Privilege Blog

Exploring Boundaries, Both Artsy And Of Age

Few of us adhere purely to one way of dressing. We’ve all taken multiple directions, from tried and true outfits, to the adventurous, to the best of breed. In my High WASP world, Style Archetypes limit the discoverable area.

If this was as Sturdy (Sturdy is kissing cousin to prep) as I get without wearing my son’s khakis, if this was as Grande Dame (little black dress for the win), then the skater dress and moto boots above surely push me to the Artsy limits. Partly because, you know, moto boots. But also because I’m 56 and it’s hard to dress this way without feeling Too Young.

Artsy Cousins Do. Not. Care. About Age-Appropriate; the Sturdy do.

So let’s deconstruct.

This deconstruction will include a survey. We’ll have the unscientific Too Young Or Not Too Young results for you soon. In 3 paragraphs, to be precise. But first, how did we get here, standing by an urban entryway in the San Francisco winter, wearing a peacoat, dress, pink scarf, boots and tights that I’m calling navy blue but might be purple?

It started with the boots. They were given to me, generously.

I owned them for a year unworn. I wrote here that I thought they cried out for a sweater dress. I bought this straight-lined Bompard version but it didn’t work with the boot shape and height. I don’t always get things right immediately. Sometimes ever. We’ll deal with the columnar dress project another day.

Still determined to wear the boots before I turned 80, I decided to try a flared silhouette. I was reluctant to throw more dollars across the Pacific after European cashmere, so I found this dress at Anthropologie, via Grechen’s Closet. Great blog by the way, with a style I endorse 100% and good for plus size too.

For $118,  the dress was a reasonable experiment.

(In case you wondered, I didn’t mean for the tights to be purple, or even navy blue. But my middle-aged eyes saw them as black under the Bloomingdale’s lights. Some of us have to fall into Artsy by mistake.)

And the survey results?

  1. Late 20’s colleague with a rad rocker hairdo: “No, it’s not too young. My mom dresses like that.”
  2. Early 40’s colleague in executive ranks: “No, frankly your hair reads as blonde, on the street. If your legs were uncovered that would be too young.”
  3. Early 40’s team member with mad design skillz: “No, you’re mixing textures and colors. If everything were smooth and the same it’d be a problem.”
  4. Two late 20s early 30s web designers: “Oh I like your outfit.” Unsolicited Artsy testimonial.

So there you have it. Teetering on the edge of Artsy, not quite precipitated into the Canyon Of Mutton Dressed As Lamb. A nice detour, here and there, even for the Sturdy.

One more question. Once we remove the Dressing Too Young filter, does the outfit succeed? Jury’s still out. At the detail level, there are issues. My lower legs might be too skinny for bucket boots. I might want a heavier-weight, longer dress. But at the highest level, turns out Sturdies love a dress, tights and boots because they are inordinately comfortable and innately non-serious.

Also turns out that Sturdies feel Artsy dressing inspires Degas poses.

It’s a gradual process, evolution. In developing an articulated but classic personal style, explore your boundaries to map the center.

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96 Responses

  1. I love everything about the outfit. The purple tights are great – I think black tights might be too much black.

  2. This post speaks my language – I have an entire wardrobe of skater dresses, boots, coloured tights, and cashmere ballet wrap cardigans to wear over the dresses when a bit more warmth and elegance is required. You look very well indeed in this ensemble: young and free and contemporary classy.

  3. I love the boots, but think they’re meant to be worn with skinny jeans or pants and an oversized, slouchy sweater. I know how you feel about skinny jeans, so I’m not going to push it, but that’s the silhouette that I think would work best.
    The whole thing still looks cute though, and I love your hair that way.

  4. Lisa, you are a beautiful woman no matter what you wear…however, those boots scream for pants tucked into them.

    As far as whether it’s age appropriate, you need to visit the blog ADVANCED STYLE (sorry don’t know how to link) I think it will give you some ideas.

    Hope you have the happiest of holidays.

    1. Well thank you. However, can I confess? I don’t care for Advanced Style one bit. I doubt I will ever dress like that. Of course, I’ve been known to eat my words.

    2. Lisa, you have at least 30 more years before Advanced Style could be an inspiration, but by then maybe you’ll have cast off sturdy completely and can play wildly in the artsy realm.

  5. I like it all separately but don’t love it all together. It’s definitely not about your age to me (although I did laugh loudly at the accidental purple tights — I’ve done that before, too). Speaking of tights, I just recently tried Wolford for the first time, and sticker shock aside, I am hooked! Have you worn them?

