Pippa Middleton wears Self Portrait for Wimbledon Day 3: cute or tragic?

2017 Wimbledon Championships

I was really looking forward to my day off on the Fourth of July because Wimbledon had scheduled Roger Federer and Novak Djokovic’s first round matches and I was prepared to tuck in for a long day of tennis-watching. Unfortunately for everybody involved, both Federer and Djokovic’s first-round opponents retired less than an hour into their matches. It really killed my holiday and I can only imagine how aggravated the fans were, especially if they paid big money for a Center Court ticket. I was also surprised that none of the Middletons came out for Federer’s first-round match. Federer is apparently close to the Middleton family, because Carole is in love with him and Pippa invited him to her wedding (and he came!). I’m sure the Middletons will show up later in the tournament for Fed though.

Meanwhile, Andy Murray is playing today (he’s up against Dustin Brown), and Pippa and James Middleton went to his second-round Center Court match. These are photos of Pippa and James outside of the All-England Club. This her brother James, to be clear. Lord knows where her husband, the honorable Terribly Moderately Wealthy James Matthews is today. Perhaps he’s working. Perhaps he too is waiting until further into the tournament to make an appearance. Pippa and James were invited to sit in the Royal Box, by the way. When they sat in the Royal Box in 2015, the Daily Mail went on a tear about how the Middletons are pushy, useless and Kardashian-esque. That critique still holds up.

As for Pippa’s dress… it’s by Self-Portrait and I’m sure it costs a lot. Unlike Kate, Pippa doesn’t have to pretend that she buys her clothes for full-price though, so I’m sure this dress (like most of Pippa’s honeymoon looks) were given to her for free because she’s a “celebrity.” Anyway, this dress is seriously fug.

Last thing: please go to the Daily Mail for a moment to check out how Pippa and James rolled up to the All-England Club. They came in what appeared to be a fortified TANK. It’s actually a bright green Land Rover Defender. Because they don’t want attention.

2017 Wimbledon Championships

2017 Wimbledon Championships

Photos courtesy of WENN.

You can follow any responses to this entry through the RSS 2.0 feed.

88 Responses to “Pippa Middleton wears Self Portrait for Wimbledon Day 3: cute or tragic?”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. Clare says:

    Wow, these sisters have a knack for taking otherwise lovely dresses, and making them look terrible.

    It’s like the Middleton super power is to make everything drab and ill fitting.

    • Jennifer says:

      Droopy boobies alert

      • Cherry says:

        See-through-showing off-hoo-ha-alert.

      • NotSoSocialButterfly says:

        That’s why she is smiling so hard behind the shades. Another Middleton in an ugly doily dress flashing the public. Whoop-ti-do.

      • TomatoGirl says:

        I wonder what is the custom among British married couples regarding finances – do they open a joint account? For just because Pippa married a wealthy guy doesn’t mean that she herself has that kind of money. I don’t think she made much from her failed book and article (whatever happened to her offer to host at NBC?) and she hasn’t worn outrageously expensive stuff before marriage. Maybe she makes profit off her share in the Party Pieces business? She doesn’t work and Does he just give he the card and tell her to spend it? Do married people in Britain have one credit card after marriage?

      • Chrissy says:

        I don’t think that Pippa would marry a somewhat rich man if she didn’t have access to his money. It would go against everything Carole taught them in her Gold-digging 101 class.

      • Clare says:

        @TomatoGirl Idon’t know if there is a ‘tradition’ between British couples. My husband (British) and I (American) have a joint bank account, and also had one before we got married. We basically are disorganised academics and have no ‘system’ as to who deposits money in the account…basically when it starts to get low, one of us transfers some money in. We have friends who have completely separate finances, and friends whose paychecks go directly into their joint accounts…
        I think it just depends from couple to couple? With these two, I’d imagine she has access to some of his money, at least? Shrug.

      • Grumpier than thou says:

        @tomatogirl I’m sure there is no real ‘tradition’ these days as to how us brits deal with their finances post or pre marriage. I have friends who set up joint accounts etc as soon as they move together and know others who never merge. I personally recently got a joint account after five years of marriage and a child. For me it felt like a huge deal to do so -and so it had to be on a very limited basis! Haha

      • What could be more flattering than a dusty rose doily with a Peter Pan collar?

    • Merritt says:

      This particular dress was never going to look lovely.

      • WeAreAllMadeofStars says:

        It would if she were in a revue based on Sister Wives. If the material were a lighter weight and the capelet were burned, it would probably be a nice dress. I still find it hilarious that people get that dressed up to go to a tennis match. Heels are for the office, people.

