Wednesday, January 19, 2011

Walking the halls, not the streets

Last week, I noted my personal discomfort at flirty tights in the workplace and posed a question to you, my readers--Are there any items you just don't feel comfortable wearing to work even though they're not expressly forbidden by the dress code?  Several ladies brought up the question--can you wear knee high boots with a skirt in the workplace without looking like a hooker?

Yes. Unless the answer is no.  Skirts and knee-highs should be avoided in conservative business professional dress code offices.  But since most workplaces are some kind of hybrid business casual, the answer is yes.

Aside from your office's dress code, here are some things to consider.
  • Heel. Flat heels come off as more casual, but not all high heels are created equal, either.  A thicker stacked heel reads better than a stiletto.  Avoid very high heels on boots (maybe 3" tops), which will add to the hooker-ish ambiance.
  • Color. Stick to browns and blacks. Grays are a great casual neutral, but may stand out a bit in the office.
  • Material/finish. For office wear, opt for a matte leather (or faux, whatever your preference) rather than shiny or patent, which will just serve to bring more attention to the fact that you're wearing knee-highs to the workplace.
  • Skirt style. Pairing your boots with an A-line skirt is the safest way to avoid a streetwalker connection, but a pencil shape can be appropriate as well, as long as the material is nice and the fit is not tight.
  • Skirt length.  A nice general rule--the higher the boot shaft, the longer the skirt should be. Think of it as a meet-in-the-middle.  If your skirt overlaps with the boot, it's fine (it may feel weird in the beginning, but the overall look is not as awkward as it feels, and certainly not as awkward as being mistaken as the entertainment).  And of course, if the skirt isn't appropriate for the workplace in the first place, don't try wearing it with the boots--it won't help.
  • Legwear. From trial and error, I would recommend wearing some kind of legging or tight with boots and skirts if any knee will be showing.
  • Condition. Make sure your leather footwear is free of visible scuffs and scratches. Nothing makes you look like a novice more than a scraggly wardrobe.
  • Balance. A covered up top goes a long way in balancing out the raciness of the boot. As you'll see below, I pair all my skirt/boot outfits with at least a 3/4 length sleeve. When I wear my boots with skinny jeans, though, I often go sleeveless.  It's all about balance.
I have four pairs of tall boots--flat and heeled in black and brown. But only two of these have made it into my work wardrobe-- my brown ones! My black flat boots are completely ratty, and my black heeled ones are too big. And I've been on more of a brown kick lately.  Here are some ways I've styled my knee-high boots for the office on the blog.

Heeled boots

October 2010 - with a brown corduroy pencil skirt (a little on the short side).
I think this would have looked better with tights.

March 2010 - Having a similar (but different) brown skirt helps downplay the boots
a little and creates an elongated silhouette despite my shortness.  The color
on top also draws the eye up.

April 2010 - Layering textures in the same shade creates a cohesive look
on bottom, and details on top keep the look fun.

Flat boots

November 2010 - Volume in the skirt balances out the leg underneath,
while the belt gives some curves. A turtleneck balances out the skin shown below.
November 2010 - Flat boots with a pencil skirt work when it's not skin tight.

December 2010 - Add length by layering a skirt underneath a dress. 
I think I'm wearing tights under this, too, which downplays the gap
between boot and hem.

Working ladies -- do you wear knee-high boots with skirts to the office? How do you style them?  Email a pic or link to me by Thursday, and I'll do a round-up post of your pics Friday!


  1. This post is exactly what I needed, I'm always wondering about the appropriateness of boots at work! They way you've styled them is very professional!

  2. Heh, I'm wearing knee-high boots (almost flat, black leather, by Clarks) with a skirt (grey corduroy, straight, knee-length) & a blouse (black button-down) at the office right now! I also have several pairs of colored knee-high boots I've worn to work. Low-heel, suede, worn with straight or A-line skirts, all knee-length.

    Of course, I work in super-casual Silicon Valley, so anything goes. Still, I think these outfits would be fine anywhere but the most formal offices. Perfectly covered up, not at all risque, not too young or trendy, just a touch creative.

  3. I was laughing at wearing boots to work and "not looking like a hooker" - how very funny. But unfortunately true.
    I think your tips are head on.
    If I may add, white boots or very colorful ones could make you look like a majorette-

  4. I wear boots to work but I actually don't agree with having your hem meet your boots. On me, it makes me look shorter, and so I won't wear a skirt with high boots unless there's at least 2 inches of a gap between the 2. It works because I am short and avoid boots that go completely to my knee already, since they tend to make us short gals look shorter.

  5. I have not yet worn my new Frye's to the office. They make me feel like a giraffe. As I read over your guidelines though, I think they are spot on.

    I really like your third and fourth boot combinations.

    Rags Against the Machine

  6. I do wear knee high boots but didn't for the longest time.

    Funny story: my old manager wore boots with a black leather mini skirt. This is what made me never wear mine. Everyone talked about how she was dressed like a hooker. I did not want that. BTW our dress code specifically says that skirts have to be at the knee.

    I will send you an email later or better links but here are a few:

    I have 2 pairs of boots. Brown and black. I wear them both to work.

  7. Oh to my friends at work I call my boots my hooker boots and tell them I have to quit doing that because the name itself makes it seem not work appropriate.

