Every six months or so, our friends at Oak Street Bootmakers create a few pieces of limited-edition footwear exclusively for us. Below you’ll see our collection for spring, available only at Trunk Club.
We’re big fans of Oak Street Bootmakers for a lot of reasons:
A Trunk Club blog reader named Tyler asks:
“There was a pretty heated intra-office debate that raged on today about when it’s acceptable for a guy to wear dressier shoes with jeans. I submit that it is never acceptable. Care to weigh in?”
Before getting into the Trunk Club–specific take on this issue, we passed Tyler’s question onto Bill White, founder of one of our favorite shoemakers, Scarpe DiBianco.
Here’s what Bill had to say:
Unless you’re wearing a tuxedo or working as a referee, we suggest avoiding black shoes. Brown provides a much more versatile footwear option because it pairs nicely with every color of clothing except black (navy suits in particular look good with brown or burgundy shoes). And versatility, of course, is the key to each of the six men’s clothing essentials.
English shoemakers have a proud tradition of bench-made footwear, like these Monorgan Boots from D.S. Dundee. (We featured the Monorgan last month in our post on brogues.) But what, exactly, does “bench-made” mean?
To find out, we talked to Jonathan Church, joint managing director at Cheaney Shoes. Cheaney has manufactured footwear in the same factory since 1886, and currently makes the Monorgan Boot especially for D.S. Dundee.
We asked Jonathan to describe each stage of the bench-made process in relation to the Monorgan Boot, including as many details as possible.
He did not disappoint.
To beat the winter cold, you might be thinking about leaving town for a long weekend somewhere warm. Or maybe you plan to embrace the chill by hitting the slopes. Either way, we created this guide to help you pack.
The term “brogues” refers to any shoe with decorative perforation. Our British friends, no strangers to inclement weather, started poking holes in shoes centuries ago, as a way to drain excess water. Since then we’ve developed more effective solutions for weather-resistant footwear, but brogues have nonetheless stayed in demand. During the last few years in particular, brogues have enjoyed a huge spike in popularity as shoemakers experimented with more casual styles.
We recently talked to Jason Smith, Trunk Club V.P. of Product, about the brogues currently making the most buzz among both Trunk Club stylists and our members.
Fratelli Rossetti Wingtips
These Fratelli Rossetti wingtips are hand-painted and then washed, which creates an assortment of highs and lows unique to each shoe. The glossy sheen in the toes gradually gives way to a matte finish, creating an effect that looks particularly good in relaxed settings.
This image recently accompanied an email to Trunk Club members, breaking down different outfits for holiday parties, based on degrees of formality.
Any favorites?
If you’re a frequent flyer, the article below might look familiar. In-flight magazines have recently featured the following tips from our CEO, as we continue to help guys looks their best for all occasions, including flying.
Click (and then click again) for the larger image.
Images from the Salesforce.com blog post, “How to Dress to Get the Job Done,” featuring tips from our V.P. of Product. To read the post, click here.
In 1883, the manager of the Buffalo Bisons pro baseball team started pitcher Jim “Pud” Galvin 75 games. To deal with the intense workload, Galvin resorted to drinking an elixir spiked with monkey testosterone. (True story.)
We’ve become much more humane to baseball pitchers in the years since. Unfortunately, lots of guys continue to treat their shoes like Puds, putting one favorite pair through the wringer day after day without sufficient rest. This reduces the shoes’ lifespan, and prevents guys from looking their best at all times.
A rotation that includes the following prospects will give your shoes long careers, and keep you ahead in the count regardless of the situation.
The following is taken from our July 4th member email.
Everything’s retro these days, from cassette-only music labels to 1990s-era adjustable ball caps. Not every item from history, however, deserves a comeback. Here are four fashions from America’s past that we’re better off never seeing again.
Colonial wigs
The style, color, and size of the colonial gentleman’s wig indicated wealth and social standing. But status came at a price: Wigs were incredibly uncomfortable, in no small part because they attracted a host of insects including the infamous “wig weevil.”
Gentlemen’s gloves
Early American gentlemen found their gloves nearly impossible to keep clean, what with constantly throwing them on the ground to challenge people to duels. We modern guys, of course, have developed more civilized ways to settle our differences, like anonymous online message boards.
Square-toed shoes
Popularized by Pilgrims, square-toed shoes survive to this day—only without those humongous buckles, and despite their tendency to make a gentleman’s stride resemble a duck’s waddle. Luckily, there’s no shortage of options for more flattering footwear.
Cargo pants
We totally get it: Cargo pants are comfortable and offer plenty of storage space. Unfortunately, their sheer bulk adds on pounds and creates an untidy appearance. Unless you’re in the bush hunting big game, we suggest a better-fitting trouser.
Tim Wilson joined Trunk Club in 2010. He recently took time away from his MBA studies for some photos near our Chicago HQ. Afterwards, we sat down for a little back-and-forth.
Any good stories about how your Trunk Club clothes have helped you out?
Um … yes, although I’m going to have to be pretty vague here. I’ll just say that I was wearing a pair of red AG pants this past weekend for Cinco de Derby, and they resulted in me getting called over from across the bar to meet a girl who had been an object of extremely high interest at our table for most of the day. I find Trunk Club clothes result in introductions like that a lot.
How does Trunk Club compare to your previous shopping experiences?
There’s no comparison. Trunk Club is infinitely simpler, with a much higher satisfaction level. I feel like before when I shopped on my own, (1) I hated it, and (2) I’d end up wearing about half of the things I got, whereas now I know I’ll wear and love everything I get from Trunk Club. Plus everything fits much better now.
What’s the best part about working with Lisa? (Lisa Bubes is Tim’s Trunk Club stylist. Her Twitter: @LBTheStylist.)
My favorite part has been Lisa’s ability to push me a little bit on what clothes I’m comfortable with, while staying within the range of style that I like. For example, I’ve now got both red and green pants, as well as a pair of white jeans, all of which I wear.
Overall, how has Trunk Club changed your experience with clothing?
It’s simplified my life a lot and just given me a much higher level of confidence in the clothes I wear. It’s helped me actually enjoy buying and owning clothes.
Want to hear more about Tim’s experience as a Trunk Club member, or debate the merits of Carly Rae Jepsen’s pop-rock stylings? You can do both by hitting him up on Twitter: @twilson22.
Our signature “Tetris” layout. To have game, all you need is that square piece in the middle.
Yep, that’s a lot of shoes, but we’re not saying you have to be the male Imelda Marcos here. It only takes a few pairs of solid shoes to keep a guy looking great from the ground up.