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Welcome to the first ever PGP Style Mailbag. I’ve considered writing a recurring column like this one for some time now, but it never felt quite right, and I wasn’t sure that I was receiving the proper volume of questions to produce quality content. Now, however, after my most recent guest spot on the Touching Base podcast, I’m receiving more Instagram DMs and Twitter mentions than ever before, so I believe the opportune moment has arrived. I’ve also been inspired by Dillon’s weekly mailbag which I enjoy very much, so I’m going to ride the coattails of his success and hope that y’all like this one too.
If you’ve got a style dilemma or question you’d like answered, hit me up on
Twitter or Instagram. You can also shoot me an e-mail at firstname.lastname@example.org. While I’m not quite as knowledgeable about women’s fashion, I do pay close attention to it as well, so ladies, feel free to jump in here too.
Hey man. Really enjoyed all your fall wear thoughts on Touching Base #113 today. Care to give your thoughts on a couple more things I’ve been pondering?
• Noticed you weren’t really for the sneakers/jeans combo.. what if it’s something sorta throwback-ish like the J. Crew Nike Killshot 2? I’m thinking about grabbing a pair.
• Time for new dress shoes: Brown wing tips or plain toe oxfords for an all-purpose business casual shoe? Would be worn mostly with chinos paired with either button downs or polos. I get caught up with trying to find something not too dressy so it’ll still flow with the more casual chinos and a polo look.
Perfect, we can knock out two great shoe questions in one answer.
First, I want to clarify that I am a major proponent of the sneakers with jeans look. All it takes is a quick scroll through my Instagram feed to see that I pair these two things together all the time. What you should not do under any circumstances, however, is wear a pair of performance sneakers with jeans. If the sneakers you’re thinking about wearing with jeans were designed specifically and exclusively for running or working out, do not proceed. I feel like this is common sense, yet I routinely see guys wearing Brooks or Asics or Saucony running shoes with jeans. Stop it.
Here’s a list of some throwback style sneakers from well-known athletic brands like @crowderruss mentioned that would look good with jeans, and none of them are too rough on your wallet:
• Nike Killshot
• Nike Air Force 1
• Nike AirMax 90
• Converse Chuck Taylor
• Converse Jack Purcell
• Converse One Star
• Adidas Gazelle
• Adidas Campus
• Adidas Stan Smith
• Puma Clyde
• Puma Suede
• Vans Authentic
• Vans Old Skool
• Vans Classic Slip-on
• Seavees Hawthorne Slip-on
• Seavees Legend
Looking for something slightly dressier? Check out the Cole Haan GrandPros. Ready to jump into upper-division style courses? Look at the Buttero Tanino Low or the Frye Walker Low. And of course, I would be remiss to not mention the end-all-be-all of the elevated minimalist sneaker, the Common Projects Achilles Low. Yes, they are expensive. Yes, they are worth the investment. My oldest pair is from 2009 — they are still in phenomenal shape and look great.
As for question two, I think your go-to versatile dress shoes should be a blucher or an oxford with either a plain or a cap-toe. (Choose an oxford if your fits lean dressy, blucher if they lean casual.) Once you’ve locked down something solid in this department, then spread your wings and opt for a wingtip on the next pair. The wingtip is inherently flashier. In some offices they can even be looked upon as the shoe equivalent of a French-cuffed partner’s shirt, meaning if you’re not a high-level exec, you shouldn’t be wearing them. On the podcast, I mentioned two great direct-to-consumer businesses that make for good places to start. Click here for Meermin Mallorca and here for Jack Erwin.
Is it okay to wear shorts on a plane if you’re flying first and have no danger of the bare thigh leg rub?
We’ve chatted a little bit about airport and airplane style etiquette recently, and I gave three main guidelines to stick to:
• No flip-flops or sandals.
• No tank tops.
• No shorts.
Guideline number three is the most flexible. If both the departure and the arrival city are miserable swamps and you’re flying in August? Sure, wear shorts. Flying first class and have no risk of your bare thigh grazing a fellow flyer? Yeah, that works. On a coast-to-coast or international flight and just can’t deal with pants for four plus hours? I’m with you. The thing to remember about flying is that you’re trying to be comfortable without making anybody else uncomfortable. Just make sure you smell decent, try to look presentable, and above all else, be polite to your fellow travelers and airline employees.
I’m seeking your sage wisdom and advice regarding a conundrum I’ve been experiencing. File this away for future columns or podcasts if you want…
Is it a fashion faux pas to wear desert boots in the summer? “Desert” implies that it is a warm weather shoe, but nonetheless wearing a boot in summer still feels a bit odd. However, they look good with such a wide variety of outfits that it’d be nice to have them as an option year-round.
