Tuesday, September 27, 2011

Decisions Are the Worst*

Hi all. I seek your advice.

This morning, driving in my car on my way to work, I lamented the stupid humid weather that has been messing with my hair and sweat glands and wardrobe choices to my sister on the phone (hands-free bluetooth, por supuesto). I mentioned that I was trying to encourage crisp fall weather by wearing a sweater/skirt/boots combo for the first time this season. I thought it was a harmless comment.

My sister paused, and squeezed out the response, "Well, I kind of think 34 is to old to be pulling off the skirt/boots look."


Am I too old to wear high-ish boots with skirts to work?

For reference, I work in an office on an Army post in a rural-ish area, where many people wear Army uniforms (as befitting their status as Army personnel), and the rest of us are instructed to wear "business casual" dress. And our handbook (yes, we have one) has lots of helpful hints on what defines business casual, such as "does not include blue jeans, but colored rinse jeans such as black jeans, or denim skirts, are allowed." That's not a verbatim quote, but it's very, very close. I have seen much in the way of "business casual" in my office that indicates to me that our definition of "business casual" likely differs from the definition other organizations might use. With our group falling on the more "casual" end of the "business casual" spectrum, clearly.

But the setting doesn't really matter, does it? It doesn't get at the heart of my question, which is "Am I too old to wear boots and a skirt to work?" Should a 34-year-old professional (can I call myself a professional?) with two children retire this look? My sister seems to think so.

For reference, this is the outfit I wore today:

I'm too lazy to figure out how to create some sort of poll, so please, answer me in the comments section. My fall/winter wardrobe is depending on it.

I am not too lazy to post a bonus video for you, where M. and I try to get our cat to take a little jog on our treadmill. Enjoy. Spoiler: It didn't work.

*Can my sisters and childhood friends name the movie referenced in this blog title? You'd better be able to...


  1. You look great! It's not like it's a leather micromini! I think you look very appropriate and stylish!

  2. I have no vote on whether it is too old or not because I never wore that style.

    I will say though that if you subbed out skinny jeans for the skirt, you would be wearing the current trend! I can't wear that bc my butt is too big so I envy those who can.

  3. Since I was the person who (gasp!) thinks we might be heading past the age of no return for tall boots let me weigh in. It might be because I live down South now and work for BigFinance but I haven't seen much in the way of tall boots around here. When I have, they have been on 20 something women. I love tall boots and am toying with picking up a new pair this fall...I'm just worried I can't pull it off at work. I think I'll wait until Fall really hits and see if I can locate more women in my age range wearing them. A. - As Ted (HIMYM) would say, "You are totally pulling them off!"

  4. I am de-lurking to say No! You shouldn't retire the look, you look great!

  5. Love the outfit! Tall boots are everywhere in Madison and on everyone, not just the college kids.

  6. Clueless is the title quote! I love that movie. Also, tall boots are still okay in the NE (Boston, NY) so rock on.

  7. Sorry, MommyEsq, I was not quoting Clueless with the blog title. Any other guesses? The movie I quoted pre-dates Clueless.

  8. No way! I cannot wait to break out the skirt and boots combo - I think it is a very classic professional, yet casual look. I see it all the time at work and in transit to and from work. No worries.

  9. You looked great on Tuesday! I thought the boots were awesome, and tons of women our age are still doing tall boots, including this 34 year old!! (I was actually wearing a pair of my tall boots under my khacki pants that very same day because of the rain!)

  10. Um, once I can fit into my skirts again I fully intend to wear them with my tall boots. Go for it! I have no idea what movie that can be from? Hmmm.

  11. Ok #1- the quote/title is of course from the most beloved Jenkin classic, "Girls Just Wanna Have Fun"

    #2- My money was on Stacey for this one and she's totally wrong:)
    Many ladies still rocking the style- especially ahem my boss well into her 40s.

    I have leather boots, I have slouchy black ones, I have boots with the fur for freezing cold days at school. Nothing makes my 10 year old female audience swoon more then when I wear a khaki/corduroy skirt with- wait for it-light patterned tights and my slouchy uggish tan colored boots. I'm way hip- maybe I don't always look totally mature, but I love it.

    You rock those boots!