Jessica Simpson’s street style involves bad boots, a negligee & a Gucci coat

Jessica Simpson exists her hotel with style while in the "Big Apple"

I just realized that we haven’t talked about Jessica Simpson YET in 2018. Allow me to make up for that gossip disaster! Here are some photos of Jessica out and about in New York on Tuesday. Yes, these are really photos of Jessica this week. These photos are unaltered. You can’t even say that Jessica just got drunk and threw a coat over a negligee and called it a day – she was clearly proud of this Gucci ensemble and she previewed it on Twitter:

Even if she had Bella Hadid’s figure, this ensemble would be pretty bad. Because it really is just a negligee and a fug coat and hooker boots. But obviously, these photos are making people ask, “so, is she pregnant again?” Jessica actually shut down speculation about having a third child last year, saying she was done having babies and she got an IUD. That was after Ace Knute was a little bit of a “surprise” pregnancy just a few months after giving birth to Maxwell Drew. Anyway, Ace turns 5 years old in June, and Jessica recently told Entertainment Tonight that she does have a case of “baby fever” and that she and Eric Johnson are “always practicing” to have a third. So… there. I think she’s already knocked up. She’s only 37, by the way.

Jessica Simpson exists her hotel with style while in the "Big Apple"

Jessica Simpson steals the scene in Manhattan!

Photos courtesy of Backgrid.

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90 Responses to “Jessica Simpson’s street style involves bad boots, a negligee & a Gucci coat”

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  1. WingKingdom says:

    Oh my… the lining of the coat matches the negligee. Those are MEANT to go together. I just thought she had bad style.

  2. Shelley says:

    Streetwalker-style? Donna Summer throwback to disconnect era? Bad girls?
    What’s withe the shapewear?

  3. MostlyMegan says:

    I actually can’t believe she is 37. She seems so… not together for 37. I don’t know why I think that – other than the dumb husband and horrid fashion sense. She commands a mult-million dollar clothing/fragrance empire. She isn’t as dumb as she seems, and yet I don’t admire her. And yep, TOTALLY knocked up.

  4. Liberty says:

    Pretty Woman meets 1960s Chelsea Girl meets…hm…early Amal? :-)

    Eh, I say, have fun while you can, girl, even if you sort of can’t.

  5. Shotcaller says:

    She’s Mariah Carey’s spirit animal.

  6. Nancy says:

    The 90′s called & they want their outfit back.

  7. Lala says:

    That outfitting…is…ASTOUNDING!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! I’m not even gonna look at Jessica regarding this one…I AM LOOKING AT THE HAUS OF GUCCI!!!! FA WHY DOE?!?!?!?!?!

    • DrunkNachos says:

      A lot of top fashion houses seem to have run out of ideas, frankly. Chanel & Gucci are 2 big offenders. They prob think this is “street style” and “youthful” but it looks like a 1st year community college fashion student’s final project.

  8. Smokey says:

    An escort leaving a hotel would try to dress less conspicuously then this outfit.

  9. ida says:

    She looks like coming from or directly going to the Playboy mansion.

  10. Mrs. G says:

    She sure looks pregnant… You could see the outline of her bump

  11. grabbyhands says:

    1994 is calling and they want their look back.

  12. Jillian says:

    She looks so different. I hardly recognized her.

  13. Bridget says:

    That outfit needs to be burned. But yeah, that’s a pregnant lady.

  14. Tanesha86 says:

    She literally looks like she just rolled out of bed and imo she’s sporting a pretty sizable baby bump

  15. mkyarwood says:

    What in the Sargeant Pepper’s Grandma hell?

  16. Snowflake says:

    She and Britney have the worst style

  17. DragonWise says:

    I almost feel bad for her tacky, clueless self. She gets an (ugly, tasteless) Gucci outfit, previews it on Insta, goes out clearly feeling herself, only to be greeted by a rousing chorus of “Is she pregnant??” 😂

  18. hey-ya says:

    …better than cycling shorts & all other lycra stuff…its nice to see someone outside the k.klan circle…

  19. NΞΞNΔ ΖΞΞ says:

    It’s the hat that sends this ridiculous getup over the edge…

  20. Snigs says:

    The body shaming on this post far outweighs the tackiness of the outfit. If she had Bella’s figure? Is she pregnant? Outline of baby bump? Just wow.

