Jeans for Men over 40: Your Ultimate Guide

18 minutes read
Jeans for Men over 40 Your Ultimate Guide

A pair of Men’s jeans are the epitome of a wardrobe staple. They’re versatile enough to wear for both casual and smart occasions (within reason), and when cared for, will last for years. However, jeans are a deceptively simple item of clothing when you’re over 40 – the slightest change in a seam can make a world of difference. This makes choosing the right pair a challenge for even the most style-savvy gent.

To make shopping for the perfect pair of jeans a little less painful and lot more successful, our ultimate guide to jeans for men over 40 covers the origin of jeans, fit, styles, denim varieties, colours, top brands to consider and the most important decision – ready-to-wear, made-to-measure or bespoke?

This guide is packed with information, so click on the list below to jump to a specific point that you’re interested in:

The origin of jeans

Why jeans are so popular

How to find the perfect pair of jeans

How to wear jeans and look great every time

Which is best – made to measure, bespoke or ready to wear jeans?

The top jeans brands for men over 40

The origin of jeans

Jeans were created and patented by tailor Jacob Davis and cotton seller Levi Strauss in 1873. A customer asked Davis to make a pair of hardy trousers that could handle rough farm work without ripping or tearing and from this humble request, the first denim jeans were born.

What made them so revolutionary was the use of rivets to strengthen the trousers at points of tension. They were such a hit that Davis asked Strauss, from whom he’d bought the fabric, if he’d like to form a partnership and the rest, as they say, is history.

Over time, men’s jeans transitioned from a functional piece of work clothing, into a fashion sex symbol – helped along by early cowboy films and James Dean’s films Rebel Without a Cause and The Wild One in the 1950s. Jeans simultaneously became a worldwide symbol for rebellion and casual wear, something that many other items clothing haven’t managed on such a scale.

Why jeans are so popular

Two simple factors: versatility and durability.

The durability that jeans offer comes from a construction method not found on any other trouser type. Rather than thread, rivets are used to join areas that face the greatest strain (such as around the pockets and the side seams). Using rivets to reinforce the seams, and a rigid fabric that becomes more comfortable as you wear them without losing strength, makes jeans one of the hardiest items of clothing around.

Jean’s versatility comes from the variety of fabrics, dyes and styles available that span the fashion gamut from minimalist and smart, to ripped and edgy. One pair of well-made, non-ripped, straight jeans can take you from Friday drinks at the pub to hanging around the house on Sunday morning.

How to find the perfect pair of jeans

What’s the best type of denim?

The traditional fabric for jeans is denim. The word denim was derived from a sturdy material produced in France called “Serge de Nîmes”, named after the region, where it was created.

Italian textiles producers in Genoa (hence the word Jeans) tried to replicate it but ended up with another twill-like fabric that became denim.

There are hundreds of types of denim from French and Japanese to raw and selvedge. A few of the more common types are:

Indigo– the ‘warp’ threads (those that run the length of the fabric) are dyed indigo, while the ‘weft’ threads (those that run the shorter width of the material) are white, so the denim is dark on one side, and white on the other.

Stretch– the thread is a blend of cotton and elastane or other plastic components to give it stretch and comfort.

Crushed– the denim treated so that it has a wrinkled appearance. Very 1980s.

Acid wash– the denim is treated with chlorine and pumice stone to give it a marbled, worn look.

Selvedge– has a tightly woven edge or ‘self-edge’ that prevents the denim from unravelling. You can see the edge when you roll up the cuffs of your jeans.

Raw– this denim is not washed or treated, so it has rough, stiff texture. It can leave traces of indigo dye behind if it rubs against anything.

Japanese – this type of denim is quite expensive as it is made on slow antique wooden shuttle looms, rather than the faster projectile looms used for most denim these days.

You’ll also find jeans made in fabrics other than denim such as cord or cotton twill.

Our Verdict: slight stretch
We believe that denim with a slight stretch is ideal for comfort and movement. Jeans made from raw denim are too stiff and can be quite uncomfortable.

What’s the best colour for jeans?

Initially, manufacturers made jeans with a dark blue (indigo) dye that would hide stains from the workmen that were wearing them. By only dying one of the two types of threads used to make the fabric (three blue to one white), the dye was kept on one side of the fabric and prevented the dye staining your legs (not a good look!). This method was particularly advantageous for workers who would sweat when doing heavy hands-on work.

