Mating, Dating, Relating, Medicating

Feb 06

Important Questions

I have a much more interesting blog post percolating about ambition, but for now:

1. What would you wear with this dress? I particularly need shoe help. I want the most comfortable ones possible that are also kind of hot. And I obviously can’t go bare-legged this time of year, so do people still wear nude stockings? The idea makes me feel like I’m suffocating, frankly, though I am a big fan of tights.

2. What do you use at work to keep track of your to-do list and stay organized? I generally use a mangy legal pad, but I’m hoping to trick people into thinking I’m better organized at my new job. (I’m also hoping to trick myself into BEING better organized. Or organized at all.) In my current gig, I always kind of know what’s on my plate and don’t have to think about it much, but I’m anticipating a steep learning curve at the new place and want to be ready. Or is there an electronic device I could justify buying for this purpose?

3. Do you have a work bag that you love? I don’t need to carry a laptop often, but ideally the bag should be big enough to accommodate one, plus other files and my Kindle and probably a pair of shoes. I need a shoulder strap, and I’m partial to buttery leather in a not-so-neutral color, like blue or purple or green. But still profesh.

4. Finally, have you ever read or received any advice on starting a new job that you have found helpful? It’s been a long, long time since I’ve walked into a place without knowing the lay of the land, or at least had a strong ally on the inside who could direct me. I want to WIN at being the best new employee ever…and I want to avoid mistakes early on that will hem me in later. (Like saying cheerfully that I love 7 a.m. meetings and then having one on my calendar every day for the next five years if I have another option.)

5. Back on shoes, two questions: Can I wear boots with a skirt or dress in an office that is technically business casual but where I am trying to be very professional? Knee high boots and a dress are my uniform October-March. Without this uniform I am helpless.

And finally, are these shoes the worst idea ever or the best? I know myself and I cannot wear shoes that hurt my feet. I have a closet full of pretty shoes that I never wear. But I am also theoretically opposed to Crocs on principle (the principle being that single women should not own multiple cats, Christmas sweaters, or shoes that appear to be TOO too comfortable.) (These are my own issues, and I own them: I’m sure your cats are lovely.)

Leather Crocs Heels? Possible or Putrid?


PS–I am addicted to Pinterest. I know, so predictable. I am indulging my¬†embarrassing¬†obsession with graphic quotes and obsessing even more about work clothes over there. Let’s be friends.

13 Responses to “Important Questions”

  1. Slauditory says:

    I think those Crocs heels don’t look like Crocs, so they’re cool. They look like regular pumps. Regarding boots: I teach and tutor and I wear boots with dresses; so do higher-up admin people, so I think it’s cool, as long as they’re sleek boots. To do list: a combination of a paper planner and slips of scratch paper. Don’t be like me. I think also digital calendars that can transfer to a smartphone are a good idea because you can assign alarms to certain tasks/events. Pantyhose: I wear them pretty frequently because air conditioning is ridiculous. Make sure to choose something really close to your skin color, unless you go with sheer black. Starting a new job: be quiet at first and listen. Watch how people interact. Find your place in there and be helpful (but not crazily, 7 am meetings all the time helpful). No work bag suggestions; I carry a tote bag, which is super not cute.

  2. CarrynM says:

    In the spring, when it is warmer, I would say you could wear something similar to these with a slightly rounded toe.

    And I think you could wear tights with this dress if it hits you a little higher on the leg. And then I would pair either navy (the dress is navy yes?) or dark charcoal sweater tights with the dress with a very dark brown knee boot. Making sure to balance your look by layering a crew neck t or turtle neck underneath the dress.

    And as far as nylons go, I would do them maybe if I could find one with a subtle texture or pattern.

    I see no problem wearing your boots in a business casual environment as long as they are not cowboy boots. I’ve never seen a dressed up cowboy boot on a women that looked business appropriate. Even in Texas, where I lived for almost 5 year.

    The shoes at the end of the post….you’re too young for them.

    I hope this helps some. :D

    • I have the same exact thoughts as Carryn. All the same. We are thought twins.

      Boots I saw that were cute (but sadly kind of spendy): Frye Melissa button boots. They’re this kind of reddish brown that goes with everything. *looks off dreamily at zappos* Do it!

