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How I Dress Up Now That I Am Over 50 (Actually 60)

August 2017. Our 4th anniversary at Boulevard, in San Francisco. “Muse” dress by Miranda Bennett via Garmentory. Shoes: Valentino Tangos ||Tights: Wolford || earrings: Vicente Agore

I thought I’d conclude 5 years of monetized style blogging with a post crammed full of shiny stuff. Game?

Let’s dress up!

The point of fancy is

  1. to feel spectacular
  2. to look your best in accordance with both your persona and the occasion
  3. to feel spectacular

How to do this in one’s later years? Advanced Style is an option for some, but Sturdy Gals don’t do outrageous, we have our ways.

Color, silhouette, fabric, those are my chosen tools. Oh, not to forget makeup brushes and white eyeshadow.

The photo above illustrates our principles. I found this blue silk noile dress is at a wonderful online resource called Garmentory. (Go to Grechen’s site and use her link for a $20 credit.) See, were I not easily bored I could wear blue every day of my life. It’s my color. This shade is a little brighter than I’d usually choose, but the intensity works for dress up.

Side benefit, my comfort in the color allows me to wear an Artsy silhouette unembarrassed, which in turn allows me to eat without discomfort. Booyah!

I added large earrings, because simple and architectural. A small two-solitaire diamond pendant because sentiment, but also to highlight my décolletage and its bony structure. We are our own accessories. And, to tone this down a bit, for San Francisco restaurant culture, I wore black tights and shoes. In retrospect, I needed sheerer tights – the shoes looked better than you can tell from this photo. (I also might yet trim off the low part of the high-low hem, or when the fashion for raw edges passes, hem the sleeves.)

But I hope to wear this dress many times over many years – full on fancy or date night, either way.

How to find your similar dress-up outfit, should you be so inclined

  1. What’s your single best color? What do you wear to a constant chorus of, “Wow you look great!”
  2. What skin do you like to show? Collarbone? Ankles? Back?
  3. With these principles in mind, lurk. Check out places like Yoox and Farfetch for unusual pieces. Install Shopstyle on your phone and while away your standing-in-line time hunting for the perfect dress. You will find her.
  4. Choose shoes that play up your color strategy
  5. Wear statement jewelry but not too much
  6. Use makeup to highlight the structure of your features.

Dresses In Knockout Colors, In A Range Of Prices

A Portfolio Of Shoes To Dress It Up Further

If we ever did go to a gala, or the opera, I could have worn my cobalt blue dress with these navy crystal-embellished satin slingback Manolos. Added red-gold jewelry for a little contrast or amethyst for complement.

Again, color. Don’t match, we’re not Little Edie Beale Bridesmaids. Aim for contrast, i.e. purple with your orange dress, and/or complement, i.e. pink with red or navy with cobalt.

Even Grande Dames approve, whether Mano-lo or Mano-no. Sorry. Couldn’t help it.

Lightweight Earrings From My Old Friends At Blue Nile

If you’re a big necklace person, I am useless to you. My apologies. But I can help with any heavy earring problems. Although Blue Nile may skinny down their earrings to reduce costs/prices, our earlobes are grateful. (Selected pieces 25% off)


  1. Gold quadrangles
  2. Pearl drops (25% off with code BRIGHT17)
  3. Diamond bars

Or these, if you tolerate the metal, in silver for less. Silly to spend money just to spend money.

Date Night Makeup

To set expectations, I’m talking date night in San Francisco, an Artsy town whose citizens on any given night show up in zero makeup, full face socialite, or full face tattoo. So, date night makeup for a no-makeup look. I’m making myself laugh, but it’s true.

In essence, I intensify the process that I reviewed in my previous video by adding shadow and light. Here’s my little kit.

(Speaking of videos, I tried to respond to Kathy’s request for a second one on makeup.) But the only space I have for such a thing is my bathroom, where the light made me look like, again, Little Edie Beale. When I reviewed the video, my voiced “Yes!’ (in approval of my fuchsia lips) brought to mind a demented woman displaying Christmas decorations made of rolls of paper towels and spiderwebs.)

