When You Get Your Outfit Wrong, And You Don’t Care


This jacket doesn’t work with this dress. I didn’t much care, last Tuesday.

What with the travel surrounding Mom’s surgery, my September 30th birthday didn’t get celebrated until October 9th. So Significant Husband took me to Boulevard, one of San Francisco’s stalwart delicious, fancy-but-unpretentious places to eat.

I had thought to wear my Dries van Noten shift with the biker jacket, but I  left that dress down at my house, so put on this 2010 Prada instead. I expect I will be alternating these two for the next decade of dinners out. I had also imagined higher heels, but my foot issues put their, well, foot down.

Why doesn’t the outfit work?  Because the dress depends on a tightly fitted bodice which the jacket disguises, awkwardly. Saved from disaster, however, by the quality of the Prada fabric. The weight, the drape, the flow nudged inept in the direction of insouciance. Almost as though I were the sort of woman who frequented Milan in proper Italian frocks but threw on her biker jacket to ride a Vespa rebelliously to Sicily.

But not quite. Also it might be hard to ride a Vespa to Sicily and Sturdy Gals would surely check Google maps before the attempt.

The light that evening, on the other hand, was perfect. We arrived a little early, and walked over to the promenade that fronts the bay to wait. The sun full on the other side of the bridge.


The jacket still didn’t work. But a grin, quality materials, and good lighting compensate for all kinds of mistakes.


AllSaints biker jacket
Prada full-skirted dress
Beautifeel captoe pumps
Old Coach bucket bag from the back of my closet

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  • There is beauty in imperfection!
    You look fab!

  • Actually I think the combo is wonderful and totally ‘works’! Fab. Happy birthday :)

  • Works for me! I mean, I see your point, and I’m sure the dress is even better appreciated with the bodice visible, but I love the unfussiness combined with verve. Or something. I can easily imagine you strapping on your helmet. . . or would you even bother? perhaps just scarf that hair back out of your eyes. . .

    7:30 pm
    Lisa said...

    Gotta wear a helmet in SF. I’ve ridden on the back of my brother’s scooter, if you can believe it. But thanks, I do think it was the unfussiness that appealed me.

  • Well, if had not told me all the reasons why the jacket does not work, I would have thought: different, but not bad. :)

    Happy belated birthday!

  • I love the outfit and disagree with your assessment that it doesn’t work. I think it makes you look like a very well dressed badass, which is a delightful combination.

    7:31 pm
    Lisa said...

    Oh if I could be anything in this world, a well dressed badass might be the thing.

    9:11 am
    materfamilias said...

    I was once called a well-dressed dictionary — I tip my hat (from the uncool sidelines) at the well-dressed badass, so much cooler a designation. #seriousenvy

  • Happy Birthday. You look beautiful. Isn’t the October light in San Francisco extraordinary? I had breakfast at the renovated Boulette’s at the Ferry Building on a recent gorgeous autumn morning. These are soul-lifting days.

    Boulevard is wonderful. I particularly like the counter at lunch time, with a cocktail in hand. (I’ve never felt the proscription against drinks before six was a sensible one.)

  • I think the outfit works. But, I suspect it doesn’t quite portray the image you wanted that evening. I have those Beautifeel pumps. I’m on my second pair, having worn the first ones beyond repair.

  • Happy belated birthday. I think the outfit works fine and that you look great in it. The heels are a perfect height. If you hadn’t said why you didn’t like this jacket with your dress, no one would have been the wiser.

    In an ideal world, one where your closet magically contained precisely the right item for every occasion, what outerwear would you have paired with the dress?

    7:33 pm
    Lisa said...

    A very light, very simple coat. With no ornamentation. Thank you:).

  • And don’t you adore the Audiffred Building? What a treasure. I’m glad it was renovated and saved to hold Boulevard on its first floor. My lawyer, who was also the author of the book Paper Chase, had his office there for a time.

    7:34 pm
    Lisa said...

    Yes, it’s a real San Francisco landmark, from the days Herb Caen always wrote about.

