Who would wear paintings as buttons? The Cooper-Hewitt has the full story of these remarkable fasteners - and it purportedly involves Toussaint L’Ouverture, the legenedary slaved-turned-leader of Haiti.
abitofcolor:

Blazer Buttons - Classics found at Cable Car Clothiers San Francisco. 

There are a million choices when it comes to blazer buttons - try searching for blazer button sets on eBay, visiting a great fabric and notions store, stopping into a trad store like Cable Car Clothiers, or looking online somewhere like Hwa Seng. The actual replacement of the buttons won’t cost you more than ten or fifteen dollars, and the possibilities are endless.

abitofcolor:

Blazer Buttons - Classics found at Cable Car Clothiers San Francisco. 

There are a million choices when it comes to blazer buttons - try searching for blazer button sets on eBay, visiting a great fabric and notions store, stopping into a trad store like Cable Car Clothiers, or looking online somewhere like Hwa Seng. The actual replacement of the buttons won’t cost you more than ten or fifteen dollars, and the possibilities are endless.

Getting Your Buttons Down
Knowing how to properly sew on a button is perhaps one of the most useful clothes-related skills you can pick up. Buttons occasionally fall off even the best of garments, and need replacing, or sometimes we wish to swap out the manufacturer’s buttons for something else. A mid-tier cardigan, for example, can be made much better looking if you change out the plastic buttons for some horn ones.
There are many good instructional guides online that’ll show you how to sew on a button. I like these by Nicola Donati and Savile Row tailor Matthew Farnes. Valet also has a nice "toothpick trick" for coats. The things you’ll need before practicing with these guides are quite basic: some button thread, a sewing needle, some scissors, and, of course, your new buttons. You may also want to have a seam ripper to take off your old buttons, and a thimble if you’re trying to sew through tough cloth. All these things should be available at your local supermarket for two or three bucks each. Once you have what you need, it takes about ten minutes to learn how to sew on your first button, and maybe a few tries before you get the technique down.
As to where you can score some nice buttons, I recommend Britex if you’re in San Francisco. They hold sales twice a year, which you can find out about by signing up for their newsletter in-store. In Los Angeles, there’s B. Black & Sons, and in New York City there’s Tender Buttons (arguably the most famous button store in America). For online sources, you can turn to Isles Textile Group, Hwa Seng Textile, and MJ Trimming. I personally prefer buying things in a brick-and-mortar store, especially with things that can have so much visual variation such as horn or mother-of-pearl buttons, but if you don’t have a good button store near you, you still have options.
For something truly affordable, try checking thrift stores. Something made by a reputable company such as Oxxford, for example, might be damaged and can be had for under $20. These will have all the manufacturer’s original buttons, which should be made from high-quality horn or metal. A smart way to pick up nice buttons for a fraction of the cost you’d spend otherwise. 

Getting Your Buttons Down

Knowing how to properly sew on a button is perhaps one of the most useful clothes-related skills you can pick up. Buttons occasionally fall off even the best of garments, and need replacing, or sometimes we wish to swap out the manufacturer’s buttons for something else. A mid-tier cardigan, for example, can be made much better looking if you change out the plastic buttons for some horn ones.

There are many good instructional guides online that’ll show you how to sew on a button. I like these by Nicola Donati and Savile Row tailor Matthew Farnes. Valet also has a nice "toothpick trick" for coats. The things you’ll need before practicing with these guides are quite basic: some button thread, a sewing needle, some scissors, and, of course, your new buttons. You may also want to have a seam ripper to take off your old buttons, and a thimble if you’re trying to sew through tough cloth. All these things should be available at your local supermarket for two or three bucks each. Once you have what you need, it takes about ten minutes to learn how to sew on your first button, and maybe a few tries before you get the technique down.

