Privilege Blog

LPC Belatedly Answers A 3rd Round Of Questions

The time felt right to answer a few more questions. In some cases, I’m asking for the community to chime in, as you offer a veritable cornucopia of knowledge. Although I’d previously cut out the complimentary remarks, I decided to include them here, as it feels discourteous to ignore kindness. And, as my mother says, A Simple Thank You Will Suffice.


Q: Can a plumpish Jewish almost-50-ish girl who has been dressing like a sad sack soccer mom for the last 20 years, thinking I might figure out my personal style if I ever got thin, transform into a High Wasp Sturdy Gal or Arty Cousin? Or is it just too late?

A: Not to go all Cheerful Charlene on you, but it’s never too late. I think there are two primary paths to style, in light of where you are right now. Method number one, and probably the more daunting, would be to get your body into a silhouette you enjoy. I’ve written a few posts here on how I eat, and what I do for exercise, but the best advice I can give is find a community and get started, with support. Could be Weight Watchers, could be a few women who walk every morning together, could be an online forum. Method number two, and perhaps more immediately rewarding, is to investigate the Artsy way. If you’re Artsy it just doesn’t matter much about your silhouette. You can decorate yourself with color, with fabric, with accessories. Your body becomes a canvas, rather than the work itself. Take a look at Ari Cohen’s Advanced Style, and then dial that back about 50%, and you can come up with a way to dress that’s fun and doable.

Q: Since recently discovering your blog, I find myself returning on a daily basis to take advantage of the wealth of information you share with your readers.  It is really quite amazing.

I have two primary questions that I need some help in sorting out:
1.  I have a granddaughter’s wedding coming up in September, and I have finally found the right dress for the occasion.  The color is navy blue (a very nice shade of navy–not too dark and not too blue), and I am debating about what color shoes would be appropriate.  I am thinking black leather pumps or black patent leather pumps.  Please give me your opinion.

2. Also, there will be two bridal showers this summer, and summery dresses and sandals will be worn by myself and I presume many other attendees.  Since sandals will be acceptable, can you guide me in choosing a polish for my toes.  Most women go very bright, but I often go soft pink.  Please advise.

Thank you so much, Lisa.  I am enjoying your blog tremendously.

E. Jane

A: So sorry to be responding late. You’ve probably already been to the showers, but here goes. With toes all bets are off. Soft pink, red, magenta, blue. Foot owners’ choice. In the High WASP culture your feet don’t actually exist as style constructs, they are for walking. We don’t see them. This allows for highly imaginative pedicures and woe be to anyone who care to comments. As for what shoes to wear with navy, the High WASP honorary color is the pigment equivalent of toes. That is to say, just about any shoes in the world – except another shade of navy – will work. Black is always good, but purple, pink, or green are wonderful.

Q: Hi Lisa, I am curious to hear your perspective on the recent factory fires in Bangladesh. As a business manager, woman who appreciates style/fashion, and writer who expresses great compassion (as well as a one-time traveler to South Asia), what do you think consumers or retailers can do to improve conditions? It’s interesting to note that European retailers like H& M have signed on to fire safety regulations in their factories, while US companies like the Gap have not. I would love to hear any insight you have to offer!

A: I am a believer in overseas manufacturing. I have no issue at all with Made In China, precisely because I believe honorable American business practices are our best ambassador, and benefit Americans and host countries alike. As a result, I think it’s critically important that US overseas factories uphold the highest possible standards of safety and quality. It becomes important therefore that we as consumers support retailers with good practices.

Q: I just discovered your blog by accident today, and it’s great – just delightful. But also, it was my 50th birthday yesterday, which brings a couple of questions to the top of my mind:
1) My teeth, always a bit yellow and crooked, are getting worse. Should I get them straightened/capped? My dentist says they’re fine as they are, good strong teeth and not terribly ugly; I am afraid that if I start messing with them, they’ll never be strong again. What, honestly, are the downsides to cosmetic dentistry undertaken in middle age?
2) You promise comfortable footwear that aren’t like shoe-muffins – can you fill me in on these please? Flat, comfortable, for walking in cities, but without that giveaway shoe-muffin look.
All tips gratefully received.
Many thanks
Jessica Thomas

A: I can’t say that I know anything about cosmetic dentistry – my apologies. I do find that over-the-counter teeth whiteners like Crest Whitestrips work well enough, and are good for a little morale boost now and again. I plan to do a week program for my wedding, for example. As for comfortable shoes, I have posted several brands. My absolute favorite is Beautifeel. You can go classic, or Artsy, with a pair of red desert boots. What else could a Sturdy Gal need?

Q: Hello.

I am about to embark on an exciting year long docent training program at a culturally rich and  prestigious museum in Sarasota, Florida.  I want to look “like a docent,” without looking any older than my 45 years.  Any tips on how to dress stylishly, yet appropriately for conducting lengthy museum tours in my warm climate?  Your thoughts are greatly valued by me, as I love your approach to style.

