“Much confusion arises about Astaire’s style because his style changed subtly over the years: his coats were tighter in the earlier years, a bit more roomy in the 1940s, and slimmer again later on; in his later films he wore fairly slim trousers. In other words, Astaire followed fashion a bit too.” Bruce Boyer on Fred Astaire

How I Learned to Stop Worrying and Love the Wear

Like anyone who feels guilty about how much they’ve spent on their shoes, I’m fairly good at taking care of my footwear. I apply cream and wax polishes every few weeks, and leather conditioner even more frequently. Before any pair goes out for wearing, it gets brushed down to remove any dust or dirt.

I’ve learned, however, that some shoes look better the less you take care of them. This includes work boots, engineer boots, camp mocs, boat shoes, and almost anything that’s considered extremely casual. These still get treated to leather conditioner, just not that often (maybe once every six months to a year). Things such as cream and wax polishes, however, never get used, and shoe trees never get inserted. If you’ve ever wondered whether these things really make a difference, just try going without them for a year. You’ll see that creases develop more quickly and set on deeper when they do. Scuffs and scars will also show up more without the “cover-up” of polish. 

For certain shoes, however you want this kind of “damage” to appear. It gives them character and makes them more lived-in. This gets back to a very fundamental idea that nothing looks good when it’s too new or too stiff. That doesn’t just go for certain styles of footwear – it goes for things such as tweed jackets, briefcases, and almost all kinds of outerwear. It’s perhaps for this reason why there are stories about how Fred Astaire used to throw his new bespoke suits up against the wall before wearing them, and how Charlie Davidson of The Andover Shop won’t even wear a new jacket until it’s been sitting on a hanger for a year. 

Of course, with dressier shoes, careful polishing, edge dressing, and even the occasional bulling can be great. Those will give your shoes a certain kind of luster that’s in keeping with the style. With everything else, however, all you need really is the occasional treatment of leather conditioner. As you can see in the last photo, as long as you buy shoes of good quality - and keep the leather supple so it doesn’t crack - they can be repaired to good effect. And why would you want to recraft an old pair of boat shoes when new ones can be bought for not much more money? Because the old ones look a lot better.   

(Photos via Andrew Chen of 3sixteen, Mister Freedom, Oak Street Bootmakers, and Rancourt)

Q & Answer: Can I Wear A Button-Down Collar Shirt With A Suit?
Timothy asks: In the pictures accompanying your post “That Enviable Roll,” several of the gentlemen appeared to be wearing suits. I thought OCBDs should not generally be worn with suits. Can you provide some insight?
Button-down collared shirts are the most casual long-sleeve dress shirts you can wear. So casual that I thought twice about describing them as dress shirts in that last sentence. They were developed for wear during sport - that’s why Brooks Brothers still calls them the “polo collar.”
Of course, the story of American style has been, over the last hundred years or so, a march towards the casual. Starting sometime around the middle of the 20th century, that included wearing button-down collared oxfords with suits. It looks great on Paul Newman (above), or on Fred Astaire (who was always about to break into dance), but what about you?
Generally, I’d discourage it. If you’re a J. Press man, wearing nothing but traditional soft-shouldered, undarted, single-vented “Ivy League” suits, I think you’re fine. I think the aesthetic coherence of that style trumps the conflict between the casual collar and more formal suit.
In practice, though, that’s rarely what I see on the street. Generally, I see men who have combined these elements thoughtlessly, perhaps because their wives bought them a dozen shirts one day at Costco and they went from there. That’s a look that does nobody any favors.
So, when to wear a button down? With an odd jacket, blazer or sportcoat, especially a casual one, like something linen or tweed. With a bowtie. When you’re committing to an American “trad” aesthetic. When you’re not wearing a coat and tie at all.
Hope that helps.

Q & Answer: Can I Wear A Button-Down Collar Shirt With A Suit?

Timothy asks: In the pictures accompanying your post “That Enviable Roll,” several of the gentlemen appeared to be wearing suits. I thought OCBDs should not generally be worn with suits. Can you provide some insight?

Button-down collared shirts are the most casual long-sleeve dress shirts you can wear. So casual that I thought twice about describing them as dress shirts in that last sentence. They were developed for wear during sport - that’s why Brooks Brothers still calls them the “polo collar.”

Of course, the story of American style has been, over the last hundred years or so, a march towards the casual. Starting sometime around the middle of the 20th century, that included wearing button-down collared oxfords with suits. It looks great on Paul Newman (above), or on Fred Astaire (who was always about to break into dance), but what about you?

