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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Yes, I had a torturous time this past weekend attempting (semi-successfully) to do a ruthless shoe purge from my closet.

What motivated this frightening action, you might ask?  I’m moving.  Yes, folks, I’m leaving New York.  It’s been a good few years, but it’s time to go.

Where to, you (may or may not) want to know?

London, I tell you.  Never fear.  I’ll be covering footwear on the other side of the Pond.  And Twinkletoes will have the New York City beat well in hand.  Or, I guess, on foot.

But all this means that I have to pack up my rather large shoe collection and put most of it in storage for the year that I’ll be abroad (horrors!).  And since storage space is limited and I’m unwilling to give up the shoe boxes in which I store my darlings, a reduction of the collection was required.

So, what got added to the donation pile?  10 pairs.  I’m quite pleased with myself at 10 pairs.  And I shall show them to you.

1. Luau-rific flower-adorned flip flops.

2. Turkish bazaar slippers.

3. Havaianas kitten heel flip flops.

4. Paul Green “Dream” tan slip-ons.

5. Biviel kitten heel pumps.

1. ECCO boxer boots (lovingly blogged about here, but always a tad too small).

2. Doc Martens maroon oxfords.

3. Valerie Stevens black leg-wrap wedges.

4. Cole Haan G Series Irvington mules.

The 10th is this pair of Giraudon boots.

They are fun and funky.  They are walkable.  They are stylish.  But like the ECCOs above, they are ever-so-slightly too small in the toes.  So are those cute Biviels up there.  This is due to a lack of smart shoe-shopping in my past, but let it serve as a lesson to all that you REALLY shouldn’t buy that cute pair of shoes that almost almost fits but doesn’t quite.

I love you all, my dears.  I have had lovely times wearing all of you.  And now it’s time for you to go on and decorate the feet of someone else.  I wish you all well.

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As Natalie Portman put it on last week’s episode, Kenley’s like some 40s broad.  She styles herself well, although the jury’s still out for me on her designs and her personality.  But she does indeed work the 40s style, and with that in mind, I’m taking it upon myself to suggest a pair of pairs she might want to look into.  No, they’re not vintage 40s, but they’re certainly styled that way.

The first is the Cole Haan Camilla Air.  This one comes in 3 colors, but trust me, Kenley, this is the one you should go for.  It looks like it belongs on the foot of a Hollywood starlet back in the era of the Glamorous Silver Screen.  Get yourself a matching green alligator purse, and you’ll be the belle of any ball.

And for those special nights out (when you won’t have much walking to do), the YSL Tribute Pump in this spectatorlicious (sorry… channeling Blayne there for a minute) satin/patent combination in a black and seafoam color combo that says clean Lauren Bacall chic like nothing else.

Think about it, Kenley.  Lots of people work this style.  If you want to do it a cut better than the rest (and no, that’s not a Project Runway sewing pun), here’s the footwear to (literally) lift you up above the competition.

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After packing last night for a weekend of beachy fun, I’m currently sitting here thinking recently about a phenomenon I’ve observed in myself for quite a while.

I feel pretty safe in asserting that anyone reading this blog has has a multitude of moments of coveting a shoe.

The one I’m currently coveting the most?  It’s the pewter Palladium Key Largo gladiator sandal that Shoesense posted about back here (don’t rush to buy them, though, they’re pretty much universally sold out by now).

But that’s not what I’m talking about here.  What I mean is just what the title says; I covet an entire category of shoes.  Yes, it’s true.  I covet those sporty slip-on “casual athletic” shoes that so many companies offer these days for women on the go.

There’s no rhyme or reason to this covetousness.  It’s not a type of shoe I actually wear all that often, and I’ve got two excellent and much-loved pairs of them: my Puma Mostros (mine are actually teal and brown, but they’re several seasons old, and you can find this shoe in just about any funky color combo you could dream of)

and my Tsubo Pingers, which I simply adore, and rarely leave my feet in the summertime.

 Now, like I said, I’m not really a big wearer of this kind of shoe (a bit more girly and funky with my style and less athletic), but every time I see a new offering in this category, I fall for it.  Something about how cute and comfy they all look.  Like I could walk around in them for hours without feeling a twinge.

The newest one to spark my covetous nature is the Teva Makayla.

How cute and fun is that shoe, I ask you?  Asymmetrical and flirty in a no-nonsense kind of way that I love.  I’m even more smitten by the red version.

Cole Haan always has a few of these, with a slightly girlier, more refined look that I think was designed to worm through all the non-purchasing willpower armor I have.  The one I love every season is the Bria, which comes in several variations.  It’s the Bria Ballet that makes me swoon, and in this season’s “vintage silver” color and stitched pattern… well, I’m having to restrain my purchasing fingers from running away with my mouse on me.

And the multi-metallic mary-jane version?  Oh, save me from the gods of impulse shopping!

I have to go.  I will be off, and thank my lucky stars that I didn’t sit here at the computer one minute longer, staring and lusting over shoes I surely don’t need, but want desperately nonetheless.

Happy weekending, Shoeblog readers.

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Comfortable low-wedge peep-toes in patents or metallic are so hotttt right now it makes me wanna throw my panties at them. You drive me wild with desire, low peep-toe wedges! Few things turn me on like well-designed, relatively well-priced, trendy, pretty shoes. Throw in some Nike Air technology and I’m hooked.

Ok, so this Cole Haan Air Elly OT ballet is not exactly the most original design, but OMG, it’s so practical and cute and comfy and coming in all sorts of fun colors, that–INSTANT LOVE! My favorite colors are the metallic pink and (are you surprised?) the yellow:

The can be found at Zappos for $189 (limited colors) or at ColeHaan.com for $185 (plus S+H). Oh, and while you’re there, check the matching patent wristlets–too cute!

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