Fashion is ever-evolving, but some styles have stood the test of time, thanks to iconic men who have shown us the power of classic combinations. These timeless outfits have been embraced by celebrities across generations, demonstrating how enduring style never goes out of fashion. Let’s dive into some of these beloved menswear staples that every men’s wardrobe should have.
1. The Leather Biker & White T-Shirt: When you think of rebellious cool, Marlon Brando’s iconic look in The Wild One might come to mind. The combination of a black leather biker jacket, white crew-neck T-shirt, and selvedge denim jeans has become an eternal marker of style across the decades. From the hippie vibes of the 1970s to the indie rock scene of the 2000s, this look has adapted but never faded. The key here is simplicity. Steer clear of over-accessorizing; the jacket, tee, and jeans do all the heavy lifting.
2. The Shearling Jacket & Grey Jumper: Robert Redford solidified the shearling jacket’s place in fashion history with his effortless pairing of a grey jumper and shirt in Downhill Racer. This look is not just warm but stylishly reliable. The beauty of this ensemble is its versatility – it pairs well with jeans, tailored trousers, or chinos. Just be cautious with tan chinos unless you’re aiming for a retro commentator vibe. A shearling jacket is an investment, but one that pays dividends in style.
3. The Sweatshirt & Chino Trousers: Paul Newman had the knack for combining a preppy classic like chinos with a relaxed sweatshirt, creating a smart-casual look that works for almost any occasion. The contrast between the formality of chinos and the laid-back nature of sweatshirts creates a harmonious balance. This outfit is ideal for those off-duty days when you still want to look put together without much effort.
Product on Amazon: JMIERR Men’s Chino Pants Casual Stretch Waist Tapered Trousers with Pockets
Brand: JMIERR
Price: 32.99 USD
Rating: 4.3 Total reviews: 269
Top Review from US: “JMIERR has truly impressed me with its quality and fit! Despite being a budget-friendly brand, their clothes feel premium, fit perfectly, and look great. I wasn’t expecting such amazing quality at this price point. Whether it’s casual wear or something more formal, their pieces are stylish and comfortable. Highly recommended for anyone seeking great fashion without breaking the bank!”
Shopping on Amzon >>
4. The White T-Shirt & White Jeans: Channel your inner Steve McQueen with this monochrome combination. While it might seem simple, choosing the right shades of white can elevate this look to summer-ready perfection. McQueen’s tactic of wearing jeans slightly darker than the tee adds depth and flair. If it’s chilly, swap your short sleeves for long sleeves or add a bomber jacket for that extra layer of cool.
5. The Casual Shirt & Tailored Trousers: Alain Delon mastered the art of looking both relaxed and refined with a casual shirt paired with tailored trousers. This look is a blank canvas, allowing for personal experimentation. Whether you add a shawl collar cardigan for a preppy touch or leave the shirt unbuttoned for a more laid-back feel, the possibilities are endless. This combination is versatile enough for almost any outing.
Product on Amazon: Floerns Men’s Fold Pleated Tailored Pants Work Office Business Trousers Pants
Brand: Floerns
Price: 43.99 USD
Rating: 3.7 Total reviews: 23
Top Review from US: “Very nice pant. Very good quality. Very well made.”
Shopping on Amzon >>
6. The Breton Top & Tailored Blazer: James Dean’s affinity for the Breton top layered under a tailored blazer is a lesson in effortless style. This ensemble not only celebrates the classic nautical stripes but also introduces a touch of formality with the blazer. For a more polished version, pair the Breton tee with a full navy suit. This timeless combination has been a staple since the days of Dean and continues to make waves in men’s fashion.
7. The Roll Neck & Double-Breasted Blazer: Michael Caine’s embrace of the roll neck under a double-breasted blazer exemplifies winter sophistication. The roll neck’s practicality and the blazer’s sharp aesthetics create an unbeatable duo. Whether you’re headed to the office or a night out, this look is both warm and polished, suitable for various settings and events.
Product on Amazon: Men’s Slim Fit 2 Piece Suit Double Breasted Business Wedding Prom Tuxedo Suits Blazer & Pants Set
Price: 69.99 USD
Rating: 4.2 Total reviews: 557
Top Review from US: “Had to change and tighten some of the buttons but this was a hit. Fit as expected. Very comfortable and good quality”
Shopping on Amzon >>
8. The Field Jacket & Button-Down Shirt: Montgomery Clift showed us how to transform a military staple like the field jacket into a menswear marvel. Layering it over a button-down shirt brings a casual yet thoughtful touch to the ensemble. This pairing is best complemented with slim-fit chinos or jeans, creating a look that is as timeless as it is stylish.
Product on Amazon: Legendary Whitetails Men’s Navigator Fleece Button Up Shirt
Brand: Visit the Legendary Whitetails Store
Price: 39.99 USD
Rating: 4.6 Total reviews: 11972
Top Review from US: “This flannel is warm and very classy, colors are brief I love thst, very soft and fits perfectly. I will buy many many more from this company. Worth every penny…🙂”
Shopping on Amzon >>
Fashion should be fun, and experimenting with trends is part of that enjoyment. However, it’s vital to ensure your outfit has a cohesive theme. Pick a couple of trends you want to highlight, and build your outfit around them. This approach results in a polished, intentional look rather than a trendy mishmash.
Related posts:
9 Menswear Looks That Will Never Go Out Of Style
