Poll of the Day: Will You Wear a Peep-Toe Bootie to Work?

So I have been seeing the peep-toe bootie every.where this season, usually styled with skirts or cropped pants.  And I always think the same thing — “Cute!  But definitely in that ‘I’m-so-hip-I-don’t-need-to-wear-flattering-clothes way.'”  You know, like harem pants and those huuuge 80s-ish glasses that some kids wear.  The peep-toe bootie trend also strikes me as completely inappropriate for the conservative office, at least when worn with skirts.  (Pictured:  Sam Edelman ‘Wakefield’ Wedge Bootie, available at Nordstrom for $199.95.)

But then I started wondering — is my gut reaction shared by others? After all, peep toes have come a long way, baby…

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Readers, what are your thoughts? Which newish trends will you be trying at the office this year?

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  1. I would very happily wear a peep-toe bootie to work, but not one with a high wedge. I think I would probably not wear a high wedge to work.

  2. Not a fan of peep-toe booties. They don’t make sense to me– boots are to keep your toes warm.

    • I know, I get way too much cognitive dissonance looking at them. That said, they’re better than those boot flip-flop things, which I find atrocious.

      • Those are so bad. The ones with almost-completely-open foot and then the cuff around the ankle? Blech. I have yet to see one person in real life who looks good in those.

        • All I can think of when I see those is “wow, I bet her ankle is sweating.”

    • i agree. i feel like the designer made a pair of boots and then ran out of material for the toe.

    • Cognitive dissonance is exactly the problem for me as well. I think that is the point of them – it is supposed to be a little shocking/surprising to have a boot covering everything up and then have the toes peeking out. It almost makes seeing the peeping toes too intimate for comfort. I saw a magazine ad recently where I finally got what they are going for – they looked kind of fabulous on the model, who was totally covered in monochromatic boots/tights/long-sleeved dress and only her toes were showing – but there is no way in a million years I could pull them off (or would want to, really). All that being said, I still see no excuse for the boot flip-flop things.

    • Yes…they are as illogical as corduroy shorts in winter, short sleeved sweaters, and “flirty” business suits… what’s truly amazing is that someone thinks of these idiotic ideas, and at least one other person agrees and says yes… Can’t wait to snicker at them on the clearance rack at TJ Maxx in a few months

      • Anonymous Today :

        Hey, I love short sleeve sweaters! They are great for layering.

        • I think Shayna was maybe referring to thick, heavy-knit sweaters that are inexplicably short-sleeved as opposed to something like a cashmere short sleeved tee that is awesome for layering and very versatile. Just guessing here.

          • Anonymous Today :

            I also layer thick, heavy-knit sweaters, but over blouses instead of under jackets.

          • I do the same, I have 2 heavy short sleeved cowl neck sweaters that I wear over really thin long sleeved blouses.

      • I love short sleeved-sweaters too! I have a hell of a time finding button-down shirts/blouses that fit, so I wear short-sleeved sweaters in the summer because they’re dressier than t-shirts.

      • I love corduory shorts in winter, I wear them on weekends with wool hose (leggings?)

  3. They’d be fine in my office on non-court days, but I wouldn’t wear them, because they are just not my style.

    • Ditto – I don’t think they’re inappropriate, I just don’t like them. (You wouldn’t wear them barefoot, right, because they’re boots? but what’s the point of peep-toe with socks? Too confusing!)

  4. No, really? I am in the ‘when pigs fly by my window camp!’ And, yeah, why wear a boot that has a hole over your toes – defeats the purpose. Maaaybe for the verrry young, not at the office EVER, but for me, just never.

    • Agree. These would never meet my feet on a work day or play day.

    • Agreed. Totally skipping this trend.

      They’re definitely not for work. Plus, with the very few opportunities I have to wear shoes on the weekend that are not running shoes or flip flops, I am sure as heck not wasting a cool-shoe opportunity on these abominations!

  5. Gaaah, I am really not a fan of the peep-toe bootie! It seems to defeat the purpose of both peep-toes and boots. Also, if you can’t wear socks, don’t your feet get all sweaty except for your toes?

    • Socks, maybe not, but they have toeless tights/pantyhose which have a sandal-like strip of fabric that goes between your big and second toes. Kind of like mini-stirrups.

