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Would You Wear… Penny Loafers?

25 Comments

Alexa Chung in Loafers
Photo Credit – 1

It’s time to pull the penny loafers from the back of your closet and start rocking the look again, because this 1950s-style shoe has once again become popular. After the rise of the flat oxford, it comes as no surprise that the penny loafer has been seen on everyone from celebs to college girls over the past few weeks.

Alexa Chung (pictured above) has worn loafers to dress down a feminine outfit, while Kate Moss loves to rock hers as part of a sleek look. As these celebs show, penny loafers are great because they can be worn with nearly anything in your existing wardrobe.

On the other hand, some people find this trend unflattering or outdated – I know I remember rocking these in elementary school. But whether you like or dislike this preppy shoe, you’ll have to get used to seeing this classic style everywhere, because it’s definitely back.

This is how I would wear them…

Penny Loafers Sample Outfit
Product Information: Dress – Miss Selfridge, Turtleneck – Old Navy, Coat – ModCloth, Tights – The OutNet, Shoes – TopShop, Bag – Asos

Would YOU Wear Penny Loafers?

Penny loafers are easily some of the most comfortable shoes to wear, but some think they are unflattering. So.. I want to know how YOU feel about them!

Do you think this preppy footwear trend should stay in the past or do you love the throwback? Would you mix them with a feminine frock or match them with a more masculine outfit? Leave a comment!

Posted on on November 23, 2010 / Filed Under: Would You Wear? / Tags: , , , , ,

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25 Responses to “Would You Wear… Penny Loafers?”

  1. 1
    November 23rd, 2010 at 2:38 pm

    yes i love them! i got a pair off etsy over the summer and they are adorable.

  2. 2
    November 23rd, 2010 at 2:45 pm

    I think penny loafers have the potential to be very versatile, but they can turn an otherwise spot-on outfit into something blase. I love to see them in an androgynous look with skinny cropped pants or with shorts as Alexa Chung likes to wear them- the key is to find a pair of penny loafers that flatters instead of makes you look frumpy.

    x.S

  3. 3
    November 23rd, 2010 at 3:26 pm

    I love them! My grandma had a pair of white ones that I love so I ordered myself a pair!

  4. 4
    November 23rd, 2010 at 3:26 pm

    i think that penny loafers are soo cute! yeah,i’m definitely goin’ to wear them. They can be a great alternative to ballet flats..
    (but,i gotta say this, you’re a lil bit in late in the US…penny loafers have been trendy for 2 or 3 years here in italy..:P)

  5. 5
    November 23rd, 2010 at 3:44 pm

    I’m still on the fence about black penny loafers, but I think tan and/or white ones are too cute! They instantly dress up an outfit in a way flats otherwise cannot.

  6. 6
    November 23rd, 2010 at 4:04 pm

    i bought some tan ones over the summer and love them

  7. 7
    November 23rd, 2010 at 4:17 pm

    As I tend to love menswear-esque shoes (I have just one pair too many brogues.) I think I should love these. And on other people, I do. But I was required to wear them as part of a uniform in high school. So – just like plaid, polos and knee socks – I have to steer clear of them.

    (But, hey, if I ever change my mind they’re at the back of my closet waiting. My mom forbade a uniform-burning party at the end of senior year.)

  8. 8
    November 23rd, 2010 at 4:35 pm

    Hmm, no thanks. I think only someone like Alexa Chung can pull off penny loafers, so i’ll leave them to her and stick to my boots and flats :)

  9. 9
    November 23rd, 2010 at 4:41 pm

    I think they work with skinny jeans or bare legs or skirts, but not with wide leg jeans and too masculine pieces.

  10. 10
    November 23rd, 2010 at 4:44 pm

    Oh if i was taller i would love them… But considering my size i dont think it’s a great idea..

  11. 11
    November 23rd, 2010 at 4:59 pm

    I’ve worn my penny loafers in almost the exact same way: dress, slouchy cardigan, OTK socks.

  12. 12
    November 23rd, 2010 at 5:46 pm

    They were part of my high school uniform and yeah, I don’t see myself wearing them anytime soon.

  13. 13
    November 23rd, 2010 at 6:09 pm

    Yes, I’m a fan! I want some tan ones.

  14. 14
    November 23rd, 2010 at 6:14 pm

    I haven’t quite decided on this one yet, but I have to say, the outfit you’ve put together might just convince me!!

    Charlotte xxx

  15. 15
    November 23rd, 2010 at 7:31 pm

    I still cannot disconnect the association of penny loafers with my Mom or Grandma. My friend wore it once and I think it was just … ok. I think you really need great legs to pull them off (like Alexa Chung) without looking too frumpy

  16. 16
    November 23rd, 2010 at 8:38 pm

    Yes…already did long ago, and would again. In those days, we put dimes in them because it was enough for a phone call :) I’d probably put foreign coins in for decoration now.

  17. 17
    November 24th, 2010 at 12:16 am

    Love penny loafers, have a pair from Topshop myself. Although I think this trend already started last year. I would wear mine with tights or over the knee socks.

  18. 18
    November 25th, 2010 at 12:07 am

    i really like it when you feature loafer-styled MOCCASINS instead of loafers — loafers extend further back onto the foot.

    can we please at least find an image of THE RIGHT SHOE

  19. 19
    November 27th, 2010 at 2:55 pm

    I’ve never owned a pair, even in elementary school (to fancy for kids really, everyone had sneakers) but I have been looking for a pair for a while. Couldn’t find anything that calls my name, but I know they’re out there.

    They are totally cute and not outdated, but classic.

  20. 20
    January 13th, 2011 at 10:42 pm

    I have been hooked on penny loafers for years. So comfortable and easy to wear with almost anything. I just added a pair of Bass Wayfarer’s in a candy apple red color. Now these are classic and I love how they fit. I’m a penny laofer fan from way back in the Weejins and Dexter Jessica style days.

  21. 21
    April 25th, 2011 at 5:01 am

    I’ve worn penny loafers for a great deal of my school years (like ALL of them). It was fairly standard with the uniform.

    I didn’t get to wear them again until a few years back, but I got the dark brown one from Sanuk. It was fantastic. It went with my casual (I live in a tropical climate) wardrobe. But now I’ve hit my 30′s, I might invest on a loafers that are a bit more dressy, but the rule is that no penny loafers in black. :)

  22. 22
    July 17th, 2011 at 10:59 am

    The shoes pictured are moccasins, not penny loafers.

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