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What A Polished Tomboy Wants To Wear To Those Daytime Events, Or, Saturday Morning at 10:01am

(Note: Although I no longer monetize new posts on this blog, the images below are pay-per-click. That’s because the tool I use to search for ideas, ShopStyle Collective, automatically includes their links in generating the widget. It would take me forever to try and replicate this what with Photoshopping and cutting and pasting. Please forgive my inertia.)

So, daytime events?

My issue is as follows:

Flowing or floral dresses are not me; fancy structured trousers are for work, not parties.

Which lands me, paradoxically, for daytime celebrations, in a world of structured dresses and flowing or floral trousers. Well all right then!

Here are some dresses I quite like. What do you think? A couple of florals because never say never. Comme des Garçons animé for our Artsy Cousins, Diane von Furstenberg or Victoria Beckham for the Grande Dame. She’ll change for dinner, by the way. The Veronica Beard ruching, not before noon.

My favorite is that blue Max Mara Weekend shift, because, blue. With low block-heeled sandals which I happen to own.

And what about flowing trousers? That’s what I ended up wearing to my daughter’s graduation. And this believe it or not is the best photo I have. (Yes I got a haircut, my very long hair was unsupportable.) Patent leather J. Crew slippers and belt. Jigsaw sweater.)

Well, maybe the trousers are not so much flowing as purchased 10+ years ago for work when Armani was wide-leg friendly. I would like to up the festive quotient.

Here are some slightly more convincing options. The search made clear to me that flowing FLORAL trousers are just too much for a Study Gal. Blush or white, OK, but black, gray or navy and we’re right back at work.

Which brings us some further deconstruction. I realize that I am motivated me in this exercise by my relationship to being a woman. For a long time my career in the tech industry required that I take as gender-neutral role at work as possible. Navy, gray, black, structure, all tied forever to myself as a work person. But I’m quite pronouncedly inhabiting my non-gender-neutral role as a woman, in a family no less, at daytime celebrations.

I am the aunt, the sister, the mother, the daughter. But, and here’s the thing, I’m not a kid, I’m not in search of a romantic partner, I am not selfless. So I want to fill a narrow space. I’m a woman, not a girl, female but not fatale. A mother with her own identity.

I also just want to eat salad, grilled meats, and cake, also hug my beloveds, but we’re talking cerebral style. As we do.

I prefer a shift to a waisted dress – waisted dresses feel too, what, girly? Too Betty Draper? And the shift has to be loose, tight dresses are for nighttime. I know, I know, overthinking. That’s what I pay myself for.

Finally, social media has been abuzz recently with a photo of two friends, a girl and boy, who wore matching suits to prom. Like so. From ASOS.

Part of me wants to show up like that to every single baby shower, bridal shower, graduation and brunch I have the good fortune to be invited to in the next 30 years. Iconic. You leave off the jacket when you want to make somewhat less of an impact, add a tunic. Just watch your color choices to avoid human wallpaper and/or too preppy if that’s not your thing.

Or you wear the jacket with white jeans and a tee.

Let’s conclude, however, with the wiser words of Alyson Walsh of That’s Not My Age, in response to my query here. She said in an email,

“…when effortless style is the aim, special occasions can be a bit tricky…It’s always better to take the comfortable option – in all senses of the word. The aim is to feel like yourself on a good day, and not get too gussied up….A ‘not-too-dressed-up dress’ and flat sandals would look chic and relaxed. Or a shirtdress over wide-leg trousers. A long shirt and cigarette pants with velvet slippers. Keep it chic and simple.
 If you want my advice on dressing for special occasions, it’s this: don’t buy anything new. Occasion wear is dead. Spend money on a blow dry not a blowout. Take the less is better approach…”

So go buy her book. It is a great read.

And have an excellent weekend, no matter the shape of your trousers.

(The image links are pay-per-click, text links are not. I don’t track you with cookies of any sort, it’s possible that ShopStyle will. And that’s all I know about that.)

68 Responses

  1. Oh, Lisa. You make me laugh. In the good way.

    You and Alyson keep me grounded in the Land of Don’t Overdo It.

