Alden 403 Moc Toe Boot - Brown Chromexcel - $680 The classic "Indy" style Alden Boot in the classic Horween brown Chromexcel. 
Grant Stone Diesel Boot Dark Olive Chromexcel - #395 Goodyear welted, Horween Chromexcel, classic good looks. 
Himel Bros. - The Ross Mk. 1 Leather Jacket Classic D-pocket motorcycle/aviator style jacket. 
At least you live somewhere where it actually gets cold in the wintertime. I own an Eastman B-6 and I feel like the biggest poseur in the world wearing the jacket here in the San Francisco Bay Area. I have found that is one of the nicest jackets in the world to wear while taking an afternoon nap on the couch on a chilly day.
In my experience, Chicago is the coldest place in the country, irrespective of the actual temperature. I have spent a lot of time in NYC, and it is temperate compared to Chicago.
I was born in Chi Town, and lived there till I was 9. Then, moved to NYC. Even though I haven't live there since the 80s, I'm basically a New Yorker. I remember being cold in both cities as a kid. Been in CA. a long time now, got soft. Having said that, in my 20s I spent one winter in a small town in Northeastern Wyoming, just South of Billings Montana. 30 degrees below 0 F., without windchill, and the winds howled on the plains. Made the "Windy City" seem like a Spring breeze. Had to put in a block heater in my car and plug it in every night. Everyone left their cars running when they went into a store to shop (really small town). I could have really used the Aero Hercules CXL steerhide shearling/alpaca I just bought. Can't wear it in the SF Bay area. I also put it on and wear it around the house sometimes. Damn thing weighs 10 Lbs. Would look pretty silly wearing it in public.
Thgank you for your usefull advice, Dr Macabre!
I bought two Chevignon leather bomber jackets from the 80s, one black, one brown. Heavy leather and affordable pricing of these on ebay intrigued me, didn't expect much from them but wow, these are quality. Beautiful thick leather, perfect craftmanship, multiple inner pockets, everything you wish for. They have the sturdiness of a Vanson but a much more casual pizzaz to them, in a very good way.Both of them easily beat my very comparable Schott bomber jacket in every aspect. Look out for these, real bargain if you find one in your size.
Anyway, the black one arrived first and unfortunately, the lady who sold it to me, wasn't too good or maybe unprecise with the measuring tape, because it is way larger than described. And I am not talking 0.25"ish off, I am talking 2"+ off. I liked the jacket so much I kept it anyway, because who knows, maybe I'll get fat with age, I like to eat a lot after all and anyway, with some layering under it, I might get away with it.
Today it was cold, so I thought I'd give it a try. Put on a very thick wool sweater and wore the jacket out. The shoulders are drooping, and it still is quite the baggy fit, but it's very comfortable to wear, much more so than my tighter jackets. Very baggy overall, but I think I can get away with the look.
Came home to find the brown jacket having arrived, quickly took a snap of that as well. A thing to say about the color of this one: You know that thing with brown leather where you see a leather jacket in a movie and think: damn, I want one in that exact shade of brown, it's perfect. And two years later you have owned a dozen brown jackets and while they may or may not have been nice to look at, none of them quite had this color you once saw and were always looking for. Well, I'm telling you, this jacket is just that shade of brown. It's nicer than anything else I have seen and I have seen a lot. An incredible rich chestnut brown; medium-dark with the slightest faint of red in it. I will try to find someone with a decent camera to take some daylight high quality pictures of this because this one doesn't do it justice at all, overlighted, artificial light and an overall lousy camera on my old iphone. Anyway, loving this jacket. And the good news, this one fits a bit smaller than the black one, in fact it fits me pretty great, I believe! The collar is snap-on and it has an additional snap-on lining for those colder days.
i have one just like that cockpit usa
