The Highsnobiety Fall Fit Toolkit is your manual for dressing well this season, from wellies to weather-ready running gear.

The stage is set for us to take our fall fit playoffs up a notch; the drop in temperature means more layers, more accessories, and more chance to leave your mark. The real question is who will emerge the winner in each category. We’ve assembled a crack team of Highsnobiety editors to make the call. Thom Betteridge, Christopher Morency, Noah Thomas, Haley Culp, and Herbert Hoffman have assembled to hammer out the ultimate fall wardrobe.

This time around we’re talking hats. The hat is an essential all year round, it’s the crowning characteristic of so many personalities, and never is it more important than in fall. From everyday baseball caps to not-so-everyday balaclavas and bucket hat-cum-balaclava hybrids, every corner of the hat world has been scouted for the best and brightest talents.

Brunello Cucinelli isn’t your typical designer. Yes, he sells ultra-lux, cashmere sportswear to the rich and famous (he was the first to do so!), however, he gives back, renovating the entire town he lives in from the library to opera hall to churches. He lives outside of fashion, so I like him even more. Plus, I dig his style. So yes, this is an overpriced $350 baseball cap with a simplistic Velcro strap, but I’m saving up. It’s Brunello Cucinelli.

I’ve had my eye on this unconventional 69-us sunblock hat pre-pandemic but it makes even more sense in today’s climate. A baggy look would compliment this statement piece well.

The Balaclava for me is the best hat option because it can also be a beanie when rolled up. It’s a secure feeling to know at any moment you can pull your hat down and your whole face is covered and warm. It’s about smart buys these days and Raf has truly made a very useful winter item. The colors are also beautiful.

This red-brown AFFIX cap features one of my favorite color combinations. It’s so simple and amazing. Reflecting on the past few months, I have to mention my beige SPRITZ cap — it makes it easy to see where your head’s at when you wear it. You can also buy the Calamari, Negroni, or Grappa version.

I’m not one for warm headwear. In fact, the feeling of cold wind blowing directly through my buzz cut and into my skull is like a second cup of coffee for me in the morning. But as far as my normal rotation of dad hats goes, you’ll catch me this fall in Praying’s Hebrew remix of a Yankees cap. Especially since COVID’s got me grounded in the Big Apple until further notice.

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