    I think I am just partial to a more timeless look. Alas, not an Artsy bone in my body, accidental or otherwise. I do admire it in others, though.

  6. An enthusiastic yes to everything but the purple tights. I can see black, gray, truly navy, aubergine, burgundy, dark green, but not purple.

  7. I would be more inclined to wear those boots with pants and the dress and tights (love the adventursome color!) with either more delicate shoes or tall boots, but then I’m not always so good at testing my Sturdy boundaries. It’s good of you to experiment for me.

  8. Child, it’s your shoulders + Degas hair that scale this whole look straight to Perfection. Such a jealous narrow-shouldered mop-haired wreck am I. It’s like when you say Context is all, in my profession Scale is all. The flare at the top of the boots reaches for, finds and partners first with the flare of your skirt, then continues upward where it’s all capped and unified by your shoulders. I wonder if that makes sense to anyone but me. I love what you’ve done here. But I’m Artsy. Well, I’m Artsy Tasteful [rather than Artsy-could-give-a-s**t].

  9. I think like this Artsy outfit looks really good on you. Not too young, at all. Like the boots, dress & purple tights – though in my humble opinion, the jacket doesn’t quite work with the skirt length. But I am a bit anal about that kind of thing. And I’ve had the ‘my mum’ comment before!

    1. Yes, maybe next time you could try a black leather (motorcycle-type) jacket instead of the pea coat. It would be a bit edgier, but proportionally might “click”.

      And I love it! The purple tights, pink scarf and your bun go so well with the dark dancery-dress.

  10. Love the dress, scarf and tights.Fab with high boots!

    For me the boots would go better with slim jeans and a layered top and flyaway type of sweater to offset the chunkiness of the boots.

    Art by Karena

  11. Mid-30s here loving your outfit (especially the tights!) and wishing I had your “skinny” legs – I’d fill those boots out in an instant!

    The peacoat on top is a double win. You look great.

  12. I agree with some of your final comments regarding the boots or dress, though in my world this kind of outfit is purely so classic as to look wonderful on you in every way. Your hair is just beautiful and everything together is so inspiring to me!

  13. OK, love the whole look including the Degas pose but, but I think your delicate aristocracy is showing in your ankles. Looked at your post of the boots and did you notice when you showed other boots the tops always “fit” the ankle in a complimentary way. I think the width at the top of the boots is the only thing that bothers me. Otherwise you look fab!

    How about that outfit with tall boots? Short tighter boots? Make those boots work with some of the suggestions above.

  14. Like the dress, tights, scarf and coat. Sorry, but hate the boots. Maybe they would be ok with jeans? Guess I am way to conservative. Btw. This has nothing to do with age. Wouldn’t like them on a 20 year old either. Call me curmudgeonly.

  15. I don’t find it to be too young at all. In fact, I am 46, but found myself studying it to see if something similar would work for me. Is it artsy? Definitely. Edgy? Probably, but in a sophisticated way. I love to see women over 50 who pay attention to style rather than resigning themselves to dowdiness. Well done!

  16. So, first, I love the outfit, and would wear it. I would want the dress a little longer, but on me it would be longer as I am I think 2″ shorter than you. I would wear it with my black Frye engineer boots, which would come higher up the leg (but not all the way to the knee).

    Some additional thoughts on pieces and proportion: The scarf is a really important part of the outfit; without it, the dress-tights-boots look unfinished, to my eye. (Also the pink scarf talks beautifully to the purple tights.) It’s hard to get a good look with the photo angle, but I could entertain the argument that your ankles are so delicate that the gap at the top of the boot is too wide. The answer to that might be a chunky black sock folded down just inside them, which would recapitulate the chunkiness of the scarf.

  17. I really like the overall philosophy/colours, but I might tweak a couple of proportions. I had originally thought that the boots were unzipped, so something closer to your ankle might be even more flattering. And if the dress were mine, I’d either hem or roll up the sleeve an inch or so–I have a *thing* about where my short sleeves hit my upper arms.

    That said, I will be going into NY in a couple of days to pick up a pair of moto boots on hold for my Xmas gift. I’m hoping I can wear them with a dress! xxMC

  18. Not too young at all. I have a curiosity about ankle boots as well; can’t figure out how to wear them, and definitely one of the problems is skinny ankles/calves. It’s such a sudden change in volume. But I think the purple tights actually help there, because that’s already a visual chop, and then the flare of the skater dress echos the volume change.

    Perhaps you are wearing this in the cold today. But, yesterday, were you wearing a purple tweed skirt? I so, I can claim a Privilege sighting. I’d be the woman who gave you the strange smile at Fremont and Mission.

