Tuesday, May 24, 2011

On the Street….Alessandra, Milan

I saw my friend Alessandra when I was in Milan last week. As you can see, her style has evolved from a sportier gamine aesthetic to a more languid bohemian-femme mood.

What I love about her look here is that even though her dress is a casual cotton dress that could be bought anywhere (and in a wide range of fabrics and prices), she still finishes off the look with very special details.

You know what else I love about this look? I know a lot of girls would throw on a big cotton dress like this and call it done…almost a “fashion day-off.” Alessandra, however, adds a dramatic necklace and a thoughtfully executed hairstyle and it elevates the entire look. The hair in this look is so important. I think the reason the girls I saw in Savannah looked so great, even as casually dressed college kids, was because they all seemed to have great hairstyles.

I think this shot is a great example of clothes as a plain canvas for the fashion in the rest of the look…as roasted chicken is to a complicated French sauce.

On this look, let the Summer games begin!!


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  1. Анна

    May 24, 2011 at 9:32 am

    I love this look! So natural, gentle and chic! Beautiful sandals!

  2. Laura

    May 24, 2011 at 9:35 am

    I totally agree. Blows my mind when I look up teenage hairstyles of 1905.

  3. Anonymous

    May 24, 2011 at 9:35 am

    Lovely in every way but the arm tats. The future will be filled with senior citizens regretting their faddish scarrifications.

    Or maybe I'm just a silly fogey…

  4. Andi Cui

    May 24, 2011 at 9:36 am

    Such a beautiful picture!
    Love the necklace!!!


  5. Beatrice B.

    May 24, 2011 at 9:37 am

    I love her tattoo and the hairdo… so diverse and gorgeous together


  6. Nomadic D.

    May 24, 2011 at 9:38 am

    A roast chicken to a french sauce indeed! Lovely photo, and I agree with you about the additions of the necklace and the thoughtful hairstyle. Also just wanted to say I love these posts where we get to see what goes through your mind when you make your selections, love to read your wordier musings.


  7. Lauren

    May 24, 2011 at 9:43 am

    Love, love, love this dress. And you're right, it is a perfect canvas for building a look. So many possibilities!

    The Styleseer

  8. Anonymous

    May 24, 2011 at 9:52 am

    radical tattoos!!! I'm thinking about her in some 15 years… good enough?

  9. Bohemian Style

    May 24, 2011 at 9:56 am

    So Pretty!! Love the tats with the gold.


  10. caribbelle

    May 24, 2011 at 10:00 am

    the accessories make the outfit. so simple yet elegant.

  11. Anonymous

    May 24, 2011 at 10:01 am

    i usually cringe at tattoos, especially on women, but… wow!

  12. Marta.!

    May 24, 2011 at 10:03 am

    I love her sandals! She looks elegant and really relaxed.
    Sorry for my English, I'm spanish.
    And I'm following you ;)

  13. s

    May 24, 2011 at 10:05 am

    Just…. LOOOOOVE <3

    The shoes and the necklace are perfect ;)


  14. Angela Jessyana

    May 24, 2011 at 10:05 am

    i love her necklace. great photo!


  15. monkeyshines

    May 24, 2011 at 10:11 am

  16. all-in-the-silhouette

    May 24, 2011 at 10:17 am

    Great tribute to summer. Clean and cool, right down to the makeup. Classy, but practical.

  17. Alice Olive

    May 24, 2011 at 10:18 am

    Agree – her attention to detail makes this simple and elegant.

  18. Adinapup

    May 24, 2011 at 10:26 am

    I like this!!

  19. Prisoner of Fashion

    May 24, 2011 at 10:26 am

  20. Anonymous

    May 24, 2011 at 10:27 am

    Yup hair is important in the South, for all races…..

    "Never does a Georgia Peach make even a supermarket run without hair and nails done."

    …….aaaaaand thats why i moved to the northeast :)

  21. Easy and Elegant Life

    May 24, 2011 at 10:39 am

    How nice to see a chic white sandal instead of the flip-flops that are more common in my college town. That helps to elevate a look, too.

  22. comme fraiche

    May 24, 2011 at 10:40 am

    I like the white in her sandals as they mix a little color in with what she's wearing

  23. Maryam Maquillage

    May 24, 2011 at 10:41 am

    her anchor tattoo is so fitting! i don't even like tattoos…


  24. Caddy

    May 24, 2011 at 10:47 am

    I concur! :D Her adding accessories and styling her hair the way she did, elevates her look.