  • I agree with all of the above – I think it works just fine, and you look great.

  • I think the jacket fits wonderfully with the dress. On the other hand a slightly shorter jacket would have been ideal, but not a must. Another alternative would have been a super size shawl in a delightlly beautiful cream shade – adds light to an already dark ensemble.

    7:35 pm
    Lisa said...

    I agree, a shorter, more fitted jacket, would also have worked well. Or a shawl, yes.

  • Love it! The combo intrigues. The photos are flattering, taken, as they are, with you posed at an angle. Perhaps you felt that from straight on, the moto jacket over the full skirt created an undesirable columnar line? A potential solution (barring significant wind or chill): wear the moto draped over your shoulders, which would allow your fitted bodice and waist some visibility. The “cape” idea would work as long as you weren’t carrying an over-the-shoulder purse. A smaller purse with a pop of color might raise the bar a bit without detracting from the outfit’s delightful insouciance.

    7:35 pm
    Lisa said...

    Of course! Over the shoulders would have been the thing. We needed you to come and give the advanced course:).

  • I was just about to issue a travel advisory re rebellious Vespa journeys to Sicily but anyway you certainly look more than presentable and that looks like the perfect outfit & night for that stroll along the promenade. Happy belated b-day; we are fellow Librans-one week apart.

    7:36 pm
    Lisa said...

    Why thank you. And happy birthday to you too.

  • I think this outfit is perfect and perfectly you. Your smile is the best accessory! Happy Belated Birthday!

  • It may not work completely, but I think the smile on your face makes the whole outfit come together. Your hair is the perfect accessory to the whole outfit. love

    On the other hand, I find myself wanting a biker jacket (that’s your influence).

  • Happy birthday! I think the outfit works because you look so happy and comfortable.

  • i disagree – the dress looks gorgeous with your leather jacket! you look confident and stylish :D such a prefect fall layering look.

  • Dear Lisa, You look fabulous and a very Happy Birthday! I do believe it works and you probably took your jacket off during dinner.

    I have the very same Coach Vintage bag and it is still like new!

    2013 Designers Series

  • Actually, I think it looks pretty good. And vintage Coach elevates every outfit.

  • First, a Happy Birthday to you ( though coming late ).
    The dress looks so good, that I didn´t even notice your jacket.
    A big shawl could have been an easy alternative, but then I don´t know what temperatures you are having on the evenings.

  • Lovely pics, you look beautiful and have the aura of walking on air.

    7:36 pm
    Lisa said...

    Some nights are like that, right?

  • You have never looked so beautiful. I could care less if the jacket works or not it’s the happiness in your face that glows above all!

    6:08 pm
    Candace said...

    I agree completely with Sandra! My eyes went immediately to your beautiful smile, the look of joy on your face and your hair blowing in the breeze. Relaxed, glowing and happy!

  • Please thank Significant Husband for letting us see that grin.

  • I actually like the jacket with the dress.

  • I thought you looked great! But then again you always do! This outfit has a nonchalantness (is that even a word?) that I think really works.
    Me on the other hand…I am barely capable of dressing myself in an appropriate manner when I go out into public. I am surprised Stacy and Clinton haven’t accosted me yet.

    7:38 pm
    Lisa said...

    They are retiring, you know that? What will we do without them.

  • Happy Birthday!

  • The smile on your face would make any outfit work. Happy belated birthday.

  • I wish I wore the outfits I got “right” half as well as you wear those you get “wrong.”

    I think it all works quite well, and you are gorgeous as usual.

  • Darling Lady, I think you are wrong! This may be one of your best ensembles – creative, casual and elegant. It says “I’m chic, it comes naturally and I don’t have to try to be so”. Love it!

    I hope your Mother is doing better and recovering well.

  • p.s. Happy Birthday!

    7:38 pm
    Lisa said...

    Thank you!

  • I do this all the time if it’s any consolation. Right combo of elements, but the silhouette is just slightly off. I think you are totally right that a cropped leather jacket would have been perfect. What you ended up with is far from bad, but it doesn’t quite have the look I know you were after. It happens to the best of us.

