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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I know I’ve written about gladiators before, trying to find a pair that was both good looking and relatively inexpensive, because, let’s face, my shoe budget is not on the level of Gwyneth Paltrow or Lindsay Lohan or numerous other stars who’ve been spotted around town in these Giuseppe Zanotti stunners (about $650 at Zappos):

No, I’m more on a Nine West budget here (especially with some recent fashion expenses that I shall leave nameless for now).  Speaking of Nine West! It seems that they have made my perfect gladiator sandal and then they promptly got sold out of it:

Seriously, I can’t find this multicolor version of the Nine West “Jobilyn” for the life of me–although I can find it in about 12 other color combos, most of which are on sale for a little over $50 at Endless. Oh! Le sigh.

But then, the gladiator-shod gods smiled down at me as they made me discover this:

Palladium “Key Largo” sandal, rich in buckles and studs and overall gladiator-y goodness. I can’t decide between the pewter version or the orange version–they’re both very appealing, I must say! And only about $80 at Shoes.com or Endless (shipping included):

I’ll probably go with metallic (metallic is the new neutral, remember?), as I can probably accessorize it better. But I still love the orange! Bonus points: Palladium is a brand known for comfort, and I can already see that, unlike its cousins with ultra-thin, slippery soles, this “Key Largo is seriously padded. Score!

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We’ve talked before about how Nine West has been upping their style quotient in the past few seasons. Some of them get mighty close to directly copycatting high end designer shoes, which I’m generally not into.

But some of their shoes have been hitting exactly the right trend notes, including these, as seen on the feet of a super stylish friend (who’s already made it to our Shoes on the Street forum with another pair of colorful, fun pumps).

Wouldn’t you believe those on a shelf at Saks? I know I would!

Update: You can purchase the Nine West Drazly at Zappos for $93 (in yellow dual straps), Endless for $44.90 (black with white straps), or Piperlime for $54 (in black with either red or white straps).

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It’s time again for Ask the Shoebloggers, and this time it’s not shoes for the bride, but for her bridesmaids.

Here are the initial parameters for this, our newest mission (which, of course, we chose to accept):

My best friend is getting married in September and we’re trying to find the perfect bridesmaid shoes—please help! Our dresses will be black, and she’s hoping to find a black shoe with some red and/or yellow on it (the colors of the wedding and bouquets). Our dresses are knee-length, and very 50s style with a wider skirt and fitted top—not too fancy.  Our location is in the U.S., we’d love to keep the price below $75, but could go up to $100 if need be. A mid- to high heel would be great!

With that, our very own Shoesense went on the hunt and came up with a first round of suggestions. First up was the gorgeous, but too pricey (at $270, and that’s on sale at Piperlime down from a full price of over $400!) Sophie by Cynthia Vincent.

Piperlime also has the Nine West Drazly 2 pump in black and red for $80.

From Nordstrom comes the pretty red/black version of the Boutique Nordstrom Melina pump (also $80).

And finally, the all-black Bruno Premi Deja-Vu slingback ($85).

That was our first round of suggestions. Then our bridesmaid-to-be responded with this:

Thank you so much for your help! We took a look at what you suggested and our bride thinks she would prefer to do a solid yellow shoe, and then put a sash on our dresses or a headband in our hair or something. So now we have changed the focus to yellow. I liked the style of the Nine West one you sent, and we really like a few at J. Crew, but they are a bit out of our price range.

The J. Crew styles she particularly liked are the Gwendolyn satin t-straps ($225)

and the Cleo patent leather t-straps ($195) that are so juicily lemon colored I want to make them into footwear lemonade.

And so now I’ve taken up the call for a yellow shoe, the official Shoeblog favorite color of spring, and very hot right now.

The rsvp Daina is a pretty lemony yellow patent leather sandal ($70) with a swooping heel detail I pretty much love.

The Nine West Argent in yellow satin is a pretty good substitute for the J. Crew Gwendolyn’s, but it’s only $64 at Endless instead of over $200. This one also comes in a yellow leather, but the color doesn’t pop nearly so much as it does in satin.

In other Nine West yellow options (of which there are several), there’s the Doverly ($80), which isn’t solid yellow, but might work anyway.

And if you want to go the super-dainty feminine route, there’s the lovely, refined Solelyn ($64).

The Jessica Simpson Chasie slingback ($100) has that same dark heel/yellow combination as the J. Crew Cleo, though with a heel of 4.75″ I can’t imagine dancing the night away in these at the reception.

There’s a new batch of suggestions for our wedding planners. Let’s see if any of them work out.

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What’s its name? It was just on the tip of my tongue. I guest the gods of onomastics must not be with me today.

You know what I’m talking about:

They’re these new hybrids that fuse approximately 51 trends into one, which could be practical, you know: in one shoe, you hit all the new spring trends! Clockwise from the top:

- Christian Louboutin “Sometimes Lace-up Sandals”–4 1/2 inch heel, platform, and tassels, $860 at Saks;

- Jimmy Choo “Evita” sandal, $1000+ (see their website for more details);

- Manolo Blahnik heels-$900+–call their NY Store for availability;

- Nine West “Heathers”–which I’ve already blogged about–for a fraction of the price of any of the above (about $90).

I have the suspicion that none of these styles would look that good in a low/flat heel, and since wearing the 4″+ heels is out of the question for me, I’m afraid I’ll have to pass on this trend. Not without a pang of jealousy, though, for those of you who can trot merrily in these styles.

(Via NYT T-Magazine.)

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