One of the must-have items of the season is, apparently, the good ol’ penny loafer. I’m all for that: school season is knocking on your neighborhood’s door, and even if you’re not in or around a school at the moment, you must feel the buzz of books and the studious energy in the air. No? It must be me, ahem; still, you are probably seeing a preview of collegiate fashions by now. And if you indulge one of my pet peeves for just a second: I for one would LOVE to see young women sporting an elegant, well-made penny loafer rather than a flip-flop way into November, as I often see, and which is just….wrong.

Penny loafers were named as such because they could be decorated with a penny (or often, a dime). I didn’t realize there was actually an urban legend behind this:

In 1934 John R. Bass (a bootmaker in Wilton, Maine) started making loafers and called them Weejuns (meant to sound like Norwegian). These had a strap across the upper part of the vamp that was shaped like a pair of lips (said to be John’s wife, Alice Bass, kissing each shoe on its way out the door). The mouth opening soon was used to hold an ornament (such as a penny), and thus penny loafers became a style. Penny loafers often held a dime instead of a penny. (From Wikipedia).

Edited: Correction: Allison in comments points out that it was actually George Henry Bass (and not John R.). Thanks, Allison, for pointing out again why Wikipedia can’t be entirely trusted!

In the days of yore, the penny loafer was a low-heeled shoe through and through, with a strong masculine vibe (it makes sense, since it started off as a men’s shoe). These days the penny loafer, just like the oxford, has gone through a high-fashion transformation, and the New York Times’ T Magazine is eager to present these options to us:

Clockwise from top: Christian Louboutin shoe, $1,050 a pair. Go to christianlouboutin.com. Yves Saint Laurent shoe, $770. Go to ysl.com. Tod’s shoe, $545. Go to tods.com. Nine West shoe, $99. Go to ninewest.com. Cole Haan shoe, $275, and Anna Sheffield for Cole Haan coin, $45. Go to colehaan.com.

This style is a classic that’s been around for decades and is bound to stay in style for a long time; in theory at least, you can’t go wrong wearing a pair of well-made penny loafers. I do admit to having misgivings about the 3+ inch height of the models shown in T Magazine; but again, I also have misgivings about models that look so masculine I have no desire to wear them. Therefore, I have also scoured teh interwebs for more pleasant AND easier on the feet loafer-options and found a few. Behold:

From top to bottom:

Marc by Marc Jacobs patent loafers (available in other colors, too), $264 at Zappos.

Marc by Marc Jacobs high-heeled loafers (2 & 3/4″, also available in other colors), $354 at Zappos.

Kate Spade Lindsay loafer (also available in other colors), $199 at Zappos.

Givenchy gold calf loafer, on sale for $204 at Zappos.

Tory Burch Clayton Loafer (also in red), $275 at Nordstrom.

Celine tasseled low-heeled brogue, $460 at Yoox.

MariaCristina low-heeled loafers, $178 at Yoox.

L’Autre Chose tasseled loafer, $68 at Yoox (only one size left!)

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Truly, Madly, Deeply have I fallen for this shoe; raised blood pressure, heart all a-twitter and breathing harder than is seemly in polite company.

If I had any true poetic talent in my soul, I would compose an ode to this breathtaking beauty.

Alas, I must add this to my list of shoes loved, yet destined to be unrequited; $795 at Bergdorf Goodman, such an unplanned shoe crush makes me wish for a world without household budgetary constraints. Sigh.

May I introduce Stella McCartney’s Flower Metallic Pump:

Seriously, I can’t stop drooling.

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People Magazine gives us the scoop on these glittery heels Cate Blanchett donned at Australia’s Helpmann Awards: they are “a pair of limited edition Roger Vivier Limelight America platform heels with sequined star detail and Swarovski crystal buckles.” Wait, that’s not the best part: They cost $11,000! Eleven. Thousand. Dollars.

I’m sure they were a gift (really, what self-respecting celebrity would fork that kind of cash for shoes, no matter how fab?). At any rate, it appears Cate also wore them to the premier of her Bob Dylan movie “I’m not here”–so at least she got some mileage out of them!

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Lipstick Jungle, huh?