  8. Hmmm, it never even occurred to me that this was a question! In my business-casual office (more business than casual--no denim allowed, etc) several women, including myself and the CEO, wear knee-high boots with skirts regularly. Now thigh-high would be something else entirely!

  9. Such a great post, A! This was something I always struggled with when I had a corporate dress code. Really solid advice! :)

  10. Thanks so much for this post! Your advice definitely helps me with the outfit I had planned tomorrow!


  11. @ kinsey - thanks! glad you found it helpful.

    @ trystan - I've never tried colorful boots, but I do imagine that with a knee-length skirt it'd look great!

    @ lorena - good call on the white boots! I just giggled imagining a majorette walking the halls at work.

    @ sara - good point. I don't think the boots have to touch the hem, I just think that the shorter your skirt, the lower your boot shaft (or shoe top) should be. Just like a longer skirt and ankle straps doesn't work. I'm not that tall myself (barely 5'4 on a good day), but I don't have that much experience dressing a smaller body than my own.

    @ terri - oo frye's. I covet frye's (and I really try not to covet). I say go for it!

    @ colleen - haha yeah I have some friends that joke like that, too (well, not with mine...I think black boots are more likely to be called "hooker boots" I don't know why).

    @ christa - You must have a natural knack for wearing them. My boss and I both are fans of the boot, so we do it often in my workplace as well.

    @ keira - Thanks! Your stamp of approval means a lot!

    @ phoebe - sweet! glad i could help. :)

  12. I was hesitant to wear boots to work at first (I am a under-30 health care provider, and many of my patients are conservative older folks) out of concern that it would look too young or too provocative compared to my heels and flats.

    What changed my mind was seeing a manager several decades my senior wearing tall black boots with a skirt that barely hit mid-thigh. Should I take fashion cues from someone who wears a pleated mini-skirt to work? No. Does it make wearing boots with a conservative knee-length skirt and suit coat seem reasonable? Absolutely!

    I am careful to keep my skirts to the knee, fitted but not tight, and I always wear hose or tights. My boots have a low heel, are a well-maintained neutral brown, and (importantly) don't click and clack on the hospital floors. I've had no complaints so far.

  13. Hello all, I'm actually a guy, I found your link via Twitter, your tweets works! I had no idea how much planning women go through regarding their dress for work. I'm an entrepreneur myself, and have been quite interested as I read through the entire page here including all the responses. I have a whole new meaning to how much women go through to dress for work...and I too got a kick out of the don't want to look like a hooker in boots at work, you literally had me laughing out loud, that means your blog is successful, people love humor! As a man, I truly think boots with a skirt on women in the workplace looks fine as long as its presented right...which you all seem to know how to bravo and well done...cheers

  14. i love seeing the different looks here! i've had troubles with the same issue but find wearing a dark pair of tights under the boots helps tone it down a bit.

    cute and little
    come join the Color Brigade!

  15. I'm completely befuddled by the idea that gray is too casual a color for the office. Black, brown, navy, and many shades of gray are basic, conservative neutrals.

    I see a fair amount of gray and gray pinstriped office options (suits, skirts, etc.) on Corporette, and those women work in a more formal environment than any I've ever even interviewed in. ;-)

    Maybe it's a function of office culture?

  16. I really like your November 2010 look. I wear flat knee-high boots to work with opaque tights and skirts/dresses and think it works fine. I'd be hesitant, however to wear both a high heeled stiletto boot and a miniskirt to work! Great post, informative and well illustrated!

  17. @ anon 1 - yikes! mid-thigh? Sounds like you've found a nice medium with boots, though!

    @ anon 2 - thanks for the feedback! Yeah, I don't know if most guys go through the same dilemmas as gals when it comes to dressing for the office. But hey, it's fun!

    @ kileen - Yup! I think so, too.

    @ anon 3 - Thanks for your comment! I am a fan of gray as a color for the office. However, this post is specifically about tall (knee-high) boots. For this purpose, I think a gray boot is better for casual wear (or Casual Friday in the office). But yes, every office varies, so my tips are far from rules!

    @ vanessa - thanks!

  18. I wear boots all the time in our business casual environment. We can only wear denim on Friday. I have worn over the knee boots with dresses, skirts and pants. I don't think I look like a hooker. I have red, brown, black and raspberry over the knee boots. I also have 2 pair of knee high black boots and 1 pair of grey suede. ALL of them have been worn to the office. I spend 90% of my day in a cubicle so I don't have to deal with the public at all.
    I love how you have mixed everything in your photos above. I have to say I am a "shorty" too at only 5'3" tall. Flat tall boots accentuate my vertical challenge so I don't wear them really.
    Please check out how I style tall boots with tall heels on my blog:

  19. Hi Yvonne - I don't think tall boots define the "hooker" look--it definitely depends on how you wear it. And from the looks of the outfits on your blog, you wear it well! Your raspberry boots are super neat, and it's really cool that you can wear those in your office! Thanks for stopping by!

  20. I wear low heeled (1 1/2 ") black suede boots with a long black dress.With shorter skirts, I like the look of tights and nice,polished loafers. I also wear boot-lets under pants. But a full-on heel of any type of footwear is asking for trouble in a school building with waxed floors. Plus, my feet would look great but my face would show my back's pain...

  21. @ teija - yes! Comfort and practicality is always key! I need to get some bootlets.


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