Menswear-Inspired Fall Fashion in Honolulu

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From smartly tailored trousers and button-downs to oversized watches and brogues, fall’s boyish good looks will have you reaching for menswear-inspired staples at every turn.

Pop of Collar

A removable neckpiece and gentlemanly fedora give strength to easy-going knitwear. Marni sweater, $400, Marni collar, $105, Marni resin earrings, $330, Neiman Marcus. Gibson twill jersey trousers, $325, Diane von Furstenberg. Fedora, $54, I Am. Legacy leather clutch, $238, Coach. Leather oxfords, $595, Escada. Gold-plated bracelet, $65, Marigold gold-plated ring, $75, J.Crew-on-the-island. Meegan Reelitz Sagitta ring, $112, Fighting Eel.
 

Fine and Dandy

Skip the monochrome for mix-match suiting finished with decidedly dapper accessories. Reade cotton blouse, $228, Kate Spade New York. Blake twill jersey blazer, $465, Diane von Furstenberg. Jil Sander houndstooth pants, $550, Neiman Marcus. J.Z. Richards silk pocket square, $39.50, Nordstrom. Stevie leather booties, $198, Banana Republic. Riyo bone earrings, $77, Sonya Renee Drusy ring, $108, Fighting Eel. 
 

In Focus

Shoot for tough in structured numbers highlighted with hints of gold. T By Alexander Wang shirtdress, $285, Marni beaded bracelet, $210, Neiman Marcus. Pyramid stud bangle, $238, Coach. Meagen Reelitz bib necklace, $112, Fighting Eel. Marigold earrings, $65, J.Crew-on-the-island. Vintage Rolex Day Date President 1803 18K gold and gator watch, price upon request, Honolulu Time Co.
 

Cuff Love

Boy meets girl in a crisp-to-flowy shirtdress and handsome, rose-tinted timepiece. Cotton and poly-blend shirtdress, $238, I Am. Céline leather tote, $1,100, Aloha Rag. Marni necklace, $710, Marni earrings, $295, Neiman Marcus. Vintage Rolex Cellini Prince 18K rose gold and gator watch, price upon request, Honolulu Time Co. Resin ring, $98, Kate Spade New York. Padma & Pickles pyrite ring, $40, Fighting Eel.
 

Pretty Boy

A classic tuxedo jacket gets a softer spin thanks to a slip of Ultra-feminine lace. L’Agence lace top with cami, $390, Nordstrom. The Row leather shorts, $1,200, Aloha Rag. Rag & Bone gabardine tuxedo jacket, $535, Marni rings, $230 each, Neiman Marcus. Painted Jewels resin necklace, $295, Kate Spade New York. Chameleon leather and snake clutch, $920, Fendi.
 

Tie One On

Anything but run-of-the-mill, fall’s shirt and tie combos come in prep-cool plaids and CHIC, ladylike cuts. Wool shirt with tie, $1,570, Salvatore Ferragamo. Hooked Up Hawaii gold-fill earrings, $77, Fighting Eel.
 

Shopping Guide: Look Sharp

Art Direction: Tiffany Below. Model: Whitney Hay, Niche Models & Talent. Makeup: Kecia Littman, Wilhelmina Hawaii. Hair: Ashlee Valeros. Photography Assistant: Trevor Sakanashi. Location: Honolulu Museum of Art.