Date Night Makeup Technique

  1. Focus on your skin; exfoliate,  moisturize, plump it up with hyaluronic acid. Use the foundation and concealer that work for you, spend some time blending.
  2. Stick with tried and true shades – I tried to wear products called “Redwood” or “Apricot” for years. When I was young I could just manage. Now I stick to “Rose” or “Pink Pearl.”
  3. Intensify your look with shadow and light: black and white; gray and pale gray; or brown and vanilla. I rarely wear eyeshadow these days. Oh, I try, but I always wind up having to clean it all off. How then to do nighttime eyes?
    1. Cover eyelid with a skin color shade (not the color of your eyelids per se, the color of your face)
    2. Line eyes from middle of eye to outer corner, using a very soft pencil. Smudge the line a lot with a brush. (I cannot tightline it makes me gag)
    3. Curl your eyelashes. Yes, it really does make a difference.
    4. Use a white-for-you shadow (cream, light tan, pearl white, ivory) shadow, with a pony tail brush, to emphasize the shape of your eyes. For me this means a dab right above my pupils, one on each lower outer right corner below the lash line, and one on the upper inner corner aligned with the top of the iris. This opens my eyes quite round. Your eye shape is different, your highlighting will be different. Experiment.
  4. Find good brushes and tools.
  5. Use a hair highlighter for sheen.

Old Favorites And Tempting Possibilities

A Few More Recent & More Casual & Less Colorful Going Out Looks

Just in case you’re shaking your head and saying, “If it ain’t neutrals I’m not playing.” For my birthday, in the ladies’ room at the Four Seasons Palo Alto. Vintage Issey Miyake top, Vince trousers, J. Crew patent leather loafers.

And for Thanksgiving. A vintage Chanel jacket from the 1990s, diamond studs, doubling down on the Vince trousers, and Marant Dickers from way back here.

And, why not, from days past. Thanksgiving 2015, a holiday party and sequins on New Year’s Eve, and a 60th birthday bathroom selfie. As Garth says, “Party on.”

Links may generate commissions. And so in a semi-epic ends my spate of monetized fashion-blogging, at least for now. Saturday posts will continue, and will often include style thoughts, but, no new dollar-generated links. I’m not editing older posts to remove them though. Thank you for your support these past years.


37 Responses

  1. That blue dress is so San Francisco Perfect! It’s a lovely color on you too. Your comment about tightlining cracked me up. I can’t apply liner to the top of my lids to save my life.

  2. You look fabulous in all the outfits. I’m pining for the Manolos. Your description of “a demented woman displaying Christmas decorations made of rolls of paper towels and spiderwebs” is hilarious. Oh, please share your fuschia-lipped video!

  3. I love your sense of humor and your fashion sense. Will miss your fashion/make up/house posts.

    1. @MaryAnne, Thank you very much. I will still post clothes and house stuff, just with less detail, not monetized, not so “shoppable” or elaborate. Just like a personal blog of someone who likes style, but isn’t making a business out of it and also thinks about other stuff. xoxo.

  4. I think the taste for sheer stockings is generational. I like them because I think they show off curvy legs, but I see enough opaque or bare legs to think there is a cohert that wouldn’t consider them.

    1. @Roseag, Yes, I think it’s generational, but also that the pendulum may swing back. A nice sheer stocking, even with a little glimmer, or fishnet? Very nice.