    And, yes, this is what we pay you for. ;)

  2. I love that Max Mara shirt dress as well. And those flowery suits on the kids. Partly because you could wear the pants and the jacket all kinds of ways. Partly because I love to see high-schoolers eschew the whole prom ethic. Not sure what it’s like in California, but here it’s hugely expensive dresses worn for two or three hours, mostly for the benefit of photos, then changing into another new outfit for the “after party” with the white stretch limo to deliver these teenagers to all the various “events.” And, I was sad to learn, prom doesn’t even involve a dance anymore, just cocktails (huh?) and dinner. Wonder what’s with that?

    Recently a friend posted some of our grad shots on FB, long inexpensive cotton peasant dresses or ones made by Mom being the most common. Then we changed into our cut-offs and tee shirts for the “after-party” as someone’s “camp” which is what we call the summer cottage at the lake where I come from. Back then in the mid-seventies, we didn’t even have a prom… too fifties for us.

    1. @Sue Burpee, Yes, we have prom hubbub here too. I don’t get it, just like I don’t get making a performance out of a wedding proposal. Generational, I suppose.

      And I didn’t have a prom really either. That is, we had one but the band played Jimi Hendrix cover songs and was so bad nobody could stand to go in the building and we all milled around outside;).

  3. Lisa, I see you have recovered from your trip.

    Thanks for reminding me of why I never seem to pull the suited dress pants from my closet.

    Successful aging is all about finally knowing who we are and embracing it. I think you have a wonderful sense of self though it may not always feel this way to you.

    Thanks for helping me understand my reluctance to wear certain clothes and my enjoyment of others.


    1. @luci, Thank you! Yes, I have recovered. It was a wonderful day:).

      And thank you for keeping me company and reaffirming that these are shared responses to style, sometimes, not just odd individual quirks.

  4. I enjoy your humor and descriptions. I am clearly very much out in left field as, while I like a shift type dress, to me, the Max Mara dresses look like what my mom used to call “a gunny sack”. I guess I like a little more shape and since you are in such good shape . . . .

    1. @Jeannine, I think I’m actually the one in left field, I think most people prefer more shape than I do, even in the daytime. I am glad you can laugh even though my silhouette choices are, let’s continue the metaphor, off-base;).

  5. I love all these clothes. I hate being short. Not a single item would fit. Beautiful choices, Lisa.

  6. Like you, I have difficulty with floral dresses. That said, when watching the royal wedding, I saw a couple dresses I rather liked and I have sourced them. For me, the alternative to a floral dress is a sheath dress in pastel. That is as close to floral as I tend to go. Btw – Your new haircut is great.

  7. I don’t understand your affection for shapeless clothes, when you are in such great shape yourself!

    The best of the bunch you feature is the yellow flowered Madewell dress (“sold out” for a reason!), but with those silly sleeve ribbons removed. (Of course, I would have to be taller and thinner to wear it … )

    Your new haircut is terrific, and the outfit you pulled together shows it off to perfection – very clever. And now YOU can be “the one with the beautiful hair!”

    1. @Victoire, Readers have brought up the question of why I do not like to dress to “flatter my figure” more often.

      So I must not have explained sufficiently.

      First, imagine some trauma when a nerdy, hyper-verbal girl matures late and suddenly finds herself with flesh in the socially approved locations, and is besieged by male attention she doesn’t know what to do with. Which is then compounded by unwanted attention in her jobs.

      Second, imagine one desires to dress to emphasize those aspects of onself in which one feels pride. I feel pride in what I’ve come to understand about design, about my nonconformity. I don’t feel any particular pride in my silhouette – it’s an artifact of genetics, privilege, an early eating disorder, and self-discipline.

      Third, inasmuchas I do dress to flatter – those broad shoulders make a great hanger for potato sacks;).

      I hope that makes some sense.

