Pippa Middleton wore one of the worst maternity looks to Wimbledon last week

Celebrities at Wimbledon 2018 Day 11

I’m late to posting these photos, but it’s never too late to talk about Pippa Middleton’s fashion, right? Pippa Middleton loves Wimbledon and she comes out for some of the men’s matches every year, as does Mother Middleton (Carole). The Middleton women are ride-or-die for Roger Federer, so Pippa attended three of Roger’s matches during the fortnight – two on Center Court, and the one match Roger played on Court 1, the less prestigious court, and the court where he lost to Kevin Anderson. After Roger lost, I don’t think Pippa went to Wimbledon again. Which is too bad, because she missed some other good matches. Still, I get it: she’s ride-or-die for Federer. Roger even came to her wedding.

Anyway, on of her Wimbledon outings, Pippa wore this absolutely heinous Anna Mason dress. I’m loathe to criticize a pregnant lady’s maternity style, especially when they’re mid-pregnancy and still figuring out maternity wear. But this dress is just bad. Wasn’t it especially hot at Wimbledon this year? Why a long-sleeved, long-skirted boho dress?? Why the ruffles? WHY DOES THIS DRESS EXIST? Also: Terribly Moderately Wealthy James Matthews looks nice in these photos.

Celebrities at Wimbledon 2018 Day 11

A few days earlier, Pippa wore a much nicer look – a Ralph Lauren shirtdress which was billowy enough to mask her bump. By my count, Pippa went to Wimbledon with her brother twice and her husband once. My favorite thing about this look? She actually wore flats!! Also: James Middleton’s pants are what I would expect from someone who has lost millions of dollars in a marshmallow scheme.

Pregnant Pippa Middleton and James Matthews arrive at Wimbledon

Photos courtesy of WENN, Backgrid.

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44 Responses to “Pippa Middleton wore one of the worst maternity looks to Wimbledon last week”

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  1. HelloSunshine says:

    My god, dressing a baby bump really isn’t that difficult lol with her money and stuff, she should be dressing her cute little bump better. I buy all of my maternity clothes at target and none involve ruffles and looking overworked lol

    And obviously she can dress it well, that second dress is really cute and she looks nice and comfy!

    • Jan90067 says:

      I think she has to stop with those double tiered drop waist dresses, esp. while pregnant. It does her long-waisted torso no favors. I like the RL dress, and I usually like espadrilles, but these ankle tied ones just cut off her legs and make her look stumpy.

      She’s rocked other looks while pregnant, and I usually like a lot of what she wears, but these… nope 😊 Still, if *she’s* happy and comfortable, that is all that matters.

      • DesertReal says:

        She looks like a sister wife in the first picture, and the first wife in the second.

  2. Babs says:

    Well, I like the first dress minus the shoes. The second dress is awful, as are the shoes, so, cohesion. Espadrilles are never right under 50.

    • OkieOpie says:

      Agreed. It is the shoes that wreck both looks. The first dress is nice but not on someone with her body shape. She is a pear shape and that dress only accentuates it.

  3. Thatsallfolks says:

    She likes espadrilles and flowery prairie dresses.

  4. perplexed says:

    She has terrible style, but I’m starting to think she might not care. Everybody is going to make fun of what she wears and she’s just going to keep on truckin’.

  5. Morning Coffee says:

    Clearly she wasn’t in the Royal Box either day as her dates were not wearing coat/tie. That’s a plus.

  6. Maria says:

    Both dresses and shoes look bad to me. Kate wore much nicer maternity clothes. And her brother? WTF? He looks like he just rolled out of bed, or couldn’t find clean clothes.I guess he’s so busy trying to rescue his marshmallow empire he doesn’t care what he looks like.

    • Rhys says:

      How does James make his living these days? Does he live off his parents?

      • Maria says:

        Trying to sell marshmallows I guess.. living in his parent’s flat, pretty sure he can’t afford his own place.

      • Aurelia says:

        He lives off the money he cons out of his crap marshmellow investors.

      • magnoliarose says:

        Yep. A real prize. None of the Middleton have had careers. It is odd to me since they aren’t rich enough to leave any of them set for life.

  7. Nancy says:

    Not going to lie, don’t hate it. It appears she walks rather heavily and it doesn’t allow the dress to flow. The solid blue is a disaster, wouldn’t get near it, nor either pair of the shoes.

  8. Citresse says:

    In the first dress, she looks like an extra from Little House on the Prairie.

  9. Apalapa says:

    I don’t like how Terribly Moderately Wealthy James is walking in front of and not beside her. Body language experts to the stars, analyze it!

    She looks like she may have gained some fluid through her legs and feet, although I know wedges were beloved by her before. If that is the case I can see why she chooses extremely roomy and flowy dresses. Pregnancy can be so uncomfortable!!

