What should men over 40 wear?


Life begins at 40.
Image source: Samuel Windsor

Anyone with half a brain knows that being 40 plus is a triumph, not a tragedy. You’re at peak earning power, you’re still young enough to do anything you want, and you know your own mind. Men over forty should dress with class – anything else is less than you deserve. Here are the simple wardrobe staples that will show you how to dress in your 40s and help you look your effortless best, with ease.

A good suit

Model 2 wearing onic Grey Suit From Samuel Windsor

A suit that fits well will look good at any occasion.
Image: Tonic Grey Suit From Samuel Windsor

Nothing is more depressing than a middle aged man in a badly-fitting suit. It doesn’t matter whether you’re a CEO or scratching away at the admin coalface, show some pride in yourself by dressing like a success story.

Can’t afford Savile Row? It doesn’t matter – an off-the-peg suit that fits you well is a fine thing. Go for a regular cut with structure to the shoulders and some shape in the waist. Trousers that fit are a must, and do be careful to get the length right. A half-break is the most wearable option.

The Idle Man says that if you’re 40 plus, you should: “[pay] more attention to the fit of your clothes and a colour palette that suits you.”

It’s worth bearing in mind that as you age, your skin tone lightens. Go for darker colours like navy or charcoal grey, and accessorise with bright socks, ties and pocket squares.



Featured product: Samuel Windsor jackets

As the Modest Man says, “some things (like distressed jeans) are especially inappropriate for older, more mature gentlemen.”  We agree. Why would you want to dress in clothes that suit youngsters still in their experimental stage? Tailored separates are the casual wear of choice for smart gents.

Buy yourself some jackets, and pair them with indigo jeans, chinos, moleskins, or grey flannels. Do check out the range of tweeds too – from mossy greens and heathery lilacs though to steely greys and blues, this most traditional of fabrics is supremely versatile. For a super-sophisticated look, wear a tactile cashmere mix pullover underneath.

And don’t forget your top layer too. Wool overcoats for winter and lighter weight Bomber and Harrington jackets for spring and autumn. Quilted jackets are another smart choice, ideal for both urban and rural wear.



Slacks cut a far more dashing figure than jeans.
Image source: Samuel Windsor

If clothes could talk, trousers would tell a tale of distress. As the team at GQ points out:

“Unless you’re hitting the gym every day, you’re probably going to have to relax your fits slightly from those drainpipe shapes you wore in your 20s and 30s.”

The rule for clothing your legs is super simple. Whether you’re wearing jeans, cords, moleskins or chinos, you want to be able to pinch roughly an inch between the fabric and your skin. For most gents, this equates to a standard straight cut trouser, but go slimmer or wider depending on your body shape.

When you’re over 40, try swapping your go-to trouser of choice from jeans to grey slacks. Easily dressed up or down, this wardrobe staple goes with everything from a long sleeved t-shirt through to a shirt, tie and blazer.

How to dress casually when you’re 40 plus


Confidence is the most important thing to wear.
Image source: Samuel Windsor

Relaxing at the weekend? Meeting friends for lunch? As a man in your prime, you need to look your youthful best without losing the gravitas your years bestow. Your clothing choices need to communicate uncluttered confidence.

We’re talking plain tees worn under quality cotton weekend or casual shirts. Try thick corduroy shirts for winter; for spring or summer, go for a simple stripe, gingham, or a classic check shirt. It’s important to keep your look clean, so if you do wear a patterned top, pair it with plain trousers like chinos or flannels.

Your forties are a great time to experiment with texture. Think cords or soft touch moleskin trousers, chunky Aran knit jumpers, and rugged tweeds. Hair wearing a bit thin? A linen flat cap looks great on men who’ve stood the test of time. For more advice on how to put together a casual outfit tailored to your specific size and shape, check out Samuel Windsor’s infographic guide to ‘Looking good over 40‘. Whether you’re short, tall, large or thin – it’s packed with helpful tips to keep you looking smart as you hit your prime.



Wear invisible socks for a streamlines, casual look.
Featured product: Samuel Windsor deck shoes

You know by now that there’s no substitute for Oxfords or Derbys for office or other formal wear. But once the working day is done, it’s time to switch to something more suitable for smart casual and informal engagements.

Over forties look fantastic in classic shoes and boots, but that doesn’t mean your footwear has to be boring. Suede brogues, for example, come in a range of colours besides tan, making them an excellent way to give your look a colourful lift.

Alternatively, why not give penny loafers a try? They’re the height of men’s fashion at the moment, but they really look best on older men. Wear yours with no-break or half-break trousers, and colourful contrasting socks.

Casual options like deck shoes come into their own when you’re 40 plus. The ultimate summer wear for mature gents, they’re the only option that really works with shorts. Wear yours with invisible socks to avoid looking like an overgrown boy scout.



A good quality watch and pair of sunglasses speak volumes
Image source: Samuel Windsor

You’ve done your experimenting, now is the time to show the world you know that less is more. You don’t want to be a clinking heap of cheap bling – apart from your wristwatch and wedding ring, you should really only wear a maximum of one other item of jewellery. The guys at Fashion Beans say: “Your forties is the time to raid your children’s university fund for wrist candy with real clout.” You might have grown up wearing a Casio calculator watch, but now’s the time to go strictly analogue. Buy the best you can afford.

Finally, leave wrap-around sports sunglasses for the young and inexperienced. Your eyewear should ooze sophistication – aviators, clubmasters or wayfarers are top picks for over forties.

Top tips for how to dress in your 40s

  • Own at least one decent suit that fits you properly. That way, you can look distinguished at the drop of a hat.
  • Switch the hooded sweatshirt for a smart casual jacket or blazer for a more mature look.
  • Swap your jeans for lightweight chinos, moleskin trousers or cords.
  • Layer up, and play with textures. Maturity is your friend when it comes to classic casual style.
  • Invest in a pair of penny loafers. This classic style looks best on older men.
  • Keep the accessories classic with an investment timepiece and sophisticated eyewear.

Do you have tips for dressing for the over 40s? If so we’d love to hear from you. Do pop over to our Facebook page and leave us a message.

Posted in What to wear guides.