      • thecookingpan says:

        Couldn’t have said it better😂

    • vava says:

      awful dress. What a strange hairstyle.

    • Pineapple says:

      Someone mentioned she was overdressed for the wedding too – was it really such low-key wedding?

      On another note: I wonder how Pips manages to get invited to her friends’ wedding these days? Most of them are private citizens and I wouldn’t want paps lurking and disturbing my day. It would be so unpleasant!

      • SoulSPA says:

        Giggle. Do you think she has her PR or some insider friend with the press informing the paps on photo opportunities for stories? With Pips at social events because she hasn’t shown much since bagging her hubs.

        I don’t think that Pips is followed all the time: someone must inform the press on her participation at public events. Or maybe businesses send press releases on her participation to “raise” their image.

        She is not an important person even though she think she is. And what can be talked about her? Lack of style in clothes, hair, make up, work? Oh she is a socialite. That is a full-time occupation.

    • What's Inside says:

      Dress is tragic. Forget the lace doilies and get something that has a great cut.

  2. Goats on the Roof says:

    I think some Self Portrait dresses look cute, but this isn’t one of them. Tragic.

    • Megan says:

      It looks like a giant doily.

    • Olenna says:

      Agree. It’s lacking femininity and is just too old fashioned to be considered retro. She could pop an Amish bonnet on her head and it wouldn’t look more out of date and unattractive than it does now.

      • BeamMeUpScottie says:

        @Oleanna, LOL ! Perfect description.
        I can just see her face under the bonnet! Lord help me!!! DWL

    • MacScore says:

      It reminds me, immediately and 100%, of all of the lovingly made, crocheted-by-hand, anti-macassars that my female forebears carefully crafted (to hang over the back of the wing chairs or armchairs so that their beloved husband’s Victorian hair oil wouldn’t ruin the fabric of the chair back). So, I suppose we can credit her – perhaps? – with some very astute/ironic referencing to British handicrafts? Can we?
      Is it attractive? No. Should we applaud a return to the crocheting trend? No, we should not.

  3. Cleo says:

    Because I’m a sucker for lace and I really like the color, I would wear it really hard if the sleeves were taken off.

    • L84Tea says:

      I agree. Remove the collar and the net-cape-thing–while it would still be a doily, it would be an okay looking summer dress.

  4. slowsnow says:

    It’s a fun dress. I could see Kiki Dunst wearing it.

    Unfortunately, Pippa does not have the it factor to carry it off. Those shoes and clutch are wrong for it. It needed a good sandal. Also not a good dress for her skin tone, it either needs someone darker or lighter imo. The hair is a mess.

  5. Digital Unicorn (aka Betti) says:

    This is a bad look but she’s like her sister, can’t wear clothes for sh!t.

    Wonder when we’ll see Ma and Pa there – no doubt mugging in the royal box. That whole family are fame hungry grifters.

    • SoulSPA says:

      Andy’s match is coming up, so I will check out if any of the Middletons’ court shows up on the Centre Court. But most importantly let’s hope for another great match after the victories of Johanna and Heather today.

      Love delicate lace dresses and that particular design is not my cup of tea. Pips lacks style and composure and has more access to money than sense.

      *edit*: looking forward to seeing Kim’s gorgeous mane. I find her hair is always impeccable. Pips should take a leaf out of Kim’s book and visit the hairdresser’s before appearing at high-profile events.

  6. TomatoGirl says:

    I think she now believes she is a star and trend setter :) )))

  7. dodgy says:

    The collar and the heavy black band at the waist spoil the look, actually. Self portrait’s stuff is pretty cute, and works if you’re trim and under a size 10. I’m gobsmacked that Pippa couldn’t carry this look off at all.

    • paddingtonjr says:

      +1000. It looks like three different dresses sewn together.She *might* have looked better if the dress was all one (different) color and was lined and she wore a fun shoe with a lower heel. As it is, WTF???

  8. OSTONE says:

    Oh boy arriving in that car. I have second hand embarrassment for them. The dress had potential but failed miserably and all I want is for Boomf Middleton to shave.

  9. Sage says:

    What an ugly dress. But she loves attention so I can see why she chose to wear it.

  10. MinnFinn says:

    I normally dislike lace dresses in part because the lace patterns are all so similar and cheap-looking polyester. But I like this one for the interesting pattern along with a 2nd pattern in the capey thing that forms the sleeves.

  11. HK9 says:

    London is one of the best places in the world to shop. You actually have to go out of your way to look bad. I have no idea why this look is so tragic but alas, here she is.

