FAVORITE: Dog Days Of...Fall?

Right when I'm settling into a happy routine of sweaters, wool socks and layering, the temperature spikes up to the mid-80s. I shouldn't be surprised. It's just like you to do this, Midwest—every damn year. Ah, well. When summer is as fleeting as it is in the northern half of this region, you've gotta cherish every last day even if it comes in the middle of autumn.

And when you find a piano on an abandoned freight railroad track, what do you? You were going to say "take some senior pictures," right? Right. (You're all invited to my high school graduation in two years.) Thankfully, the talented Rob Culpepper was on hand and in the mood to shoot some medium format film on the Bloomingdale Trail, Chicago's undeveloped and still super-secret future answer to New York's High Line.

A note on the trousers: Dockers? Yeah, you read that right. Your dad's favorite brand has updated some of its offerings with more tapered silhouettes that look like like khakis but wear like jeans. They're called Alpha Khakis, and I've been wearing the hell out of 'em. Along with a second green pair, they've become fast favorites. 

It's still fall, right? I got hooked on yerba mate in Argentina and have it with me most days when it gets late in the year.

On Seth: Indian cotton button-down (sale $30, reg. $75) by J.Crew; "Alpha Khakis" in British khaki (sale $59, reg. $68) by Dockers; natural veg leather belt by Cause and Effect; thrifted loafers by Giorgio Brutini; "Weekender" watch ($25) by Timex with Horween leather strap ($95) by Buckshot Sonny's.

Oh, and if you're a Mizzou Tiger, you're headed into a special weekend. Cam and I will see you at Homecoming, suckers.

Photos by Rob Culpepper.

NORTHERNGRADE: Chicago Edition

Ladies and gentlemen, NorthernGRADE is coming to Chicago. This edition of the legendary pop-up market will be produced by our friends over at Well Spent and Pierrepont Hicks, so if you're in town you've really got no excuse for missing out on the festivities.

Having been to Minneapolis, the place where it all started, we saw firsthand what all the fuss is about and we can tell you that NorthernGRADE is one of the gems of the Midwest. You can expect beer, camaraderie, and damn fine American-made goods. But don't believe what you're reading here: take our word for it. 

When: Saturday, Oct. 27 (10am – 6pm)

Where: Open Secret Studios (401 N Racine Ave)

Who: Made-in-the-USA vendors!

1. Penelope's (Sponsor) - Chicago, IL
2. Haberdash (Sponsor) - Chicago, IL
3. Red Wing - Red Wing, MN
4. Tellason - San Francisco, CA
5. Winter Session  - Chicago, IL
6. Pierrepont Hicks - Minneapolis, MN
7. Oak St. Bootmakers - Chicago, IL
8. Independence - Chicago, IL
9. Portland General Store – Portland, ME
10. Field Notes - Chicago, IL
11. Archival Clothing – Eugene, OR
12. MidNorth Mercantile - Minneapolis, MN
13. Stormy Kromer – Ironwood, MI
14. Sir & Madame - Chicago, IL
15. Locally Grown - Des Moines, IA
16. Corter Leather – Boston, MA
17. Inland Clothing – Chicago, IL
18. Heritage Bicycles - Chicago, IL
19. Drift Eyewear - Chicago, IL

GIVEAWAY: And The Winner Is...

Alright, you filthy animals! The time has come.

We want to thank you guys for your interest. We've loved reading the stories of your old, faithful, ratty backpacks. The new opportunities, the ending chapters. The big-boy jobs and the style transformations. We feel like we know each of you a little better, and that's a wonderful thing in our book. 

Our winner is Josh Krasovec, the Kansas City police officer who plans to use the Bleecker Utility Tote to schlep around gear for his newborn daughter, and then pass along this beauty of a bag to her when she comes of age. Brilliant. (And we're already picturing you motoring down the road on your motorcycle with this thing, Josh. Badass.)

To be honest, all your stories were excellent. We especially loved Jerry Stoffl's hilarious empathy for the duped New Yorkers. Brad Rice's philosophizing on the process of reinventing his style. And of course, ThreadWise's courageous husband, who's soaring above Iraq and Afghanistan and protecting our freedom. A humble thanks to both of you.

BUT: Before you walk away with heads hung low, know that we've got several more giveaways just ahead in the coming weeks—everything from winterwear to illustrated stationery. Don't miss 'em!

And, of course, a huge thanks goes the team at Coach for their generosity and damn fine bags.

GIVEAWAY: Coach + The Sartorialist Tote

UPDATE: Don't forget to "like" the Coach Men's Facebook page! Extra props for tweeting at @Coach and @TheMidwestyle, too.

These giveaways just keep coming, eh? And there are even more on the way.

