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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 In fact, that’s what originally made them popular with students, who wanted something comfortable and smart, but sufficiently casual to avoid looking corporate.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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Nothing softens the look of a leather jacket like suede. A plush, napped leather can be a good way to tone down the utilitarian origins of a bomber jacket or cafe racer – making them friendlier versions of their rugged counterparts. Want to wear a leather A-2 without looking like you’ve just stepped off the set of Top Gun? Or a double rider without people mistaking you for a Hells Angel? Get them in suede. 

The material can be particularly nice in the warmer months since it absorbs light. That gives the jacket a softer, more sophisticated appearance on a bright day than some of your smoother, shinier leathers. Plus, much like suede shoes, you can use them to add texture. A suede jacket lends visual interest to a plainer t-shirt or henley, but it also won’t clash with a patterned shirt. In the colder seasons, you can team one with a speckled Donegal sweater or cabled Aran for a texture-on-texture look. 

I recently picked up this suede five-zip from Maison Margiela (on sale at the moment at SSENSE). The design has been with the company for over ten years now, making it one of the more enduring non-traditional styles. It has long, diagonal zips across the chest – giving it an edge – although it’s still easy enough to wear with slim jeans or wool trousers. Pictured above: my Margiela jacket with a Barena henley, pair of 3sixteen jeans, and some Saint Laurent sneakers (the quality of the sneakers is admittedly terrible, especially for the price. Readers would be better off with Common Projects Achilles mid-tops in white). 

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One of the nice things about working with Steed is that they’re able to produce a single-piece back. Traditional patternmaking dictates that a center seam has to be put into the back of suit jackets and sport coats (if you pick one up, I’m sure you’ll see it). Much like darts, that seam is used to add shape – which is important since your spine naturally curves from the nape of your neck down to the small of your back, and then out again towards your seat. 

The problem is that the seam disrupts patterns. It’s unavoidable, really. If you think of how a pattern runs on a fabric (usually like a straight grid), it will naturally look off once it curves at certain parts. You’ll notice this most easily on pinstripes, where the spacing between the stripes is widest at the shoulder blades, before they curve in and touch at your waist. 

Steed solves this by getting all the shaping out of the side seams. So, without that center seam, your back has a smooth, uninterrupted pattern. 

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Summer calls for a different kind of necktie – one that’s brighter in color and lighter in weight than its cold weather relations. Mogadors, linens, and slubby silks are often the choices this time of year. Mogadors are favored for their vibrant colors, whereas linen, tussah, and shantung are used for their texture (see Mark Cho for inspiration). 

There are also Panama silks, which are woven in a way that’s similar to Panama hats (two wefts up, two down). Unfortunately, much like ancient madder silks, the texture here is hard to appreciate in photos. You really have to handle them in person to get the appeal, but so goes the travails of shopping online. 

When you do get a chance to feel them, however, you instantly understand why they pair so well with cotton and linen jackets. “It’s the dry hand and matte finishing,” says Drake’s Creative Director, Michael Hill. “Especially in dustier colors, such as this series we recently made, they just complement casual forms of tailoring.” 

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The term bespoke has a lot of marketing cachet nowadays. It’s used to describe anything and everything. There are bespoke salads, crackers, bacon, bicycles, cardboard boxes, and financial services. There’s even a ready-to-wear clothing line called Bespoken. 

Most of this is just harmless marketing hype – a way for brands to defend themselves against commodification – but some of it is disconcerting if you care about actual bespoke tailoring. Lots of made-to-measure and made-to-order services these days describe themselves as bespoke, even when they’re not, which makes it difficult for the casual consumer to know exactly what he’s getting. 

A couple of weeks ago, Simon Crompton wrote a basic primer on the differences between ready-to-wear, made-to-measure, and bespoke (it’s the start of a longer guide on how to buy tailored clothing). The info here will be nothing new for anyone who’s been interested in custom clothes for a while, but it’s the kind of thing that helps sets parameters for those just getting acquainted.  

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Saint Crispin’s might be the closest thing to bespoke shoes without actually being bespoke. It’s not just about their construction – Vass, Enzo Bonafé, and Meermin’s Linea Maestro line offer handwelted shoes at lower price points anyway – but rather the shaping. Saint Crispin’s puts a lot of shape into their shoes. Whereas other companies just sharpen the angles on their toe boxes, Saint Crispin’s cuts a tighter waist, higher arch, lower vamp, and curvier heel. As a result, their shoes look a lot more refined – which is why they go so well with tailored clothing. 

On the downside, there’s also much less room for error. Most ready-to-wear brands build a little more room into their shoes, which allows them to comfortably fit a wider range of customers. With Saint Crispin’s, however, you’re painfully made aware of every bump and misaligned angle if your shoes don’t fit perfectly. 

This problem must have been obvious early on because the company has an ingenious made-to-order program. Along with being able to change the leather and any design details, they can also customize their lasts. That means rasping off parts for a closer fit, or building up places that need more room. You can see one of Saint Crispin’s workers modifying a last in the video at the end of this post. 

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I’m fairly straightforward when it comes to tailored clothing. For shirts, I mostly wear light blues in stripes and solids – the latter in slightly more textured weaves than poplin (which I find too boring). End-on-end, oxford, and a heavier twill works well. A bold butcher stripe is a nice way to add visual interest to a tie-less, sport coat ensemble, while a solid blue shirt will serve as a nice background for any tie and jacket combination. As usual, I find if you limit the number of patterns you wear to two, you don’t have to think as much about pattern coordination. 

In contrast, my casualwear is all over the place, but lately I’ve been wearing shirts that are slightly more off-beat than your standard button-ups (or even the ever-reliable white tee). Outerwear tends to be simpler this time of year – assuming you can wear a jacket at all – so sometimes wearing an interesting shirt is about as much as you can do on a warm day. Four options I’ve been relying on: 

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