    After ten years of investment banking, 37-year-old Saukok Chu Tiampo ditched the boardroom to launch her own bridesmaid-dress collection, 57Grand (57grand.com). Last year, she sold the line to the Dessy Group and founded Professionelle (professionelle.me), a shoppable site for style-minded career women. “Over the years, even Wall Street has gotten less buttoned up,” notes Chu Tiampo of the changing standards in 9-to-5 dressing. “Today, the power look is having the freedom to set your own rules—in work wear and everywhere else. It’s more relaxed but still polished.” With that in mind, we hit the streets of midtown and the Financial District to see how city slickers are redefining corporate attire.

  2. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Karen Rothstein, retired preschool teacher; Kansas City, MO

    Rothstein looks comfortably chic in Chicos pants (1310 Third Ave at 75th St, 212-249-9105 • 2300 Broadway between 83rd and 84th Sts, 212-579-4572 • chicos.com), a snakeskin-print sweater from Old Navy (locations throughout the city; visit oldnavy.com) layered over a Brooks Brothers collared shirt (locations throughout the city; visit brooksbrothers.com), and a leather jacket from Macy’s (151 W 34th St at Seventh Ave;212-695-4400, macys.com). A structured Marc by Marc Jacobs satchel (301 W 4th St at Bank St; 212-929-9455, marcjacobs.com) enhances the outfit’s polished vibe. “I love how she mixed upscale [labels] and really street brands,” says Chu Tiampo. “She looks like a million bucks.”

  3. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Karen Rothstein, retired preschool teacher; Kansas City, MO

    “It’s a great mix of details,” says Chu Tiampo of Rothstein’s gold accessories, including an 1870s bangle that belonged to her great-great-grandmother in France. “It’s called a slave bracelet,” explains Rothstein. “The women wore them on their shirts to hold up their cuffs.” Rothstein had her stacked wedding ring custom made in Kansas City.

  4. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Karen Rothstein, retired preschool teacher; Kansas City, MO

    Stuart Weitzman leopard-print flats (locations throughout the city; visit stuartweitzman.com) pop against dark neutrals.

  5. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Jennifer Kapahi, 30, senior manager of global product development at Revlon, Soho

    Kapahi, who works in a more creative office, dresses up Rag & Bone jeans (locations throughout the city; visit rag-bone.com) with a floral top from Phillip Lim (115 Mercer St between Prince and Spring Sts; 212-334-1160, 31philliplim.com) and an R13 fur-lined vest (r13denim.com). “I love how she played with the seasons a little, but it still feels transitional,” says Chu Tiampo. “The floral shirt picks up the deep green of her bag so it doesn’t feel spring, it feels fall,” she adds, referring to Kapatti’s Céline satchel (870 Madison Ave between 70th and 71st Sts; 212-535-3703, celine.com). Suede booties from Walter Steiger (417 Park Ave between 54th and 55th Sts; 212-826-7171, waltersteiger.com) further the look’s autumnal appearance.

  6. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Jennifer Kapahi, 30, senior manager of global product development at Revlon, Soho

    Edgy accessories, including a woven-leather spiked bracelet from a Prince Street vendor, a Cartier Love bangle (653 Fifth Ave at 52nd St; 212-446-3400, cartier.com) and an Annelise Michelson double-crown ring (annelisemichelson.com) toughen up Kapahi’s sweet floral top. “All the spiky pieces don’t necessarily work for a more conservative office, but for a creative environment it’s perfect,” says Chu Tiampo.

  7. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Jennifer Kapahi, 30, senior manager of global product development at Revlon, Soho

    “Mixing gold and silver is hard to do but because her outfit is eccentric, it’s able to absorb the difference,” says Chu Tiampo. Kapahi blends the two metals by stacking a Cartier watch, antique bracelets from her grandmother and crystal beaded styles from a friend.

  8. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Russell Kelly, 39, brand manager at Tudor Watch USA, Upper West Side

    Kelly uses color to subvert a classic work look. “He’s got a little bit of character going on, but people aren’t going to be like, ‘Are you kidding me?’” assures Chu Tiampo of the office-appropriateness of Kelly’s Hertling for Haberdash (haberdashmen.com) canvas chinos. The vibrant pants are successful when paired with a traditional blazer and button-up, both from Sid Mashburn (sidmashburn.com).

  9. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Russel Kelly, 39, brand manager at Tudor Watch USA, Upper West Side

    Kelly swapped in a vintage-leather strap on his Tudor Heritage Black Bay watch (tudorwatch.com), and wears a Billykirk wrap bracelet (billykirk.com) on his other wrist. “It was natural leather when I got it, almost white,” admits Kelly of the accessory, which is engraved with both his and his wife’s initials.

