Fall Work Outfit Ideas—Including Dressed-Up Sweatpants!—From Madewell’s Main Man

You should know that I have a tiny (but totally professional) crush on Somsack Sikhounmuong at Madewell. He’s so kind and warm and, ya know, regularly turns out timeless pieces for today’s girl that are somehow what I want to wear before I even know it. When the brand released its fall look book, it was predictably chockablock with combos I’d like on my body, right this instant. Because he’s somewhat of a genius at putting together outfits, I threw out my hardest questions and he took them all in stride.

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On denim at the office:
“It definitely depends on your office. I suggest pairing our Slim Boy Repair jeans with a great T-shirt, leather jacket, and heels.” If that sounds too laid-back for your workplace, take heed. “An easy swap would be a longer menswear-inspired blazer instead of the leather jacket.”

On sneakers worn 9-to-5:
“It’s all about how you wear it. I recommend that from the ankles up you go a little less casual.” If your profession doesn’t require a super buttoned-up look, consider sharp suiting paired with skater sneakers or Adidas Stan Smiths.

On whether sweatpants are ever OK for work:
“The ones I currently love are less sweatpants, more pants cut in sweatpants fabric. They swing toward a relaxed pant, [like] more of a cool-slouchy vibe and less ‘I put these on to eat ice cream and sit on the couch.'” Need a visual? This is the sort of pair he’s referring to.

On loving to layer:
“I love to layer! The Madewell outerwear plays heavily with it this season, and there’s a great rivet and thread olive quilted coat as well as a vest that take their cues from the linings and interiors of coats. They can be worn on their own as true outwear pieces in early fall and go under coats come winter.” My favorite is the disheveled-preppy combo up top, with a button-up, a sweater, and a blazer. Perfect.

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“This vest is one of my favorite pieces! It’s reversible and has patterned wool on one side and dark navy nylon on the other. I suggest wearing it with jeans and heels.”

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For fall days with extra bite, I love this idea: Wear a boxy coat over a thinner jacket belted at the waist.

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And, brilliantly, I can now totally envision wearing overalls into fall. Keep it grown-up sexy, not little-girl sweet, by wearing a high bib with nothing else underneath, and top with a tailored overcoat.

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