    • SoulSPA says:

      HK9, I think that in case she improved her style she would think she’d acknowledged the public’s criticism. Or, that marriage gave her access to more funds so she would afford better style. But still no hope. I think that, as a comment on the thread said, she’s a legend in her own mind. Also please add “accomplished” before the following: cook, event planner, charity promoter, runner, model, cyclist, skier, as a member of a self-made family (cough cough, where is Gary?).

    • L84Tea says:

      Years and years ago one of my sisters went on a school-related trip to London, Madrid, and Paris. She said of all the places, London had the best clothes. Your comment triggered that memory!

  12. justcrimmles says:

    The sleeves… Were they made out of that plastic mesh stuff you can line your cabinets with? Also, I am out of the fashion loop, because seeing Self Portrait, I thought she’d worn a shirt with her own face on it 😂

    • frisbee says:

      Yes and me, I thought that too and was about to launch a blistering post on rampant narcissism, I was quite disappointed that it was only lace and that she looks a lot like Maria Von Trapp in it.

    • Indiana Joanna says:

      I thought the same thing! Pips in a t-shirt with a photo of her her faux coy side glance and giddy grin.

      The Midds remind me so much of the Trumps. It’s all about leveraging their deluded self importance. Their “job” is to tell the world how special they are.

      Neither Kate nor Pippa look elegant in anything. Always an awkward edge about how they dress. Meghan in contrast mostly looks effortless and elegant no matter what she wears.

    • Indiana Joanna says:

      I thought the same thing! Pips in a t shirt with her own giddy grin.

      The Midds remind me so much of the Trumps. It’s all about leveraging their deluded self importance. Their “job” is to tell the world how special they are.

      Pips head looks really out of proportion in this dress. It overwhelms her. But she and Kate never look relaxed in anything. A couple of paper dolls in perpetual search for attention. In contrast, Meghan looks put together and elegant.

    • Janetdr says:

      Me too! And ditto on the shelf liner-haha. What a hideous dress and on top of the special ugliness of it, you can see through it…too awful.

    • Elaine says:

      #PippaTip: If you can only find a Moderately Wealthy Giraffe to marry, and need to save money, wear a dress made out of shelf liner. Look fashion fresh all day, line shelves all night.

    • JUstBitchy says:

      ITA, shirt with her face on it. I don’t know fashion but I know that this is wrong

  13. Sharon Lea says:

    There is a woman sitting behind her (see DM) in a way better, classy dress in this style in cream. Poor Pippa, having someone upstage you in the seats can’t help.

    • SoulSPA says:

      Pips will “win” over everyone with her wide grin and display of “keen interest”. Just like her sister.

  14. Tan says:

    The top portion of the dress is cute
    Beautiful even and the cheery summer color

    The lacey weird bottom portion, which could have been a plain material , ruins the dress

    Too much of everything ruins it all

    When will the designers learn it?

  15. Alisha says:

    When I first read that headline I thought “self portrait” meant she was wearing something with her own face on it, so I’m slightly disappointed.

  16. Natalie S says:

    I didn’t like the green dress Pippa just wore to a wedding but the color was flattering and the fit was beautiful on her. Quite often the fit of her clothes gives Pippa a frumpy, stumpy look but she looked elegant and beautiful in that green dress. (I’m choosing to ignore her choice of headwear)

    And now here we are back to this; the Lena Dunham route to attention except I’m pretty sure Pippa thinks she’s rocking that dress. Pippa isn’t tall enough for some her choices in clothes.

  17. BlondieR says:

    Clearly, I know nothing about fashion as I expected to see a picture of Pippa in a t-shirt with her face on it.

    • SoulSPA says:

      You were ahead of me, BlondieR. I hadn’t properly grasped what SP was. I had to google it. Still not sure whether it’s a brand or an e-boutique.

  18. Connell says:

    I think this is a beautiful dress, which would look better on a 5′ 10′ model. She is overdressed again, just like she was for the wedding in Ireland this past weekend. Pippa does not understand the concept of understatement. It’s so funny to me, how important Pippa thinks she is.

  19. Maria says:

    That top part looks like one of these night jackets women used to wear over their nightgowns. Bottom is okay, but a pink lining would have been better, also more casual shoes.

    • detritus says:

      If they removed the capelet and weird collar, this actually would be fine
      Especially if it was on someone else.

  20. Summer says:

    When I read Self Portrait, I thought you meant like an actual t-shirt with a Self Potrait of herself on it. Lol I really like this outfit. Then again its obvious that i know nothing about fashion.

  21. PettyRiperton says:

    This chick steps out with looking like my grandma’s table cloth.

