So, this is a very complicated time to get dressed. Times photographer Bill Cunningham declared the death of "dress down Friday," as he was seeing people dressing way, way up. And while he's always right, that doesn't necessarily mean that it's true in your office. But what it does mean is that you can often dress in the way you see fit. Often, it's easiest to start dressing from the shoes up.
And do you even know what kind of shoes you're wearing right now?
Get ready. This is going to be intense.
KINDS OF SHOES
Oxfords, derby shoes, gibsons, bluchers and balmorals.
Yup, this is all going to be terribly confusing, because different countries call these different things. You may not even know what is on your feet. Look down! Look up! Cry! Okay don't panic. In America, what we call an "oxford" is really a derby. (Annnddd... that's when you clicked "close tab.") The difference between the two is a bit of technicality: basically, if it has a "flap" atop the shoe that has the lace holes into it, it's a derby shoe.
This is a derby shoe.
See how that top leather part-thingie is sewed atop the shoe? That makes it a derby. This is an oxford.
That's all! One has a little thing sewed on for the laces, the other just has lace-holes.
Basically you can die now, right? Well bad news, the "oxford" is also called a "balmoral," and you know what, don't worry about that. (Unless you go to Barneys, where the official terminology is "balmoral.")
So the true oxford shoe makes for a very sleek profile and front view, as it's so close to the foot and because the laces draw it completely together; the derby shoe, with its little bulk-adding flap, often has a little more manly chunk to it. I often feel too much like a lady in an oxford shoe! But that's totally personal. Dudes like what dudes like.
Brogues and wingtips.
A wingtip can be any of those! "Wingtip" just means they're decoratively punctured. (You might use an awl to do the leatherworking!) The short version here is that a "wingtip" shoe is a "full brogue" and it is easy to identify: it has a "W."
Other kinds of perforated shoes are kinds of brogues too.
Here is something important to know about wingtips: people nowadays see them as very formal and fussy "banker and lawyer" shoes. This was not until recently the case!
The saddle shoe and the spectator shoe.
This is like a trick question, because the saddle shoe, no matter what color, has a saddle.
And spectator shoes do not. 
So you would basically never wear a spectator shoe unless you were going to a "Gatsby"-themed lawn party.
But you can wear a beat-up saddle shoe on the weekends and look nice and not totally silly! Also these are both brogues. DO YOU WANT TO PASS OUT YET?
Monk shoes.
It's a "monk shoe" if it has a buckle, basically. I have never met one that I liked. This is an extremely expensive Berluti shoe. No thanks! Not for me! If you take five people shoe-shopping with you and they all agree you look amazing in a buckle shoe, then knock yourself out.
Loafers (as in, "Venetian-style" shoes, or "slippers"). Oh, a tricky one. You can actually wear a nice version of a Venetian loafer to the office of a Friday.
This is a Brooks Brothers "classic" Venetian loafer.
That is not an office shoe.
But this, this could be (or a nicer version of it), if you were wearing nice jeans or something.
Regular loafers, boat shoes and topsiders.
For your boat or your lawn.
TOES
I am not going to torture you about the shape of your shoes' toes. Toe caps are like skirt styles; they come in and out of vogue. There were two horrible years when every shoe was pointy; there was a revolution when every toe was squared off. I say split the difference for safety—and if you love it, wear it! But you should know these are extremities of style and it's easy to make enemies at either end of the spectrum. (I personally cannot wear pointy shoes without feeling like I'm in a witch costume.)
COLOR
According to How to be a Gentleman, a book to which I do not subscribe at all, brown shoes are some scary, risky thing. Hogwash! Brown belt and a not-black suit and you're golden for brown shoes. Blue summer cotton suits and brown shoes are great. They're not funereal—although they're also not, obviously, super-formal. If you are wearing separates, there's no reason not to wear brown.
THREE BRIEF THOUGHTS ON SHOES
• If your work shoes are uncomfortable, you're doing it wrong. Shoes don't hurt. (With rare exceptions. I'm looking at you, vintage Dirk Bikkembergs.)
• If you have a ton of cash to spend on shoes, go on up to John Lobb, even if just to look. They're incredibly well made, if overly traditional for some of us. Like, really well made. And they'll answer your questions and stuff!
