Jenna Bush Hager Has Worn Some Inappropriate Outfits

While Jenna Bush Hager is usually a class act who looks stunning even without makeup, she doesn't always make the right calls when it comes to fashion. Now, to be fair, she isn't in the fashion industry; Bush Hager is an author and journalist, better known for her Read With Jenna book club picks than her outfits. She also doesn't use a stylist, so we can't really fault her for occasionally missing the mark when it comes to clothes.

Still, as the daughter of a politician, Bush Hager has been in the spotlight for years, so she's had plenty of practice at dressing for a public event. However, the author told InStyle, as of 2024, she doesn't even plan her outfits. While we can respect her spontaneity, unfortunately, on more than one occasion, she has made some questionable style choices that were ill-suited to the time and place.

In 2022, Jenna Bush Hager attended the Greenwich International Film Festival in a shiny suit that looked a bit like a matching pajama set. Rather than making the suit seem more elegant and evening-wear appropriate, the fabric choice just made the trimmed suit look intended for a sleepover. The bedtime-meets office wear ensemble was out of place on the red carpet, which tends to be a venue for tuxedos and gowns instead. This is another instance when the clothing pieces themselves are lovely but its poorly suited to the context since Bush Hager ended up looking more professional than glamorous.

Jenna Bush Hager welcomed pop star Ciara as a guest cohost on "Jenna & Friends" by wearing a long black shift dress with a lace hem. Although it was a lovely LBD, it's hard to deny this was oddly formal for the daytime show. While this would be a great ensemble for a night out, it looked overly done up for the morning television taping. Black might be a universally flattering color but it's really just too harsh for daywear, particularly when it's in more lavish textures like this dress. We'll give Bush Hager some credit, though, as it seemed to be part of a theme – Bush Hager and Ciara spent a portion of the segment taste-testing espresso martinis. 

For a segment with guest co-host comedian Michelle Buteau, Jenna Bush Hager donned a maxi length black leather skirt, paired with black boots and a patterned top. While the bright top was perfect for day wear, the leather skirt seemed a little too stiff for the cheerful daytime segment. In one clip, Bush Hager jumps around to greet Buteau, and the tight leather skirt looks uncomfortable and restrictive — the wrong choice for a playful television spot. The skinny heel on the boots just solidifies that this look would be better suited for a night out.

To announce her September 2023 book club pick, Jenna Bush Hager shared a photo on Instagram of herself wearing a lime green two piece set featuring a double breasted jacket and pleated shorts. While it's understandable she may have been trying to coordinate with the book cover, the summery color felt like an unusual choice to wear during the fall, when styles are already shifting toward darker textures and palettes. Plus, the formality of the double breasted coat style was strangely at odds with the casual vibe of the linen shorts, which appeared wrinkled from sitting. For this appearance, Bush Hager would have been better off in a darker color, like ruby, which would have appeared less rumpled and more seasonally appropriate.