  10. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Russell Kelly, 39, brand manager at Tudor Watch USA, Upper West Side

    “He looks like someone who can get down a bit and be casual,” says Chu Tiampo, referring to Kelly’s worn-in Alfred Sargent for Sid Mashburn shoes (alfredsargent.co.uk). “It’s sort of a Thom Browne look.”

  11. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Allison Chin, 24, analyst at Wells Fargo Securities; Valley Stream, L.I.

    “I love how she’s wearing jeans and a blazer but in order to pump it up a little bit, she added a pretty lace shirt,” says Chu Tiampo of Chin’s relaxed but professional ensemble, consisting of a J.Crew tailored schoolboy blazer (locations throughout the city; visit jcrew.com), a Lost neon eyelet top (lostenterprises.com) and Rag & Bone denim.  

  12. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Allison Chin, 24, analyst at Wells Fargo Securities; Valley Stream, L.I.

    Chin accessorizes with a Tory Burch patent-leather wallet (257 Elizabeth St between E Houston and Prince Sts, 212-334-3000 • 38–40 Little W 12th St between Ninth Ave and Washington St, 212-929-0125 • 797 Madison Ave between 67th and 68th Sts, 212-510-8371 • toryburch.com), a J.Crew bracelet, a Michael Kors watch (locations throughout the city; visit michaelkors.com) and a Pandora ring (pandora.com).

  13. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Allison Chin, 24, analyst at Wells Fargo Securities; Valley Stream, L.I.

    Kate Spade wedges (locations throughout the city; visit katespade.com) keep Chin’s casual-Friday outfit grounded.

  14. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    James Cho, 29, analytic consultant; Astoria, Queens

    “There’s a juxtaposition between the jeans’ rolled-up hem with the blazer,” says Chu Tiampo of Cho’s raw-edged camel topper and distressed denim, both from Zara (locations throughout the city; visit zara.com). He wears them with a tuxedo-style shirt from Topman (478 Broadway between Broome and Grand Sts; 212-966-9555, topman.com) and Ray-Ban specs (ray-ban.com).

  15. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    James Cho, 29, analytic consultant; Astoria, Queens

    Classic accessories, such as an Invicta watch (invictawatch.com) and a Michael Kors belt, elevate Cho’s low-key office wear. “He is very well-groomed, which speaks to going to work,” says Chu Tiampo.

  16. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    James Cho, 29, analytic consultant; Astoria, Queens

    Cho rocks his Zara tasseled loafers sans socks.

  17. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Katherine French, 22, administrative assistant at Star Foundation (starfound.org), Upper East Side

    “She is able to look professional while still having a bohemian vibe,” says Chu Tiampo. French balances an oversize Marc by Marc Jacobs jacket and flowy Zara blouse with fitted trousers from Rag & Bone. “It works together because it’s all within the fall color palette, which really highlights her red hair.”

  18. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Katherine French, 22, administrative assistant at Star Foundation (starfound.org), Upper East Side

    “[This] fun bag is the cherry on top,” says Chu Tiampo of French’s portfolio bag, a vintage souvenir from a recent trip to Berlin. “It’s exactly the kind of shape that’s professional, but having the colorblocking on it makes it much more fun.” French adds some sparkle with rings from Alexis Bittar (locations throughout the city; visit alexisbittar.com) and Tiffany & Co. (727 Fifth Ave at 57th St, 212-755-8000 • 97 Greene St between Prince and Spring Sts, 212-226-6136 • 37 Wall St at William St, 212-514-8015 • tiffany.com).

  19. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Jesus Ortiz, jewelry salesman at Chopard, Washington Heights

    “A lot of times accessories are overlooked, but I think that’s what makes the outfit with work wear [when] you can’t really go too far out,” explains Chu Tiampo. Ortiz pulls together a box-check suit from Barneys New York (660 Madison Ave at 61st St; 212-826-8900, barneys.com) with a patterned Hermès tie (691 Madison Ave at 62nd St, 212-751-3181 • 15 Broad St between Exchange Pl and Wall St, 212-785-3030 • hermes.com) and classic John Lobb footwear (800 Madison Ave between 67th and 68th Sts; 212-888-9797, johnlobb.com). “The fact that the shoes are beautifully tailored helps to elevate the look of the outfit.”