As to where you can score some nice buttons, I recommend Britex if you’re in San Francisco. They hold sales twice a year, which you can find out about by signing up for their newsletter in-store. In Los Angeles, there’s B. Black & Sons, and in New York City there’s Tender Buttons (arguably the most famous button store in America). For online sources, you can turn to Isles Textile Group, Hwa Seng Textile, and MJ Trimming. I personally prefer buying things in a brick-and-mortar store, especially with things that can have so much visual variation such as horn or mother-of-pearl buttons, but if you don’t have a good button store near you, you still have options.

For something truly affordable, try checking thrift stores. Something made by a reputable company such as Oxxford, for example, might be damaged and can be had for under $20. These will have all the manufacturer’s original buttons, which should be made from high-quality horn or metal. A smart way to pick up nice buttons for a fraction of the cost you’d spend otherwise. 

It’s On eBay
Ten-Piece Holland & Sherry Blazer Button Set
One of the most impactful and reasonably-priced aesthetic alterations you can make to a blazer is button replacement. I have a blazer with traditional brass buttons, but it’s easy for brass too look, well, country-club-ish. Replacing gold buttons with something more distinctive, like the ones above, or with mother of pearl (in white, bronze or black) or bone (in white or brown) can make a big difference.
I recently acquired two coats - one a Chester Barrie double-breasted with spectacularly homely metal buttons, the other a Kiton suit jacket with dark plastic buttons. I hopped over to Hwa Seng Textile, and ordered white bone buttons for one and black mother of pearl for the other. Silver-colored metal is also an option, but as long as you don’t go with black or navy (which will look like an orphaned suit coat), the world is your oyster.
A tailor will typically charge about a dollar per button to attach whatever you bring him.
Starts at $24.99, ends Friday, April 8th

It’s On eBay

Ten-Piece Holland & Sherry Blazer Button Set

One of the most impactful and reasonably-priced aesthetic alterations you can make to a blazer is button replacement. I have a blazer with traditional brass buttons, but it’s easy for brass too look, well, country-club-ish. Replacing gold buttons with something more distinctive, like the ones above, or with mother of pearl (in white, bronze or black) or bone (in white or brown) can make a big difference.

I recently acquired two coats - one a Chester Barrie double-breasted with spectacularly homely metal buttons, the other a Kiton suit jacket with dark plastic buttons. I hopped over to Hwa Seng Textile, and ordered white bone buttons for one and black mother of pearl for the other. Silver-colored metal is also an option, but as long as you don’t go with black or navy (which will look like an orphaned suit coat), the world is your oyster.

A tailor will typically charge about a dollar per button to attach whatever you bring him.

Starts at $24.99, ends Friday, April 8th

Here’s a thrifting tip - that works at regular stores, too.
One sign of a high-quality dress shirt is natural buttons. Plastic buttons are cheaper and more durable than mother of pearl, but they lack the natural pearlescent sheen of the Real Deal. The difference is marginal, but it’s one way a fine shirtmaker distinguishes his product.
If you’re not experienced at spotting natural buttons, there’s an easy way to test. Grab a sleeve, and touch the cuff button to the top of your upper lip. at the bottom of your philtrum. (I use this spot because putting it on the part of my lip I use to eat is kind of gross.)
Natural buttons are more conductive to heat than plastic ones, and will feel cold against your lip. The difference is marked, and easy to feel.
The real trick, of course: explaining to store clerks why you keep eating sleeve buttons.

Here’s a thrifting tip - that works at regular stores, too.

One sign of a high-quality dress shirt is natural buttons. Plastic buttons are cheaper and more durable than mother of pearl, but they lack the natural pearlescent sheen of the Real Deal. The difference is marginal, but it’s one way a fine shirtmaker distinguishes his product.

If you’re not experienced at spotting natural buttons, there’s an easy way to test. Grab a sleeve, and touch the cuff button to the top of your upper lip. at the bottom of your philtrum. (I use this spot because putting it on the part of my lip I use to eat is kind of gross.)

Natural buttons are more conductive to heat than plastic ones, and will feel cold against your lip. The difference is marked, and easy to feel.