  21. Lucy2 says:

    It looks like she’s about to go onstage at a, um, gentlemens club?

  22. Chloeee says:

    I have a nightie that bubbles awkwardly like that in the tummy area. But if she isn’t preggers, I’d ditch that outfit because it def gives that impression

  23. eeeeetrainnnn says:

    She actually looks much less bloated than the last time she was pap’d in NYC which leads me to think she is pregnant (besides the bump)…she had to quit drinking.

  24. Veronica S. says:


    …like the coat?

  25. Snappyfish says:

    Wow, what a mess…all the way around

  26. JRenee says:

    Homage to Julia Roberts in Pretty Woman..

  27. Beatrix says:

    For someone with a successful “fashion” line, this woman has always had THE WORST taste.

  28. Andrea says:

    Is it a dress or a nightie??

  29. flebel says:

    Just getting fat – again. Adding her yo-yo weight and dieting to her love of booze cannot be doing her well-being any good.

  30. LittlefishMom says:

    I love her, but not her style. She’s a sweetie pie tho.

  31. ... says:

    The only comment I can come up with is…… why?

  32. joanne says:

    all this slut shaming, hooker boots, escort, gentlemen’s club. body shaming, is she pregnant, booze bloat, fat, sloppy. yet, we all claim to be feminists here and support other women. i’m all for gossiping about behaviour and actions not denigrating women because i don’t like them. anyone can critique fashion without using slut words. you can critique women without shaming their appearance. this is getting to be a nasty trend.

    • Mabs A'Mabbin says:

      Hellooooo…cele–bitchy. When you get out and about today let us know if you come across an outfit as hideous as this. Can we not discuss anything negative? The outfit Jessica Simpson is wearing sucks ten bushels of lemons. Those are, indeed, boots that command certain designations (by the masses). Is she not covering her bodice with something akin to lingerie? It looks exactly like that to me. In fact, I’m struggling to locate something positive about her look. I like that crescent necklace. Maybe her bag. There.

      • joanne says:

        as i said, i have no problem with the critiquing of her look. my problem is with how it’s done. there’s a huge difference between saying her outfit sucks and saying she looks like an escort wearing hooker boots. being bitchy is not a problem, it’s what you’re being bitchy about.

      • Mabs A'Mabbin says:

        I hear ya. But the escort comments are the result of a general consensus of a sucky outfit and what it resembles. Jessica isn’t a hooker. But she allowed herself to look like one. Apparently. As several posts indicated. Lol

  33. Sansa says:

    She looks good to me, if she going out for a night out, good on her.

  34. Jayna says:

    She’s making the Jersey Real Housewives look like they have fashion sense. LOL

  35. Sarah says:

    Ahhh! Gucci’s Pregnant Hooker line! I ❤️ it! 😛

  36. Lisa says:

    That’s just not a good look.

  37. happy girl says:

    She looks as absurd as she sounds (can’t stand the sound of her slurry, locked-jawed yodel).

    I hope she takes a few minutes every day of her life to thank the universe for her good fortune because it’s impossible to fathom how a dumbass like this has achieved wealth and fame.

  38. Green_eyes says:

    The hair is too much, the outfit is too much.. and she looks like she is expecting.

    Hello Hooker Barber meets growing tummy Skipper.

    My sister had a growing up Skipper doll when we were little & I had Disco Barbie, she reminds me of a combo of the two. Especially w/ that hair. Disco Barbie had crazy hair.

  39. Anare says:

    Finally someone mentioned the hair, thank you Green Eyes. I know y’all are blinded by that Beefeater + Hooker ensemble so go back and check out her hair. Be sure to wear eye protection. It’s like looking at a solar eclipse with the naked eye. What is that color? Neon Clorox?

  40. SJhere says:

    This outfit is ugly.
    I can’t believe she did her hair and makeup and left the house wearing that outfit.
    With all her $$ she really has zero style/taste.
    I do like the purse.
    Her hubby seems OK and I’m all in favor of house hubby or house wife if it works for you and you can afford it, why not? He is no K-Fed IMO.

  41. Mar says:

    She has the worst style I have ever seen. God awful.