How to Dress Like A Badass In Your 40s

If you like having fun with fashion, growing into your 40s and beyond doesn't mean you should stop. For these dapper men in their 40s and 50s, wearing clashing pieces and bold prints is not a fashion faux pas - it's a fashion statement. These gentlemen are popularizing men's style and individual expression at any age.

Eric Rutherford wearing Black Chinos, Hot Pink Crew-neck Sweater, Grey Floral Blazer
Go for sophisticated style in a grey floral blazer and black chinos.View Details
Alessandro Manfredini wearing Red Lapel Pin, Olive Camouflage Chinos, Light Blue Dress Shirt, Brown Plaid Waistcoat
Bump up your off-duty style game in this combo of a brown plaid waistcoat and olive camouflage chinos.View Details
Nick Wooster wearing Brown Wool Dress Pants, Blue Chambray Dress Shirt, Olive Camouflage Wool Waistcoat, Olive Camouflage Wool Blazer
Pair an olive camouflage wool blazer with brown wool dress pants to look like a modern gentleman. For something more on the daring side to finish this outfit, complete your look with brown leather casual boots.View Details
Domenico Gianfrate wearing Black Leather Tassel Loafers, Black Chinos, Black Overcoat
Inject personality into your daily styling arsenal with a black overcoat and black chinos. Why not introduce black leather tassel loafers to the equation for an element of refinement?View Details
Men's Black and White Polka Dot Scarf, Brown Chinos, White Dress Shirt, Dark Green Camouflage Wool Blazer
Marrying a dark green camouflage wool blazer with brown chinos is an on-point option for a casually sleek look.View Details
Men's Blue Beanie, Black Leather Derby Shoes, Grey Check Wool Dress Pants, Camel Overcoat
A camel overcoat and grey check wool dress pants are absolute essentials if you're piecing together a classic closet that matches up to the highest sartorial standards. When in doubt about what to wear on the footwear front, complement this ensemble with black leather derby shoes.View Details
Men's Navy Beanie, Grey Chinos, Blue Denim Shirt, Dark Brown Houndstooth Blazer
If the situation calls for a polished yet kick-ass look, you can rock a dark brown houndstooth blazer and grey chinos.View Details
Men's White Pocket Square, Dark Brown Suede Oxford Shoes, White Dress Shirt, Navy Vertical Striped Blazer
Go all out in a navy vertical striped blazer and a white dress shirt. To give this ensemble a more polished spin, why not complement this getup with a pair of dark brown suede oxford shoes?View Details
Men's Dark Brown Leather Oxford Shoes, Navy Chinos, White V-neck T-shirt, Navy Blazer
This classic and casual combo of a navy blazer and navy chinos is very easy to pull together without a second thought, helping you look amazing and prepared for anything without spending a ton of time combing through your wardrobe. Dial down the casualness of this outfit by sporting a pair of dark brown leather oxford shoes.View Details
Justin O'Shea wearing Black Dress Pants, White and Purple Vertical Striped Long Sleeve Shirt, Black Waistcoat, Violet Blazer
You're looking at the solid proof that a violet blazer and black dress pants look awesome when worn together in an elegant getup for a modern guy. A pair of dark purple leather dress boots can integrate really well within plenty of combos.View Details
Justin O'Shea wearing Black Dress Pants, White Dress Shirt, Black Waistcoat, Dark Brown Paisley Overcoat
A dark brown paisley overcoat looks so elegant when worn with black dress pants for an outfit worthy of a British gentleman.View Details
Men's Brown Leather Loafers, Orange Chinos, White Dress Shirt, Grey Plaid Blazer
Dapper up in a grey plaid blazer and orange chinos. Brown leather loafers are a fail-safe way to breathe an added touch of refinement into your look.View Details
Men's Navy Leather Double Monks, Beige Floral Chinos, White Dress Shirt, Navy Wool Double Breasted Blazer
This smart casual combination of a navy wool double breasted blazer and beige floral chinos is super easy to put together without a second thought, helping you look stylish and ready for anything without spending too much time rummaging through your wardrobe. For a more refined twist, round off with navy leather double monks.View Details
