How to Wear Booties to the Office

how-to-wear-booties-to-the-office2017 Update: We still stand by our advice on how to wear booties to the office, but you may want to check out our recent roundup of sleek strappy pumps for the office if you are in search of other options to wear with tights, or our most recent discussion on what boots to wear with tights to work.

After years of tall knee boots, I’m personally thrilled that ankle boots and booties are 100% back. I started out writing our usual Hunt feature but then realized: There are so many styles now, it’s worth discussing: How many booties/ankle boots do you have for work, ladies, and how do you wear them?

Pictured at top, clockwise: tall bootie / boot-pump / Western boot / low ankle bootie.

To my eye there are a few major styles, with distinct ways to wear them — and not all of them are for work:

how-to-wear-low-ankle-booties-to-the-office1) The low ankle bootie, such as the Petty, pictured — this looks best when worn with ankle pants or possibly wider trousers, but it can be difficult to wear with skirts and dresses unless you are very young and/or attending Coachella. Still, these have been around for years and are the most established and probably the easiest to wear to work. Examples: Sam Edelman (note these come in wide widths sizes 4-13), Vionic, BP., Dolce Vita.
how-to-wear-western-booties-to-work2) The almost Western bootie with a chunky heel, possibly with a dip in the front of the boot (such as the Margot, pictured) — wear them with ankle pants, skirts, trousers, and dresses, but note that these have a more casual connotation because of the Western vibe. Examples: Rag & Bone (buckles), Rag & Bone (sleeker, pictured), Dolce Vita ($142), and UGG.
The Best Kind of Booties to Wear to Work (and they're $99!) | Corporette3) The sleek bootie/pump, probably with a skinny (and high) heel. These come and go in terms of popularity — they were out for a while but seem to be coming back now. These are in many ways the easiest to wear because they’re just like a pump. Anything goes — wear them with pants, trousers, skirts, tights, hose, bare legs, whatever — you can even dress them up to wear with a suit. Examples: this highly-rated $99 pair from Bella Vita (pictured – note that it comes in four widths), this pair from Aquatalia, or this pair from Ecco.
perforated-booties-for-the-office4) The sandal/open bootie, often seen with perforations, a peep toe, a sling back — these are best for transitional weather, and often read to me like bulky sandals. If you can’t wear sandals to work, don’t wear these. Examples: Adam Tucker by Me Too (pictured), Frye, Isola, Free People, Vince Camuto, Paul Green.
how-to-wear-tall-booties-to-work5) The tall ankle bootie, often seen with a block heel — this is the most modern version, in my mind, and I’m still getting used to seeing it around.  I first spied it on BrainDead (this GIF is the best screenshot I can find right now), and thought to myself, well, hey, she’s supposed to be a bit of a rebel/outsider, so it’s fine — but now I’m seeing more and more of them, particularly with skirts (knee length or lower), culottes, and more, including in fun fabrics like velvet. (Nordstrom has a dazzling number of velvet booties right now, including these $89 boots.) Know your office and yourself here — if you have any doubts, I’d say it’s best to save it for the weekend right now. Examples: Vince Camuto (pictured, only $140),  Prada, TopShop ($150!), Paul Green (water resistant), Steve Madden (platform!),
clog-booties6) Weekend booties: definitely save these for the weekend, unless you work in a very creative office: moto booties, clog booties, lug soles, and anything with shearling or a harness. Pictured: the best selling clogs at Zappos from Dansko.

Ladies, what are the major types of booties in your work wardrobe — and how do you wear them to the office? 



  1. If anyone is looking for a lower priced dupe of the Rag and Bones, I really really like these by Lucky. Very walkable, and lots of great color options.

  2. #5 is the only one I could see myself wearing.

    I think I see them working well with skirts + black tights. I also see them working with pants (I wear bootcut pants with 2″ block heels anyway) and also jeans (not skinnies, but all others).

  3. 1 (with nice-and-not-too-tight skinnies on casual Fridays) and 5 (not as strappy, though, with black tights and a pencil skirt) are the only two that would work for my office. The others are firmly in Weekend Only camp.