  • I understand that the jacket doesn’t quite work with the dress in the ways you write, but to me just owning and wearing a jacket like that brings anything into conformance with it! You look authentic and not try-hard or costumed. Your hair and smile are so pretty, and a wonderful lesson or example in your sharing this is the LIFE in you, compared perhaps to others of us who in such standards of fussiness might have been inhibited from going out in something not just “right”.

  • Yes, agree with your assessment wholeheartedly! You do look great but the proportions are a bit off and the beauty of that narrow bodice wants to be outed. Quality fabrics do save the day. Along with your lovely smile! So enjoying your blog and your high intelligence. Thank you.

    7:39 pm
    Lisa said...

    Very nice to meet you. Welcome. I wish I could pin a fabric swatch to the blog page here:).

  • Belated Happy Birthday,I like the combination you look chic…..if that is your idea of getting your outfit wrong you have not seen our rural outposts!!

  • Belated Happy Birthday Lisa! I hope you treated yourself to your birth year necklace.Your outfit looks great to me.

    7:40 pm
    Lisa said...

    Not yet. I’m getting ready to.

  • I discovered your blog a few months ago and JUST LOVE IT!
    Thank you for inspiring me, confirming that style is ageless and a great attitude can carry the day as long as you have a smile…no matter what you’ve got on! Even more cudos for those of us who choose to look our best as Mother Nature gently eases us forward.

    7:40 pm
    Lisa said...

    Welcome! The comments, BTW, are always the best part of my posts:).

  • You look fabulous – whatever you’re wearing!

  • Happy birthday! We share it, by the way, and I find it so nice because I really like your blog, I like the way you write – aaand I like your style a lot as it seems to be the same as mine. I count this as serendipity.

    7:41 pm
    Lisa said...

    Happy birthday! Stars align!

  • Sometimes a jacket is more functional than stylish. Not that the style is completely disregarded, of course, but when the choice is a match that’s less than ideal, or freezing arms? I’ll take the jacket any day

    7:41 pm
    Lisa said...

    Hahahahaha. True. Goosebumps are not, as m=y mother would, say, very attractive.

  • Oh, p.s. You look nice here. All the rest is quibbles. Wishing speedy recovery to your mother.

  • If only you had your Harley, then it would all work just fine.
    Good health to your Mother.

    7:42 pm
    Lisa said...

    You’re right. What was I thinking;). Mom is doing very well, by the way, surprising us all. Thanks.

  • It looks OK in the photos. Didn’t you have a cartigan sweater with it originally?

    7:43 pm
    Lisa said...

    Yes, but it’s beige/peanut colored and didn’t suit my mood. I felt more saucy than beige.

  • I don’t see what is not right about this looks at all…
    it looks great IMO.
    Happy Belated Birthday Lisa!
    Hope your mom is doing well.

  • Happy Birthday! Your smile says it all. And yes, great light is a blessing. I’m glad you showed us this outfit even if you did not see it as ideal.

  • Fab outfit! Happy Birthday a little late! And I had no idea your hair was so long — it’s beautiful.

  • Love the dress. And adore the riding boots from the previous post. Hope you are doing well, my friend!

  • I love Coach, but I think that a smaller, envelope style purse would have worked better. I don’t like to add any bulk with fuller skirts. Wish the photo of the jacket made it easier to appreciate. Hope you had a nice piece of birthday cake :)

    7:44 pm
    Lisa said...

    You can see more photos of the jacket in the post I linked to. Maybe I will do a post solely on the jacket, for those who want moto-spiration.

  • I think you look fabulous! Had an occasion lunch at the French Laundry a week ago and wore something similar; swingy, gored skirt, knit shell, large pearl necklace, and black biker jacket. I just love, love, love the opposition inherent in the combo of girly dress and masculine biker jacket and it is kind of a new go-to for me. Happy belated birthday, by the way!

  • You look great – effortless. Beauty in slight imperfection.

  • It’s the shoes. They seem to be shrinking away from the jacket like middle-aged ladies on the bus trying to sit farther away from the guys with tattoos.