  25. 2heels1flash

    May 24, 2011 at 10:49 am

    The very clean shoes are perfect with the sport dress and the tatoos


    Hope to meet you some day. we share almost all the opinions!!!!!

  26. haka

    May 24, 2011 at 10:53 am

    I love this shot, the shoes are so chic and simple, mixed with the dress and bangle. perfect outfit


    May 24, 2011 at 10:55 am

    this is so sublime!


  28. Sing

    May 24, 2011 at 10:56 am

    Totally agree. Even casual pieces can be amped up with hair and accessories. Her necklace is beautiful.

  29. Anonymous

    May 24, 2011 at 10:58 am

    In my humble opinion, to me, this is what 'fashion' is about. It's taking something that can be fairly simple and making it your own. I feel like most of the looks out there are so pretentious, too thought out, too complicated, too much stuff, too much trying to show the world what you're about and shouting "this is my identity!!", too much complicated outside, no substance inside. Whilst perhaps Alessandra considered the shoes, the accessories, or the hair, it still speaks volumes of simplicity, so if I had a conversation with her, her personality would hopefully shine, rather than her clothes taking over the conversation.

  30. Martha

    May 24, 2011 at 10:58 am

    She's got great tattoos! M X

  31. Liege'

    May 24, 2011 at 11:14 am

    I love everything about this look, especially the necklace!


  32. Miss Top Ten Image

    May 24, 2011 at 11:19 am

    LESS IS MORE. One of my favourites fashion mantras!!


  33. Angel

    May 24, 2011 at 11:27 am

    So Nice, I think the simplicity is so elegant on how she pulls this off.

    Angels Point of View – Street Style Photography

  34. alessandra de leonardis

    May 24, 2011 at 12:14 pm

    during my fashion designer life I always tried to reach the inner beauty…so: let's go simple!!!

  35. proletarian Great Gatsby

    May 24, 2011 at 12:26 pm

    Elegant, natural and personal at the same time…And the most important is the woman you show us,not was she wears.You got it one time more!

  36. SarahV

    May 24, 2011 at 12:37 pm

    She's so chic, kind of bohemian too!


  37. Shervin nassi

    May 24, 2011 at 12:42 pm

    SIMPLE ELEGANCE love is so deep!

  38. givea

    May 24, 2011 at 12:45 pm

    true goddess

  39. dinamita.paquita

    May 24, 2011 at 12:53 pm

    I looove the tattou!!

  40. Elisabethbaysset

    May 24, 2011 at 1:03 pm

    Tranquille , cette belle personne est là , très belle ,
    très Italienne .Un plaisir ! EB

  41. TruetoTrend

    May 24, 2011 at 1:16 pm

    The necklace makes everything work; I love how ancient Greek style sandals are all the rage this summer.

  42. zoom

    May 24, 2011 at 1:22 pm

  43. Anonymous

    May 24, 2011 at 1:28 pm

    the tshirt dress. looks like it might be the thing these warmer seasons. it's too reasonable and such a cheat – getting to look chic and feel like you're in your nightie.

  44. Victoria Regia

    May 24, 2011 at 1:31 pm

    She's very elegant. Love her dress!

  45. Emma

    May 24, 2011 at 1:35 pm

    I love it =)

  46. mon sac by me

    May 24, 2011 at 1:40 pm

    Very Chic tatoo…… !


  47. Aimes

    May 24, 2011 at 1:57 pm

    GORGEOUS!!!!! So simple, casual, elegant.


  48. Anonymous

    May 24, 2011 at 2:05 pm

    nice toes ;)

  49. Marcel Da Chump

    May 24, 2011 at 2:07 pm

    Inspires me to sing "Sophisticated Lady".

  50. briannelee

    May 24, 2011 at 2:08 pm

    LOVE the necklace. Amazing!

  51. balthasar

    May 24, 2011 at 2:19 pm

    absolutely adorable!



  52. BASIIK

    May 24, 2011 at 2:34 pm

    I love this so much, her tattoos also add a really great touch to her style.

    Kate – BASIIK Blog

  53. laurakly

    May 24, 2011 at 2:49 pm

    This is very beautiful!

  54. Marly

    May 24, 2011 at 2:59 pm

    Great look – relaxed, yet chique.

    Also I love it when you write down your thoughts on the look and why you like it.
    Thanks so much, looking at your blog always makes my day.

    Love from Germany.

  55. Evan

    May 24, 2011 at 3:11 pm

  56. hedonista

    May 24, 2011 at 3:13 pm

    I love this.

  57. E...

    May 24, 2011 at 3:43 pm

    Cool shoes and I do love the grey outfit!