  6. Love the trend and would wear a peep-toe bootie but not a wedge one because I wouldn’t wear a wedge. I already started wearing booties two years ago (in Biglaw) so this is just the next step. I can see how they would not be appropriate for all offices, though.

    My one caveat is that I don’t wear peep-toes in the winter because of the pantyhose issue. But for that issue, though, I would totally wear them.

    • Anonymous :

      If you like this kind of look you’d probably like peep toes with tights, especially bright tights.

  7. “Cute! But definitely in that ‘I’m-so-hip-I-don’t-need-to-wear-flattering-clothes way.’” <– Kat finally put into words the feeling I've had about this look since it started! : )

  8. It seems fashionably unique and applicable in a corporate setting, but IF and only if you’re comfortable doing your corporate responsibilities with such unbelievably high wedge.
    Well, to each her own.

  9. Haven’t worn a wedge since I was 8 and am not about to start now…

  10. I wouldn’t wear that even if pigs did fly past my window.

    The style looks kinda “clubby” to me – like all the peeptoe/boot/sandal combos.

    • Little Lurker :

      Do you mean “clubby” as in, “it recalls the clubbing scene” or as in, “it makes your foot heavy like a club”? Because I definitely agree with the second sentiment! ;)

      • I meant I only see women going to the clubs sporting the peep toe bootie, and that other version that is like a sandal/boot.

        So I did looked through 100’s of “peep toe booties” and decided I would wear these, but obviously not to work. Maybe to a club or as part of a halloween costume! Ha, but I do like at least one pair out there!


  11. divaliscious11 :

    Wouldn’t wear peep toe booties anywhere….. do wear peep toes shoes to work though….

  12. I’m too old to jump on every bandwagon that comes along. I have muscular legs (but skinny ankles) and I look terrible in ankle boots unless there are pants over them. I love my peep-toe pumps, but these just look weird. No thanks. Other trends I will be skipping this year:
    -“Jeggings” – these were jean leggings when I was growing up and yes, I wore them then. But I was 14 at the time. Not wearing them again as I have better taste now.
    – Acid-washed denim (see above)
    – All-leather outfits
    – Jumpsuits
    – Pleated denim in any form
    – Socks with pointy-toe or maryjane pumps (this has been all over the magazines; can I just say, GAH!)
    – Military jackets. On tall, skinny girls they can look chic. On me, I look like I am actually in the military, and got the wrong size BDU issued to me.

    • I love the socks with pointy-toe shoes look! I saw it in several magazines too and I can’t wait to try it when classes start back up.

      • No offense, but the fact that you’d be wearing them to school pretty much tells me all I need to know about who that trend is aimed at. And it ain’t me. :)

        • Anonymous Today :

          I wouldn’t be so quick to judge regarding the target demographic. I am in my late 20’s and did the socks with t-straps after it was prominently featured in J. Crew’s catalog last year. And I got a lot of compliments on it. To be fair, my office is business casual.

          • The socks with pointy-toe shoes trend was popular in Japan when I lived there 7 years ago. I don’t think it’s new or aimed just at younger women. They had some socks there just for that type of shoe that were fantastic. I haven’t been able to find anything similar here and am disappointed.

          • late 20’s here too. I wouldn’t wear them to my fall externship with my judge, but I will to class/shopping.

          • Yeah. I’m not in my late 20’s, either. I am old enough to remember when Olivia Newton-John et. al. wore this trend the first time around, which means I am definitely too old to go near it this time. But for those of you who are not, hey, feel free. (as long as it’s not to work. Yikes.)

          • Anonymous Today :

            I still disagree that it’s aimed exclusively at younger women. I remember when this trend was popular the first time around, too. The way it’s generally worn now is much more polished and less…loud, for lack of a better word. Incidentally, my late 30’s sister and early 40’s boss also like the look. I think it’s more a matter of personal style than of age.

          • My colleagues from Japan wore this look when they were visiting for a conference a few years ago (I think back in 2007). It’s difficult to pull off and seems to go with a very specific style – they wore very “girly” items along with the socks and heels. They’re also very petite and look very young for their age so they pulled it off really well. Can’t say it fit into the American corporate setting but they had some leeway because they’re not based out of headquarters.

    • Amy, I feel your pain. :) If these are the trends this year, can the stirrup pant be far behind?

      • It’s here. But the stirrups have moved further north….