  8. I like a more tailored look – defined waist. It suits my body type. I’m all for wearing pants when I can get away with it. A flowing pant with a fitted top, a pair of smashing heels and I can go anywhere with confidence.
    Those kids in almost matching suits are adorable. One of my granddaughters would wear that. She’s smart, active, outgoing and fun. I like it!

    1. @Joanna, Going anywhere with confidence is, in my opinion, the ultimate goal. To say nothing of granddaughters who are active, outgoing and fun:).

  9. I think you look nice. Graduation from professional school isn’t a wedding.

    Congratulations to all.

  10. That is a great haircut. I love the length. Personally, I don’t like any of those dresses, and would have to agree with Jeannine’s assessment.

  11. I agree with you about flowing and flowery dresses, although the girl in me who grew up in the 1960s is tempted by the Johnny Was – or at least I am until I think about whether, especially at my age, I would feel foolish in it rather than glamorous. My solution is often a more fitted dress (although not necessarily with a waist) in an abstract print, or sometimes tighter pants with a looser top. No gunny sacks for me; they just make me feel awkward and klutzy. You’ve got the right idea about being comfortable, because then you can relax and enjoy yourself.

    1. @MJ, So, question. My Dries van Noten dress that I’ve won here several times. Does that look like a potato sack? Because I never feel like one.

  12. I attended 4 graduations this year (technically 3 graduations and a professional showcase for the 4th person). In all cases, I was supporting cast (not the parent), which gave me some leeway. In only one case did we have “spring” weather, and in most cases there was lots of walking on varied surfaces. All but 1 involved an overnight stay for convenience, and more than one had events on different days, such as a dinner the night before the graduation. So my priorities were different: comfortable but not casual shoes, versatile clothing, layers. Why, yes, I did wear black pants with different top parts depending on the event, and flat Mary-Jane-style shoes, and I’m fine with that choice. (In one case, the weather in the SF Bay Area made me wish I’d brought boots for warmth instead.) Comfortable but festive was what I was trying for, without having to try too hard.

    1. @Cathy, PS – the Victoria Beckham is closest to my style, if I could have a different color and a lower price.

    2. @Cathy, That is so many graduations! I hope they were happy events!

      I hoped to make clear that my thing about black/blue pants was my own issue. Everyone else should wear them all they please.

      Perhaps I’m out of practice with this style post business, I need to be more explicit!

  13. I love that last Comme des Garcons dress but I’m not sure that I am tall enough to carry it off. I rather like the other Comme des Garcons as well. I guess I just favor the slightly off-beat.

    Just want to say that I really like your new haircut. So polished and modern! Trousers suit you well and that look is good with the sleek, modern haircut.

    1. @Jane, I favor the slightly offbeat too these days. I hadn’t realized how much I’d veered off the classic track until I read the responses to this post!

      And thanks on the haircut but it’s so funny, I find it too short now. It will grow of course, but I think it’s yet another sign of just how much Alt-Style I’m comfortable with now. I said I wanted to go Artsy, I guess I meant it.

  14. Thanks for the mention, Lisa. I like the outfit you wore to your daughter’s graduation, the haircut, everything. I’ve started to wear dresses and kaftans, as a bit more in summer – maybe it’s the menopause?- but the aim as always is to look like a grown-up tomboy/Gentlewoman.

  15. I like your outfit (and a beautiful haircut)
    Feeling good and positive is my goal-even wearing floral or loose (or loose floral :-)) MM dresses,as well as black or navy (or white ) trousers (or the floral suit,rather in different combinations than as the suit))
    A woman is wearing a dress (or trousers :-)),not the opposite,you walk,gesticulate,move……it is not “potato sack” any more….and I adore your Dries van Noten dress

    1. @dottoressa, Thanks.

      You bring up a good point. Dresses look different and move differently on different people. I am pretty sure I am drawn to dresses that look like sacks on the rack because after years of experience I know that they are likely to hang in such a way that it’s just obvious enough (and no more) that there’s a woman underneath.