This was an e-mail I’ve had filed away for a few months, and even though summer is now officially over, I’m still going to address it since there are many of us with at least 6 more weeks of heat ahead of us. If there was ever a shoe that fits the definition of multi-seasonal, it’s the trusty desert boot. Suede, as a fabric, is generally considered great for at least three seasons, and when rendered in a low cut and floppy boot like the Clarks Original, for example, it’s perfect for summer as well. Pair them with lightweight chinos or white jeans and a t-shirt.
As an aside on desert boots:
A month or two ago, a contributor to the PGP subreddit reduced my fashion guidance to telling everybody to go buy a pair of chukka or desert boots. My rebuttal is that I see this as a really important early step when a guy is trying to graduate from his college style to something more grown-up. After living in a rotation of New Balance 991s, deck shoes, Rainbows, and western boots for four years, it can be hard to escape that routine. Putting on a pair of ankle boots to accompany your new slimmer, darker denim and your shorter, less preppy flannel is the quickest way to transform your look. It’s an approachable and subtle change. It’s not scary, and you will still feel like yourself. It opens the door to buying more expensive clothing, to taking bolder fashion risks, and to learning more about the world of fashion. If the very first thing I mentioned to you guys was that I swear by $400 Common Projects sneakers, y’all would recoil in horror like a scared turtle, and I’d never get any of you to give up the bleached Wranglers and the Sperrys.
I’m a little late to the party but I just listened to the DDB podcast you were a part of about a week and a half ago (Author’s note: nearly a year ago now, sorry!). You made an excellent point about button-down shirt length, and I had a question about flannels. I’m looking for some good quality flannel or “flannel-esque” button downs that can be worn untucked. Unfortunately, a lot of the ones I’ve found are either way too heavy (I live in Houston) or too long. Any suggestions on brands?
If you like to wear your shirts untucked, length is the biggest part of the equation. This is especially true for shorter guys as we’ll revisit further down the page. If you want to keep it in the family, RVCA is the brand I’d recommend for you on Man Outfitters. This is probably my favorite one on the site right now. RVCA definitely designed this shirt to be worn untucked, so I trust that the length keeps that in mind.
I’ve also had a really good experience with my J.Crew slim fit flannels as well as the ones I have from Gant Rugger. I also feel like I have to address a brand called UNTUCKit here since, as the name suggests, they based their entire line on this exact style issue. I have zero experience with their product, but to be perfectly honest, I don’t think the shirts look very good online, and for the price, I think you’re getting a better looking and more fashionable garment from J.Crew or Bonobos.
Long time listener here. Love your takes on all of your appearances on TB.
Even more so, I love the depth of knowledge you bring to OCC. Keeping characters straight is one of my major flaws as it comes to TV watching, and the fact you can name them, both character and actor, during your analysis makes listening even more enjoyable.
You probably have touched on this on any number of the Touching Base appearances you have made over the year, so if you’ve already answered this, forgive me. I’ll go back and listen and figure it all out.
Do you have any advice, do’s and dont’s, for dressing as it relates to body type? I know the number one rule is to typically get your stuff tailored, but I mean more so, like styles of clothes, patterns, colors, etc?
Case in point: I’m 5’9″ and stocky. I personally know the slim fit stuff looks tight and uncomfortable on me, but the word “tailored” in the shirt description typically does okay. Jeans, I may as well buy one that’s a size too big, knowing I’ll need to get the waist brought in, and the pants tapered and likely shortened is easier than actually searching the rack for brands that fit.
Any advice for someone like me who can’t fit into anything at H&M and is trying to have a more grown-up version of the button down and jeans?
What about for the tall and skinny guys?
I’m including this e-mail for a couple of reasons.
First, it’s a great opportunity to plug the podcast that I co-host with Ross Bolen and Veronica Ruckh, Oysters, Clams & Cockles. It’s the number one podcast in the realm for Game of Thrones fans that party like Tyrion and slay like Danerys. We’re currently doing a rewatch of the entire series to get prepared for the final season. We’re doing one episode a week, and we’re still on Season 1, so it’s the perfect time to jump on this crazy train and re-watch with us.
Second, this is the perfect submission for readers to help with and chime in on. I’ve definitely gotten this question from the bigger dudes out there a few times before. I think the best piece of advice I can give is that you don’t have to wear baggier clothing just because you’re bigger, but I understand that it’s much harder to find things that are cut right. IIRC, some of you have highly recommended the Athletic fit pants from Bonobos. I would also recommend finding a celebrity that’s got a similar body type and looking up street style photos of them. For 5’9” and stocky, Jonah Hill comes to mind.
Figure out what you like about how they dress and then do your best to emulate it.
As for colors and styles, I can tell you that black and navy are always flattering and always slimming on virtually everybody. For us shorter guys, pants with no break and cropped outerwear will make us look taller. On the flip side, untucked shirts that are too long and pants that bunch at the ankles will make you look shorter. Vertical stripes on shirts can also elongate the silhouette, while horizontal stripes can accentuate and further widen a stockier frame.
To the tall guys and the bigger guys out there, what say you? Help me with the advice here in the comments..