  20. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Jesus Ortiz, jewelry salesman at Chopard, Washington Heights

    Vintage sterling-silver cufflinks from the 25th Street Flea Market (W 25th St between Broadway and Sixth Ave; 212-243-5343, hellskitchenfleamarket.com) and a Chopard watch (709 Madison Ave at 63rd St; 212-223-2304, chopard.com) complete Ortiz’s weekday attire. “He looks really polished and high-end without being boring,” says Chu Tiampo.

  21. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Puja Parekh, 28, vice president at a private-equity firm, Tribeca

    “This outfit is proper and conservative but at the same time really fashionable,” says Chu Tiampo. Parekh mixes separates—a tweed jacket from DKNY (168 Fifth Ave between 21st and 22nd Sts, 212-989-3438 • 420 West Broadway between Prince and Spring Sts, 646-613-1100 • 655 Madison Ave at 60th St, 212-223-3569 • dkny.com) and a Zara pencil skirt—to put her own spin on a suit.

  22. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Puja Parekh, 27, vice president at a private-equity firm, Tribeca

    “She’s not being crazy with color, but if you look closely, she’s playing with details,” says Chu Tiampo of Parekh’s enamel bangles from Henri Bendel (712 Fifth Ave at 56th St; 212-247-1100, henribendel.com).

  23. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Puja Parekh, 27, vice president at a private-equity firm, Tribeca

    The subtle cutouts in these Christian Louboutin stilettos (59 Horatio St between Hudson and Greenwich Sts, 212-255-1910 • 965 Madison Ave between 75th and 76th Sts, 212-396-1884 • christianlouboutin.com) lend standard pumps sex appeal.

  24. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Kelly-Ann Philip, 34, business planner at Gucci, Inwood

    “This is actually a perfect work look because she’s wearing pants and a blazer, but she’s upped the fashion ante by wearing a gorgeous pink windowpane check,” remarks Chu Tiampo of Philip’s bold silk J.Crew trousers. A velvet blazer from Parisian boutique Galeries Lafayette (galerieslafayette.com) makes her outfit more winter-ready.

  25. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Kelly-Ann Philip, 34, business planner at Gucci, Inwood

    “It’s the right size for work but it’s got that beautiful gold bamboo toggle,” enthuses Chu Tiampo of Philip’s vintage handbag from a Paris thrift shop.

  26. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Kelly-Ann Philip, 34, business planner at Gucci, Inwood

    The low, sloping cut of these Enzo Angiolini suede high heels (enzoangiolini.com) aesthetically lengthen Philip’s legs.

  27. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Logan Sawtelle, 25, sales associate at Bergdorf Goodman; Long Island City, Queens

    Sawtelle juxtaposes a playful Etro floral shirt (720 Madison Ave between 63rd and 64th Sts, 212-317-9096 • 89 Greene St at Spring St, 646-329-6929 • etro.com) with a proper wool tailcoat from Comme des Garçons (520 W 22nd St between Tenth and Eleventh Aves; 212-604-9200, comme-des-garcons.com). “It doesn’t look stuffy because he’s got relaxed pants and fun glasses,” notes Chu Tiampo of his Club Monaco trousers (locations throughout the city; visit clubmonaco.com) and Ivory + Mason frames (ivorymason.com). A silk ascot from Neiman Marcus (neimanmarcus.com) and Wolverine 1000 Mile boots (254 Elizabeth St between E Houston and Prince Sts; 212-226-7869, wolverine1000mile.com) round out the offbeat ensemble.

  28. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Jort Possel, 36, social-media director, Upper West Side

    “He’s wearing a really classic style—perfect for a business-casual meeting, and it works for almost any industry,” enthuses Chu Tiampo of Possel’s Banana Republic trousers (locations throughout the city; visit bananarepublic.com), and Suit Supply blazer and open-collar button-down (453 Broome St at Mercer St, 212-828-7250 • 635 Madison Ave between 59th and 60th Sts, 855-784-8464 • suitsupply.com).

  29. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Jort Possel, 36, social-media director, Upper West Side

    Possel bought this Rolex timepiece (665 Fifth Ave at 53rd St; 212-758-7700, rolex.com) to celebrate the birth of his first child. “It has the birth date of my daughter on the back,” he says. “I got the smaller size so she can wear it when she grows up. She’s two now.”

  30. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Jort Possel, 35, social-media marketing consultant, Upper West Side

    These lace-ups are from John Spencer (johnspencershoes.com).