  58. Judith Ross

    May 24, 2011 at 3:45 pm

    Hi Scott,
    Thanks so much for your commentary about why this look works. I found it very educational and helpful. And, yes, I agree, the details elevate a plain dress into something special.

  59. That's Not My Age

    May 24, 2011 at 3:45 pm

    I do like simple, easy-to-wear clothes – as Alessandra proves with the right accessories they can look very chic.


    May 24, 2011 at 3:49 pm

    Your reaction to this ensemble is interesting to me. Actually, I had an opposite reaction. Often women think that more is more and so they stack on accessories, when in fact, they detract from a clean and polished look. Though her neckless is beautiful, though here it just looks cluttered. The hair and nail polish were sufficient alone.

  61. songbird

    May 24, 2011 at 3:51 pm

    the neck piece and the hair style absolutely makes the look..i usually go without accesories but i like having a statement piece on even on plain clothes.


  62. Giada

    May 24, 2011 at 3:55 pm

  63. Rachael

    May 24, 2011 at 3:58 pm

    So pretty! Love the casual maxi dress and the beautiful chunky necklace.


  64. Anonymous

    May 24, 2011 at 4:02 pm

    The tatoo is a nice part of the look.

  65. Anonymous

    May 24, 2011 at 4:05 pm

    Love the tattooed tripart band on her lower arm… very striking.

    Speaking of ink: I honestly don't understand why some folks find tattoos off-putting. Could anyone explain his/her negative response? (That's a serious question–I'm genuinely curious.)

  66. Lenita

    May 24, 2011 at 4:14 pm

    great look! I think the tatoos helped a lot

  67. Anonymous

    May 24, 2011 at 4:59 pm

    I agree, and I really love the tattoo- Tattoos can really add a whole other element to an outfit, that no accessory can do! Love the look- And I prefer this much more feminine look too- Less aggressive, more fluid and inviting- Without comprimising herstyle. Bravoooo

  68. The Foolish Aesthete

    May 24, 2011 at 5:17 pm

    Beautiful. Simple doesn't mean boring. That necklace is gorgeous and was the perfect touch.

  69. Meredith Howard

    May 24, 2011 at 5:25 pm

    I love the necklace. Gray and gold seems to be the hot color combination right now.

    - Meredith

  70. Anonymous

    May 24, 2011 at 5:56 pm

    I'm so glad to see Alessandra again! I've been quite taken by her esthetic ever since I discovered her here on The Sartorialist (or was it that Crate and Barrel ad?) I find her evolving look and innovative vision to be inspirational and have a hard time knowing how to find more of it.

    Thanks! for the photo :)

  71. Anonymous

    May 24, 2011 at 6:58 pm

    Gorgeous. The hint of white from the sandals is just so refreshing.

    The Re-Stylist

  72. rose

    May 24, 2011 at 7:27 pm

    loving the tattoes! she wears them so very well…

  73. FashionableAwkward

    May 24, 2011 at 8:00 pm

    This outfit is so perfect. I love her choice in accessories when it comes to the simple dress. I also love your description on what makes this outfit so wonderful.


  74. Violet Cadburry

    May 24, 2011 at 9:05 pm

    So Grecian. Tattoos don't bother me. I have seen some pretty ugly old arms that could use a tat or two if just to connect the age spots into something more attractive.

  75. Maryanne

    May 24, 2011 at 9:56 pm

    the elements of white and silver enhance the steel grey.

  76. ADJ

    May 24, 2011 at 10:10 pm

    She is so graceful and elegant!


  77. nikki kulot

    May 24, 2011 at 10:46 pm

    love her style :) and tattoos :)

    Don't live life on fast forward. Coast Thru Life.

  78. olya chess

    May 24, 2011 at 11:04 pm

    great outfit !! i like it !! stanning!!


  79. yv

    May 24, 2011 at 11:50 pm

    her necklace!

  80. Ambica

    May 25, 2011 at 1:19 am

    how gorgeous is this. effortless chic :D

  81. Anonymous

    May 25, 2011 at 1:24 am

    Please. Where can i find that dress?

  82. Vasilieva

    May 25, 2011 at 2:28 am

  83. dvj

    May 25, 2011 at 2:52 am

    Fabulous casually stylish look! Love this lady's aesthetics… adding a touch of gold (neckpiece and bracelet) to her otherwise grey outfit lends a rich-esque feel. The tattoo, black woven in the bracelet and black polish give a bohemian twist to the look and the white chappals extend the casualness of the dress. the overall look is leant a very clean and 'I know how i like it' effect by the hairdo. just love the melange!