    1. Yes! That was surely me! Did you look at me quizzically? Short wavy hair? I remember thinking, hmm, wonder if she reads the blog? Well, hello!

  19. I like the outfit. It’s not too young because you are covered and the proportions work. I have a great pair of short boots which I pair with tights, wool skirt and pullover sweater for a ‘walk about the property’ look.

  20. As you might expect, I like this — it’s comfortable territory for me, and I think it looks great on you as well. And I like the unexpected hit of colour in the tights.
    I’m struck by a tension-vulnerability I sense in that top photo, around your shoulders — and I wonder if that signals permission for viewers to project “too young” onto the outfit. By the time you begin “owning” the look — adding the pink scarf, the peacoat — you relax into it, and it looks completely congruous. Probably the top and bottom shot were taken closer together than this narrative suggests, but I can imagine you gaining comfort and bringing that into the outfit so that by the bottom Degas pose, your Sturdy-Artsy is completely credible, and absolutely age-appropriate, selon moi. And my, you have slim ankles!

    1. Yes, I think of this as Dressing Like Mater. But it’s so interesting your interpretation. I can see how that might have been the case. In fact, I took the photos with the full getup first, because it was quite cold that morning, for SF. The tension in my shoulders is the instinctive pulling in against the cold, as well as my hurrying because my camera was about to run out of battery and people were beginning to pull into the parking lot I’d chosen and want me to get out of their spaces!!!:)

    2. Dressing Like Mater — love it!
      I can imagine that posing in the parking lot would def. cause some shoulder tension! as would the cold. You’re an inspiration, doing this for us!

  21. i don’t think it’s too young for you at all. after all you are young!

    like kathy way up there i’d like to see the boots styled with skinny jeans and a chambray shirt or a thick sweater.xo

  22. It does me good to see these photos. It’s a lovely outfit—fun and fresh and comfortable and pretty. I wear things like this all the time and they feel just right, until I go out in public and then I see women my age (53) dressed very differently, and I have a spasm of insecurity that I am dressing “too young.” It is encouraging and it helps me to trust my own eye to see you looking so fantastic in this outfit. Love every bit of it.

  23. You look amazing! I’m 20 odd years younger than you and jealous of your figure and graceful posture (did you do ballet as a child?).

    Keep rocking the boots!

    1. I was a terrible dancer, but I did it anyway. My daughter was a serious, and talented ballerina as a teen. So I saw a lot of good work and am emulating.

  24. Let’s celebrate that you look so healthy! Everything is in tip top shape. I think you look comfortable without being dowdy, and age-appropriate. Something “artsy” my Mom does is wear a solid obaque colored tight (like blue) with a patterned hose over it. Adds fun texture to an otherwise plain outfit. One time she did that and coordinated the blue to the threading in her cowboy boots. No, I’m not kidding. She was an artist for a long time. :)

  25. You are gorgeous and can wear anything.

    I found the photo jarring. It is so different from what you have shown us before, so different from your usual uniform. I like each piece. I prefer those boots with a much longer skirt, something funky like rundholz or comme des garcon or rick owens. I love the purple tights and do that look frequently myself but with only a hint of color between ankle boot and skirt hem. One problem for me is that I lived in this look a decade or so ago while home with kids. So it no longer feels new. Also, since I am very short/ petite it starts to feel very young on me at this age. little girlish. You are taller. I am not sure if I like the exposed knees. It is a lot of leg. I wonder if it is a look for someone our age that works better in certain regions/urban centers than others? I am sure you are always appropriately dressed.

    I hope this isn’t too critical. I love the post and find the very different look very intriguing.

    1. I don’t mind the criticism one bit. I asked for it, as this is clearly a departure. One additional piece to the story is that I cannot stress enough just how untraditional my work place is. I’m inspired by my colleagues to stretch. It is a regional thing.

  26. It’s an OK look, not too young. Everything fits you nicely.

    If you only have room for one gray dress and are getting rid of that Lela Rose gray dress just let me know, because it’s my favorite!

    How about layering some other socks over the tights? Too arty? Your tankles trim ankles, the opposite of cankles – calf/ankles, could take a little more bulk.

  27. In case anyone thinks I’m insane, Lisa asked me to find her some sweaters that I think would work with slim jeans tucked into her moto boots. So, I found 3, and have posted them. I think you’d rock all of them.

    1. Thank you Kathy! I am still unsure that the sweaters will prevent the bowling pin effect caused by upper thighs that are wider than my hips, and long waist that causes said upper thighs to show up lower than I want them too. I should measure, and then I’d know the required sweater length.