  31. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Anisa Moolani, 22, investment-banking analyst, Financial District

    “A very classic look, but she’s added a nice pop to it with a geometric necklace,” says Chu Tiampo of Moolani’s Forever 21 statement piece (locations throughout the city; visit forever21.com). “It’s noticeable in a good way.” The bauble adds pizzazz to Macy’s house-label trousers and a blouse from H&M (locations throughout the city; visit hm.com).

  32. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Natasha Kingshott, 22, investment-banking analyst, Tribeca

    "The colors are very classic but at the same time the jacket has a lot of cool detail,” says Chu Tiampo. Kingshott adds some spunk to traditional suiting through design elements, such as the frayed edges and metallic piping of her Zara tweed blazer. She keeps her look formal and within her industry’s dress code by pairing it with a solid J.Crew shift dress and L.K. Bennett nude pumps (10 Columbus Circle at Broadway; 212-309-7559, lkbennett.com).

  33. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Natasha Kingshott, 22, investment-banking analyst, Tribeca

    “She accessorized beautifully with a chunky necklace, which is perfect for a conservative office but at the same time really edgy and fun,” says Chu Tiampo of Kingshott’s Kate Spade bauble. She keeps the rest of her add-ons—a Christian Bernard watch (christian-bernard.com) and a championship ring from her college squash days—subdued to compensate.

  34. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Natasha Kingshott, 22, investment-banking analyst, Tribeca

    A Michael Kors satchel in a cheery hue enlivens corporate dressing.

  35. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Brandon Messina, 33, lawyer, Chelsea

    “I like how his bag is a little more casual,” says Chu Tiampo of Messina’s Barbour tote (123 Wooster St at Prince St; 212-941-7524, barbour.com). It serves as a foil to his Hugo Boss suit (locations throughout the city; visit hugoboss.com) and Ralph Lauren button-down (109 Prince St between Greene and Wooster Sts, 212-625-1660 • 867 Madison Ave between 71st and 72nd Sts, 212-606-2100 • ralphlauren.com).

  36. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Brandon Messina, 33, lawyer, Chelsea

    Messina rounds out his courtroom look with a with a whimsical silk Hermès tie, an IWC watch (535 Madison between 54th and 55th Sts; 212-355-7271, iwc.com) and Warby Parker glasses (819 Washington St between Gansevoort and Little W 12th Sts, 646-517-5227 • 121 Greene between W Houston and Prince Sts, 646-568-3720 • warbyparker.com).

  37. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Akila Raman, 31, investment-banking vice president, Flatiron District

    Raman pairs a vivid chiffon dress from Catherine Malandrino (468 Broome St at Greene St; 212-925-3415, catherinemalandrino.com) with her staple Christian Louboutin pumps. “I love how she accessorized with that necklace to make it more edgy,” says Chu Tiampo of Raman’s Lizzie Fortunato sparkler (lizziefortunatojewels.com).

  38. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Akila Raman, 31, investment-banking vice president, Flatiron District

    A studded Valentino handbag (821 Madison Ave between 68th and 69th Sts; 212-772-6969, valentino.com) doesn’t detract from Raman’s Rolex timepiece and David Yurman ring (712 Madison Ave at 63rd St; 212-752-4255, davidyurman.com).

  39. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Stefanie Jay, 35, leverage finance vice president, Tribeca

    Jay admits her strategy for dressing for work while pregnant is to minimize the bump. “I don’t like to attract too much attention but [you should also] embrace your body,” she says. She layers a Diane von Furstenberg shift dress (874 Washington St at 14th St, 646-486-4800 • 135 Wooster St between W Houston and Prince Sts, 212-542-5754 • dvf.com) under a Theory blazer (locations throughout the city; visit theory.com). “The pattern and colors of the dress are fun, but the addition of the blazer keeps it polished and professional,” notes Chu Tiampo.

  40. Photograph: Jena Cumbo
    Photograph: Jena Cumbo

    Stefanie Jay, 35, leverage finance vice president, Tribeca

    Christian Louboutin pumps in a bold color help draw the eye downward.

Street fashion with Saukok Chu Tiampo, founder of Professionelle

For our latest street fashion edition, Professionelle founder Saukok Chu Tiampo takes us on a search for well-dressed workers in midtown and the Financial District.

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Professionelle founder Saukok Chu Tiampo regularly covers stylish office attire on her career-fashion website, so we had her guest-edit Time Out New York’s street-fashion column, scouring midtown and the Financial District for well-dressed workers. We spotted classic Hugo Boss suits and printed Hermès ties, as well as trendier gear from Rag & Bone, Zara and Warby Parker.

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