This type of dark denim is still popular today and looks the most elegant for office casual and smart casual occasions.

Although they are trendy, light, faded jeans won’t cut it for the man over 40 who cares about his image. A lighter shade of jeans will not only make your legs look larger than they are but can detract from rest of your outfit. Quite simply, light jeans don’t look great unless you’re under 30 or a member of WHAM.

Our verdict: dark
At Alexandra Wood, we always recommend that you buy a richly dyed, dark blue pair with minimal detailing to give you the most flexibility for dressing up or down. We’ve created three shades which work well for a variety of looks and occasions.

Some jeans with a strong blue dye will fade over time to look more ‘worn in’. We’ve chosen fabric that has been designed not to fade, so your jeans always look as fresh as when you first bought them. This does, however, mean you need to dry-clean them. It isn’t an arduous task, despite expectations from our customers to the contrary. The jeans don’t need dry cleaning all that often, and the extra work is worth it.

What’s the best style of jeans?

The humble jean has seen quite an evolution since it was first designed in 1873. From flares to baggy legs, skinny to slim fit and boot cut, jeans have followed each and every fashion cycle. Here are just a few styles you’ll find hanging on the rack:

Skinny – This style is tight from the hip down to the ankle with a tapered leg opening. It generally is a low to mid-rise and a zip fly.

Stovepipe – Like the skinny but falls straight down from the knee—a very vintage style and best for extremely tall and slim men.

Slim fit – Slim but not tight, this style sits at the hip and flatters the line of the leg. It usually has a mid-rise and a zip fly.

Straight – As the name suggests, these classic jeans are cut straight up and down. There is a bit of variety in this style as they can sit on the hips or waist and have a button or zip fly.

Bootcut – Bootcut jeans generally sit at the waist and are slim through the thigh before widening from the knee downwards to fall over a pair of boots.

Relaxed/Baggy – These sit at or below the waist and are roomy in the seat and thighs with a straight leg. They are rarely flattering.

Flares – A style best kept for the vintage fashion lover, flares sit firmly at the hip and thighs before flaring out to the ground. These often have a button fly in keeping with the vintage style.

Our pick: Straight or Slim
They look good on everyone, go with everything and when made well, will flatter you for years.

How should jeans fit?

Not too tightly but not too loosely, either.

The high street has sold many skin-tight styles, from the stovepipes of the 1960s to today’s ripped skinnies, but only a tiny fraction of the population is young and slim enough to make them work.

Look for a pair of jeans that are slim enough to make you look sleek and elongate your legs, yet not so wide that they look in any way baggy. You should be able to see your shape, but they shouldn’t cut in or pull at any point around the waist, bottom or crotch. If you can’t sit down comfortably without adjusting them or worrying that your shirt will come untucked at the back, they aren’t for you.

They should also be longer than your legs to give you a half or full break in terms of length. This break is where the fabric bends above the cuff, so a portion of the hem sits on the top of your shoes. If there is no break, your jeans are too short. If they are too long and bunch up at the ankle, please see your tailor and have them properly hemmed.

What details should I look for when buying jeans?

The most important details are the rivets and the seams. Ensure the stitching is firm, and there are no loose threads.

Some brands place decorative stitching on the back pockets, but this isn’t necessary and draws attention to your rear end, which may or may not be a good thing.

Where should rivets be placed on jeans?

The top button should be riveted in place rather than sewn for strength, as should the fly if it’s a button-up style.

Jeans look the best when the buttons and stitching are subtle in colour and finish. After all, you want the fantastic fit and shape to stand out, not your buttons!

Settling the debate: zip fly vs button fly on jeans

It’s a matter of preference.

When Davis and Strauss invented jeans, a button fly was the norm – they didn’t add zips to Levi jeans until 1947.

Buttons are certainly more durable and less prone to snags and breakage than zips, and for denim puritans – this is the only option.

On the other hand, zips are far easier to use and work better visually on slimmer styles of jeans. Just lock the zipper by folding it down flat against the zip to prevent it from coming undone.

How and when should I alter my jeans?