  16. Although I think you looked great for the graduations, I wore something very similar to a charity luncheon and also felt I looked as if I’d stepped away from the office.
    I like the Max Mara dress but have a strong feeling it would look not “fine” enough for the type of event we’re talking about – more of a vacation dress.
    I do love your haircut. Other than that – no answers, only as lost about it as ever.

    1. @KSL, I am lost with with good company;). I think you are right about the Max Mara, looking closely it appears to be more of a coverup than an actual dress:(.

  17. I cannot offer any advice as I do not gravitate towards any florals….except bouquets and the garden!
    In clothing…I do wear polka dots and stripes.
    Your hair looks amazing!

  18. I’ve always been flummoxed by special occasion dressing, whether day or night. And wouldn’t you know (great minds, similar vibes) I just purchased a printed shift dress and some soft, flowy pants when I was in Paris! So I feel like I might finally have those bases covered….

    Your hair looks *fantastic* BTW…

  19. Your Dries Van Noten does not look at all like a potato sack because it’s cut closer to your body. Indeed, it’s the kind of dress that I would choose for these kinds of events but for the fact that the black would be unflattering on me. The Max Mara, by contrast, looks much wider and so just strikes me as looking shapeless. I think some of us are just not comfortable with extra fabric.

    1. @MJ, You’re right, the Max Mara is wider, way boxier. And of course what I really want is the Dries dress in sky blue with short sleeves, like, a daytime version!

  20. Yeah!…That over white jeans,,,I, too, am searching to find the style for “event” which is true to my style…Not precious or pretty or expected but true to my casual, chic, rate (rough around the edges) style…THX for bringing this to the forefront…

    1. @Deede, My pleasure:). I do need a little bit of rough around the edges, or at least the capacity to take it there if necessary.

  21. The TIME it must have taken you to assemble these thoughts, these thumbnails, these personal deconstructions. Someone around here already said it best: “Thank you for your work.” Yes, I do think the Polished Tomboy has shed a skin on her way to Polished Artsy; I look forward to being joined on the Artsy side [while I’m shedding toward Artsy Grande]. Again, thank you Lisa.

    1. @Flo, Artsier and Artsier! Sort of curiouser and curiouser:). And I look to you as a beacon. Artsy Grande must be downright spectacular.

    1. @Nancy, I thought about a jumpsuit! I had one back in the 80s. I guess I had the usual worries, taking it off and on in the bathroom etc., compounded by the fact that I injured my shoulder while shrugging on a motorcycle jacket so might be high risk for a jumpsuit. :p.

  22. How I’ve missed these posts.
    Your haircut, great. Your outfit, great. I was right, you look adorable.

    I think we get to a certain age and comfort and appropriateness are the main goals.

    1. @MaryAnne, You are a doll!

      I am going to add to comfort and appropriateness, which, yes, and say, I want to communicate who I am, not who I should be, or who I might worry I am not.

      Meaning, I am going to want clothes that are thought out, and probably overly intellectual. xoxox.

  23. Damn, you’re chic! And I love the new haircut – very fresh and modern.

  24. Not finding time or Wifi to comment much, but I’m still reading and need to say how much I enjoyed everything about this post — especially having you back on this particular gig, which you’re so good at! xo

  25. PS “Part of me wants to show up like that [crazy print skinny-legged suit] to every single baby shower, bridal shower, graduation and brunch I have the good fortune to be invited to in the next 30 years.”

    Exactly! That’s just it! I too am looking for the same golden mean northsoutheastwest, hotcold, urbansuburban, youngold, outdoorindoor outfit that cruises its way around the globe, effortlessly. We will FIND it, onward!

  26. Lisa, interesting you should mention Dries in your comments, it’s my go-to for dressy occasions. Not an entire outfit, but one judicious piece to turn a sophisticatedly boring outfit into something personal and expressive.

    1. @Redolence, Now there’s a thought. Maybe a pair of Dries trousers, or one of his blouses. I keep looking for a dress – these days he’s big into yellow and I can’t do large scale yellow. Thanks.

  27. Hi! I want to throw in a recommendation: the Marshalls stores (there’s one about 10 miles north of you, in my town) usually have shift dresses by laundry Shelli Segal and they are just the thing for our body type. I love your blog, thanks so much. Long time reader, first time poster. Cheers.

