On dresses
It’s been almost a year since the last time I wore a dress and high heels to work. (One of the big perks of Silicon Valley start-up life: Everyone wears jeans. Every day.)
That said, this look only lasted about four hours. After some important meetings, I changed into my usual uniform for a flight to New York (where my closet is full of dresses, the only thing I want to wear on humid weekends).
On the one hand, I’d wear dresses every day if I could - they’re just easier. On the other hand, they require often very painful footwear (hello, I wear a size 12 or 13!). If I had one more hand left, I’d point out that wearing dresses in an office full of guys in jeans and free conference giveaway t-shirts (sometimes a polo shirt if someone important is stopping by) could look a bit try-hard.
Ladies, where do you stand on all this? I’m seriously considering converting to a skirt- and dress-centric wardrobe.
Filed under: Life


That’s almost all I wear– with tights in the winter, with bare legs in the summer. I actually get a ton of compliments on my dress-centric style (and people think I’m ill if I wear anything other than a dress and heels).
Plus, I wear a ton of wrap dresses which conceal the fact that I am an expanding food blogger. Oof.
Don’t you look styley! Very nice.
I do have a dress/skirt-centric wardrobe - my firm is a formal workplace and I have to look smart all the time. And, for me, dresses and skirts make that easier - for some reason, British-made trousers are often cut wrongly for me, so dresses and skirts are easier.
You’re totally right, though - the clothes are lovely but it’s a pain to wear heels every day. And while I like dressing smartly, I would LOVE to wear jeans every now and then. On days when I’m not leaving the office it would be great to kick back a bit.
Jacq, I definitely appreciate jeans so much more after I’ve been wearing a dress with tights - even if only after a few hours! Tights are probably the most annoying thing to wear, paired with the least annoying (dresses or skirts). This is a curse on women to go along with the pain in childbirth thing, but was edited out of the Bible many centuries ago.
Julie, I’ve got a couple of wrap dresses, but I’m always afraid they’re going to come untied. In fact, an ex-bf’s mother accidentally almost made me come out of my dress by playfully tugging at the fabric of the belt. It was funny at the time, but could have gone horribly wrong…
My biggest issue with wrap dresses is that they often seem to cross over at a scandalously low cleavage point - far too low for a conservative law firm, anyway! In the UK, I find that Hobbs do good wrap dresses.
Jacq, that’s why I own roughly six dozen camisoles of varying fabrics, colors, and vintage. You can never have too many camis!
Hobbs has been getting so much positive buzz for its offerings in the last year or so. M&S needs a little bit of the Hobbs magic as far as reinvention…
I say wear what you are most comfortable in, and you will come across as comfortable. Short of pajamas, which I’m seeing a lot of at the airport these days.
As for the shoe issue, I have solved that: I no longer buy uncomfortable shoes, period. No matter how cute. I have wedge sandals and loafers that look great with dresses and are as comfortable as anything. Life’s too short for foot pain.
BTW, do not under any circumstances take your fashion cues from geek guys, or even take their habits and opinions into account on any level! That is the primrose path to fashion hell.
Sage advice, Hill! (It also reminded me of when Cathy Seipp dismissively referred to someone as “a woman who only wears comfortable shoes,” the implication being that she didn’t care about her looks and was unsexy as a result. How I miss that lady!)
Being large-busted, I will often safety pin the top, or wear a camisole, so as not to be scandalous in the office. :)
In cooler months - or in an office with overactive air conditioning (like Qik HQ) - a scarf that hangs to perfectly cover up cleavage works well.
Dresses are the easiest thing to wear, I think, but tights are a big pain: I often end up in trousers just for that reason, if it’s not warm enough to go bare legged. OTOH American trousers don’t fit me (opposite of Jacq’s problem!)- I think they’re cut for more curves- so I started wearing leggings and short skirts, which I’m guessing is possibly a bit weird & Bananarama for you, Jackie.
In general though, sod what other people think is quite a good rule; if they’re only going to see you once it doesn’t matter, and if they see you all the time they’ll get used to it anyway!
I also hate painful shoes- the comfiest heels are usually wedges with ankle straps, but they’re hard to find among the fad for totally ridiculous shoes right now.
I enthusiastically support you in wearing mostly skirts and dresses, as I do myself. American pants don’t fit my long legs + curves and I’m pretty sure English ones wouldn’t either. It’s not as fun when it’s cold, but I love wearing pretty grown-up dresses. Knot the bow on the wrap dress after you tie it–it’s easier to undo than knotting it before. And thank God for this extended flats moment we’ve been having!
Alice, I should start travelling Stateside for my trouser shopping, then - UK trousers don’t fit me because of my curves! I’m a fairly standard size and shape, but I definitely have a bit of an hourglass thing going on, whereas British trousers seem to be cut more for women with a less pronounced waist and narrower hips. It’s very frustrating!
Yes, Jacq, for some reason British fashion houses think that most women are shaped like boys. If you can find them on sale, Prada trousers are well-cut, and I find Burberry an exception to the rule when it comes to trousers (though they are often far too wide in the thighs and require tailoring).
Jackie, I can’t get over the fact how much weight you’ve lost since the last time I saw you in person. I am almost tempted to call you bitch - in a nice way though and only because I’m jealous ;-) Honestly, you look like a billion dollars. And I love that dress you are wearing.
We don’t have a dress code in my office either, everyone wears what they want and you can always tell when we have demo guests in because the men turn up in suits and the women turn up in a dress or a blouse and skirt.
I ought to wear more dresses, too, because whenever I wear a dress I feel very different. Different in a good way.
I always wear high heels. I spend a lot of money on shoes and they are always comfortable.
I haven’t worn a skirt in over 2 years, and may never again - I wear formal, expensive, pantsuits and sensible shoes (I WILL NOT ever wear shoes I cannot run in - EVER) everyday. I don’t ever do business casual, I think it looks sloppy, so good slacks and flats everyday.
I’m weird, I know it, but dresses are too “girl” for someone who is very uncomfortable (and not terribly happy about) being a girl. I don’t want to be the person, or the thing, in shoes I cannot run in and an outfit that makes me feel like a “girl” instead of a human being.