8 Preppy, Nautical Summer Looks for Men

Menswear prep with an urban upgrade.

Photograph by Jeff Elkins

Preppy style is easy to pick out because of how little it changes. Specific items may fall out of favor (never again, pleated-front khakis), but the primary colors and classic cuts remain signature elements that work for men of all generations. Which is precisely how a city kid like Tim Downing ends up in outfits only a few shades off from what you’ll see on golf courses at suburban country clubs.

“My style is not too far from the old Connecticut guy’s,” says Downing, a designer at the Bethesda needlepoint company Smathers & Branson. “What I do differently is keep the cuts of my clothes slim and modern. And I’ll make things interesting by incorporating tropical, African, or other big patterns.”

Accessories also play a role. Eyewear sometimes happens in neon hues, and loafers (he usually looks for shades other than black and brown) up the modern factor. Belts are a heightened area of focus for the Dupont Circle resident these days, as Smathers & Branson is debuting a line this fall that matches his style. It’s called Parlour, and the tattoo-inspired motifs are “dapper with an edge”—just like their designer.

What He’s Wearing: The inside leather of Parlour’s Shipwreck belt is deep teal. Downing wears his father’s Bulova watch from the ’80s. “Pairing a dressier shoe with casual clothes makes an outfit look more expensive.” J. Crew’s slim-cut short-sleeved shirt looks cool in the summer heat. Bonobos makes a brighter, slimmer take on the traditional Nantucket reds chino.

How to Get Tim Downing’s Preppy Look

All Aboard

Leather boat shoes, at Brooks Brothers ($148)

Make a Splash

Horizontal-stripe swim boxer, at ($88)

Batten Down

“Claud” blue-and-white button-down, at Billy Reid ($295)

Anchors Aweigh

Rope bracelet with anchor, at ($80)

Snappy Sunnies

Krewe du Optic “St. Louis” sunglasses in matte clear, at ($195)

Camo Carryall

Signature West Branch tote, at L.L. Bean ($159)

Rising Tide

Jogger pants in garment-dyed cotton/linen, at J. Crew ($75)

Light Layer

Tommy Hilfiger “Chase” crewneck sweater, at ($119)

This article appears in our June 2015 issue of Washingtonian.

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Sarah is the Editor-in-Chief of Washingtonian Bride & Groom, and writes about weddings, fashion, and shopping. Her work has also appeared in Refinery29, Bethesda Magazine, and Washington City Paper, among others. She is a Georgetown University graduate, lives in Columbia Heights, and you can find her on Instagram at @washbridegroom and @sarahzlot.