A household name for decades, Coach wanted to reward you guys, our readers, with a new bag as midterms end, new jobs begin and the seasons change. We leapt at the chance, of course. Earlier this year, Coach teamed up with The Sartorialist, who did his usual good work photographing stylish urbanites carrying Coach's latest Legacy Series collection. Have a look:

The Bleecker Legacy Utility Tote, photo by the Sartorialist for Coach

GIVEAWAY DETAILS:

• What you'll get: The tote pictured above.
• Contest starts: Now, October 18, 2012.
• Contest closes: Sunday, October 21, 2012 — at 11:59:59 p.m.
• Announce winner: Monday, October 22, 2012

HOW TO ENTER:

• Answer this: "Why you need to ditch your current bag and update to this beauty?"
• Like the Coach Men's Facebook page and us, of course!

We've been fans of Coach for quite some time, and we know firsthand just how well their product holds up over time. Here's Jeff's recently acquired Coach backpack:

And Seth's Legacy Field Bag has become an instant favorite:

Hell, it only gets better as the leather ages and softens, as you can see from the vintage Coach finds we've stumbled across. What are you waiting for? Let's hear it!

midweSTYLE: Double down

Let's dish out another take on wearing a double-breasted jacket today, yeah? Cam brought his game with a Barena find last week, and I'm continuing with an Aspesi gem.

This is my first double-breasted jacket, let alone my first year-round + Italian designer jacket. I added in plaid shirt, thrifty slim carpenter pants, leopard-print hat and Nike Safari sneakers. So many red flags, styles clashing and seasons colliding in one outfit. But I was comfortable and in a hurry to meet up with Yewon Kim to snap some photos. Be warned when you meet up with Yewon: She's in a league of her own.

Ladies, take note of Yewon's outfits. Guys, take note of Yewon's outfits. Everyone, follow the Yewon.

Story time on the wine-stained trousers: These Levi's slim carpenter pants are favorites because of the lore behind them. A halloween-plus-birthday party was thrown at my house in Logan Square last year.  I remember neither my costume nor the song, but I swatted a wine glass out of the hands of some white girl with bangs (or rather her flailing arms swatted me.) The wine glass splattered and shattered on my computer and all over my pants. The white girl with bangs didn't skip a beat and kept on dancing. The computer spluttered out, however, and a part of me died that night. The following day, I took it to the Apple Store, where they took a look and said, "Well, we tried to turn it on, but it smelled like wine and beer. It's toast, bro." 

Let's review: My computer smells not just like "alcohol,"  but specifically, "wine and beer." Noted, Genius Bar guy. My computer smelled like booze, I GET IT.

A day later, I emptied my bank account to get a new laptop. 'Cuz Internet. A week later, I finally washed my wine-splattered carpenter pants. But the stains remain...and somewhere I think I still have that wine-logged laptop, too. 

 Photography by Yewon Kim

On Jeff: Double-breasted cotton blazer by Aspesi from Mr. Porter; checkered button-down by A.P.C.; carpenter pants by Levi's; Air Safari sneakers by Nike from St. Alfreds in Chicago; five-panel cap by Reed Space + Publish from St. Alfreds in Chicago; frames by Warby Parker.

MIDWESTYLE: Camo is for outside

*This post contains the use of what we call "the hillbilly hem job," a term loveably applied to the folding under of excess fabric at the hem of one's pants. We, in no way, endorse this tactic as a longterm solution to long pantz. Go to a tailor. But, in the short term, what the hell? Plus, this entire photo shoot was unplanned, I was caught by one of the many street style photographers in the middle of Missouri while I was on a lonesome hike through the woods in my double monks, and I needed a quick solution. You're not still cuffing your pants, are you? Besides, that's why the ROTM dudes put a lug sole on those monks, guys. For hiking. They want you to do more hiking.

BACK TO OUR REGULARLY SCHEDULED PROGRAMMING

Have you guys heard of Barena? It's Italian tailored, casual #menswear. And it's awesome. Tailored casual is king. Jersey everything. Fleece, everywhere. Your grandpa's sweatsuit and your blazer can be made of the same thing now. Anyway, I found this double breasted jersey sport coat on Yoox for, like, not very much money. The fit is spot on and it's unlined, unstructured, and unbelievably comfortable. Notice how it's layered over an aran knit sweater? That's for texture. The internet told me fall is about texture.

I don't care if you hate camouflage, these Baldwin joints are on point. Word is that Hova wears them a ton. If you hate on something Jay-Z rocks all the time, no offense, but who the hell do you think you are? I'll trust your opinion when your net worth is around $500 million.

Oh, and double monks on a lug sole? Phew, never thought I'd see the day. That is, of course, until the Run of the Mill guys dropped these bombs on us last fall. As a man who's notoriously obsessed with resoling shoes with soles that have no business being welted to the uppers I've chosen for them, these struck a deep, deep chord with me. Couldn't drop $435 on 'em, but I found some on StyleForum at a steep discount. And seriously, it's completely normal for guys to walk around in the forest with double monks! That's what lug soles are for! Welcome to the 21st century. 

On Cameron: double-breasted jersey blazer by Barena; cotton aran knit sweater by J.Crew; The Ryan pant in camo by Baldwin; scotch grain double monks by Run of the Mill; thrifted scarf. 

Photos by Christine 'Big Cat' Cover