A Fall/Winter Hat Guide

Hats for Men - Fur Felt Fedora Mens Winter Hat Outfit Idea - He Spoke Style

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If you think an ascot is stuffy, put a lid on it!

Men's Fedora Hats Fall Outfit Idea - He Spoke Style

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Throwback Thursday! All the way back to last week! I'm pretty sure this look is still relevant, however.

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Or perhaps you would like to spend more, say, on this Borsalino Rabbit Felt Fedora at $395?

Hats for Men - Newsboy Cap with Plaid Blazer and Layered Cardigan Outfit Idea Fall Winter - He Spoke Style

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Rob comes up with names for all of these looks. He titled this one Highland Lad.

Hats for Men - Newsboy Cap Fall Winter Outfit Idea - He Spoke Style

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Get rich quick by incorporating jewel tones into your looks!

Though you should have a hat for every season, there’s no better time to wear one than in the late-fall and winter, when you get the practical benefit – keeping your head warm – as well as the style benefit. Here are a few of my favorite hat styles right now.

1. The Narrow-Brimmed Fedora

Hats for Men - Mens Winter Hats Goorin Bros Felt Fedora Hat - He Spoke Style

As worn last week. A narrow-brimmed fedora is a great starter hat for those just beginning to wade into the headwear waters. A feather is optional but adds a nice sartorial touch.

2. The Newsboy Cap

Hats for Men - Mens Winter Hats Wool Newsboy Cap - He Spoke Style

This is my go-to casual hat. I tend to wear it most on weekends and while traveling – times when I don’t feel like or don’t want to comb my hair.

3. The Fur Felt Fedora

Hats for Men - Mens Winter Hats Christys Fur Felt Fedora - He Spoke Style

A classic men’s hat. With a bit of a wider brim, it may not feel like the right hat for a headwear novice, but once you feel ready, this is one you’ll want to have. Like all classic menswear items, it looks great dressed up or down.

MORE: Explore looks with hats in the Style Guide.

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

Photography by Rob McIver Photo

Chime In

  • MNuta

    Great article! Wearing a hat is definitely a dying art, unfortunately!

    I’ve been wanting a wool newsboy for a long time now, but all I find online are either expensive, or don’t look or fit right (I love caps that are a bit full, or puffy). Any suggestions?

  • http://www.tailormade-style.com DJ

    Would you say that there’s a hat for every head ‘type’? I’ve wanted to give one a shot myself but I’ve worried about this.

    DJ | http://www.collegestyleguy.com

  • http://www.lefrenchboy.com Cedric

    Fedora hats all the way ! ;)

    C├ędric / http://www.lefrenchboy.com