  84. Sasha

    May 25, 2011 at 3:23 am

    this is how i want to look all summer long!

    i love how her simple tattoos are such a strong accessory paired with the geometric shape of her necklace.

  85. Monia

    May 25, 2011 at 4:18 am

    I love the mix, sport + elegant!
    Monia, Rome


  86. IS THIS IT? models review

    May 25, 2011 at 4:19 am

    "a great example of clothes as a plain canvas for the fashion in the rest of the look…as roasted chicken is to a complicated French sauce" – haha absolutely, I totally agree, great point…


  87. †ELMO†

    May 25, 2011 at 4:23 am


  88. Hair Romance

    May 25, 2011 at 4:25 am

    I so agree. Your hair is your best accessory and completes your outfit. It doesn't cost anything to style your hair well either.

  89. Trine

    May 25, 2011 at 5:47 am

    Love the second girls circle-tattoos!!


  90. Anonymous

    May 25, 2011 at 5:48 am

    She has got very beautiful feets.

  91. BeLighter

    May 25, 2011 at 7:15 am

    I couldn't agree more with you!
    It's all about those details; the accessories, including hair!!!
    It does make a huge difference, when the clothes you're wearing are this "plain"

    Great post!

  92. fashionxxi

    May 25, 2011 at 7:41 am

    Nice outfit!

  93. Misha

    May 25, 2011 at 8:23 am

    the pose, the tattoo, the clothes, the hair, reminded me of Rosie of "We can do it!" . Indeed she can :-)

  94. Queen of Hearts

    May 25, 2011 at 8:26 am

    She looks very "ancient Roman" to me (the necklace, the hairdo, even the sandals…).
    I love this look, for its simplicity yet for its thoughtfulness as well.

  95. Anonymous

    May 25, 2011 at 8:54 am

    Lovely look and though i am not a fan of tattoos these do add stylish enhancements. If she were standing and her head turned to a profile shot she would look as if she stepped out of ancient Egyptian pyramid.

    To the commenter on why some folks don't like tattoos.
    1.) They are permanent . 2.) older generations associate them with tough, anti social pose, and less elegant- I realize it is a hip look like long hair on guys in the sixties 3.) They don't look good as the body ages-one needs to be more attentive to appearance as the years go by. 4.) Older folks associate tats with men, who often sheepishly said they were young and drunk when they thought tattoos were a good idea.
    Yet if that makes one feel good about themselves and they can enjoy the ink as they grow old, certainly enjoy them.

  96. Kera

    May 25, 2011 at 10:17 am

    simply lovely.

  97. Anonymous

    May 25, 2011 at 11:34 am

    reminds me of Carla Sozzani.. !!!!

  98. Anonymous

    May 25, 2011 at 12:03 pm

    Who makes that dress and sandals? Does anyone know?

  99. Anonymous

    May 25, 2011 at 12:09 pm

    I too love the hair, but there is no style to it so I'm confused. It's just pulled back – which I love, but to emphasize that it's a "style" is silly. Plus you can't really see what it is because she has her hands wrapped around the ponytail?

    I think American women overdue their hair way too much by straightening etc. I love the French and Italian style which is no style at all even if your dressed up. Just let it do what's it's going to do and concentrate on your clothes. Very sexy.

    Love the sandals and dress. Not crazy about the necklace and dislike the tattoos very much.

  100. Kacie

    May 25, 2011 at 12:52 pm

    Total casual elegance. You're so right about the hair. I'm going to start doing mine daily. Even though I have a newborn I can still refine my look and be comfortable!!!


  101. Lisa :*

    May 25, 2011 at 1:01 pm

    Beautiful dress ! :)


  102. Anonymous

    May 25, 2011 at 2:59 pm

    @ Anonymous 8:54–thanks for your response (and for your respectful approach to those who think differently).

  103. Anonymous

    May 26, 2011 at 12:34 am

    Your friend is a work of art; I long to know her thoughts. Fluidly elegant from head to toes! The neckline garnishment, however, appears to armor her appearance.

  104. Midge

    May 26, 2011 at 6:20 am

    Mmm simple, comfy and mega-jewelry. Perfect outfit for a casual day.

  105. Anonymous

    May 26, 2011 at 6:37 am

    Just perfection !!!

  106. Bernadette

    May 26, 2011 at 8:35 am

    Your friend Alessandra combines the contemporary with elements that could have jumped straight out of the Iliad (hairdo/jewellery); the result is edgy and timeless. Innate style. Just Gorgeous.


