There comes a time in a woman’s life where she trades in her heels for flats, but not today. Instead I’ll be wearing Nike’s. You really learn a thing or two in school, like whenever indecisive just go with C (the Nike’s) and go home and make a sandwich — a well-deserved one, because you probably just aced your chemistry exam and because you’re about to make the most comfortable decision of your life (thank me later.)

That being said, I took close notes at NYFW (once again) where Mason Margiela taught me that oversized blazers are cool and cuffed trouser pants are even more so. If ever unsure about what to wear, it’s OK — throw on gym sneakers and that button-down you shoved in the back of the closet because sporty is in and sneakers are everything. Now go on, steal dad’s blazer (and tie) and call it a day. An extremely comfortable day.

Below I’ve styled two ways to tackle menswear this fall. I’m taking a classic, masculine approach, whereas I have Ms. Ashley chanelling a more chic, feminine take on Menspiration.

Take One: Classic

Menspiration 3   Menspiration 4

Take Two: Chic

Menspo 2   Menspiration 7

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