#OOTD: The Best Way to Wear A Henley This Fall

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

So it’s not exactly the middle of summer anymore, is it? That’s a strange sensation if you’ve been used to dressing for the heat or packing up stylish beach gear. But if  you’re anything like this #menswear writer, you relish the chance to dress for seasonal transitions and break out some of your favorite seasonal style staples. We’re talking pieces that are rugged and refined, ready for casual wear or able to be worn with a bit more tailored style in mind. And in the case of this week’s #OOTD, we’re looking at an outstanding piece for a seasonal transition — the ever-reliable slim long-sleeve henley.  With its athletic-minded origins and rugged good looks, a great henley certainly works in the summer as well as the in-between period between summer and fall. But particularly when it’s made with marled fabric and plenty of quality and comfort, it’s the ideal early (and middle, and late) fall style piece — think of the below #OOTD as a weekend workhorse look. To get your mind right when it comes to stylish henleys, check out last year’s picks for the best men’s henleys for fall — and know that we’ll have a similar feature coming on this site in the weeks ahead. Oh, and how exactly should you style this durable staple? We won’t drop any hints up here — scroll below to check out the #OOTD, join in on the men’s style conversation at The Sty le Guide’s Facebook page, and check out this guy’s Instagram for daily style tips.

Best men's henleys for fall
Just one way — but perhaps, the best way — to wear a henley this fall.

The Henley: Flint & Tinder Marled Long-Sleeve Henley, $62  — So, the henley shown here is a bit more expensive than you might be used to paying for a basic layering piece. But the quality, fit and styling potential is top-notch, and given the fact that it’s part of a slew of new additions to the Flint & Tinder product line, you should definitely pick up this slim henley.

The Coat: Old Navy Canvas Coat, $69.94 — It might initially be too hot to wear a canvas coat atop that henley, but know that when it gets slightly chilly and you need a crisp top layer, this rugged canvas coat is the perfect finishing touch.

The Chinos: JACHS NY Grey Bowie Fit Stretch Cotton Chino, $89 — Why go with chinos here as opposed to slim, dark denim? They lend the look a bit of high-low style appeal, and the fabric and slim fit are nice positives.

The Boots: CAT Footwear Russell Boot, $150 — Boots that blend different fabrics and textures (like wool and leather) with a sturdy ankle boot, moc toe combination are the perfect way to nod toward the chillier temperatures of fall — not to mention the rugged-refined vibe of this outfit.

The Socks: Flint & Tinder Inventor Socks, $17.98 (Three-pack) — If we’re going with a Flint & Tinder henley, might as well go with crisp, stylish and comfortable Flint & Tinder socks, ehh?

The Watch: Timex x Red Wing Waterbury Chrono, $158 — The Timex x Red Wing Heritage collaboration is a certified Style Guide favorite, and it’s the perfect mixture of toughness and style to offset the other fall-appropriate pieces in this #OOTD.

The Belt: Anderson’s Stretch Woven Leather Belt, $195 — If you want a belt that’s going to work as hard as you do, last forever (truly) and add some subtle texture to this overall look, the Anderson Stretch Woven Leather Belt is the way to go.

The Everyday Carry: United By Blue Lakeland Laptop Bag, $119.98 — Looking for a durable, dependable bag to haul around your laptop? This United By Blue laptop bag merges function and fashion, and it does so while promoting a good cause (the brand removes one pound of trash from oceans & waterways for every item sold).

Are you ready for some fall weather yet? Hopefully so. Dressing for the transitional period between the heat of summer and the chill of winter can seem taxing if you’ve grown used to wearing that short-sleeve chambray shirt for months on end, yet reaching for the right pieces can make it an enjoyable task. A marled henley is an essential for the colder months, and when mixed with dependable boots and refined chinos, it can work in even more style situations. On top of that, sharp socks that add a pop of color play nicely off dressy touches like that textured leather belt and rugged leather watch. And if it gets truly cold in the weeks ahead, you can always add a crisp shawl cardigan to this same ensemble. Have questions or more suggestions for the #OOTD series? Shoot me a note on Twitter.

Make room in your closet for a great henley — and stay stylish in the meantime!

-Beau

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