    I would not wear booties with a suit because if I need to be in a suit, I definitely need to be in more conservative footwear.

  4. This would be a much more effective post with visuals of the “how to wear them” rather than just picture of the booties themselves.

    • Ooh, yes! Good idea.

    • I wear bootie’s to the office onley when I know I am NOT goieng to court. They are best worn with jean’s, ankle pant’s or even yoga pants (if your tuchus is not to big). They do NOT go at all with dresses, unless you want to look like a model. Again, you must have the tall, thin look, not the short, squat look like I do. FOOEY!

  5. Disagree on the low ankle bootie. I am not particularly young and I am not attending Coachella but I wear my Petty boots with dresses (in my very casual office) all the time. But open-toe booties make my blood curdle.

  6. Another Waxing Q :

    I have a male friend coming to visit this week. Tomorrow night or Wed he gets in, dependent upon other things. I was thinking of getting a surprise Brazilian wax but I’ve never had that done before. Will I still be able to “garden” effectively if I get it tonight? Will it hurt too much and leave me useless as a gardener?

    • Anonymous :

      I would highly recommend doing a close trim rather than a full wax if you’ve never done that before. Without knowing how sensitive your skin is, it’s hard to say how tender (or worse, irritated) you’ll be.

    • If you get it tonight you’ll be fine Wednesday but not tomorrow most likely. Most waxers recommend no friction in the area or even a hot shower/bath for the first 24 hrs. I am usually “back to normal” tenderness/redness wise by 36 hrs but 48 is ideal for LGP.

    • Anonymous :

      If you are concerned about pain, make sure to take a pain reliever before your appointment. It will help cut down on tenderness.

    • Definitely wait at least 24 hours after the wax to garden or to be seen in uh, LGP mode. I look all red and have little pinpricks where some deep hairs were right after a wax. It takes at least 12 hours to look “normal” again for me.

  7. Dressy Casual? :

    I RSVP’ed to an evening event in the NYC area that says “dressy casual.” When I asked the organizer to be a bit more descriptive about what correct attire was, her response was that a daytime dress would not be festive enough, but a cocktail dress would be too fancy.

    I need help! Can anyone translate this dress code into English for me?

    Many thanks.

    • Shopaholic :

      Black dress (sheath maybe) with a statement necklace?

      that would be my best suggestion but I have no idea what the dress code means in English

  8. Dressy Casual? :

    I RSVP’ed to an evening event in the NYC area that says “dressy casual.” When I asked the organizer to be a bit more descriptive about what correct attire was, her response was that a daytime dress would not be festive enough, but a cocktail dress would be too fancy.

    Men have been told that sport jackets and ties would be nice but not required.

    I need help! Can anyone translate this dress code into English for me?

    Many thanks.

    • Your favorite work dress with fun accessories?

    • Anonymous :

      Sounds like the perfect occasion for a “day-to-evening” dress, the kind that is usually too dressy for day and not dressy enough for night. MM LaFleur has some dresses that might fit the bill.

    • Anonymous :

      I think it means your shoes / accessories need to be decidedly not every day.

    • Legal Cancuk :

      I would think skirt and nice blouse with a statement jewelry piece and shoes. If jackets and ties are nice but not required for men, they mean they want the men in them. This is the worst way to describe a dress code.
      I went to an event that was dressy casual and people were in jeans ranging to full on tuxes (I wore a black and white dress with a leather blazer and stillettos). Girls were ranging from cocktail dresses to jeans.

      It was so hard to figure out what to wear on these events.

  9. hilarious :

    that’s an annoying dresscode

  10. Putting my comment here in case anyone comes back to this post… I bought the Bella Vita shoes (#3) this week and they are very comfortable. Amazon has a number of different colors, although I stuck to black suede to wear with skirts/tights and with slacks.

  11. Bootie problems :

    I am getting ready to interview at several residency locations in medical settings. Many are in cold locations and we will be walking several blocks. Can I wear plain, 2-in heeled, black booties with a dark navy suit? Are booties with a suit a non-option for interviewing?

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