    1. @Kim, I know the one! I bought shoes for my daughter there, when she started her first job post-college. Thank you for reading, so nice to meet you:).

  28. Thank you, Lisa for your timely voice. As a newly minted Mother of the Bride (wedding next spring in southern California), I am already fretting over what to wear. I sew all my own clothes, including jeans, and love my me made wardrobe, but this special occasion project has me confounded….. I want to feel special, elegant, photogenic, but still myself. It’s a tall order….. Any words of wisdom to add to Allyson’s?

    1. @Kathleen, I love nothing more than to sort out a special occasion outfit;). If you want to email me at the skyepeale address, I will happily discuss at more length! Because it so depends, on the time of the wedding, the kind of location, your silhouette and preferences and coloring etc. Which is exactly why these things can be so confounding!

  29. Take the less indeed. I could not agree more. Recently attended a wedding and wore trousers and a beautiful new shirt. It was so comfortable and turned out to be exactly right for the setting and the weather. Beautiful sandals made it look elegant but not overdone. After all, I am not the bride and I (like you) am not out there to be catching the eye of Lotharios. Just to celebrate and look good. That prom pic is fab. They both deserve to have a wonderful and comfortable time.

    1. @Annie Green, Now I’m dying to see a photo of your outfit:). One burning question – was it all structured? Or was some part of it slowly? And if some part was flowy, top or bottom?

  30. Repeating the congratulations already conveyed on Instagram – because a new graduate and her Mum can never get too many congratulations!
    And what a fascinating couple of posts, this one and the one before it, on graduation wear choices. Some very different style considerations/traditions to the UK. At my own children’s graduations the styles were subtly different to each other (Glasgow and St Andrews), and somehow I had anticipated that without articulating it to myself beforehand. What complex social codes we live by!

    Am having an enjoyable Saturday read back through posts I’ve missed on your blog – including your trip to Scotland. Haste ye back! (No rain here in whisky country of Speyside for the past 3 weeks – so you might be lucky)

    1. @Linda, “and somehow I had anticipated that without articulating it to myself beforehand.” This is pretty much why I started writing this blog about style to begin with? I felt the unspoken dress codes so vividly, had to articulate them for my own sanity:).

      I would LOVE to come back to Scotland. It’s now perhaps my third favorite part of the world, behind only my home, and Hawaii. Could be tied with Hawaii if it were closer in distance and time zones:). I love your Instagram, keeps me in touch, along with a couple of others. xox.

  31. Long time reader, but first time commenting. I appologize for being so lazy, I love your writing, “female, but not fatale”, dang that’s good.
    And I also love your haircut.

    1. @Susan Beach, No apologies – you owe nothing, reading is more than enough! And my haircut but mostly my words thank you:).

      So nice to meet you. xox.

  32. I love the way you delineate the underlying issues. up front and I love your choices, dress wise, especially the shift dresses and the more unusual prints, which don’t particularly read as “girly” but might still be considered feminine.

    I love shift dresses for daytime, and even perhaps for evening with a little more something. I can’t say what yet. It is not that I don’t look good in a fitted dress, I can look very good, but usually it draws attention in a way I don’t necessarily want; somehow I feel like I may become more visible but less interesting if that makes any sense. Probably to no one but me.

    Still trying to figure it out here, and I am often, its seems, either over or under, where I want to be on the style spectrum. But articulate posts like this one inspire me.

  33. Re the beautiful wedding shirt. I am not keen on having my photo taken…so there isn’t one available. The shirt was quite fitted but not tight, had a collar you can pop and it was the sleeves that made it: they were large and sort of flounced and ruffled. Sadly, when I got home one must have flounced in the direction of a cigarette but a clever, sewing friend showed me how I could hide and repair it. The shirt was a lovely pale, soft pink. Slim black trousers. Semi-high black suede sandals. Vintage tiny black handbag. Tried to copy photo of shirt but it would not send. Sigh.

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