• If you feel really super good and strutty about your shoes, it doesn't matter what dirty looks you're getting on the street. You're the one that matters.
Sponsored posts are purely editorial content that we are pleased to have presented by a participating sponsor, advertisers do not produce the content. This series/post is brought to you by Gillette. Learn more about Gillette and its products at Gillette.com.
I have forwarded this to my boss who insists on wearing the crappiest shoes wherever he goes.
Could we have a picture of a wingtip awl?
Whither thou, mandals?
You have to throw them in your murse so you can wear them to and from the office.
@deepomega- Get your murse and mandals over here so I can Veet your toes, you. It's time for the summer ritual!
@scroll_lock You'll probably also need a manbra for your moobs.
What Lawyergay's Wearing
sponsored by Mama Celeste's Frozen Pizza
On the left foot: A vintage Kleenex gold, bronze and chocolate foil "lilypad" facial tissue-box design from the 1970s, with several still-intact tissues lining the sole.
On the right foot: An updated classic "Stewart's Shops" logo paper bag sized for ice cream and other luxury dairy products.
@lawyergay <3
I think you left out page two with all of the neon high tops? I want to know if convertible highs are dressier folded up or down.
@deepomega- It depends on the dress you're wearing.
@scroll_lock Short black cocktail dress. What do I look like, a farmer?
@deepomega- Showing a bit too much cleave for 3pm, aren't you?
@scroll_lock How else am I gonna get a free drink before happy hour?
@deepomega - And stop taping them up.
@scroll_lock YOU WEREN'T SUPPOSED TO TELL THE WHOLE INTERNET ABOUT THAT
@deepomega Hey, at least I kept my word and didn't mention your glute implants.
but how does the steel toe fit in there?
@Abe Sauer- It's on the foot of the man in the factory making these other shoes.
@scroll_lock Is "man" the Tagalog word for "14 year old girl?"
@Abe Sauer - If the steel toed shoe fits...
If Tom Ford could get someone to pay $1,500 for a pair of white bucs he would declare them the very thing.
An entire article on mens' footwear and not a single word about the importance of polishing one's shoes?
I can see I've returned with not a moment to spare.
@jolie No, seriously, I don't know a damn thing about shoe polish. How does that work?
@boyofdestiny Is this another one of those times where you try to convince me that men are thinking "I'm nailing this chick" while doing sex to a lady? Or do you really not know how to polish your shoes?
@jolie Most men in our age group don't know how to polish our shoes, Jolie. My concern is always that I'll fuck up the stitching or something? Is that something I should be worrying about?
@deepomega if you're using black polish on brown shoes then yes. first rule of polishing your shoes? get polish that matches your shoes.
@jolie I would never make a sarcastic comment about something so serious.
Really, though, I've never shined a shoe in my life.
@deepomega *lies down under desk, sobs*
@boyofdestiny *lies down under desk, sobs*
@jolie It's easy. You go to Grand Central Station.
Or, if you work in a decent office building, a man comes through the building once a week and shines them at your desk.
@roboloki Even if the polish matches won't it fuck with the stitching? Am I being insane here?
(I have polished my dress shoes a few times, and each time I was left wracked with fear uncertainty and doubt. A quivering pile of nerves.)
@jolie Does it help that I saddle soap and mink oil my hiking boots? We're talking about the same skillset, at least, right?
@Choire Sicha Both of these answers are correct, yes. I love polishing my own (and/or my boyfriend's) shoes though. So satisfying!
@deepomega fear not! polish is not going to harm the stitching.
@boyofdestiny it is the same skill set, just a few extra steps.
Polishing your brown shoes with black polish makes em look awesome.
I'll just jump in here and point out that if you buy really quality shoes, you'll only have to polish them about once every other month. The rest of the time, before you put 'em on, just brush them vigorously with a sturdy shoe brush for about 15 seconds apiece and you're good to go ... good leather just needs a little perking up, not layers of nasty old dust-attracting polish.
OK, if you scuff them badly you may have to touch-up a little with a bit of shoe cream (not polish! shoe cream! I like the Allen Edmonds stuff because it smells like Manly Endeavours). Rub a tiny little bit on with an old sock (or one of those dauby brushes if you're that kind of a guy), let it dry 'til it gets cloudy and dull-looking, and then go at it with the aforementioned sturdy shoe brush.