The real trick, of course: explaining to store clerks why you keep eating sleeve buttons.

Ambrosi pants via A Rugged Old Salt.
A button fly doesn’t really have much of a functional advantage.  It’s a bit less dangerous, and a bit harder to accidentally leave open.  It’s mostly a symbolic thing - it says that these pants are made the way pants used to be made, despite the extra work involved. 
Those extra buttons on the side of the fly (or sometimes along the waistband) do have a purpose.  They keep the top block and waist of the pants straight, which is not a given.  Without them, the pressure of your gut could bow the front of your pants into a V, which is less than flattering.
Some details are symbolic, some functional.  Of course, symbolism has its function, too.

Ambrosi pants via A Rugged Old Salt.

A button fly doesn’t really have much of a functional advantage.  It’s a bit less dangerous, and a bit harder to accidentally leave open.  It’s mostly a symbolic thing - it says that these pants are made the way pants used to be made, despite the extra work involved. 

Those extra buttons on the side of the fly (or sometimes along the waistband) do have a purpose.  They keep the top block and waist of the pants straight, which is not a given.  Without them, the pressure of your gut could bow the front of your pants into a V, which is less than flattering.

Some details are symbolic, some functional.  Of course, symbolism has its function, too.

Q and Answer: The Three-Roll-Two
Benjamin writes to ask: I inherited a handful of my grandfather’s tasteful suits a few years ago  and am slowly having them tailored and integrated into my wardrobe.  Among my favorites are a very classic Brooks Brothers navy blazer and a  cotton khaki suit. Both include three-button jackets, however the lapels  were folded as two-buttons leaving the third button hole exposed on the  lower part of the lapel. Being under 6’, I tend to prefer a two-button  jacket, so I would like to keep them folded the way they are now. But I  would also like to know a little more about the style, what’s the deal  here? Was it a style years ago? Is it considered tacky?
What you’ve got is probably the most classic suit buttoning style, the 3-roll-2:  three buttons, with a roll in the lapel that rolls under the top button, making the coat functionally a two-button.
Three-button suits were the style of the “Friends” era, and two buttons the style of the “Cheers” era.  The 3-roll-2 is a compromise.  It’s found on many Savile Row single-breasteds, and is the classic buttoning for the undarted Ivy League-style “sack” suit.  It’s the opposite of tacky - the epitome of class.
The great challenge will be preserving the lapel roll as such.  On cheap and mishandled suits, the lapel doesn’t roll at all - it folds.  Often dry cleaners will press the lapel down into the chest of the suit, flattening out the suit’s three-dimensional shape.  They’ll also often press a 3-roll-2 into an awkward three-button, so be vigilant.  A good tailor can steam the lapel roll for you to preserve its shape.

Q and Answer: The Three-Roll-Two

Benjamin writes to ask: I inherited a handful of my grandfather’s tasteful suits a few years ago and am slowly having them tailored and integrated into my wardrobe. Among my favorites are a very classic Brooks Brothers navy blazer and a cotton khaki suit. Both include three-button jackets, however the lapels were folded as two-buttons leaving the third button hole exposed on the lower part of the lapel. Being under 6’, I tend to prefer a two-button jacket, so I would like to keep them folded the way they are now. But I would also like to know a little more about the style, what’s the deal here? Was it a style years ago? Is it considered tacky?

What you’ve got is probably the most classic suit buttoning style, the 3-roll-2:  three buttons, with a roll in the lapel that rolls under the top button, making the coat functionally a two-button.

Three-button suits were the style of the “Friends” era, and two buttons the style of the “Cheers” era.  The 3-roll-2 is a compromise.  It’s found on many Savile Row single-breasteds, and is the classic buttoning for the undarted Ivy League-style “sack” suit.  It’s the opposite of tacky - the epitome of class.

