Style Suggestion: How to Dress for Fall Weather

Editor’s note: For a full set of style suggestions for fall, click here.

We’re slowly (but surely) creeping toward fall — it seems like that’s been the case for a couple of weeks here at The Style Guide, but it’s certainly no more true than right now. Dressing for football season has started, there’s a bunch of great new music out — that signals tons of fall tours and rock concert style — and it’s high time to, well, get with the times. So, grab your fall style wish list and get hip to the scene. Even if it takes a while to get chilly, you’ll still want to have the proper gear on hand when it does. I know temperatures have been high here in NYC, but I’m definitely anxiously awaiting fall. For all of you loyal Style Guide readers (I know you’re out there), it signifies a really fun time of year in terms of menswear. If you’re one who tends to get sick of the oppressive heat — and even tires of heading to the beach — it can be a welcome change of pace to throw on heavier layers and incorporate durable texture into your #menswear ensemble again. And being able to play around with deep fall colors and textures — as some of the picks do below — is another reliable signifier that the season is changing. Everywhere you look, it’s about that time. Wthout further ado, here’s a look at how to dress for fall. Catch more style tips daily on the ‘Gram or Twitter, and leave any thoughts on this look in the comments.

The Jacket: Old Navy Canvas Coat — $69.94

Not as heavy as a winter parka, not as lightweight as a spring jacket -- hence, a great fall coat.

Not as heavy as a winter parka, not as lightweight as a spring jacket — hence, a great fall coat.

You feel a crisp breeze in the air, but a lightweight spring jacket won’t cut — and it’s not heavy winter topcoat time, either. What’s your reliable go-between? A cotton canvas coat in a rich shade that’s perfectly primed for fall. Although the interior of this jacket is lined with a neat striped cotton, it should prove reliable and not too heavy for layering. Details like the front patch pockets call to mind workwear of days past, and the rich Bandolier Brown color is going to handsomely offset the blues in the rest of this ensemble (although we don’t want to give too much away yet).

The Shirt: Taylor Stitch Everyday Chambray Shirt — $104.98

Beautifully made, able to withstand anything and certainly able to make that transition to fall.

Beautifully made, able to withstand anything and certainly able to make that transition to fall.

Were you expecting something other than a stellar Taylor Stitch chambray shirt here? I hope not, because I’d bet you’re disappointed right about now. The brand takes the same attention to detail that’s made its Standard Issue Chinos beloved by The Style Guide, and applies that process to a heck of a chambray shirt. Featuring sturdy double-needle construction, a midweight 7oz. chambray fabric and a fit that’s modern yet mobile, it’s the ideal contrast to that handsome brown jacket. Plus, it’s got the type of classic looks and styling potential that’ll work the rest of the year, too.

The Denim: Flint & Tinder All-American Slim Tapered Jeans — $98

New denim from a menswear line that gets essential fall basics right.

New denim from a menswear line that gets essential fall basics right.

The brand that produces your favorite set of American-made boxer briefs and other stellar fall menswear delivers again with new denim that’s part of its deepest product offering to date. For fans of versatile, timeless style, that’s very much a positive. These jeans are every bit an essential pair of fall denim, made from 12oz. Cone Mills fabric and featuring one percent of stretch  — that touch will make it easier to wear ’em on fall hikes or walks in the park. The slim fit is a must-have these days, although the brand’s waist sizing does go up to 40. Grab one pair of these, wear the heck out of them and watch them tell the story of a great fall season.

The Boots: JackThreads Kimbo Chelsea Boot in Brown Calf Leather — $110

Part of a new set of footwear offered from the excellent E-commerce retailer.

Part of a new set of footwear offered from the excellent E-commerce retailer.

