If James Bond wasn’t such a well-dressed man, this blog would not exist. But sometimes James Bond is not the best-dressed man in the room. On a number of occasions, Bond has made some poor choices regarding his clothes. What are these poor choices? And how could these outfits have been improved? Following are 13 of James Bond’s worst outfits and suggestions relevant for the time each film was made on what could have been done better.

15. Die Another Day: Hawaiian Shirt

Loud is not Bond’s style, so there’s no reason why Bond would have purchased a blue floral-printed shirt to wear in Cuba. It’s not any sort of disguise. The medium blue shade recalls the colour of many shirts Bond’s creator Ian Fleming specified for Bond in the novels, but the large print does not. Since the shirt has only two colours, it’s better than a true Hawaiian shirt that could have many colours. Other men Bond encounters in Cuba are wearing much worse clothing.

Instead of a pattern, a solid or semi-solid medium blue cotton or linen made in the same shirt style would have been a more appropriate and tasteful choice for Bond.

14. Tomorrow Never Dies: Oversized Clothes in Vietnam

The blue shirt in Tomorrow Never Dies isn’t so bad on it’s own, but on Pierce Brosnan it’s much too large. The colour is something that Ian Fleming’s Bond would have worn, but it would have also been made to fit Bond. Though it follows the 1990s trend of baggy clothes, nothing else Brosnan wears in his films is so baggy. A man who has given up on life wears stretch jogging trousers, not James Bond.

The shirt would be fine if it were properly fitted to Bond with the shoulders narrower, not halfway down his forearms. The black jogging trousers should instead have been navy cotton chinos, to bring in Fleming’s Bond’s love of navy trousers. The overall effect of this outfit would be a more refined version of what Brosnan already wears.

13. On Her Majesty’s Secret Service: Brown Golfing Outfit

People think of leisure suits as a 1970s atrocity, but the concept started much earlier. Brown was also trendy before the 1970s. George Lazenby wears a 1960s example of a brown casual suit in On Her Majesty’s Secret Secret. The suit of matching light brown blouson and trousers with an orange polo neck looks horribly dated today, and the warm colours do no favours to Lazenby’s cool complexion. Despite how poorly we may view this outfit today, it was probably the outfit George Lazenby was most comfortable wearing in the film. Though he wears his suits well, he didn’t think wearing suits was cool. On the other hand, he must’ve thought this golf outfit was the hippest thing.

A blouson and polo neck aren’t necessarily bad, but this would be a much better outfit with a touch of Fleming. Straight out of Fleming’s Goldfinger, I’d make the blouson the “faded black wind-cheater” and the trousers the bottom half of the “yellowing black and white hound’s tooth suit”. These are the two key parts of the literary James Bond’s golfing outfit. Houndstooth trousers would have been flashy enough to still look trendy at the time. And instead of the white sea-island cotton shirt that Fleming specified, I’d keep the polo neck and make it white to update it to the 1960s. Such an outfit would combine classic Bond and still have enough of the fashionable look of Lazenby’s outfit.

12. Licence to Kill: Faux Morning Dress for Felix’s Wedding

One of the worst things Bond has been forced to wear is the morning dress that Bond’s pal Felix Leiter hired for his wedding in Licence to Kill. The medium grey morning coat belongs with a matching morning suit and should never be worn with the traditional striped trousers, as Bond wears it here. The shirt’s attached wing collar and pleated front don’t belong in any form of dress, and the clip-on cravat looks cheap. The outfit is neither historically accurate for Edwardian morning dress nor does it follow the modern form that royalty established a few decades later. It just looks like a cheap hire, which works in a sense because it’s what Felix would have gotten for Bond to wear as part of the wedding party.

If Bond is going to wear morning dress, it should be either the morning suit that Roger Moore wears in A View to a Kill or the more traditional form of morning dress that Q wears in A View to a Kill. But what Bond wears was not Bond’s decision; it was the decision of an American with little taste and appreciation of tradition. I’m talking about Felix and Della Leiter as well as Licence to Kill‘s costume designer Jodie Tillen.

11. Diamonds Are Forever: Pink Tie

Pink ties are difficult to wear, even for Sean Connery. And they certainly don’t fit with James Bond’s usual style. The pink tie that Sean Connery wears with his cream linen suit in Diamonds Are Forever stands out because it is so unusual for Bond, and it stands out in a very bad way. What makes this tie even worse is that it is too short for Sean Connery, though the tie’s length is not apparent when Connery has his suit jacket on. And in being such wide tie, the Windsor knot it ties is too big. Too short and too wide makes it look like a bib! Though the suit and shirt that Connery wears with the pink tie are nice, Connery messes up the suit’s lines by fastening the jacket’s bottom button.