  10. Lisa Giametti says:

    I think she looks comfortable and obviously she likes her choices, and that is all that matters.

  11. Becks1 says:

    oh my gosh that first dress is truly awful. WHY PIPPA WHY. I love the second one, but I love a good shirt dress in general. Hate the shoes.

  12. kate says:

    I … actually like the first dress. **runs away**

    • JanetDR says:

      As you should! Lol! I pretty much had this dress , but in my defence, it was the late 70s.

  13. Veronica S. says:

    Eh, I don’t hate the dresses, honestly. It’s the shoes that I dislike. Just go with a straight espadrille – the tie up is just never that flattering to the calf.

  14. Amelie says:

    I wonder if she’s self conscious of her changing body and wearing these ugly patterned dresses to mask her baby bump? I don’t know because she carries pretty well!

    James Middleton looks like a Brooklyn hipster from Williamsburg, hahaha how does that look even go with Wimbledon? People still do dress like that in hipster Williamsburg even if the look is considered so dated at this point. Hipster Brooklyn is no longer considered cool to move to though since they are soon shutting down the L train (the subway line that goes through most of Williamsburg and now more recent hipster enclave Bushwick) for major work.

    • magnoliarose says:

      He is creepy to me. Like the guy in a Greenpoint bar who smiles at you and you nudge your friend and tell them it is time to go as a preemptive measure. Or the try hard faux artiste who parks himself at sidewalk cafes in Brooklyn so he can be seen drinking Pernod.

      • Amelie says:

        Ugh I recently had an encounter with Hipster Brooklyn with a capital H. I live in Brooklyn in the non-hipster part (though unfortunately I am being forced to move again) and I went to meet up with a friend at a cafe in Williamsburg. I don’t do hipster cafes if ever, and everyone there was on their laptop, working furiously away on… their Great American Novel?? Everyone was dressed like James Middleton. I felt so uncomfortable and so did my friend because just speaking out loud felt like I was in a library. We didn’t want to upset the creative hipstery atmosphere! We moved to a creperie where we could be more mainstream haha.

      • magnoliarose says:

        I don’t like those places either. There are some cool spots in Brooklyn but the hipstery try hard places are exhausting and make me want to burst out laughing. I go down to Brighton Beach to get Russian fixes and I find that more fun than watching trustfunded faux artistes pretend to be important.

  15. Beth says:

    Ugh, those shoes are horrid. The only shoes that should have tie up straps are ballet pointe shoes

  16. Naptime says:

    She loves those unflattering lace up espadrilles, doesn’t she??

  17. Mitzy says:

    Kill the shoes. With fire.

  18. magnoliarose says:

    These looks are confusing. Has she given up trying to be a thing and was caught by accident? Is she trying to look like a fundamentalist member of some strange Pioneer cosplay cult? Do they hold major stock in an espadrille company?

  19. Millenial says:

    Carole has better fashion sense than both her daughters. For that matter, she’s also the brains of the whole Middleton operation. For my money, Carole should the be a duchess and/or married to a terribly wealthy aristo, not her daughters.

    • perplexed says:

      I think Kate’s dad has some kind of aristocratic lineage. That’s the impression I got from reading a bio on Kate. But for some reason everybody goes on about Carole’s origins and nobody talks about the dad’s lineage. However, I think the dad might come from a somewhat posh background. If I am wrong, anyone please feel free to correct me.

      • Aurelia says:

        Mike MIddleton’s ancestors were strictly middle class. More media myth making derspo to elivate kate’s station.

  20. Vava says:

    Can’t say I am fond of many of the Middleton ensembles………..The dad is the best dressed of the lot.

    These garments are meh. Particularly the first one. It seems as if puffy sleeves and ruffles are coming back as a fashion fad. Ewwwww…… I’ve seen this on a lot of fashion bloggers, too, and they rarely get it right either.

    The shoes are not something I would buy, but I think if one loves them, then they look better with a shorter skirt or with shorts. More leg exposure.

    • YankLynn says:

      Instead of a Wimbledon day she looks like hubby is taking her out to meet her new sisterwife …

  21. Case says:

    I feel like it’s not that hard to dress a cute little baby bump when you have tons of money, and yet…

  22. liriel says:

    And the shoes. Seriously hideous. I’m wondering if Kate and Pippa are as close as usual. Maybe Pippa’s kid will bring them closer, playtime but I get an impression Kate’s all about her kids, Pippa is old news. Is Pippa happy in the background?

  23. TyrantDestroyed says:

    What in the world is Marshmallow’s King wearing? Those pants areally beyond terrible

  24. raincoaster says:

    Love the shirtdress, and I’m pretty sure the floral thing was my party dress in 1974 when I was in grade school.

  25. Antonym says:

    “Also: James Middleton’s pants are what I would expect from someone who has lost millions of dollars in a marshmallow scheme.”

    I am rolling 🤣