Nick Sullivan wearing Dark Brown Leather Oxford Shoes, Light Blue Chinos, Grey Crew-neck T-shirt, Tan Double Breasted Blazer
This combo of a tan double breasted blazer and light blue chinos will add effortlessly elegant essence to your ensemble. A pair of dark brown leather oxford shoes will give a more sophisticated twist to an otherwise standard ensemble.View Details
Justin O'Shea wearing Black Leather Derby Shoes, Charcoal Dress Shirt, Black Waistcoat, Navy Suit
You'll be surprised at how super easy it is to throw together this classy getup. Just a navy suit worn with a black waistcoat. A pair of black leather derby shoes introduces just the right amount of casualness to this outfit.View Details
Alessandro Manfredini wearing Charcoal Dress Pants, Beige Long Sleeve Shirt, Olive Wool Waistcoat, Beige Field Jacket
Get into dapper mode in a beige field jacket and charcoal dress pants.View Details
Aiden Shaw wearing Black Suede Derby Shoes, Black Floral Chinos, Burgundy Crew-neck Sweater, Black Suede Bomber Jacket
This relaxed pairing of a black suede bomber jacket and black floral chinos is a tested option when you need to look stylish but have no extra time. You can get a bit experimental with footwear and complement your look with black suede derby shoes.View Details
Men's Black Knit Scarf, Pink Floral Pocket Square, White Dress Shirt, Grey Vertical Striped Suit
Pair a grey vertical striped suit with a white dress shirt and you'll be the picture of polish.View Details
Men's Dark Green Plaid Canvas Tassel Loafers, White Chinos, White Polka Dot Dress Shirt, Black Cotton Blazer
Marrying a black cotton blazer with white chinos is an on-point choice for an effortlessly smart outfit. Dark green plaid canvas tassel loafers will bring a dash of refinement to an otherwise mostly dressed-down look.View Details
Alessandro Manfredini wearing Beige Floral Bow-tie, Olive Camouflage Cargo Pants, Blue Chambray Long Sleeve Shirt, Grey Plaid Waistcoat
A grey plaid waistcoat and olive camouflage cargo pants are the kind of a never-failing combo that you so awfully need when you have zero time to spare.View Details
Nick Wooster wearing Brown Leather Derby Shoes, Navy Shorts, White Long Sleeve Shirt, Navy and White Floral Blazer
Breathe new life into your day-to-day casual fashion mix with a navy and white floral blazer and navy shorts. Rock a pair of brown leather derby shoes to avoid looking too casual.View Details
Men's Navy Crew-neck T-shirt, Light Blue Denim Shirt, White Long Sleeve Shirt, Navy Trenchcoat
Infuse style into your daily styling repertoire with a navy trenchcoat and olive chinos. Bring a playful vibe to this outfit by rounding off with charcoal athletic shoes.View Details
Men's Black Suede Loafers, Blue Jeans, Light Blue Long Sleeve Shirt, Navy Vertical Striped Blazer
Try teaming a navy vertical striped blazer with blue jeans to pull together a casually cool ensemble. To introduce a little classiness to this look, add a pair of black suede loafers to this getup.View Details
Justin O'Shea wearing Navy Vertical Striped Dress Pants, White Dress Shirt, Navy Vertical Striped Waistcoat, Mustard Overcoat
Make heads turn by opting for a mustard overcoat and navy vertical striped dress pants. Complement your outfit with a pair of burgundy leather oxford shoes et voila, your ensemble is complete.View Details
Men's Purple Scarf, Beige Floral Chinos, Blue Long Sleeve Shirt, Navy Cotton Blazer
The pairing of a navy cotton blazer and beige floral chinos makes this a really well-executed getup.View Details
Nick Wooster wearing White Dress Shirt, Black Cardigan, Grey Plaid Suit, Charcoal Gilet
For a look that's nothing less than GQ-worthy, choose a charcoal gilet and a grey plaid suit.View Details

Do you like the featured outfits? These are some of the most stylish and popular combinations out there. But you can also filter out the outfits you see to match your own clothes.

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