@boyofdestiny: Yes to saddle soap. Double yes to mink oil. Triple, absolute No to using either of those on your Nice Shoes.
@zoom: Unless you're trying for that weird pre-aged "burnt toe" look that all the shoes on Gilt seem to be going for lately, which ugh.
@deepomega : As others have pointed out, polish will not harm the stitching, and it'll come out on its own if you let it dry and then give the shoe a vigorous post-polish brushing like you should be doing anyway. But really, maybe you're using too much polish in the first place? Think "film," not "frosting."
@jolie : I'm more concerned that this is an entire article about shoes and not a mention of white bucks, dirty or otherwise.
@Choire Sicha Yes. Though I'm going to be That Pedantic Guy and insist on Grand Central Terminal. The shoe-shine gentlemen there know their stuff.
If you join a country club, you can leave your shoes at your locker when you go out for a round and they'll be all shined up when you get back. But that's a more expensive option than most.
Holy crap, was no one here in the service? Shoepolishing 101 for business types: rub a very thin layer of polish over your shoe. Allow to dry until it hazes over a bit. Brush with a shoe brush until you get a nice satiny gloss. Easy.
"Spit" shining: probably not worth doing (unless, of course, you're actually in the Army or whatever). But if you want to: get a very soft, 100 cotton rag (t-shirts are ideal). Poly blends will not work - they're too scratchy. Again, rub a very thin layer of polish on the shoe. Continue buffing more or less continuously as the polish dries. As it becomes drier and and doesn't want to buff anymore, apply small drops of water (actual spit is not recommended, although it will work in a pinch) to the shoe while continuing to buff. At some point the polish will be completely smoothed out. Now repeat that process about 5000 times, or until your shoes attain a mirror-like shine. Once you've gotten the shoe to this point once, maintaining the appearance is not that hard... but you'll never be able to use a shoe brush, as it returns the shoe to a satiny gloss.
If this is preempting a future sponsored post, stop me, but I need some opinions here.
I got into a near-friendship-rending argument over the subject of sneakers. We can all agree that gym shoes are not for going out. But I'm of the opinion that a clean pair of low-top Chuck Taylors is a perfectly fine sneaker to wear to events and in venues where sneakers are acceptable. My friend responded to this as if I told her I was going to the club wearing Wonder Bread bags on my feet. Who's right?
@boyofdestiny OOH, I am on the side of KICKS. I mean, you're not wearing them to the MET or to an estate settlement conference. It's 2011! People are lucky we're wearing shoes at all.
@boyofdestiny You are right that sneakers are ok. She is right that Chucks are the fucking worst. And I have, myself, compared the structural integrity and general foot-support of them to wearing plastic garbage bags like you're trying not to leave footprints on the grassy knoll.
@boyofdestiny Dude. *Low-top* Chucks? ::sobs in corner with Snoop Dogg::
@Matt This might be the wrong site to admit this, but I got the low tops so I could wear them with shorts...
It's 2011! You can SOO wear the Chucks to the Met! Peter Gelb is all about the youths, you know.
@boyofdestiny ...
@boyofdestiny Tell me more of this "Wonder Bread."
@boyofdestiny I'm a girl who likes boys who wear low-top Chucks.
@boyofdestiny Chucks are a classic but as a society, can we stop pretending they're hip? Ten-year-olds and angsty tweens wear them - everyone else needs to stash theirs away for a few years.
@boyofdestiny isn't the real point of contention, just where are sneakers acceptable? Some places for sure YES, like to the rock show? Because yes then Chucks have long been the very best shoes for a boy (whether of destiny, or one simply meandering through life) to wear. The low-tops are more appealing if you have nice ankles, surely. (So long as they are black! The shoes not the ankles! Or that faded blue, possibly.) But still, unless it is a very casual venue, maybe you'd be better off in a decent pair of loafers (just as comfortable, if not more so) just because it is less embarrassing to be over- than underdressed.
@barnhouse I am almost positive we have already had this exact same conversation on this website at some point in the past two years.
Vans or Chucks is about as far as I get. I have some shiny black shoes I wear if I don't want old guys looking at me crossways for carrying a dead body in sneakers.
Where are the Ferragamo or Gucci loafers?
@scroll_lock If the comment fits, you have to oh wait that's something else.