Theirs is nothing on the Internet regarding “docent style.”  Help!


A: Now that’s an interesting question. I suspect that some of the commenters here will have great advice. Analytically speaking, I’d imagine that “docent style” involves getting out of the way of the artwork one is presenting. But culturally, and socially, especially in Sarasota Florida, I’m at a loss. I put the question in turn to our community here.

Q: What would the High WASP stay-at-home mother wear? I ask because I have moved and my clothing is not always geographically appropriate and I have found myself in my mid-forties at home in Virginia with three teens and a 3 year-old. I work at home as an artist but I identify with your “Sturdy” style far more than the “Artsy” archetype.

A: In my case, the High WASP mother wore anything she could find that was clean and allowed for bending and twisting. I admire you enormously, 3 teens and a 3 year old. Am also slightly envious, to have a late-ish baby like that. In California our strategy is jeans, and shorts on the few hot days, with good classic tees, and some slightly hipster comfort shoes, like Pikolinos for example. “Trainers,” as the British call them, are to be avoided.

But Virginia’s weather might not support jeans, and the local culture might not be so shorts friendly. At a guess, were I you, I’d find myself a signature brand of khakis and wear them with high-quality button fronts – new and clean for going out, paint/materials decorated when staying in to work. Here’s a cool new LA shirt brand I saw recently. I might also invest in a few of the Dressed USA shifts, so that if I had to run errands in the heat, I could get out of work clothes fast, and pull a pretty but comfy shift easily over my head.

Thank you all for your questions. It’s a privilege to be asked.


19 Responses

  1. I am the SAHM artist who posed the question. I love your answer and have been admiring the DressedUSA shifts. You are semi-correct about the shorts. I don’t wear shorts out and about but there are so many Northern transplants that they are a normal sight among women my age. I find skirts and casual dresses to be a prettier option.
    I will definitely be on the hunt for some cute khakis.

  2. As a former docent, I’d recommend comfortable shoes and clothes (and hairstyle) that don’t require fussing or yanking around. Project neatness, competence, approachability – the kind of person you’d ask for directions in a strange town.

  3. To the new docent – I’ve been a tour guide and now oversee and train guides/docents at a Museum in Massachusetts,and I would say that you have a lot of leeway as a docent as long as you look nice and don’t wear anything revealing (no matter the age). Nice is subjective so I mean khakis or colorful pants are totally fine, nicer short sleeve shirts, blouses, any button-downs, dresses (with cardigan for tank tops), all of that is great. You can definitely go towards the artsy cousin (grand dame and sturdy gal also ok!), but not too many patterns (that might distract as Lisa suggests).If you avoid jeans, short skirts, casual t-shirts, sweatshirts, etc I think you’ll do well. Also, in my experience, if you are being thoughtful about this to begin with you are going to be just fine. Have fun in your new docent position!

  4. I can offer some insight on the later-in-life dental work…I had my teeth straightened and whitened for my 40th birthday (although the work itself started a few years earlier) and it was a terrific decision. The way to start is to get recommendations for orthodontists and schedule meetings with several (this is usually free) to see what the options and costs and any risks might be, and to see who you’d feel most comfortable working with. I recommend Invisaligns if you’re a candidate for them; they’re removable and less obvious and more comfortable than metal braces. It’s a process and an investment, to be sure, but I didn’t realize just what a difference it could make until one day a butcher stopped mid-order and said ‘You have a beautiful smile.” I’d never heard that before, and I will never tire of hearing it. Go for it!

    1. I’m with ParisGrrl. I was fitted with Invisalign braces at the advanced age of 53. I have always been a bit self conscious of my crooked teeth…but then my dentist informed me that they were actually getting worse and recommended seeing an orthodontist about braces. I held off for a long time…soooo worried if I was making the right decision. Was it too vain…too expensive, too inconvenient…too embarrassing? I mean…what was I thinking? I was too old, right? Then I found a great blog by an Australian woman who wrote about her Invisalign journey (in her early 40’s) and that helped me decide. And now that the process is complete, I am very, very glad that I went ahead. Get lots of advice from the professionals, shop around for an ortho with whom you feel comfortable..and go for it!

    2. Teeth are very important!

      Younger Americans of a certain class mostly have great looking teeth. People of our generation don’t necessarily have the greatest teeth – orthodonture wasn’t as good and parents didn’t always consider it a must-have. Straightening your teeth will do wonders for your appearance.

      If you can’t financially swing straightening yours then do consider whitening. Whitening strips can get you started. After that I recommend one of those battery operated toothbrushes like they sell at Target, plus whitening toothpaste. The battery-operated brush does wonders.