Both the length and knot size problems could have been avoided if the tie was knotted with a four-in-hand knot instead of a Windsor knot. A navy or brown grenadine or knitted tie in the Connery Bond tradition would also have been a better choice than pink.

10. Skyfall & Spectre: Undersized Suits

The fashionably shrunken fit of Daniel Craig’s suits in Skyfall and Spectre will not date well, just the same as Roger Moore’s flared suit trousers and Timothy Dalton’s baggy suits have not. Though the too-tight fit is trendy today, Craig’s suits will look like poorly fitted mistakes once the trend is over. That is if it doesn’t already look like such already. While Roger Moore would have looked like an old fogey in the 1970s had he worn tapered or straight 1960s-style trousers, today a man can still wear a suit that fits well and not look old-fashioned, so long as the suit has a close fit and not a baggy one.

Though it’s easier said than done, Daniel Craig’s suits in Skyfall and Spectre could have been vastly improved with just a cleaner fit if all else stayed the same.

9. Licence to Kill: Baggy Suits

Bond’s suits in Licence to Kill are amongst of the worst of the series and do not follow what the character typically wears. They may be in tasteful colours, but an Italian fashion cut in a sloppy fit is not what Bond would or should be wearing. Excuses could be made if Bond had to buy all of his suits at short notice in Isthmus City, but his charcoal suit in Key West early in the film before all hell breaks loose is the same style as the suits he wears later in the film. All of Bond’s suits in Licence to Kill are what an American with lots of money to spend and no taste would wear.

At the very least, the suit in Key West—which I think could more appropriately have been either a beige linen suit or a blue blazer and cream trousers—should be a classic British Bond style with a cleaner fit that hints at the full-cut, built-up trends rather than goes all out with them. Something more along the lines of the suits in The Living Daylights would have been appropriate. Since all the suits in the film are already from the same source, they all could all be from a more appropriate source for Bond.

8. On Her Majesty’s Secret Service: Highland Dress

The highland dress is not James Bond’s outfit but rather belongs to genealogist Sir Hilary Bray, who Bond is disguised as. Since Bond is in disguise and not himself, we can’t entirely blame Bond for wearing this. However, highland dress looks like a joke on Bond, and it only serves the purpose of allowing the girls to write their room numbers in lipstick on his thighs under the kilt. George Lazenby’s Bond unfairly comes off as a joke, in large part due to the highland dress.

Is this how Sir Hilary really would have dressed? Classic black tie, perhaps a double-breasted shawl collar dinner suit like what M wears in Goldfinger, would have been less comical. A black velvet dinner jacket with tartan trousers could also have worked well for the occasion.

Because the highland dress is a disguise, and the highland dress is done well, it is slightly forgiven.

7. Diamonds Are Forever: Terrycloth Camp Shirt

Sean Connery’s Bond wardrobe is still considered one of the greatest film wardrobes of all time, but he has a problem when it comes to terrycloth. Nobody told him that terrycloth is for towels, not for clothing. The design of his camp shirt in Diamond Are Forever isn’t so bad, but the material is a problem. Not to mention the colour. Beige was a popular colour to wear in the 1970s, and there’s nothing inherently wrong with beige. But beige is not a flattering colour on Sean Connery.

A shirt in the same camp design in linen or a blend of linen with silk or cotton would have been a more sophisticated choice. A lighter cream, white, icy blue or even pink would be a better colour. One of his camp shirts from Thunderball should have made a repeat appearance.

6. On Her Majesty’s Secret Service: Ruffled Dress Shirt

George Lazenby’s dinner suit from Dimi Major is an elegant, classic piece of tailoring, and it is one of the best dinner suits of the series that still looks fantastic today. But Bond messes up what could be a superb black tie outfit with a ruffled dress shirt when he visits the casino. Thankfully it’s still a white shirt with a perfect spread collar, but no matter how fashionable ruffles were in the late 1960s, they don’t look so hip today.

A classic pleated shirt, perhaps with three oversized pleats on each side for more flair, would have held up far better. The ruffled shirt didn’t take very long to look outdated. Thankfully, the rest of Lazenby’s black tie outfit is beautiful.

5. A View to a Kill: Velour Tracksuit

Roger Moore is dressed mostly elegantly and timelessly in his 1980s Bond films. The exception to this is his velour tracksuit that he wears for sneaking around Zorin’s stables at night in A View to a Kill. Though Moore’s body is slim enough to look decent in the tracksuit, the youthful garment emphasises his age. It’s also just a horribly dated piece.

Instead, Moore should have dressed in the more classic styles that were popular in the 1980s. This would have been the perfect time for him to wear the “faded black wind-cheater” that Ian Fleming dressed Bond in for casual wear. Under the wind-cheater he could have worn a black polo shirt and charcoal or black worsted trousers. This would have been a classic look for Bond and appropriate for the mid 1980s. Sir Godfrey Tibbett is actually wearing an outfit in this scene similar to what I’m recommending for Bond. But Bond would do it better.