Yep, that was the challenge for Project Runway designers last night: design an outfit for Brooke Shields’s character, Wendy, to wear on Lipstick Jungle.  I think it’s quite possible that every designer was also required to say the name of the show in every single soundbite, too.  Shill, much?

Anyway, the description that was given for the character was that she came from a bohemian background, but is now a high-powered executive, and this was supposed to be a day-to-night outfit.

What did these teams of two do?  More importantly (as far as we’re concerned here, that is), what shoes did they use?

The look I’d have handed the win to is the one Heidi loved most: Jerell and Stella’s.  And it’s also by far the one with the best shoes.  The Nanette Lepore Dotty Dame pumps are ADORABLE and have a perfect balance between grown-up and girly, as expected from the designer.

Who actually got the win?  Keith and Kenley, who, admittedly, also made a beautiful dress there.  It’s pretty primetime ready.  And so are its shoes, the Stuart Weitzman Expump (here in black patent, but also available in black leather).

Middle of the pack were Korto and Joe with their interesting “ethnic” blouse and poorly-fitted strapless dress.  And Terri and Suede, with this outfit that, to me, didn’t seem quite right for the office OR for evening.  And same goes for the shoe choice, the Charles by Charles David Savior mule that we saw way back in the first episode with Daniel’s plastic-cup dress.

And then we had the travesty that was Kelli and Daniel’s hoochie-mama outfit.  Leopard and lace and lingerie are NOT good looks for a classy, sophisticated type.  It looks like they used the Charles David Catch sandal, which is nice enough, I suppose.  But really, I don’t think there was a way to save that outfit.

If you want to check out other options for “dressing the businesswoman,” Bluefly is doing a spotlight on the peep-toe this week from their Project Runway accessories selection.  Ironically, the only one of the above shoes that shoes up on that page is the Nanette Lepore pump, and that one in a different color.

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Black Leather Boots by Marc by Marc Jacobs: 599 dollars

Vintage Black Leather Ankle Booties by Rave Review: 13 dollars

Winning one in the turf war with designer price inflation: Priceless

I fell in love with these Rave Review booties the minute I saw them. I have never heard of the brand Rave Review (and still can’t find them on the internet), but I could tell from the luster of the leather that we were going to be great friends. Sadly, this budding relationship was destined to end in near heartbreak. Being vintage, the shoes were available in only one size which was a full two sizes too small for me. Never one to be defeated by practicality, I grabbed the shoes off the shelf at Beacon’s Closet* and ran over to my shopping buddy, a girl of diminutive foot proportions. They fit her perfectly and with a little pushing, she was convinced to take them home with her. It was an act of selflessness of great proportion. But at least I know they have a good home and I got the opportunity to photograph at will.

Two weeks later, I was in the West Village and meandered into the Marc by Marc Jacobs store. What should I see as a focal point in the store but ankle boots nearly identical to those I had sent my friend home with before. Though the ones I saw in the store are not yet available online, the ones above are. These can be found at Zappos are are basically the boot version of the bootie to come.

Moral of the story: a stylish bargain shopper’s friends are oft rewarded.

*Beacon’s Closet {bē’kuhnz kloz-et} -noun: a Brooklyn thrift store/paradise of deals.
If you live in New York, you have probably heard of Beacon’s Closet, the quality establishment where my recent shoe adventure took place. If you are a Californian, think Crossroads Trading Company, but cheaper. If you are a Manhattanite who doesn’t go to Brooklyn, shame on you. If you are unacquainted or looking to visit the big apple, let me fill you in. Beacon’s Closet is a Brooklyn thrift store. It has two locations, one in Park Slope and one in Willamsburg. They are very particular about what they accept, so they tend to carry really cool stuff. Even more awesome: their prices range from about $5 - $50. Some of my past find at Beacon’s include an adorable pair of Marni heels ($50), a Catherine Malandrino sundress ($19.95), and a Dolce and Gabbana snakeskin belt ($25). These prices are actually a bit higher than the average (because I might be a tiny bit of a label whore). More common are the Abaete for Payless pumps I found for $9 and the vast array of Urban Outfitters wear available for around $13. I prefer the Park Slope location; it’s a bit smaller and more manageable.

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