      Also, you could totally rock some ankle boots with that dress too. I heart my Remont Dorndorfs and they are seriously almost as comfy as sneakers.

  3. Jesica says:

    I think grey tights would look pretty with the dress at the top, or thigh high boots and no tights. Though obviously depends on where and for what occasion you are wearing the dress.

    Regarding boots and the office, I see no reason why boots and pencil skirts or boots and “business casual” dresses wouldn’t be ok.

    And finally, I hate those shoes, please don’t buy them , in your words they are putrid =)

  4. Kinsey says:

    To-do list: I use and I would be lost without it. I keep it open and update it all day long. It lets me a plan a week or so out, mark things off, and access it at home or on my phone so I can add things I remember at midnight.

    New job advice: I started a new job about a year ago after spending 10 years in the same place, and I was completely overwhelmed for about the first two months. I had wanted a new challenge and new learning opportunities, but I mostly felt incompetent. While I was freaking out, a very wise friend told me, “If you can do everything on the first day, it’s not the right job.” I took some deep breaths, soldiered on, and now I love my job more than anything else I’ve ever done. I just had to get used to, and be comfortable with, not knowing everything.

  5. MD says:

    1. I see quite a few women wearing nude stockings in NYC. Brown is very popular however, that will not go with that dress. I would do white shoes or like a subtle silver or shiny red (if I feel like being bold). I think Calvin Klein has a nice low red heel. Check DSW – they had a ton of nice shoes when I went this weekend.
    2. Microsoft Outlook. You can made a to do list that’ll stay at the right hand side of the program and you can set alarms or reminders.
    3. I have this purse in aqua (looks like the Tiffany’s blue). That bag is magnificent. It held my laptop, large LV wallet, school books and notebooks, and a bunch of other crap. I love it.
    4. Unfortunately I don’t have any advice. I just smile a lot, listen and try to figure people out, and offer to help whenever I can.
    5.Personally I don’t like those black shoes because I am boycotting Crocs. I just bought a similar style (for an interview) made by Anne Klein at DSW. I can’t find them on DSW’s website but here’s a link to the shoe on another site.'s+Rava.aspx
    They seem comfortable and they’ll go with a lot of office outfits.

  6. asplenia says:

    I just bought these Merrells because I needed something dressy that wasn’t a boot but was also comfortable:

    They’re a little stiffer than I’d like, but then again I expect the comfort of a sneaker out of my shoes — my main criteria for a shoe is how well I can run from the serial killer in it. With the above dress, however, I’d wear tights & boots — navy boots, if I had them, and tan tights prolly. I’d have to see how it looked on. I love me some boots.

    As far as a laptop bag, I was surprised to find a huge selection of neat-looking handmade bags on etsy. I favorited these but haven’t purchased any yet:

    (No affiliation.) has the largest & nicest selection I’ve ever seen — search for messenger bag or laptop bag. Or check out Ross, Marshalls or TJ Maxx, you might score a find there.

    To keep organized, I do three things: 1. I keep a notebook at my desk and use it to create a daily list, updating it at the end of the day so I know where to start the next morning; 2. a personal little notebook for personal stuff; 3. I just started using google tasks and syncing it with my iphone to see if there’s an electronic way to keep organized: and then the iphone app is GeeTasksPro (it automatically syncs whenever you update either on the computer or phone). I’m still trying to train myself to use it.

    Advice on starting a new job, I’m not sure. I found this online: but I would add that you be honest about what you are willing to take on. People often want to stick the new person with the stuff no one else wants. Don’t take it on if you don’t want it. If you aren’t sure no is an option, buy time by saying that you would like to see how things go and decide later. If they say 7am meetings, say that you prefer your meetings at __ (whatever time). Don’t be afraid to say what you want because whatever you agree to now will end up being accepted, even if they view it as a quirk, more easily than if you adjust later. Best of luck!!

  7. Pish Posh says:

    Oh my god so many questions. Okay. first – have you started your new job yet? Do you like it?

    Now, I would wear nude/camel shoes with this dress and nude nylons or dark fun shoes with white tights. Personally I hate nylons and tights so I would probably wear flip flops. Anyway, go with camel pumps.