  • Happy Birthday! You look so blissfully happy and beautiful!

  • i’m a new reader and enjoying your blog very much!

    now i’m curious. what topper did you wish you’d worn with that dress for that occasion? i’d love to know how you’d have perfected the look.

    your comment about your bad feet struck a chord with me. i have that issue also. so many pretty shoes avoided!

  • the reason why it works for me is because of your commitment to the leather jacket. it’s you and b/c of that the outfit is perfect. to me that’s what constitutes style. x

  • I like the sweet/tough combination. Don’t fret about the heel height either.

    I had a wonderful dinner at the bar of Boulevard some years ago. I like to strike out on my own at meetings and have a meal at a good bar. Met some interesting folks, nice bistro food. Happy Belated!

  • Haha! The comments are the greatest, aren’t they?
    Good health to Mom, Happy Birthday to you … and must agree… it’s the shoes!
    Business shoes with playful outfit, street brawl ensues.
    Sneakers Woman! Black&white Converse or Keens, et voila. http://www.6pm.com/keen-arcata-black

  • Sometimes, each garment sings but they do not sing in unison together. And I would have happily listened to exactly this very personal ensemble.

  • Happy birthday! I always like it when my birthday celebration is delayed because it’s like having a birthday week.

  • there’s a cat in my lap, but not with a hat, and she is hindering my typing ability…

    happiest of birthdays to you, you beautiful woman you.

    and i think you look smashing.

    xo jane

  • Hello Lisa,
    I smiled when I saw your title… too harsh… you look gorgeous and the combination is great… I do like Rosie’s comment …and maybe that is the answer … but sometimes our feet have to be comfortable!

    I have this dress and have always struggled with what to wear over the top… I usually end up with a long, trench coat style…


  • Sometimes it’s the “I don’t care” part that brings the whole get-up together.

  • Like so many others, the things that I see first is the peace and joy and quiet elation on your face. And frankly, I think it works fine!

  • You look greatly comfortable and beautiful (the newly-wed glow). I like each piece of your outfit by itself. I think the dress goes well with the biker jacket that make you young and lively. Personally though, I would choose a classic ballet flat (you know the Chanel style) than the cape-toe pumps to go with the biker jacket.

  • Oh, Lisa! Happy Birthday! Wishing you good health, peace, joy and continued bliss! I’m with the Princess on this one: the joy on your face is the most beautiful aspect of this photograph. It transforms any imperfections you have dreamed up about this outfit. You have traded in the East Coast version of the navy blazer for the leather jacket quite admirably, I could not even dream of doing such a thing! 1/ I could not afford a great leather jacket so I would not dare a cheap one, 2/ in Florida, a leather jacket, in black, no less, would be beastly hot (saved by the tropics yet again!) and 3/ I’m not tall enough to pull off a below the knee skirt with same without resembling a troll. I opine you look smashing! I see where you would prefer the long line of the shift to lengthen the leg and balance the jacket. But, oh, well! Seated, none of that matters, does it? I am constantly amazed at the courage of the over 50 women bloggers (“Style Crone”, “Une Femme D’Un Certain Age”) to put their fashion foibles on display. You all are a hardy, gutsy lot!

  • Are you fishing for compliments?…You look gorgeous in that outfit.

  • In retrospect, IMHO, an application of one of the new Autumn/Winter Bordeaux lip colors would have delivered a bit of Zing! to your ensemble. With the notable exception of your wedding day, I don’t often notice make-up as part and parcel of your dressing. Is that part of your personal credo? With your wise choice to keep your hair healthy by not resorting to dye to cover the grey, some cheek & lip color might be something you wish to experiment with. The lipstick can always be applied to the apple of the cheek with a wee bit of water-based moisturizer to it spread using your ring and middle fingers to keep pressure light should you not want to invest in blusher but be assured of a match. I employ this trick to keep inventory down in my cosmetics case with very good results.

  • You look great. The jacket looks terrific with the dress for this occasion. Lipstick would be good.

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