  5. Blue and army green are probably my best colors, but I wear what I like..particularly becoming or not. Camel for example. After a black tie wedding last weekend, I’ve sworn off heels – I’m done done. Went out the next day and got two pairs of fancy flats.
    I like the dress on you, but prefer you in pants – I feel the same about me. For next year I’ll be looking for a dressy pantsuit for all occasions.
    Your hair has inspired me to finally transition to silver – thank you for all of your wonderful style posts over the years, and I totally understand your disinterest in doing them now. XO

    1. @KSL, Kathy and Lisa: (I hope you can both see this reply.) All my life, I’ve worn what I wanted to wear, full stop, so age or color issues go past me. Kathy, I like a 3″ heel height in short boots at times, but I like it in a block heel, which is stable. I’ve never been a fan of a skinny high heel, so for (rare) formal I have a couple of black dressy 2″ tapered heel choices. Lisa, I agree with Kathy, I adore you in pants that highlight your lithe figure, and I prefer to wear pants. Both of your neutral outfits (Neutrals! Yay!:) look great on you. Adore your Chanel jacket. Also? Skinwise? Yes to hyaluronic acid! I’m loving Twelve’s Ideal Moisture Level Serum for a hyaluronic (Ayla S.F.), and my toner, MUN’s Anarose, has hyaluronic acid in it. (Expensive, but excellent yearly sales.) Until recently, I didn’t understand that there’s a difference between dry skin, which I don’t have, and dehydrated skin, which I do have, particularly in the winter, which is hydrated by hyaluronic acid. Regarding makeup? I rarely use any, but when I do, I use a pale powder or cream shadow over my lid, for example Kjaer Weis Cloud Nine, or Alima Pure Gamine, or for slightly more pigment, but still neutral, Rituel de Fille Sigil or Phosphene Luminizer, which is a highlighter, but works on my lids, a cream blush, and lipstick. I’m experimenting with the Bite Beauty (Fillmore Street brick & mortar) Multistick in Biscotti for both lips and cheeks, (it may be too matte, the search goes on), then curled eyelashes and mascara. I’m trying to use mascara, but I don’t like it. 1000% with you on tightlining, which gives me chills. I line nothing. BTW, Kjaer Weis is expensive, but the containers are gorgeous (designed by Marc Atlan) and refillable, though heavy, and the products are organic and effective, though they expire. You buy the container version once and then buy refills. You can also buy refills initially and put them in a magnetic container. You might like the blush Embrace. (A subset of the lower-priced Alima Pure is also in refillable containers of black metal.) I hope soon to narrow my makeup to the simple routine I had with conventional products: five products, five minutes, out the door. Lisa, I also agree with Kathy about the beauty of your silver hair. I’d grow my hair out if it weren’t presently half very dark brown and half gray, and not in a pleasing salt and pepper way. I need more gray before I stop coloring it. Finally, I echo Kathy’s thanks for all your style posts. It’s been absorbing and fun to watch it all unfold. I also understand why you wish to change your focus now. Happy anniversary, Lisa. Boulevard is lovely. xoxoxo to you both.

    2. @KSL, I was thinking about this, how there is a point in dressing up where something just makes me feel like I’ve got to wear a dress. Maybe it’s cultural, personal history, I don’t know. Maybe it’s also that if I’m dressing up for a fancy event I feel more protected and am therefore more willing to be vulnerable, legs showing etc., in a dress. Hmmm.

      Must think. xox.

  6. Sorry to see your style posts going the way of the dodo bird. I do love your choices. May not be right for me but love them on you. You always open up my eyes to some delicious item. So thanks for the memories.

  7. I enjoyed this look through Outfits Past. What I love about your blue dress outfit, apart from it looking fantastic, is how you took it from casual, as shown in the shop photo link, and make it into something elegant and now. And the shoes, I noticed them right away. Verrrry nice.

    The red Bregazzi dress, I could sure use that! Hahaha. With feminine, green satin, bejeweled shoes. Blue is my usual go-to popping colour.

    Write on. Style, schmile.

  8. I love your style posts, I will miss them too. You’ve introduced me to so many wonderful brands over the years and I usually love everything you wear. I especially love your jewellery finds. I’m glad you are leaving the old style posts up!

    1. @Patricia, Thank you! I will definitely leave them up. And will share any good new brands I find, just far less elaborately and less-well-photographed. I really appreciate your support.