Since when does JackThreads make footwear? Since this season, that’s when. It’s part of the brand’s mission to expand on its stellar menswear line and take up some serious real estate in your closet. When they’re able to churn out crisp pieces like these refined Chelsea boots for just a shade over $100, that’s very agreeable. A stylish Chelsea boot works nearly any time of year, yet they seem particularly fitting for fall. They’re not nearly as clunky as some thick winter boots, and they feel especially sleek alongside slim denim and a chambray shirt (some stylish leather chukka boots could also work here, though).

The Socks: Mack Weldon Everyday Striped Socks — $14.50

Easygoing socks for daily wear -- in a color that plays along nicely with the rest of this outfit.

Easygoing socks for daily wear — in a color that plays along nicely with the rest of this outfit.

The folks at Mack Weldon are consistently churning out everyday basics that’ll have you covered from the ground up, from its Vesper Polo to pieces like its Merino Long-Sleeve Tee, and if you read this blog as much as I think you should, you’re well-acquainted with those pieces (wink, wink). So, it only makes sense that you should round out your wardrobe with some striped Mack Weldon socks that add a nice bit of color contrast to the deep blues and browns of this outfit. Ya feel me?

The Watch: MVMT Watches The 40 in Rose Gold/Brown Leather — $120

A stunner of a watch for a stunningly low price.

A stunner of a watch for a stunningly low price.

Are you familiar with MVMT Watches? If not, you definitely should be. That is, if you’re a fan of stylish, affordable eye-catching watches — and who isn’t? There are some watches that are so refined in their design, you can wear them more casually — that’s certainly the case with this MVMT Watches timepiece, crafted from a rich brown leather-brown dial-rose gold case combo that’s a heck of a looker. It’s a way to offset some of the more rugged pieces in this outfit, like the canvas coat and chambray shirt. More importantly, it’s dressy enough to wear later on this season with, dare I say, the Taylor Stitch Telegraph Suit?

The Belt: J. Crew Suede Belt — $55

Texture in the form of a refined belt for the season.

Texture in the form of a refined belt for the season.

This suede belt first made an appearance in this site’s suggestion on how to dress for a football game, and it’s back here and adding a change of pace to this outfit in the process. The look is already quite heavy on rugged style, to be sure, so it’s fitting that a suede belt comes into play. Fall is the perfect time to try out texture where you might not do so normally, and for more than $50, you better get a lot of wear out of this belt to justify the initial price (although this particular pick is suede, a handsome leather belt like the Tanner Goods Classic Belt would work, too).

The Sunglasses: MVMT Watches Runaway Sunglasses — $75

Equal parts retro cool and affordable style from a watch maker who knows how that stuff works.

Equal parts retro cool and affordable style from a watch maker who knows how that stuff works.

Wait a second — MVMT Watches does sunglasses? Yes, they sure do. And why do we have sunglasses in this post? Well, as this is transitional style and all, it’s still going to be a bit sunny out there most days, whether you’re taking a hike through a park, heading to a bar crawl or taking in that football game. These sunglasses aren’t too precious to take a beating, and more importantly, they’ve got a distinct air of retro cool about them. Just like the watch, they’re perfect to pair with everything from that Taylor Stitch chambray shirt to … wait for it… the decidedly modern Taylor Stitch Telegraph Suit.

And there you have it, folks — pick up one, all (or heck, none?) of the above items and prep for fall in style. As we always aim for at this #menswear blog, reaching for pieces that are going to have your back the rest of the year is a solid bet no matter the season. And if given the chance to wear a durable chambray shirt with a crisp canvas coat, take it. The combo is just the right amount of rugged with venturing too far off the beaten path, and pieces like slim, dark denim and brown leather Chelsea boots keep things modern. A refined watch and cool-as-heck sunglasses are items every guy needs, yet not every guy has — except you. And you can never go wrong with accessories from staple players like Mack Weldon and J. Crew. Head-to-toe, there might not be a better time to be a style fan — and that’s what makes fall menswear so great.

What’s your take on this ensemble? Have you picked up any of these pieces?

#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