Generally, I’d discourage it. If you’re a J. Press man, wearing nothing but traditional soft-shouldered, undarted, single-vented “Ivy League” suits, I think you’re fine. I think the aesthetic coherence of that style trumps the conflict between the casual collar and more formal suit.

In practice, though, that’s rarely what I see on the street. Generally, I see men who have combined these elements thoughtlessly, perhaps because their wives bought them a dozen shirts one day at Costco and they went from there. That’s a look that does nobody any favors.

So, when to wear a button down? With an odd jacket, blazer or sportcoat, especially a casual one, like something linen or tweed. With a bowtie. When you’re committing to an American “trad” aesthetic. When you’re not wearing a coat and tie at all.

Hope that helps.

This photo of Fred Astaire in a pair of true natural waisted trousers (trousers that come up to your natural waist) reminds me of the "Happy Pants" song. 
"Put on your happy pants, in your happy pants, you’ll laugh a while!" 
(Photo via A Suitable Wardrobe)

This photo of Fred Astaire in a pair of true natural waisted trousers (trousers that come up to your natural waist) reminds me of the "Happy Pants" song

"Put on your happy pants, in your happy pants, you’ll laugh a while!" 

(Photo via A Suitable Wardrobe)

PTO Man: G. Bruce Boyer

In this special bonus preview for Season Two of the menswear series Put This On, writer G. Bruce Boyer talks about his distinctly rumpled style. He says the clothes you wear are an armor against the slings and arrows of life, and you should enjoy them.

"You play to your strengths, you know? And my strengths happened to be rumpled."

G. Bruce Boyer’s latest book is Gary Cooper: Enduring Style.

Season Two of Put This On premieres March 13th at PutThisOn.com, along with the DVD of Season One.

Directed by Benjamin Ahr Harrison
Executive Producers Adam Lisagor & Jesse Thorn
Producer Andrew Yamato
Director of Photography Ryan Samul
Sound Andrew Reardon

Special thanks to Leonard Logsdail

Steven Hitchcock shows off one of his high armholes. Such armholes will allow you to lift up your arms without moving the rest of your coat. As Steven writes, “You will be in control of the coat not the other way around.”
Of course, there are other things that facilitate a comfort and movement, and it’s best not to get too fixated on armholes alone. However, whether you’re buying off-the-rack or getting something custom-made, it’s important to lift your arms a bit to see if you have a good fitting jacket. You don’t just stand in front of mirrors all day, after all, you move. 
For a very interesting read about Fred Astaire’s armholes, which are kind of legendary among bespoke enthusiasts, check out this interesting article by Kerry Goodrich. Sometimes photos like this are posted when the topic of movement comes up, but as Goodrich explains, there are important trade-offs. 

Steven Hitchcock shows off one of his high armholes. Such armholes will allow you to lift up your arms without moving the rest of your coat. As Steven writes, “You will be in control of the coat not the other way around.”

Of course, there are other things that facilitate a comfort and movement, and it’s best not to get too fixated on armholes alone. However, whether you’re buying off-the-rack or getting something custom-made, it’s important to lift your arms a bit to see if you have a good fitting jacket. You don’t just stand in front of mirrors all day, after all, you move. 

For a very interesting read about Fred Astaire’s armholes, which are kind of legendary among bespoke enthusiasts, check out this interesting article by Kerry Goodrich. Sometimes photos like this are posted when the topic of movement comes up, but as Goodrich explains, there are important trade-offs. 

“Be yourself - but don’t be conspicuous.” — Fred Astaire’s style philosophy
“The unpadded shoulders, the three-buttoned long and boxy coat, the too-short, thin pants, and the thin ties with striped buttoned shirts in dark colors—well, I suppose this may go very well with some personalities but it’s not for me. To me, all such look like TV producers. Maybe they want to.”

Fred Astaire on the Ivy League look

(via ASW)

“It was Deborah Landis’s job to play up Jackson’s masculinity while dressing him in hip, casual clothes that were comfortable for dancing. Since the video would be shot at night in a mostly somber palette, she says, “I felt that red would really pop in front of the ghouls.” She chose the same color for both his jacket and jeans to emphasize a vertical line, making his five-foot-seven-inch, 100-pound frame appear taller. “The socks and the shoes were his own,” she says. “He took that directly from Fred Astaire, who always wore soft leather loafers to dance in, and socks. And Michael was elegant. I worked with David Bowie, who was also that same body frame, again very, very slim. Fred Astaire was a 36 regular; Michael was a 36 regular. David and Michael and Fred Astaire—you could literally put them in anything, and they would carry themselves with a distinction and with confidence and with sexuality.”” From Vanity Fair’s The “Thriller” Diaries