For as long as I’ve been interested in shoes, I’ve always favored boots, and one of the first boots I fell in love with were Chelseas. An ankle-length, pull-on boot with elasticized gussets, they were originally invented as an easier-to-wear alternative to button-boots. It wasn’t until the 1960s, however, when they really took off. That’s when they were picked up by rebellious youths in Chelsea, London (hence the name) and The Beatles (although, technically speaking, The Beatles wore a modified version with Cuban heels). 

My first Chelseas were RM Williams’ Gardener. Rounded and clunky, I found them too casual for my wardrobe, so they were replaced a few years later with Edward Green’s Newmarkets. Since then, I’ve learned Chelseas can be worn with almost anything – black ones with slim, charcoal suits for a Modish look, or black jeans and black leather jackets for something edgier. Brown suede Chelseas go well with denim and olive field jackets, or just jeans and chambray shirts. 

I’ve liked my Newmarkets so much that I recently decided to revisit RM Williams’ catalog – this time picking up a pair of their sleeker Craftsman model in tan suede. They cost a fraction of the price of my Edward Greens, but the chiseled, angular toe box lends a more distinctive look than EG’s 202 last (which my Newmarkets are built on). The pull tabs have logos, which is unfortunate, but you don’t really see them when they’re tucked underneath your pants. 

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My favorite jacket from Steed isn’t even something I own. It’s a cream-colored DB Edwin once cut for style writer Glenn O’Brien. In an old feature at GQ, O’Brien said of it: “I have a few tuxes. I guess in case somebody books me in Vegas for a couple of nights. My first-string tux is a peak-lapel Anderson & Sheppard – makes me feel like a million plus. Another is a shawl-collar double-breasted tux. The oddball in my formal wardrobe is this double-breasted white dinner jacket I had made by Steed of Savile Row. It’s not really white, but sort of ‘clotted cream.’ Somehow I rarely wear it. Maybe I’ll throw it on for a party some hot night.” 

If tailored clothing can be hard to wear in the 2016, semi-formal clothes are only more so (and none harder to wear than a cream-colored dinner jacket, as O’Brien notes). Generally speaking, such jackets are reserved for open-air social gatherings on hot, summer evenings. Think: country club dances, yacht club parties, and outdoor weddings (presuming you’re the groom).  

Much of this comes from the jacket’s origins. In the 1930s, well-heeled vacationers wanted something formal they could wear in the tropics, but without having to endure the heavier, darker fabrics traditionally found on evening clothes. So they had white dinner jackets made, originally with single-breasted closures and shawl collar lapels, although double-breasted designs later became popular. 

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End made another round of markdowns and added some new things to their sale section last night. There are some surprisingly good deals, especially when you consider that some of their prices are already lower than what you’d pay in the US (mostly thanks to them discounting for VAT). 

Among some of the more surprising finds, there are Inis Meain and SNS Herning sweaters starting at $115.  Inis Meain’s linen crewnecks, for example, are just $119 (well below the $400+ you’d pay in the US). I wear mine with leather jackets on weekends. There’s also a good selection of Barbour jackets starting at $105, raw denim jeans for $89, and Buttero sneakers for just $115. 

Some other things I like:

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It’s no secret that the key to wearing tailored clothes in the summer is to get something with an open weave. Style writers mention the same line every July: get a jacket that’s softly tailored and unlined, made from a tropical wool or porous linen. That way, you can feel every passing summer breeze. 

The same idea applies to shirts. Everyone knows you can wear a lightweight cotton or linen shirt on a hot day, but few people think about the weave. 

At the most basic level, plain weaves are often more breathable than twills, although not all plain weaves are built alike. Some can be tight; others a bit loose. I recently picked up a few things from Acorn in the UK (a recommendable fabric supplier for those who get custom shirts made. Their cloths are a good value, even if they’re not particularly luxurious). A run down of some of their summer options:

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Small companies often have charming stories and interesting provenance, but sadly, sometimes the quality just isn’t there. That’s the case with Miserocchi, the original car shoe company that invented driving moccasins back in 1942. Their most famous customer, Gianni Agnelli, wore them with soft-shouldered suits and spread-collar polos. After a car accident left him permanently injured, he found their slip-ons much more comfortable than anything stiff or welted.  

In the world of driving moccasins, Miserocchi is dwarfed by Car Shoe and Tod’s, who produce their shoes by the thousands in Eastern Europe and Italy. Miserocchi, on the other hand, still operates out of a small workshop in the alpine village of Domodossola. Supposedly, the two brothers who founded the company had a falling out many years ago. One took the company name, which he later sold to Prada. The other kept the factory, which is now run by his sons. As the marketing line goes, the company still produces everything the way they did fifty years ago, even with a bright red model named after Agnelli (which is what the industrialist wore). 

All that means little, however, once you actually order from them. Back when he was still writing, Will at A Suitable Wardrobe complained about how it took months to get his shoes, and how there were tons of unanswered emails and missed delivery dates in the process. My experience, unfortunately, was the same. It took about three months to receive my order and once I did, I was disappointed with the quality. The leathers are cheap and thin; the soles have loose stitching; and there’s visible glue at the heel. Perhaps worst of all, these just aren’t terribly comfortable. The insoles are made from a hard rubber – much harder than what’s used in my Car Shoes – which makes these feel like Italian getas. 