    • sophietta says:

      She looks like a child’s doll in that outfit. Massive miss! I really don’t get the Middleton offspring. Their mother always looks top notch…didn’t any of that rub off…think I just answered my own question.

    • sophietta says:

      She looks like a child’s doll in that outfit. Massive miss! I really don’t get the Middleton offspring. Their mother always looks top notch…didn’t any of that rub off…think I just answered my own question. Oops, think the poster above got it spot on!

    • Joannie says:


    • misery chick says:

      @ YOUR MOM-You ARE my mom!!!! My grandma made this actual frock for her toilet roll, except the pinks were more subtle, not so bright and garish! It sat proudly on the back of the loo!

      Thanks for a great belly laugh at Pips expense, and a sweet memory of my grandma 👵

  22. Lainey says:

    Do not like Self Portrait. Always looks so cheap and constricting.

  23. bella says:

    This I is a very unattractive dress. Her brother would fantastic–sans beard

  24. Erica says:

    Pippa looks way to smug in that old lady dress. Does anyone know if the middletons were photographed going to Wimbledon before or during the waity period so much as they do now?I don’t remember them turning up to Wimbledon or many royal events before kate got my precious on her finger.

  25. M.A.F. says:

    I was expecting a dress with her face on it. Not her wearing a tea cozy. Very disappointed.

  26. Wow says:

    I like the dress for Pippa. She looks nice. Everyone does not have the same style or taste. I’m sure Pippa, Kate, Camilla and even The Queen would find some of our clothing choices fugly to. To each their own.

  27. Pandy says:

    Wow, totally over dressed! Pumps at a tennis match – seriously??? And that fussy dress. She’s not royal – she can dress down. And James in a suit. Give me a break.

  28. Joannie says:


  29. graymatters says:

    I don’t like this dress much at all, but it really doesn’t suit Pippa. The jumpsuit she wore to the heart charity thing a few days ago was more her style and would work well for Wimbledon.

  30. Pumpkin Pie says:

    I like the dress but as an item in a museum of fashion of some sort. Or in a fashion show by some “fancy” couture brand.

  31. seesittellsit says:

    “Tragic” is too weak a word.

  32. Zardi123 says:

    Ugh .. its ghastly on her .. see through what a surprise not…

  33. JC says:

    On another note—regarding the well documented royal pretentions of the Middletons. Pippa now has 2 ladies-in-waiting (so to speak), etc. But, what about brother James?…his beard, haircut, even the pinky ring are oddly reminiscent of the way King George ll and his cousin Tsar Nicolas IV looked and dressed as young men at about the same age. Lots of images of the two available on line. Just a coincidence???? hmmm….

  34. Dhianna says:

    and this person is ‘famous’ because………………………………????????????

  35. Baltimom says:

    I thought she was auditioning to be Mary Poppins.

  36. Wren says:

    Ok, that is beyond hideous. It reminds me of the Afghan my mom kept on the back of the couch. Is she trying to look horrible?

  37. Reece says:

    I like this dress. However…
    This dress would be cute on someone else. Or if it were shorter ie take out the last tier.
    Her inverted triangle body shape emphasizes rather than balances this top heavy dress. Taking out the last tier would balance this dress on her.

    I really do not comprehend the Middleton lack of proper structural under garments. All the money these two women spend on clothes and neither of them seem to have a F**KING PROPERLY FITTED BRA!
    And The Shoes! *>&*${?#+___________* I quit!

  38. Mildred Fierce says:

    She would have looked much, much better if the dress was sleeveless and shortened to knee-length, but the most important items missing here are a decent bra and a slip/lining for the skirt. She and her sister’s aversion to undergarments aren’t doing them any favors.

    • Addie says:

      The droopy-boob sisters. I don’t understand their aversion to underwear either. What I’d like to see missing on Pippa is her smugness. And what’s with the retro Land Rover? James’s personal transport or yet another fashion/ attention-grabbing statement?

  39. Becks says:

    I agree with the comments about how this dress may look a lot better on someone else. It takes a certain sense of style to pull it off. I’m thinking of how Kate wore that dress in December (I cant remember the brand, with the long sleeves etc) and she looked dowdy, and Drew Barrymore had worn the same dress shortly before and she looked very fresh and hip in it (compared to Kate at any rate).

    Pippa seems to buy clothes that are expensive and that she thinks are “cutting edge” but not every fashion/style works on every person.

  40. Kaz says:

    English girls just don’t do ‘smart casual’ well. A lace doily and high heels for a sporting event. I know they probably get to go and have tea and scones inside with the other richies and snobbies but surely there must be something else to wear between a nearly cocktail dress and a bikini?