  9. I think the pants look wonderful on you. Your glasses and hair all sophisticated.
    Still, for myself it can be hard to let go of not looking like I’m thirty something. Very hard to pull of at sixty-one. What do the Buddhists say, “be here now”.

    1. @Luci, Thank you! And I definitely am most at home in pants. BTW, I’m getting new glasses and I think I want new frames and I’m thinking translucent blue. Am I nuts? We shall find out!

  10. The intensity of the blue works so well with your silver-white hair. It really amps up the dressy aspect. You look spectacular – bravo, well done! I enjoyed your thoughts and tips here on dressing up. We also love Boulevard and make it a point to go whenever we are in SF.

    1. @Jane, Thank you:). I did feel amped up. I hope I have an occasion to wear the dress with the crystal-filled slingback. Am glad you’ve discovered Boulevard. Such a great place, a real blend of old and new San Francisco.

  11. Lisa, you still have the ability to make me laugh! I’m picturing Little Edie in a cobalt blue bridesmaid dress with matching cobalt pumps, and of course, a matching cobalt headscarf.

    Stay stylish!

  12. So,it’s a farewell :-)!
    Happy anniversary!
    Lovely outfits-beautiful colour of the dress,it suits you perfectly
    Looking forward to all the topics you’ll choose to write about

  13. Love the Chanel jacket and boots outfit. Love them all really but it’s my favourite. I love cobalt blue as well. I’ve a cheap Zara blouse with fake leather trim in cobalt. I wear it with my black leather trousers.
    We don’t really do dress-up very often is ever. I have two dressy dresses…actually not sure one fits anymore. I bought it the nineties, but retirement has wrought a few subtle changes on my body. Ha. Even though I have upped my fitness regime and work out pretty much every day, I can’t seen to make up for the calories that I burned running up and down stairs at school, waving my arms around and talking to a room of 30 teenagers, or the constant stress of marking, dealing with administration, and smoothing riffled parental feathers. Sheesh. Don’t miss that at all. What’s a couple of pounds, eh?
    Hope you will still chat and muse about fashion sometimes. I just love to hear you think… so to speak. xo

    1. @Sue Burpee, A couple of pounds is infinitely preferable and better for one’s health than stress. And yes, I’ll still chat about fashion, I am sure I will have to tell you about my Alexander McQueen sweatshirt with swallows on it, for example;). I bet you look great in a cobalt jacket. You have the coloring to carry it off on a daily basis.

  14. IT’s funny how when you think of the ADVANCED STYLE WOMEN we tend to think of the VERY FEW OUTRAGEOUS ones!If truth be known that is NOT what he is HIGH-LIGHTING!
    I had an interesting conversation with ARI about that………..
    He also shoots the elegant or plain older woman.
    He is looking for COUPLES at the moment…………..
    Should I put YOUR NAME IN!!!!!!!!!?

    1. @LA CONTESSA, You are right, of course. I think the term, Advanced Style, has gotten so tightly tied to the idea of extreme looks that it’s hard to detach it. My bad.

      Also, thank you for thinking of me but Significant Husband is so private that I only those wedding pictures where he was seen from the back;).

  15. You have just given us the best Christmas present, the kind that takes dayyyys to open and savor – this post must have taken you a very long time to assemble, wrap, tie and send, thank you for all your carefully assembled parts and pieces! You look ravishing in each photo, I hope you’ll decide to revisit style topics in the year ahead, you’re just a natural arbiter of style, we’ve come to rely on you for these things…

    1. @Flo, Aw, you are so kind. Yes, of course I will revisit these topics, see today, but, recreationally. And you, with your extraordinary design sense, I am not an arbiter, just maybe a prolific gabber who is good enough. xoxox.

  16. Thank you for the time you have dedicated to all of your exceptional posts. I appreciate your diligence to the writing craft, as well as your interesting posts. I’ll continue to read your posts. Yours set the bar for the blogging world. Have a Merry, Merry Holiday season! xo

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