5 Times Bradley Cooper's Street Style Left Us Scratching Our Heads

Bradley Cooper is usually impeccably dressed. Whether he's sweeping award show categories or living out his rockstar dreams onstage with Lady Gaga, he's one of the few actors who really knows his way around a three-piece tuxedo. Therefore, we're not surprised that the "Maestro" star is praised for his fashion around Hollywood and beyond. For example, Cooper's been honored by both GQ as a style inspiration for fashionably adept men. Esquire also lauded Cooper, a father of one, for inspiring other fathers to up their fashion game. Given how difficult it is to make trips to piano recitals or sports tournaments look cool, you know this is an impressive feat. 

So why is Cooper's ultra-casual street style a bit of a head-scratcher? Fact is, for every time Cooper has gotten it right in the style department, there's been another time that has made us question whether he knows that, one, he has enough dough to fund the most fabulous wardrobe of all time, and two, if he checks the mirror before leaving the house. More recently, we've started to wonder whether Cooper's rumored girlfriend, model Gigi Hadid, has enriched his life with her fashion knowledge and pulled him down a peg. Either way, Cooper's street style is terrible. So terrible that it's almost good! Here are five times that Cooper's street fashion left us incredibly confused (but also very entertained). 

Bradley Cooper tried out a two-in-one look

Even the most fashionably adventurous people build their outfits around a theme — you know, business or casual, formal or informal. Bradley Cooper combined two looks in one when he stepped out in New York on October 24, 2023. In this case, Cooper combined formal and casual all in the same look, creating a busy, incoherent mess. While his navy blue slacks and black sweater were more than enough for a cool day in the city, the black trench coat he paired it with was definitely a bit of overkill. Basically, the individual pieces would've worked independently, but together, they created a beautiful disaster.

If you'd like further proof that wearing the jacket was a mistake, you should know that Cooper was also photographed without the oddly placed coat on the same day, and the look was definitely much more well-rounded and cohesive. The Cooper in this photo seemed confident about his destination, be it a trendy brunch spot or a cool, obscure museum. Granted, he had also capped off his look with a black beanie. Furthermore, Cooper also swapped out his eyeglasses for a pair of shades that pulled the look together. Who knew a coat could make or break an outfit? Hopefully, he learned his lesson.

Honestly, he should burn these pants

Bradley Cooper may be a heartthrob who can get away with experimenting with fashion, but not even he can pull off a monstrous pair of blue camouflage cargo pants. As you can see in the photo above, Cooper rocked the camo pants, scattered with blue stars, against a bustling city background, which kind of, you know, defeated the purpose of the whole camouflage deal. But perhaps he was aware as he paired the pants with an unassuming black hoodie and glasses, which nearly rendered him unrecognizable. Honestly, the additions almost worked, as Cooper completely buried his usual aura underneath the look.

As seen in this November 2023 post by GQ, Cooper once wore a pair of similar pants in green. And while we'd love to throw the "Silver Linings Playbook" star a bone here and say that he executed these better, that sadly isn't the case. In fact, Cooper's look here is even busier than the one above. Instead of pairing the camo pants with a reasonable neutral, he added a color-blocked sweater featuring black, green, and blue horizontal stripes and a green, white, and yellow bomber jacket, creating a dizzying visual experience.

Bradley Cooper's top ruined the whole look

We appreciate Bradley Cooper's appreciation for a good coat, but that doesn't mean we always understand his logic for layering. Take, for example, the above photograph of Cooper donning what could've been a rather debonair fit as he walked his way through whichever city he'd made home for that week. Unfortunately, the star of the look, i.e., that amazing, double-breasted tan coat, fell flat against his other pieces, mainly the forest green horizontally striped shirt underneath. Instead of screaming quiet luxury, the look screamed rush job or a general lack of coordination. And the coat had so much potential!

Plus, the tan pants Cooper added to round out the look also seemed glaringly out of place. Worse, we can't really imagine where the soft-legged pants would fit. But you don't have to just take our word for it. One of Cooper's own fans hated the pants, which he's apparently worn in the past. "Those fugly pants again," wrote one user on Instagram. And while we may not have worded our opinion quite as harshly, we can understand the frustration. After all, Cooper boasts a net worth of over $100 million and definitely doesn't have to repeat unflattering pieces of clothing. Points for saving the environment, though!

Bradley Cooper wore a tragic blue hat

So, there's really no easy way to say that the blue, checkered hat that Bradley Cooper is proudly wearing in the above photo is just really displeasing to the eye. Like, so displeasing that we kind of wish he'd take it off, store it wherever he's keeping his collection of camouflage pants, and then forget that they all ever existed. Granted, it's not really the color of the hat that doesn't quite work. Instead, it's the ridiculous shape and size. Of course, the way he plopped it atop his otherwise glorious mane of hair didn't help matters either.

Since we've established that Cooper enjoys getting the maximum mileage from his wardrobe, you should know, according to News AU, he's worn the hat, produced by Louis Vuitton's label, at least three times in public. The other two instances involved similar variations of the outfit above. Once, he wore the colossal blue hat while photographed out with his rumored boo, model Gigi Hadid, proving that, well, her fashion acumen hasn't been able to totally neutralize some of his most random fashion urges. Of course, this doesn't mean Hadid hasn't influenced Cooper's fashion, which brings us to our next point.

Bradley Cooper likes to look cool for Gigi Hadid

Even though Gigi Hadid and Bradley Cooper are still in the will-they-or-won't-they phase, their fashion influence on each other is already quite apparent. In fact, it looks like Cooper's recent push to elevate his casual wardrobe coincides with the time he's been spending with the renowned model. For example, Cooper and Hadid were photographed in many similar looks as of late. And while Cooper's look in the above photo, including the rumored couple's matching sunglasses and similar fits, isn't his worst street style offense, his hip casual energy is certainly more proof that he's channeling his inner millennial. Perhaps for Hadid's sake?

And even though Cooper didn't accompany Hadid to The Met Gala – known as the biggest fashion event of the year — he's more than proven that he supports not only her proximity to fashion but also her fashion empire. As People reported, Cooper's actually been rocking several pieces from Hadid's Guest In Residence fashion line over the past few months. One example? The color-blocked sweater that he wore a few entries up. By the way, that one piece cost a whopping $545, so let's hope Hadid extended the actor a friends and family discount. Then again, Cooper's co-sign is probably worth a six-figure fee, so maybe she's the one who got the discount.