    2. I think you have to try them on, because it’s not just about length, but also the width and slouch of the sweater that helps balance whatever problem areas you think you have. If a sweater is too long, I think it shortens the leg – so it’s a more complicated thing than just length.

  28. I agree that these particular boots would look best with pants. I would like this dress with different boots. I’m not sure about the purple tights. They are ok, but I would try other colors. None of it is too young for you! (I am 60 and would wear these styles.)

    1. Got it. They really are slightly more navy than it appears. I tried to tweak the photo but my skills weren’t up to it.

  29. I like the dress with those tights but different footwear or the dress with those boots but sheer black nylons. For some reason, the purple is a bit too bright to go with those boots for my eye. Those boots demand something a little less cheerful. But I love the experimentation!

  30. Late to the party, but had you considered gently flared trousers? I think pants over the boots + white blouse + a plain leather jacket would be an absolutely killer look. That said, the knit dress with the boots is fun and unfussy. I’m afraid the peacoat clutters the line – but a longer coat, say a trench covering the dress, would top it off nicely.

    1. I tried bootlegs – the boots are so clunky at the toe they didn’t quite look right. Were I taller it would work. As for the coat, yes, I am just not well coat-resourced:).

  31. I would have to agree with the commenter who did not like the jacket. Remember Marlon Brando’s motorcycle jacket? Something in that vein would be good. You have great legs, take them off your list of things to worry about.

  32. The flared dress line is lovely with your broader shoulders. You should do that more often! As to the boots, I have my doubts, too. Legwarmers might fill out the gap between ankles and shoe. Great colours on you!

  33. Without the scarf the dress is a little boring, but once you get that punch of texture and colour up near your face and neckline I think it works quite well.

    Definitely not too young either. Not by a long shot.

  34. I love seeing you branch out:) Looks awesome to me, but then I have been known to wear short booties with leggings and an over the buns dress or skirt..I get lots of compliments and I’m almost 63:) Young girls tell their Mom’s to wear something like I’m wearing, so I don’t think it is bad..You have inspired me..I’m looking at some short Frye boots to wear..I find the older I get, the more “tough” I like to dress..don’t want to be one of the ladies who lunch crowd heh…Coco

  35. I love it. I am envious that you can wear a knit dress without worrying about belly pooch, and I think the accidental navy/purple tights are inspired. I would not for a second change them back to black.

  36. PS the dress would look great with a long pendant necklace. Quite long. For when you’re not wearing the scarf.

  37. So, what do you think? What do you feel good in? Do you *want* to be at the edge? I have an opinion but it is really only my filter.

  38. Anything flared tends to lean towards too young, but I’m this case it’s so cute and is so flattering on you that it doesn’t matter. Purple (or even navy) tights are pretty artsy. I think the whole thing would be adorable AND age appropriate with black tights, a leather jacket, and some “important” jewelry on your wrists.

  39. I like how the blogger at odyssey home dot com wears motorcycle boots. To my mind, they fit seamlessly into the total look she has created. I think you would look fantastic in her look . You both have wonderful hair. I really like the look you have been doing. It seems ladylike/hip, elegant/edgy to me. The tweed skirt with shirt and sequin skirt with shirt were some of my favorites. I also want to say I liked the wide pants.

    Do you like the idea of wearing very different looks? I am a style purist and have been impressed with your consistency. The changes in your hairstyle seem to me to change your entire look dramatically. I love your hair, especially in this post.

    1. I never meant to be a style purist, it was a desire to be “appropriate.” I don’t fancy wild swings in my style, but a gradual nudging feels right. I’m really taking cues from my surroundings, the way people dress in my job. And it’s so funny – this is probably how I wear my hair most often, but never felt it was worth showing on the blog:).

  40. I think it is certainly age appropriate but I just don’t like the boots. The wide open top looks kind of sloppy. A trimmer boot would look nicer in my opinion.
    I really like the addition of the scarf. The coat is ok…. but I like it better without.
    Your hair looks lovely!

  41. Aha, so you found a sweater dress after all! It’s a great choice, and I like the look of it with the boots. I also liked KBG’s idea of adding a leather jacket and jewelry. You might also try the same outfit over ponte knit pants — they have the look of tights, but will fill out the ankles of the boots much better than tights do.

    We should get together soon, btw! Perhaps we could peruse the post holiday sales…

  42. love it. I would say go for booties that are less big. they have some great options out there. it is great you show your figure….it makes you look younger when u show it

    enjoy your blog, immensely

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