      • No, they cannot. The back page of this month’s Lucky had a pair of Hammer pants (they called them Harem pants but they were Hammer pants, and I can say this with authority as I met MC Hammer back in 1991). I predict we will be seeing pleated-front stirrup pants all over the place in about a year. Fashion editors will suggest wearing them with something “cheeky” like a Flashdance-style ripped sweatshirt, fingerless lace gloves, and those lace-up grandma ankle booties that have already come back a couple of times. And every time I see some version of that outfit on the street, “What A Feeling” will be playing in my head. Sigh.

        • Wait, I thought hammer pants were last summer’s bad trend? They haven’t gone away yet?

    • Don’t forget the ‘new’ denim-on-denim trend!

      Oh the recycled trends. People think they are oh so trendy and fashion-forward, but just look back 30 or 40 years and there it is!

      • Oh no, not demin on demin — someone just had denim with camel (workchic?) and I just about gagged. Having done it before means that I really shouldn’t be doing it again!

    • Agree… and I’m not old, fyi.

      Also, harem pants… no one looks good w/ a baggy crotch. Not even MC Hammer. Some of these trends died for a reason the first time around!

    • Most of these trends were popular when I was in high school in the 80s. The socks with pumps, leggings and acid wash I remember, and I cringe every time I look at those pictures. WHY OH WHY would we want to go back there???

    • Amy, thank you for adding a laugh to my afternoon.

      Signed – your presumed age peer!

    • Anonymous :

      I saw a woman wearing a single half-sock with flats (the sock only covered half her foot, leaving the toes and ball/vamp bare). It looked like an ankle brace, only it wasn’t.

  13. I don’t think they look “professional enough” in that I would never see a woman in these and assume that she held a position of power unless I was in a P.R. firm or an ad firm. They scream intern or assistant to me.

    Secondly, I just don’t like peep-toes at all – purely personal preference. It’s summer, six-degree temps outside, I’m in thick boot socks, simple black kitten heel boots under my suit pants, and my feet are FREEZING. Peep-toes are torture for my cold feet. Also, those of us with narrow feet often find enough room for our foot to slide around inside and angle themselves so that one special toe can reach out and hang over the edge of the shoe – neither professional nor sexy. And what’s the point of that?

  14. Other because I think they are hideous and would never wear them anywhere :) But then again I think most, if not all booties, are hideous, so I am probably not the person to ask!!! Clearly I am not hip at all!

  15. Anonymous Today :

    I wouldn’t wear the ones pictured anywhere. I would however, wear something like these ones to work:


    • Cute, I think the key to good booties is that the ankle isn’t covered and it has a low rise like these.

      • Anonymous Today :

        I think you hit the nail on the head as far as the booties not covering the ankle.

        And I kind of want these now! I’m upset that they aren’t left in my size.

        • This is another pair I really like (from a site that I love). They kind of bridge the gap between gladiator and bootie, obsessed with the cone heel.

    • Chicago K :

      I like these!

    • Anonymous :

      love these

  16. I am so glad that a majority said no. Maybe peep toe flats but not these wedges, I don’t know why they remind me of clogs (especially with the flying pigs comment)

  17. What’s wrong with wedges that people won’t wear them?

    • I know. I wear wedges a lot.

    • Personally, I don’t think they look good (but that’s just my taste). Every time I get a pair thinking that they’ll be more comfortable and supportive, they actually hurt my feet more than heels or flats, are clunky, and are generally heavier. I also think they’re more casual in appearance.

      • anon - chi :

        Agree that they are generally more casual. I would not wear them to court, but I have a number of lightweight wedges that I wear to work and love. The trick to work-appropriate wedges, IMHO, is to get a wedge that is fabric/suede/leather covered rather than one that looks like cork or stacked wood. I’ve found a number like this at Cole Haan over the years.

    • I also like them, but not as high as these! I look for a wedge that is narrower at the heel and agree that cloth/ leather covered is more professional, though I think there are probably stacked wood exceptions.

      With a lower heel they are more comfortable, but at 3+ inches I don’t know if anything is.

  18. I would wear them to work if they weren’t against my employer’s dress code. We aren’t allowed to wear peep toe anything unfortunately.

  19. Those are some of the ugliest shoes I have ever seen. I’m 23, generally on top of things, and I had no idea that was a trend. I wouldn’t wear them anywhere.