  107. Ms Wanda

    May 26, 2011 at 9:45 am

    Yes, totally agree, Love it!

  108. libelulaseneldesierto

    May 26, 2011 at 4:52 pm

    Is one of the best looks I have ever seen. It's really simple, sport… but IT'S AMAZING!!!

  109. ADDENDUM handmade

    May 26, 2011 at 6:42 pm

    So classy! Now I want a dress like that…

  110. Kali

    May 26, 2011 at 10:40 pm

    Her hair looks so different! How did it grow so much in under two months?! I was so inspired by her gamine look, this is a bit of a surprise. I wouldn't have associated the two identities if I hadn't done a search for your other posts about her.

    I like that the graphic pattern of the dark nail polish seems to camouflage in plain sight. I love the hard dark lines against such a soft, organic look.

    @ Anonymous 12:09 There are a lot of subtleties that make this a style. I agree with you that American women too often forget that "styled" doesn't always mean that the natural texture is done away with.

  111. Lady Maphet

    May 26, 2011 at 11:24 pm

    Great (and insightful) commentary!

  112. caroline

    May 27, 2011 at 9:00 am

    J'adore la reference culinaire sur la fin!! Bravo! :)

  113. psh

    May 27, 2011 at 10:23 am

    great, great…

  114. Fairy Ondine

    May 27, 2011 at 10:35 am

    Attractive.. I'd call it The MODERN Ancient Greek lOOk.. Alessandra has character, I can tell from the tattoo, hair, glans.. she is in a gladiator's woman shoes !!

  115. FePa Design

    May 27, 2011 at 8:09 pm

    amazing dress!!!! LOVE IT!!! is just simply an elegant… wowww~~~


  116. amanda

    May 27, 2011 at 11:24 pm

    love her styling. very greek goddess-y imho, dig the tattoos too.

  117. zoe bowie

    May 28, 2011 at 1:48 pm

    This image is inspiring to me– a striking juxtaposition of 1930s Dadaist avant-garde minimalism and flourishes of Egyptian / ancient Greek mysticism…. Shall we call it Neoclassical?

    Incidnetally, I found similar sandals on JCrew.com, Astria suede sandals in beechwood. $98

    Now where do we find such a dress?

  118. Zornitsa

    May 28, 2011 at 3:10 pm

    I just love her tatoos!


  119. lushgazine

    May 29, 2011 at 12:05 pm

    loving the simple dress and chunky accessories!

  120. Anonymous

    May 29, 2011 at 8:50 pm

    It is really nice to hear your opinion on the photograph! I always notice little things but to hear from the photographer themselves is different.

  121. The Styley

    May 30, 2011 at 12:39 am

    You've captured a lovely moment here. And I really enjoy your meditations on how various outfits are put together–during the most recent fashion week you wrote something about how to be inspired by runway looks when one can't afford them, and how to incorporate what they have to say into any wardrobe, no matter what the budget. Great food for thought.

  122. Hannah

    May 31, 2011 at 5:24 am

    Loving the simplicity of the dress coupled with the accessories!

  123. Bernd

    June 1, 2011 at 6:45 am

    What a great shot, so unique and the dress looks so simple and comfy. Great work


  124. Wang's Factory

    June 1, 2011 at 8:38 am

    Her tattoos are very eye catching


  125. il fait du soleil

    June 1, 2011 at 5:22 pm

    it's all perfect.. necklace/tatts/shoes/hair… great outfit… def not 'fashion day off'! xx


  126. Mertxe Hernàndez

    June 2, 2011 at 5:31 am

    She is very natural,, like it! very fashion and simple at the same time…!!! love love love fashionn…!!!


  127. Anonymous

    June 2, 2011 at 6:39 pm

    stunning…what beautiful tattoos.

  128. carlotta robotta

    June 3, 2011 at 6:57 am

    What a perfect combination! Love that necklace. x

  129. Anonymous

    June 6, 2011 at 12:23 pm

    Necklace is from COS a few seasons back….

  130. Hanna

    June 22, 2011 at 4:43 pm

    Beautiful,i also love the sandals. Do you know where are they from? Just looking for sandals like this. Would be very kind of you to give me an answer!

    Love, Hanna

    [email protected]

  131. Emily

    August 20, 2011 at 8:26 pm

    I have a huge crush on her.

  132. run3

    June 20, 2017 at 9:21 pm

    wow. awesome. Alessandra Milan.

  133. New Type

    April 16, 2018 at 1:11 am

    I love this look! So natural, gentle and chic! Beautiful sandals and neclace!

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