@scroll_lock: and the Teva sandals?
I once owned a pair of John Lobb shoes. For two weeks. I never wore them on anything other than carpet -- my children have to go to college some day! -- but I did suddenly understand why people drive Ferraris, charter jets, etc.
Also THANK YOU re brown shoes. An estranged friend who wrote/writes for the Times once let me know that my brown shoes were strike two. I didn't dispute the call, then when a legitimate complaint came down the road, pfft, oh well.
@dntsqzthchrmn I seriously just don't understand that proscription at all! If you're wearing a navy suit, then what's your option? Cordovan? *shudder*
Saddle shoes are for dudes in SKA bands.
@HiredGoons i miss ska like i miss the dysentery!
I don't care how trendy boat shoes/top siders got in the past 5 years, they are wonderful for most occasions and go with many outfits.
Get a knockoff of the Pope's red Prada pumps.
Vintage wingtips. Humena.
Couple of years ago I went to a Paper party at that Tommy Hilfiger store in SoHo (don't ask) and they gave everyone a gift certificate - the only thing in the store that was even remotely in my taste was a 100+year pair of refurbished vintage Oxfords.
They are the most gorgeous well made pair of shoes I have ever owned; the leather is so amazingly distressed in a way that you can't manufacture.
I had a dream. In it, I died and went to Hell.
I knew it was Hell because, outside the door, trying without success to light the remnant filter of a cigarette, stood Alex Balk, wearing Bermuda shorts with Birkenstocks and black socks, and drinking a Mr. Pibb.
He said, "I'm so hungry. Got any cashews?"
Can someone please explain what a "driving moccasin" is (car driving?) and where it fits in this shoe article...?
@jasonnn See the Venetian loafer.
Completely with you on the monk strap shoes. The men who used to come in and buy those at the shoe store I worked at also wore pin stripe blazers with denim jeans and white button front shirts with embroidery (embroidery!) tucked into the jeans. They were a mess.
@TullyMMills oh god oh god oh god
I always feel like these sponsored posts about men's fashion are from a previous generation. When summer comes, I plan to wear no shirt, flip-flops, and perpetually pee-and-beer-stained cargo shorts. Is that okay?
@Harry Cheadle: Mom?
@Harry Cheadle: me too, although I'm probably going to wash my cargo shorts. Probably.
When I was a child, I was pigeon-toed. The "cure" was a pair of saddle-shoes, connected by a metal bar. Instead of crawling, I had to drag my legs behind me or scootch around on my bottom. I have a distinct memory of doing both of those things and thinking they were very unpleasant.
Hence, I have a strong aversion to saddle shoes and POLITELY disagree with your assessment of saddle shoes, as they are the tool of the devil.
@mom, on the one hand, !!! .. but on the other? I am pigeon-toed to this very day, so .. maybe I'd rather have saddle shoe baggage?
i love these posts so much. I love my oxblood derbies, but feel they're not particularly spring-y? Boaters and white keds are basically the only shoes for spring, in my opinion.
I pretty much only wear brown wingtips (horribly beaten-up) or boat shoes. Except hiking but that's a whole other life, shoe-wise (I have climbed Monadnock in weejuns, though...).
@My Number Is My Address: Weejuns give me Daddy issues. Which is neither here nor there, but ... you know.
Explain this outfit combo:
http://i52.tinypic.com/2ylvdx2.jpg
@katiechasm holy shit
If I knew how to do it, I would send a picture of my Italian Street Runner shoes- made in China of course.
This rule "If you feel really super good and strutty about your shoes, it doesn't matter what dirty looks you're getting on the street. You're the one that matters." and this rule "So you would basically never wear a spectator shoe unless you were going to a "Gatsby"-themed lawn party." contradict. Further, every time I wear my spectators, and I have six pairs - cordovan on tan, brown on white, blue on white, black on white, black on grey, and red on black - I get nothing but compliments, various oohs and aahs, and requests for my supplier. So suck it.
@Ryan Gray@facebook Cordovan on tan :(
What kind of shoes can I wear without socks?
Expect a bill for the cost of removing all the blood from my keyboard.
Brogues icing brogues. (This post was both fun to read and very informative!)
If your work shoes are uncomfortable, you're doing it wrong. Shoes don't hurt.
Unless you are a lady.