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Pitti Uomo is happening this week. The bi-annual menswear tradeshow is mostly a place where brands and stores meet for their seasonal buys, but in the last few years, it’s also become into a jostling peacock event. Street style photographers descend on the show to take pictures of the more extravagantly dressed men – and some attendees couldn’t be happier to oblige. I can’t tell if the guys dressed like Dick Tracy villains look like that in everyday life or if it’s just a show for internet attention. 

In the sea of bad, however, there’s often some good. The key, I think, is finding the right photographer. One of my favorites is Maxime Tormen, a former tailor at Sartoria Ripense who shoots street style photos in his free time. His blog, Neo Retro Style, doesn’t have the kind of post-processing you see on other style sites (e.g. saturated colors pumped up to 100), but in some ways, that only makes his images more relatable. 

For guys who visit style blogs often, a lot of faces here may be familiar: bespoke tailors Edward Sexton, Antonio Panico, and Kotaro Miyahira; designer Yasuto Kamoshita (pictured above); and store owners Mark Cho, Simon Righi, and George Wang. I think Tormen also has some of the best photos of Our Mystery Man (who turns out to be Noboru Kakuta, although little else is known about him). 

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The penny loafer was the sine non qua of the post-war Ivy Look. Often worn with Shetland sweaters, flat front chinos, and tweed sport coats, they were the choice of Ivy League students across the East Coast, later finding broader appeal through Esquire. More than being an Ivy shoe, however, penny loafers embody the kind of casual, dressed-down style that the US has always championed (much like button-down collars, in that sense). In fact, that’s what originally made them popular with students, who wanted something comfortable and smart, but sufficiently casual to avoid looking corporate. 

Which is why they continue to be so great today. They’re dressier than sneakers, but not as formal as wingtips. They go just as well with jeans and casual jackets as they do with sport coats and trousers. The Prince of Wales even wears them with casual suits (although I don’t recommend them with dark business suits). 

If the penny loafer is an American icon, it stands to reason that the best pennies ought to be from a US company. Unfortunately, G.H. Bass – who invented the style in the 1930s by placing a vamp saddle on a Norwegian slip-on – hasn’t made good shoes in decades. That leaves Alden, Allen Edmonds, and Rancourt, all three of which are good, but I find their best pennies to be very casual. Alden’s partially lined slip-ons, for example, go well with jeans and Trad looks, but their dressier, Copley-lasted loafers don’t have as much sophistication as Edward Green’s Piccadilly (my favorite with tailored clothing). 

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When it rains, it pours. End just started their end-of season sale, where you can take 25% off select items with the checkout code SALEPREVIEW. There are some exclusions (the code won’t work on Common Projects or already marked-down inventory, for example), but it applies to most of the store. 

Perhaps the most exciting inclusion: Barbour, where export restrictions have now been lifted. For the last two years, Barbour hasn’t allowed EU retailers to ship to the US (mostly as a way to protect their other distributors). End confirmed with me this morning, however, that US orders are now fine and the code applies to mainline models such as the Bedale and Beaufort. If you need more info about how the jackets differ, refer to the Barbour buying guide I wrote for Put This On. 

I also like Margiela’s German Army Trainers. They’re little old-hat at this point for style enthusiasts, but easy to wear and incredibly versatile. Additionally, Inis Meain, Inverallan, and SNS Herning make wonderful sweaters, while Nigel Cabourn and Mackintosh are always good for outerwear (I like especially like Cabourn’s Surface and Aircraft jackets). Filson’s canvas bags are also really useful. 

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Mr. Porter’s end-of-season sale is always one of the most exciting sales events. Where else can you find marked-down Drake’s ties and John Lobb shoes being sold alongside discounted casualwear items from Aspesi, Camoshita, and Kapital? 

This morning, they dropped prices on their spring/ summer inventory by 30% to 50%. For a thorough browse, go to their sale page and filter by sizes. That won’t capture some of the Japanese brands – where you sometimes have to size up – but it’s a nice way to serendipitously find things you may not have considered otherwise. I’ve also rounded up some of my favorite items below:

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There’s been a lot of talk lately about palewave – a lighter colored, ‘90-influenced aesthetic that’s grown as a reaction to modernist streetwear. So, instead of black technical jackets with black jeans, you have light-washed jeans, white minimalist sneakers, and a general reliance on white/ beige color palettes. I think the style works on the right person, but if someone dismissed it as ‘90s normcore, hipster nonsense, I wouldn’t blame them. A lot of the clothes can be pretty ugly – maybe something like “‘90s Spanish textbook style” repackaged with a bit of irony. 

What makes palewave compelling isn’t necessarily about the clothes, however. It’s more about the color combinations. Most men rely on the same formula for how they dress: a lighter pair of pants is sandwiched between a dark jacket and dark pair of shoes. This allows all three items to look distinct. 

Palewave is the opposite. It’s about exclusively relying on light colors and minimal contrast, which doesn’t have to be limited to just casualwear. See many of the examples here for great tailored looks. 

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