    2. To do lists. Have you ever used the Evernote App? I swear you will love it. You can use it on an iPhone iPad laptop PC desktop – anywhere. You can store it according to notes and notebooks. It is a convenient organizer because not only can you create to-do-lists but you can organize files and web clippings. Otherwise I write to -do lists on post-its, small notebooks, legal pads, and index cards. To-do lists may be the key to happiness.

    3. I have a work bag that I hate but my friend has an awesome one and I think she got it from… hmm was it Zazzle? My student gave me her Mary K bag and I love it.

    4. I haven’t read any advice, but in my experience, doing more listening and less talking, and polite smiles and such go further than you think because people are weary of the over ambitious and like people to grow on them. Just first get used to the place and the people and see how things work. Nobody really expects you to break out for the first three months. Do lots of observing and listening. Whatever you do, don’t form solid allegiances or play office politics yet. Listen and watch.

    5. Yes you can wear boots with a skirt in that environment but dress it up and keep it modest. The skirt should be at most a few inches above your knee but below mid-thigh. Accessorize. Wear dark tights with them.

    The leather croc heels look like the worst idea ever

  8. Nikki says:

    My boss has some of the Croc heels and she swears by them. I think they are ugly, personally, but I’ve heard all kinds of good stuff about how comfortable they are.

  9. 1) WHERE is that dress from!? I freaking love it! I defer to Pish Posh on the tights/shoes guidance. Nailed it. I am not opposed to nude hose but as a last resort.

    2) I’ve tried everything and honestly my favorite route is just a notebook with to-do lists, with just a Dayrunner calendar in the front. Yea, I’m like 74. Oh, and Outlook reminders for errrrything.

    3) What everyone else said

    4) Oh geez, I hate to be a Debbie Downer, but I freaking hate first days. They have always gone better for me when I lower my expectations and just acknowledge that I will feel majorly awkward and weird. And that I should wait for week 3 before forming an opinion. By then I am always happy! Sorry, was that terrible and unsupportive? I’m sorry. But you will rock it!!!!

    5) My office is business and I have never thought twice about boots! Boot away!

    Bonus Croc Question: Ehh they are not my favorite but they’re not terribly offensive or anything.

    Congrats on your new job!!!! (Oh and srsly where is that dress from)

  10. Jessica says:

    Second (third?) on loving the dress! Can you please, please, please divulge where you found it?

    I wear boots and dresses/skirts ALL THE TIME in a fairly professional office. Every once in a while my style verges into “hair stylist” territory (black dress, black leggings, not-so-sleek/professional boots), but I can get away with it every now and then.

    Can’t help with the bag, as I’ve been carrying around the same GAP tote for the past 10 years.

    Second on the lists + Outlook reminders. I have a system with my Franklin Covey planner for personal + biz, Outlook for reminders, and scraps of paper for each day’s hot list.

    I was 1.5 hours late for my first day at the current job, thanks to a horrific accident that shut down a major highway and all its connectors. Back roads were a mess. I cried. Ten years later, I’m doing great and no one remembers that I was late my first day. I also remember hating the job for the first few weeks. I LOVE the advice of Sarah above, to lower expectations and expect it to be awkward…and cross your fingers to not get those 7 AM meetings on your calendar right away!

  11. C_girl says:

    You guys are awesome–THANK YOU for all of these suggestions. I have been bookmarking like crazy.

    The dress is from Macy’s! I think its their INC line

  12. Artemisia says:

    I have to laugh. Business-casual in DC is SUPER DUPER FORMAL in Wyoming. I looked hideous when I first moved to DC, and then I looked like a snobby a-hole when I moved back to Wyoming.

    I am horrible at shoe advice. I have normal-width toes, NARROW-AS-F*CK heels, and large calves. I walk right out of flats and heels. I can only get wide-calf boots. It bites.

    I have no advice for you, only bitterness.

    To do stuff: I love productivity hacks and such. Probably to the actual detriment of being productive. Anyway. I follow a customized version of GTD (Getting Things Done) as a system. I use (and on my iPhone) to manage said GTD system. When I follow it, I kick ass. I’d be happy to email you with more info if you like. Like I said, I love this shit.

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