The great challenge will be preserving the lapel roll as such.  On cheap and mishandled suits, the lapel doesn’t roll at all - it folds.  Often dry cleaners will press the lapel down into the chest of the suit, flattening out the suit’s three-dimensional shape.  They’ll also often press a 3-roll-2 into an awkward three-button, so be vigilant.  A good tailor can steam the lapel roll for you to preserve its shape.

Q and Answer

Abby writes from snowy Canada:

my boyfriend bought a vintage ralph lauren tweed suit on ebay but only the jacket fit so i took the pants and claimed them as my own… but now that i am wearing men’s flap front pants i have a question: why are there 4 different buttons and a fly? it seems overly complicated - what don’t i know about men’s pants & how they work? i realize that women’s pants often have a few different elements to the closures but this seems a bit much….

I have attached pictures, please forgive me undoing my pants for you - it’s in the pursuit of knowledge!

First of all: no need to apologize.  If being sent pictures of women undressing is the price we have to pay to be men’s style bloggers, then SO BE IT.

As to your question: they stabilize the beltline.  Pants, especially pleated ones like those, can bow and puff in strange ways when they’re pushed against by bodies less shapely than yours (ours, for example).  The three button lineup you’ve shown us ensures that the front button is part of a clean line, and not the inflection point in a weird V shape.  As for the fourth button, we don’t see it here (more pics?), but it’s presumably an extra button, conveniently sewn in so that it’s easy to find when the need for it arises.

(By the way: Abby’s boyfriend is Dave Shumka, of the very funny podcast Stop Podcasting Yourself, and as you probably already know, podcasters are very, very strong and tough.  So don’t think any impure thoughts, people.)

Q and Answer
Jordan writes:
I just bought a navy blue blazer from a thrift store.  The blazer came with old brass buttons that I’ll have to be replace.  Will I be better to replace them with new brass buttons or dark navy blue buttons?
The blue blazer is a classic menswear staple.  It pairs well with almost anything and is appropriate for almost any occasion that doesn’t call for a suit.  That said, the classic brass buttons can look a little fogeyish.  If you’re wearing them to your country club for a soiree, maybe that’s appropriate, but we’re not crazy about the idea.
Navy buttons (as seen on Kenneth, above) are fine, but they can, in some cases, make the coat look like an orphaned suit jacket.  We like a natural bone color, which will go nicely with brown shoes and is pretty neutral.  If you’re a bit more adventurous, a white bone or horn button also looks really cool.
You can find button sets pretty easily (and cheaply) on Ebay or at a local fabric store.  Your tailor or alterationist will likely charge about a dollar a button to switch them out for you.
While you’re on Ebay, by the way, be sure to check out blazer button sets in precious metals (silver and gold!) and for odd clubs and organizations.  You may not belong to the New York Fencing Society, but it might be kind of cool to have thier buttons on your thrift store blazer.

Q and Answer

Jordan writes:

I just bought a navy blue blazer from a thrift store.  The blazer came with old brass buttons that I’ll have to be replace.  Will I be better to replace them with new brass buttons or dark navy blue buttons?

The blue blazer is a classic menswear staple.  It pairs well with almost anything and is appropriate for almost any occasion that doesn’t call for a suit.  That said, the classic brass buttons can look a little fogeyish.  If you’re wearing them to your country club for a soiree, maybe that’s appropriate, but we’re not crazy about the idea.

Navy buttons (as seen on Kenneth, above) are fine, but they can, in some cases, make the coat look like an orphaned suit jacket.  We like a natural bone color, which will go nicely with brown shoes and is pretty neutral.  If you’re a bit more adventurous, a white bone or horn button also looks really cool.

You can find button sets pretty easily (and cheaply) on Ebay or at a local fabric store.  Your tailor or alterationist will likely charge about a dollar a button to switch them out for you.

While you’re on Ebay, by the way, be sure to check out blazer button sets in precious metals (silver and gold!) and for odd clubs and organizations.  You may not belong to the New York Fencing Society, but it might be kind of cool to have thier buttons on your thrift store blazer.