  5. To the plump, almost 50 woman, you do not have to wait until you are thin to look terrific. You can look your best at whatever weight you are currently. If you want to lose weight, that’s fabulous, but please don’t wait until then to enjoy having a personal style. I am a plump 55 year old who wrote a blog article about just that thing. It is posted here –
    I have a very traditional, classic style and that really works for all sizes! And to the docent, I am from Sarasota, too! The Ringling Museum is lucky to have you! I would look at what the other docents you admire are wearing and dress similarly, according to your style.

    1. Just adding my hearty, vigorous, fist-pumping, head-nodding-so-hard-I-risk-neck-injury assent to Debbi Benedict’s comment that women can be stylish at the size they are right now. In addition to Debbi, Sal at Already Pretty ( is quite affirming and articulate on this topic

    2. Thirding the comment by Debbi Benedict to “plumpish Jewish almost-50-ish girl.” You don’t have to wait until you lose weight to find your personal style, whether it be your personal version of Sturdy or Artsy Cousin, or something else entirely. If you decide for yourself that you want to lose weight for whatever reason, that’s fine, too, but it’s not a prerequisite for looking good and feeling good about your appearance.

    3. I echo and second/third/etc. that you absolutely should not wait till you lose weight in order to find your style.

      I also want to point out that depending on your body type/metabolism/chemistry there might be no way that it is physically possible for you to lose any significant weight without damaging your health. And if you are healthy at your current weight is it even worth trying?

      However there are no barriers (except the difficulty of finding good quality good fit clothes – which is significant) to finding your style. I’d start with some serious thinking about the basic pieces and any awesome flourishes that will make you happy (signature beautiful necklace?). Make lists, think some more. Then go somewhere like Nordstroms and Bloomingsdale – to be followed by some small boutiques/stores and figure out which is easier/better for you as a shopping experience and what kind of clothes work from your imaginary/well considered list. If you love things put them on hold. Go home, think, google – then go out and buy a small new wardrobe (possibly at cheaper stores) – a more or less complete small wardrobe does not have to cost an unaffordable amount.

      I think just one or two expensive items that you personally adore adore adore that are “everyday” wear in addition to very basic items that are well picked will make you feel very stylish and happy with your look.

    4. I’m sure you are beautiful at any weight, but if you are determined to lose, I can’t say enough good things about Weight Watchers!

    5. For the 50-ish Jewish woman.
      Are you from New York? If so I think you have a lot of style-leeway, but generally when thinking of the Jewish women I’ve known even if they fashion themselves towards the Sturdy Girl style they are distinctly Urban. Not to make unwarranted generalizations, but it’s something about the dark, sometimes curly hair.
      Overall I’d say my Jewish friends, who aren’t ultra Conservative, which I assume you are not because you wouldn’t be looking for style advice, run more Arty Cousin.

      As to the weight-loss issue – should you or shouldn’t you- it’s been my long-time feeling that you can’t successfully address your weight until you love yourself the way you are right now. So don’t put off assembling some great outfits with the excuse that you’re going to wait until you’ve lost weight.

  6. I am the docent (intraining) who posted the question. Thank you, Lisa, for soliciting your readers thoughts. I like their suggestions, and will use them. Thanks to all!

    LOVE this blog, and this sense of community that you have created, Lisa. Bravo!


  7. Jessica – I had braces (the conventional bands and wire type) twice. Once when I was a pre-teen, then again, at my own expense, when I was in my early 20s. Over the years, my bottom teeth became somewhat crooked again. My friends and family claimed they didn’t notice or maybe they were just being nice but at the mature age of 56, I decided to get Invaslign for my bottom teeth. It was expensive and hurt a little in the beginning but well worth it. So, I would recommend finding an ortho who can guide you through this process. For the yellowing, I use whitening strips when needed. Go for it! I don’t think you’d be disappointed in having beautiful straight white teeth.

  8. To the plump, almost 50 woman: I am 55, plus sized and struggle with finding clothes that work with my style (kind of Grand Dame) and what works for my body (more artsy cousin). Sal at the alreadypretty blog had a post on this particular topic yesterday. I think the key is finding pieces you love, realizing that every look isn’t for every body, and that it is OK to sometimes wear things that aren’t the most likely to flatter your shape if fitting with an informal dress code is more important at that time.

    1. “informal” is probably the wrong term. What I meant was informally understood, or perhaps unspoken. I wasn’t referring to the formality of dress.

  9. For the lady who is now a SAHM in Virginia, it’s going to depend on WHERE in Virginia she lives. There are some cultural differences among the different areas, so my advice would depend on her location.

  10. I love the questions and responses in this post; they are so thoughtful and so helpful.

    As a docent, I tried to wear subdued colors in simple, classical styles, without seeming schoolmarmish. Black turtlenecks with black trousers – taupe, navy, brown, also – with a stylish sweater or dressy but not formal jacket and often some piece of interesting jewelry. Since I was working in a history museum, I tried to find items that could be used with the exhibits – teaching tools – as I frequently took grade schoolers around.

    I strived for a look somewhere between classic and academic bohemian.

    It seems cliche now. But that was the 80s.

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