Chris: Esquivel Vanas wingtip boots
“George Esquivel is an amazingly talented guy, and he’s created his whole business around footwear that’s handmade in the United States. His shoes fit like a glove and they only get better with time. I like the updated toe box on this otherwise classic wingtip. George’s background is in the California punk and hardcore scene, and his designs reflect that ‘F-you’ attitude. ”
$538; On sale Tuesday at noon ET.
Tyler: Antonio Maurizi ankle boots
“I have to thank my colleague Chris for turning me on to Maurizi footwear, although it turns out that he and I differ when it comes to boot styling. I love a good wingtip, but I also subscribe to the belief that the only thing adorning the toebox of one’s boots should be scuffs from hard wear.”
$218; On sale Tuesday at noon ET.
Chris: John Smedley merino wool V-neck sweater
“This is our first time working with John Smedley, which is one of the first English knitwear manufacturers in the world. More than 225 years after its founding, Smedley still makes products in England using a combination of old-world techniques with state-of-the-art technology and design. I love the clean look of this V-neck with the bright blue trim to add a bit of color.”
$128; On sale Tuesday at noon ET.
Tyler: John Smedley merino turtleneck
“Now’s the time to locate your inner Steve McQueen (technically, there’s never really a bad time to do that) and embrace the late-’60s cool of a turtleneck under a blazer, McQueen style. This lighter weight merino is perfect for this time of year, and looks equally good with black (see below) or a gray herringbone.”
$108; On sale Tuesday at noon ET.
Chris: Corneliani wool plaid two-button blazer
“This jacket by Corneliani has a great tailored fit and a beautiful shoulder, and the fabric is sublime. It looks great for work, and just as good worn casually on the weekend with some jeans or cords.”
$598; On sale Wednesday at noon ET.
Tyler: Corneliani black blazer
“Purists who insist that brown and black should never intermingle ought to take a look at the brown leather elbow patches on this beautifully tailored black blazer. If you haven’t yet added Gilt MAN Essential #15 to your wardrobe, you’ve now officially got no excuse.”
$638; On sale Wednesday at noon ET.
Chris: Canterbury of New Zealand wool hunting jacket
“This jacket looks so cool and the price is amazing. What is surprising is that this quintessential American hunting jacket is made by Canterbury of New Zealand, a brand made famous by their signature rugby shirts. You can’t go wrong with this version—the look and fit is more modern than what you’ll find in the hunting shop.”
$78; On sale Thursday at noon ET.
Tyler: Nortwick quilted shirt/jacket
“Or, if you want something lighter weight, grab this work shirt from L.A.-based label Nortwick.”
$112.50; On sale Thursday at noon ET.
Chris: Titanium by Columbia hooded parka
“I don’t mountain climb, and no one would mistake me as an outdoorsy person, but I love this jacket by Columbia. It’s the perfect bad weather coat—it’s waterproof, breathable, lightweight, and has a hood.”
$139; On sale Thursday at noon ET.
Tyler: Titanium by Columbia Boulder Peak fleece
“With a fleece, it’s about performance, not fashion. Still, there’s no edge to be gained by a boxy fit, and you might as well go with a sharp-looking color, which is why I like this slim-fitting red jacket from Columbia’s stylish Titanium line.”
$39; On sale Thursday at noon ET.