Wes Gordon is a child of the ’90s, and over the past few seasons he’s made a business out of designing modern clothes that are nostalgic for that era, from minimalist slipdresses to chunky, high-neck sweaters.

For Fall he took it one step further, enlisting longtime collaborator Manolo Blahnik to make refined combat boots. There was a flat version, and one with a sky-high, squared-off heel. “Last season was very serene, very clean,” Gordon said at a preview. “This time, there’s a little more attitude. It’s not aggressive, but there is an added confidence and toughness.”

With every collection, Gordon moves a little further away from the idea of what an Upper East Side princess might wear, and closer to what she actually wants to wear. For instance, he showed a long coat in double-faced speckled wool as an opening look. It wasn’t overly polished, but it was the sort of thing his customer could easily throw over a gown—even though it was shown with a rib-knit pullover and skirt set that was reminiscent of long underwear. “I don’t know any girls who have a ‘dress’ coat,” Gordon said. “This was created in line with how people actually live.”

There was more to love in that vein, from a dark gray mink sweatshirt with subtle chalk-like vertical stripes in cobalt blue—designed in collaboration with New York furrier Pologeorgis—and a mock-neck, double-slit dress in black stretch crepe. These were elegant pieces, yes, but not fussy. Gordon also took less-precious fabrics and gave them a glamorous spin. A dark blue corduroy trouser, for instance, was cut ultrahigh and close to the body, its pockets trimmed in an expensive-looking Japanese denim. Jeans done in the same fabric were worn with a high-neck blouse covered in geometric Swarovski crystals.

There were times, however, when the clothes felt more ambivalent than cool. A pieced-together dress—gray mélange on top and beige double-faced satin wool on the bottom—didn’t really say anything, it just existed. You can offer realness, but you’ve still got to wow them. Gordon achieved that by playing with embroidery and lace, moving away from his favorite Chantilly and going for a gorgeous guipure, sourced at a prestigious Swiss mill. (The paintings of Argentine artist Grillo Demo triggered Gordon’s print story of lavender and buttercup yellow florals on black.) A crepe mock-neck top, worn with a lace skirt and flat boots, was very real looking, but also beautiful.

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