4. Octopussy: Clown Suit

Octopussy is one of the most derided films of the James Bond series, and a large part of that stems from James Bond wearing a clown suit. Despite his most series acting as James Bond when he wears a clown suit, people think of Roger Moore in a clown suit as the epitome is his silly portrayal of Bond.

Before he dons the clown suit, Bond wears a red shirt that he stole from circus knife-thrower Mischka. It’s a circus outfit, but it doesn’t look that silly. He trespasses onto the army base and is seen wearing this red shirt, so he is in need of a new disguise since he very well can not shoot his was through the United States Army. If it’s not a clown suit, what should this disguise be?

The gorilla suit he hides inside earlier in the film is even more silly! Just about all circus outfits would look silly. He could have found some circus-worker clothes like how he finds an Octopussy Circus jacket earlier in the film. But the clown outfit disguises his face and allows him easy access to the circus ring.

Without coming up with a new plot for the film, the clown suit gets the job done better than anything I can think of. Unlike most of the outfits and items on this list, Bond is not wearing a clown suit as a fashion statement. And thankfully, Moore’s Bond isn’t even tempted to crack his usual jokes while wearing the clown suit.

3. Casino Royale: Printed Shirt in Madagascar

Bond may be a new 00-agent at the start of Casino Royale, but that’s no excuse for poor taste. A person’s taste is ordinarily developed at a much younger age than 38. Nevertheless, he wears a loud printed floral shirt that makes him really stand out in the crowd. A spy should blend in with the crowd, and he would have been better off dressing like the locals. Instead he looks like a clueless tourist. The Madagascar shirt makes the blue floral shirt in Die Another Day seem subdued in comparison. A few other men in the crowd are wearing loud prints, but most are wearing plainer shirts. Bond has no excuse to be wearing this shirt.

I would keep the cut of the shirt and the overall beige colour. I would dress Bond in a solid or more subtly patterned beige shirt that follows Bond’s more usual tastes. Two flapped pockets on the chest would be a nice way to hint at the legacy of Bond’s safari suits, but the shirt should not be an all-out bush shirt. I would also do away with the undershirt and have Bond fasten more of the shirt’s buttons. This way he’d be dressed more like most of the locals who aren’t layering their clothes.

2. Goldfinger: The Terrycloth Playsuit

The first embarrassing thing that James Bond ever wore is a blue terrycloth playsuit in Goldfinger, and it is still one of the worst things Bond has ever put on of his own free will. A one-piece garment may work as a spacesuit, but it doesn’t look so appealing at the poolside. It’s a wonder, even with all of Sean Connery’s charm, that Jill Masterson didn’t scream when a man wearing a terrycloth onesie showed up on her balcony.

Instead, Bond should have worn what Fleming had Bond wear over his white linen bathing-drawers in Casino Royale:

This was a pyjama-coat which came almost down to the knees. It had no buttons, but there was a loose belt round the waist. The sleeves were wide and short, ending just above the elbow. The result was cool and comfortable and now when he slipped the coat on over his trunks, all his bruises and scars were hidden except the thin white bracelets on wrists and ankles and the mark of SMERSH on his right hand.

This pyjama coat—perhaps in dark blue silk—would be perfect for Bond to wear over his swimming trunks instead of a playsuit in terrycloth. Even the pyjama coat in blue terrycloth would have been better than a playsuit.

1. Live and Let Die: Powder Blue Leisure Suit

Roger Moore is not dressed overly fashionably in his first Bond film with the exception of one item: a powder blue leisure suit worn over a white vest (sleeveless undershirt). The rest of the outfits on this list have some redeeming quality: a nice fabric, part of the outfit is nice, it’s a disguise, there’s some practical value, etc. This has nothing going for it. The leisure suit, particularly in this form, does not fit with Bond’s refined image. I would imagine that even in 1973 it still would have been an embarrassing look on Roger Moore.

A light blue or brown striped camp shirt with cream linen trousers could still look fashionable enough for 1973, but it would also have the more classic elegance Bond typically wears. Bond would still have fit in with the locals wearing such an outfit. Though flared trousers don’t look so great now, they were sadly a necessity of the time for Bond to not look like a fuddy-duddy.

Note: Roger Moore also briefly wears a navy leisure suit in Live and Let Die when hang-gliding, but since one cannot even see what the garment is in the film, I cannot count it here. From behind-the-scenes photos, this navy leisure suit is the nicest example of a leisure suit I’ve ever seen. But it’s still a leisure suit.

What outfits do you think are Bond’s worst? Leave your thoughts below.