
Loafers have never much worked for me. Ridiculously, perhaps—because I’ve certainly never met a clunky-ass boot I didn’t like—they’ve just never quite felt feminine enough. But in fact, it’s probably their very diminutiveness—and that dead solid flatness—that turns me off the most; even sneakers give you a tiny bit of height. Lately, though, I’m coming around—possibly because they’re the perfect easy on-easy-off shoe for airport security, and outside of summer items, exactly zero percent of all my footwear could be characterized as easy on, easy off. Dieppa Restrepo makes some of the most covetable loafers and oxfords around, quite a few of which are on sale right now at the insanely great lower east side boutique Maryam Nassir Zadeh (another one to put on your must-visit in New York list, people). These python penny loafers feel seasonless: imagine them come spring with cropped straight khakis,

Also from Dieppa Restrepo: a wooden platform provides a nice bit of height, but without any resulting Frankenstein Foot—which is always the risk.

The braid detail on this Rag & Bone pair adds some gravity, and the slightly weathered blue leather is just unexpected and really cool.
I love these: so simple and classic and Euro-prep. And they cost way less than other very similar versions for sale elsewhere.

Does it surprise any of you regulars that I have been longing for these metallic Sperry Topsiders for ages? The only reason they haven’t been a a Crazy or Cute? is because I’ve felt certain they’d get clobbered. But the metallic is well on the safe side of crazy, and there is something deeply satisfying about the notion of reclaiming a shoe I haven’t worn in three decades (and because Candies aren’t on the table).










Not into the loafers; with a size 10 foot I never look for shoes that will make it look even longer, and loafers do exactly that. But thanks for the link to the Camay web site! What a treat!
My size 10 is not particularly fond of the choked up loafer, but occasionally I have found styles that have a shorter front. They look best with cropped trousers- no socks. The Sperry topsider looks good on no woman old or young who is bigger than a size 7. Sorry the whole shoe is too grandpa or preppy guy in structure. If they streamlined the pattern to flatter a woman’s foot it would be a must have in every wardrobe.
I have a size 11 foot and I truly do not believe that my foot looks any bigger in my bright blue suede J Crew loafers! (“Denial!!!”) I wear what I want because it gives me pleasure, and everytime I look down at my feet, I smile. (“Pole!”) I’d get the Sperry’s or the Rag and Bone.
I have those metallic Sperrys (I also have those gold clogs from a few weeks back. Maybe I have a problem?) and I love them.
Watching Isaac Mizrahi on Project Runway All Stars 2 has cured me of any desire for loafers. He wears them incessantly.
I have a closet full loafers. It’s just about the only shoe that designers actually make in attractive styles for wide sizes. I get compliments on my shoes all the time. Never once has any one ever said to me “Gee you have short, fat feet. Those loafers look awful.” Get the loafers. And the Sperry’s. You will smile every time you look down at your toes. And every one looks good when they are smiling.
I love loafers for air travel. Easy on/off and are more dressy than Toms or sneakers and more support than ballet flats. Love the Sperry’s.
I can’t bring myself to wear Sperry’s now… I’ll forever associate them with the sailors at my parent’s yacht club in the 70s and 80s. It was not a hoity toity, “Muffy, I’ll meet you for cocktail hour on the deck at five” type of yacht club. All of the usually slightly drunk old men who had spent too much time in the sun and whose clothes were always covered in bottom paint wore Sperry’s at the yacht club. They are probably still down there, wearing the same pair of shoes. Sperry’s just remind me of things I thought were gross when I was growing up. That said, they look better in gold than in other colors!
My 17 year old daughter has the metallic sperrys in rose gold color and they are VERY cute on her. As for me, I think maybe the navy blue but not the gold.
I love loafers in theory (and, oddly, I kind of like the Sperrys, despite my rather strong reaction to the gold clogs), but I’ve never really found a way to style them that didn’t look awkward or hipster-juvenile. Maybe it’s how far they come up the foot? I don’t have the same problem with other types of flats.
Loafers, in general, seem awkward. Sperry Topsiders are so specific – does that make sense? – that you can’t really own your style in them. They are cute on 17 year old girls who are cute in anything…
I used to not be into loafers but now I lurve them. I have a cream colored pair. I wore boat shoes as a teen and recently purchased a more chukka-ish Sperry style in olive nubuck and another in black pony hair. I haven’t worn such a style in decades nor wanted to so perhaps this Means Something.
i’ve been collecting loafers lately because i think they look better than ballet flats with skinny/straight jeans on my ‘hippy’ frame. and a good pair is essential for traveling!
I have the Sperrys in metallic silver, size 10, and I love them! Don’t think they make me feet look bigger unless the proportions of whatever else I’m wearing somehow highlight the feet. And I’ve been eyeing Bass Weejuns lately. Guess I’m regressing to my parochial grade school footwear style.
In 2007 I bought a pair of Rockport loafers in navy with a white inset for a trip to France with my niece. I wore those things like crazy. They were perfect for the shoe removal at the airport and perfection for walking all over Paris. I still wear them on EVERY trip and just about everyday when I’m going casual. So comfortable. I love those things and I get compliments all the time. Also, I wear a size 9 and my feet don’t look larger (and even if they did look larger I would still wear them). I don’t like gold or metallic but those Sperrys look just fine. As someone else said, wear what you love.
Count me as another who owns the metallic Sperrys, and loves them. My only problem is, I wear a lot of stripes,which just skews too nautical when I wear them together. But they are super comfy and I love the platinum gold color.
I don’t know why I prefer oxfords over loafers, but I do. Although, ballet flats are my first choice for flats. The python penny loafers are pretty cool, though! I might reconsider.
I just don’t have the right legs/ankles to look good in mannish shoes. Unless we are talking doc martins.
I like the python, assuming it’s fake, but otherwise they sort of look like men’s bedroom slippers to me. In fact, I think I’d like them better if they *were* men’s slippers. I feel bad saying this because I am a big believer in women wearing shoes that don’t hurt. Maybe I’d like the metallics if I could see them better?
And I have issues with oxfords too, maybe because they look like men’s shoes but not in a good way.
The other thing is, I’ve read that what you really want in a shoe is about a 1 inch heel. It is supposed to be good for you for some reason. I find that I can put a Superfeet insole into almost any shoe and I’m all aligned. So, I ditto the “wear what you love” people. Even if what you love is a loafer. I have a feeling I’d like them better if I could see the whole outfit.
I own those Sperry Topsiders and they add a special little punch to casual clothing I just love. Plus they are amazingly comfortable. Jeans, a huge white cable sweater and those shoes and I am good to go. My shoe collection is mostly loafers anyway!