Movies Every Menswear Enthusiast Should Watch

For a long time, ladies have been getting fashion tips from leading actresses in Hollywood, but many men have us hooked on incredible movies with their acting skills and killer style. Movies and TV shows with stylish gentlemen and stellar outfits are worth watching, especially for a menswear enthusiast.
Aside from showing you great storylines, these movies can also be a great source of inspiration, regardless of how old they are. From some eye-catching classic looks and styles that are coming back to the best wardrobe winners, we’ve compiled the must-see movies for every menswear enthusiast. Now, your movie night can double as a style lesson.

The Great Gatsby

Regardless of where you live, the 1920s summer style in The Great Gatsby (2013) will attract attention in any room. Gatsby always went for a full-suited style in the summer heat, with attractive finishes of tie pins and boater hats. Formal wear isn’t only ideal for weddings, and you can still look good in the summer heat. The 1974 version of the movie also offers great inspiration.

The Talented Mr. Ripley

This star-packed thriller offers some of the best wardrobes and aesthetics from the late 90s and will give inspiration for your daily wear. The film is set in 1950s Italy and displays a simple yet elegant fashion that will attract a second look. Some styles include short-steel separates, slacks, and lightweight suiting.

American Gigolo

American Gigolo is a 1980 movie well-known for launching Giorgio Armani’s career, and it’s still relevant in offering style inspiration today. Richard Gere provides a lot of Italian flairs, evident in the delicate fabrics and relaxed silhouettes. Some of the major clothing pieces include retro jeans, suits, and wrap coats.

Kingsman: The Secret Service

Most spy movies have their male characters in stylish attires like brogues, but Kingsman: The Secret Service takes it to another level, with secret agents that want oxfords instead. English tailored suits are featured heavily in this movie, especially how they are used as weapons. The film also features a collaboration with Mr. Porter, a luxury menswear retailer, which means you can sport their looks too.


When a menswear fan thinks of Shaft, the first thing that comes to mind is leather! Everyone knows that Shaft had a massive influence on style, especially in the aspect of leather jackets. The movie has Shaft wearing sleek leather jackets a lot of the time, with leather pants and turtlenecks while fighting crime.

The Matrix

The all-black-everything has always been a great look, and you can get inspiration for this by watching The Matrix. From their long leather trench coats and slicked-back hair to the combat boots and tiny sunglasses, the aesthetic comes with a futuristic, sleek look. Also, tiny sunglasses have become a trend again.

Rebel Without a Cause

James Dean is known for sporting and rocking an effortless look, especially in the Rebel Without a Cause (1955). Dean can wear a simple T-shirt and jeans in the movie and still look great. He is primarily known for the bold red windbreaker that gives a subtle bad boy look.

Top Gun Maverick Image

Top Gun

Top Gun had a significant effect on popular trends, even if you never watched the movie. From jumpsuits and bomber jackets to aviator sunglasses, the film introduced trends that can enhance your style at any time. You can combine some of these with your modern style.


Cher and her girl gang really excelled in the Clueless movie in terms of style. But next time you watch, you should divert your attention to Bronson Alcott High School boys. The 90s skater boy look is pretty unique and an excellent style to sport when you’re going for casual and distinctive.

Mad Max: Fury Road

Look no further than Mad Max: Fury Road if you’re searching for a wild and rugged yet fashionable style. The movie is well-known for its wardrobe full of futuristics, apocalyptic and neutral-colored costumes. You can go for worn-in-looking pieces with earthy and neutral colors to create a rugged and stylish wardrobe inspired by this movie.


While we might not be able to pull off the perfectly disheveled hair that Jude Law had in this 2004 movie, there are other ways to mimic the modern playboy style. Some outfit pieces include tied scarves, pink button-down shirts, and slim pinstripe suiting.

Crazy, Stupid Love

Although no one ever gets a style makeover from Ryan Gosling (or his abs), there are other ways you can remake the fashion choices in Crazy, Stupid Love. The wardrobe was full of body-hugging and simple clothes with modern, fashionable designs.


Looking for something classic? Grease has an entire wardrobe for you. As you enjoy this iconic movie, you can also get inspiration from their slim-fit jeans, leather jackets, and wine T-shirts that provide a great look.


You can never go wrong with James Bond, and Spectre has some much-needed wardrobe advice for you as you enjoy the movie. Daniel Craig had a lot of wardrobe changes, with one of the significant outfits being a double-breasted overcoat and turtleneck sweater. If you want even a hint of James Bond in your outfit, the Tom Ford sunglasses are a great place to start.

The Best Offer

Although this movie is not very popular, it has a couple of styling tips for fashion enthusiasts and even those interested in upper-class interior design. Geoffrey Rush serves us some classy looks with three-piece suits and subtle colors while wearing gloves at all times. If you’ve been wondering how to combine gloves with suits, you know what to watch next.


This is the love story of Wallis Simpson and Edward VII, hence the name. In real life and the movie, Edward VII is well-known for his style, as one of the most photographed men in the world in the 30s. The bold patterns, soft colors, detachable collars, and exciting outfits are enough to pique your interest.


Another movie with Ryan Gosling looking good, Drive is a 2011 heist movie that received a standing ovation at the Cannes Film Festival. But the outfits are amazing, too, mainly focusing on rugged looks and driving gloves. You will see how Gosling combines boots and denim with Henley shirts.

American Psycho

Even psychological horrors have unique looks sometimes, and American Psycho is well-known for its style. The iconic business card scene especially displays power suits that any menswear fan will love. If you can stomach the harsh themes featured in the film, you can enjoy the combinations of peak labels, bold shirts, pinstripes, and ties.

Crazy, Rich Asians

The 2018 movie is well-known for having some fantastic outfits, mainly since most of the movie is featured in the Royal Wedding of Asia. The male characters mostly wore well-tailored suits and tuxedos, and while this might seem Western-style, you will notice that this has been replicated for the Asian male physique.

A Single Man

It’s not surprising that the first movie directed by Tom Ford was a costume success, and A Single Man is a great place to look for styling ideas while enjoying the heartwarming storyline. Taking place in the 1960s, there are different style vibes for the male characters. From T-shirts and jeans to make bad boy looks to collegiate layering and gentleman suiting, every man can find their style here.

The Royal Tenenbaums

Not many films have a lot of style ideas like The Royal Tenenbaums. The movie is based on a dysfunctional family, and everyone has their signature look. From the camel suit and sweatbands rocked by Luke Wilson to the retro tracksuits, you will see on Best Stiller; anyone can get inspired here.


Steve McQueen rocked the turtleneck look in this thriller from the late 1960s, but that’s not all you get with Bullitt. The movie offered a lot of style inspiration for masculine and classic looks, mainly focused on coats and blazers with a turtleneck as the layer. No wonder the Hollywood actor is called The King of Cool.

Funny Face

Although most people focus on the style of Audrey Hepburn when discussing Funny Face, Fred Astaire also served some fantastic looks. His style shows that accessories can change an ordinary suit into something special, as he rocks boater hats and neck scarfs. Once, he used a tie as a belt around his waist, something you should try next time for something classic.

Reservoir Dogs

A group of men wearing matching black suits is now always cool, and that’s because of Reservoir Dogs. This 1992 movie inspired many groomsmen and provided a good way for any guy to look like a boss. And, don’t forget your wayfarer glasses!
Next time you’re looking for an excellent movie to watch, you can check out these popular titles. While you enjoy the storyline, you just might find great inspiration for your next look.


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