  20. I do wear peep toe pumps to work; my workplace is not at all conservative (most people wear sneakers). BUT, I dislike the peep toe bootie trend (frankly, I dislike booties, peep or no) and will be staying off that bandwagon.

  21. Not even if pigs *did* fly by my window. I haven’t felt such a strong rush of DO. NOT. WANT. in years…

  22. I would totally wear these to work for a day if Glinda the Good Witch promised to pay off my student loans – otherwise, no. These are fugly.

  23. I’ll be one of the bold and lone dissenters and say that I love them.

    • Me too! But not to work.

      However, I just bought these shoes:

      So it’s painfully clear that I am in the lone minority regarding peep-toes. (The Inga sandals I linked to are RIDICULOUSLY comfortable for 3.5″). I can’t wait for it to get cold enough for opaque hose that I can really wear them.

      (Late 20s here).

      • Didn’t make it obvious enough, but I wouldn’t wear either to work. But am quite happy rocking them on the weekend.

      • These are nice — because they don’t really look like booties, more like a sandal.

  24. I love Sha-Booties (short for shoe bootie). So high fashion. But, unfortunately, they would be incredibly misunderstood by the middle-aged, male (sorry to discrimate, but its true) partners. These beauties are for personal, not professional, time.

    • I agree, I think peep-toe shoes are ok, most (middle-aged, male) partners wouldn’t even notice honestly, but these horrors? They look extremely odd and would be noticed as such, and I’m someone who finds many of the rules touted in the comments here to be rather arbitrary.

  25. I had some sky high wedge heels (black, cloth material, with buckle) from the early 2000’s. Ca-UTE. No peeptoe, though. Got them at Nordies. Wore them TO DEATH for about 2 years. Not sure if I got rid of them (always on the fence). I hope I didn’t!! I’ll check when I’m home. LOL.

  26. I voted yes maybe for casual friday with trousers. But NOT these particular ones! **shudder**

  27. The poll isn’t cooperating w my phone so I’ll just say my opinion here:

    this shoe is so ugly I wouldn’t wear it to muck out the pigpen. It’s not stabile/practical enough for that either n

  28. These make about as much sense to me as crotchless panties . . . and look about as classy.

    • These make less sense to me than crotchless panties. At least no one who doesn’t want to see your crotchless panties has to :)

    • LInLondon :

      Haha, best appraisal I’ve seen yet! Peeptoe booties are /atrocious/

  29. I would not wear that pear (not a fan of the wedge …) but I have a pair of these: http://www.stylefeeder.com/i/rjxrhtyg/Gretta-Glendale-Rich-Brown-Footwear in black that I got in the spring of 09, and still wear frequently. I do work in a non-profit, not a law firm or anything.

  30. Anonymous :

    Those shoes are an oxymoron. It’s cold so I’ll wear a boot! It’s hot so I’ll wear peep toes! I’m a fashion victim! Help!

  31. Experienced :

    These in particular–excellent & conservative with tights.

    • I didn’t like them, but I can see how they would look nice with tights. Way too trendy for me personally…

  32. This has to be one of the ugliest shoe trends in recent memory.

  33. I’ve seen some cute ones, but with cutouts down the entire shoe and a regular heel, so the peep toe doesn’t look as out of place as it does when the rest of the shoe is whole. Similar to these:

    But I wouldn’t wear these to work, only for weekends.

  34. Anon in Midwest :

    Ok, just for curiousity’s sake, you know, to see what the kids are wearing these days, I did a search on Zappos for “peep toe bootie”, and here’s the most ridiculous example I found:


    I mean, come on, how are you going to kick some sh*t with open toes?!

    • Anon in Midwest :

      p.s. just watch the video description to see how silly they look when worn

  35. I want to wear a very toned down version of this- meaning, not really a peep toe if it is a bootie, definitely not a wedge, a moderate heel…maybe a small peep toe if it is more of a sedate pump than a bootie. Some of these styles look fairly conservative to me if the heel is moderate and there is no platform.

  36. Joy Sargent-Smith :

    On the subject of wearing the peep toe booties to the office. Never mind the office, I wouldn’t wear them anywhere. Aside from being downright ugly and clunky, they look like a sprained ankle waiting to happen.


  1. […] acceptable to wear with tights than they used to be (just for kicks take a look at our 2010 poll on peep-toe booties), the most conservative option is still, I think, pumps or flats, whether with straps or without. […]

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