More Menswear Inspiration: The Fall Hat

Fall's not just a great time for shoes and boots; it's also a fantastic opportunity for gloves, scarves and hats meant for weather that's cool but not yet cold. Our go-to hat provider, San Diego Hat Company, has turned out a number of hat styles perfect for fall trends.

As in shoes, we're seeing (and loving) the migration of traditionally masculine styles into womenswear. This fall casual newsboy caps, engineer and fishermen caps get dressed up and formal fedoras and equestrian riding helmets get a dose of urban chic. Both trends point to a season of refined dressing and smartly tailored looks tinged with pastoral romance.

In addition to boots, equestrian styling is inspiration for fall chapeaux. The traditional English riding helmet with its black velvet covering has been remade by San Diego Hat Co. in a structured wool. We love the short, peppy brim and SDHC's addition of a front band secured with eagle-stamped gold buttons. The traditional ribbons at back have morphed into a tab at the cap's peak.

Sew on a colorful ribbon at back to reference the hunt (and give you easy DIY style options). Pair with riding-style boots, but forego the white breeches and scarlet coats. Instead, riff off the formalwear with a shrunken, tailored, dark blazer. (Or go with a Prince of Wales or other glen plaid to make it really pop.)


Another great women's hat this fall is a mashup of several styles. Part Greek fisherman, part engineer's cap, this style has a softly structured, roughly cylindrical top and a short brim braced with a decorative hatband. Brando immortalized a softer, foppier version in The Wild One.

What makes this hat a seasonal fave is the vast range of fabrics and patterns being used. San Diego Hat Company's purple plaid engineer cap (shown, also in red) is a casual-chic boho example, the three-button band a nod to the rakish tilt of Brando's lid. Plaid's just the start: look for embroidery, mod herringbones and a variety of tweeds.

With hats this bold, amp up your look. Plaid cap? Add more plaid in the form of a scarf, blazer or pants. Contrast the big tartan pattern in this hat with a smaller, more subtle design in your outfit. Make it clash to make it work. And the shoes? The shoes. Or rather, the boots. High, polished, dark, heeled.

A more youthful version, the newsboy, is also well-stocked here at Lori's, the biggest difference being a larger, floppier crown (perfect for tucking away long tresses or an ad hoc role in Newsies). Throw on some oxford pumps or a wingtip pattern under pants.

Last but not least, a classic of mid-century menswear, the fedora, has found its way back into our wardrobe. Characterized by a higher, structured crown and wide brim, often with a wide fabric hatband, the fedora was a ubiquitous - and required - piece of men's attire until the '60s when style icons like JFK famously went lidless. The demise of the hat quickly followed.

Or so we thought. We're carrying some cute versions this season in more relaxed fabrics and with a short, snap brim that reminds us of fast-talking newspaper reporters. This look would be great over a structured top like a white menswear dress shirt and some spectator pumps.