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.

UNIFORM: Work From Home

When you work from home, you sometimes have to come up with elaborate ways to actually trick yourself into, you know, working. (Yo freelancers, you feel me?) One of mine is actually getting dressed. In the words of the wise scribe Blake Royer, "If you don't have pants on by 9 a.m., you're finished."

I can drink to that, Blake. It might be a throwback to the days of my high school dress code, but I do better work when I'm dressed for it. (Mention that you're a freelancer, and be prepared to hear how jealous people are that you get to work in bed wearing your underwear. That can work for some folks. But not me; I'll just end up power-eating dry pasta [think I'm kidding?] and marathoning FIFA's career mode all morning.)

That's why I put on clothes. And sometimes a tie—when I really need to make it rain.

So, when Jeff sent me his favorite one-word text ("Photoshoot?"), I was able to grudgingly hop on my bike and head straight to Logan Square to meet up with him and John.

A quick word about the tie: It's a stunner. I nabbed it from Lands' End Canvas on sale (you can, too), and I've been wearing it almost non-stop. I'd been looking for a bright tie, but what really made me notice it was the dual pattern on the narrow end. A subtle but fun detail. The only downside is that it wrinkles easily because it's cotton—but that's nothing a quick steam can't fix. Oh, and here's a bonus: It's made in America.

The shirt: I kept hearing about Modern Tailor (and other online made-to-measure clothing companies), but I was a little skeptical. Places like Reddit and StyleForum originally seemed to share my uncertainty about whether this was a good buy, but recently people have been more positive about the results. When I saw that first-time customers can customize a trial shirt (white, blue or black) for just under $20, I figured I'd take the plunge. 

I knew the blue would last longer than the white, so I took measurements from a few my best-fitting shirts. It ended up being a hybrid: the sleeves and shoulders of one, the torso of another, the tail from a third. My total came to $30, because I opted for a couple of upgrades, including mother-of-pearl buttons. I also went with the spread collar and notched cuff.

My only complaint is that the arm holes are a little high. They're snug in my pits, but that's because of the way I measured, and I can tweak it on the next one if I decide to go this route again. Otherwise, perfection. So far (after probably a dozen wears), the construction seems to be holding up—and slipping on a shirt that's made for your body creates an inexplicable feeling of invincibility. Of course, the price gets steeper (starting around $50 and going up from there except for the occasional sale), but I imagine I'll be going back.

On Seth: Spread-collar dress shirt ($30, promo) by Modern Tailor; cotton tie (sale $35, reg. $50) by Lands' End Canvas; "Kane" trousers in Aged Greystone courtesy of J Brand; self-made natural leather belt with help from Cause & Effect; woven and stitched loafers ($6, thrifted) by Giorgio Brutini; red tote (sale $40, reg. $150) by Filson; "Weekender" watch with olive strap ($29, Amazon) by Timex.

Photos by John Stoffer.