Altering jeans should be restricted to shortening hems only. You’ll get a much better look if you take the time to find a pair that fit you perfectly everywhere else.

If you need to have your jeans shortened, ask your tailor can finish them with a matching thread. A pair of jeans altered conventionally can quickly ruin them so ask the tailor to finish them in the same style.

How to wear jeans and look great every time

We attribute the humble jean’s popularity to the fact that they bridge the smart to casual gap so perfectly. It’s just a matter of selecting the right combination of shirt, outwear and shoes.

Fool proof casual looks with jeans

Jeans and a T-shirt combination
Nothing says casual like jeans and a plain t-shirt. The cut and quality of clothing are crucial to pulling off any look successfully, so for a more grown-up style, we recommend wearing a high quality, slim fit crew neck t-shirt. Make sure you pair them with clean, smart trainers.

Jeans and jumper combination

Another classic. Choose a jumper made of 100% natural cotton or wool with a bit of texture, like our New York Moss Stitch merino wool jumpers. Layer a high-quality t-shirt underneath for comfort and pair with smart trainers.

Fool proof smart-casual looks with jeans

When the dress code is smart casual, you can create an appropriate outfit with a pair of dark indigo jeans (no embellishments) in a few ways:

Sports jacket and knitwear combination

This is an excellent look for those chilly days between seasons when it isn’t cold enough for an overcoat. Pair your jeans with a fine knit sweater in merino wool and layer a sports jacket over the top. The type of knitwear is significant here – you want it to be fine and 100% merino wool to keep you cool and comfortable under your jacket.

Sports jacket and shirt combination

The very definition of smart casual is wearing jeans with a button-down shirt with single cuffs (that means buttons) and a sports jacket layered over the top. We recommend avoiding business shirts as these can look odd with jeans and opting for a printed shirt to liven up your look.

Overcoat and jumper combination

An elegant overcoat like a covert, Chesterfield or car coat dresses up this otherwise casual look. Pair this look with a lovely scarf and lace-up boots for a sharp winter outfit.

What are the best shoes to wear with jeans?

Don’t underestimate the power of shoes – they have a massive impact on whether your outfit is casual, smart casual or formal.


  • Smart trainers: This does not mean running shoes! Simple trainers in leather or dark coloured canvas look great with jeans. Look for minimalist designs with few or no embellishments. Please only wear white if you can keep them immaculately clean.
  • Loafers: These are an acceptable option, but only in summer – their holiday vibe looks out of place in winter.


  • Chelsea boots: These are ideal for a smart-casual look and work equally well with a shirt and sports jacket as they do with an overcoat.
  • Lace-up boots: These tend to have a bit more personality and look great with an overcoat.
  • Brogues: Ideal for the shirt and sports jacket combination for a more dressed up or business casual look.

Which is best – made to measure, bespoke or ready to wear jeans?

To settle this debate, we need to understand exactly what each terms means.

What are ready-to-wear jeans? As the name suggests, these items are pre-made and can be picked up from a retailer, ready to be thrown on with your favourite shirt. No customisation is provided by the designer or retailer so you may not get an absolutely perfect fit.

What are made to measure jeans? In short, made to measure jeans are laser cut using either an algorithm (used by the likes of Spoke so customers can select preferences to create their ideal jeans) or pre-defined pattern which is modified to suit your measurements. A tailor or system will enter your measurements onto a CAD machine which will then cut your jeans. After this, real humans stitch each part of your jeans to create your unique pair.

What are bespoke jeans? In short bespoke means hand cut and made by an individual or individuals. Therefore, a true bespoke pair of jeans would have to be hand cut from scratch, and hand-sewn through to the finished product: no algorithms, no laser cutting.

Will the fit of a pair of bespoke jeans be superior to ready to wear?

Absolutely! After all, bespoke or made to measure are created to fit your unique measurements, rather than a generic set of measurements based on averages for height, weight, leg length and waist circumference.

The verdict: are bespoke or made to measure jeans worth the investment?

If you are searching for the perfect pair of jeans to wear out and about on the town, and you’ve got a little extra patience – a bespoke or made to measure pair are certainly worth the investment. They’ll look and feel great for years.

However, if you need a new pair more urgently, or know that you’ll be wearing them day in and day out, a high-quality ready to wear pair (like our collection) are a better investment.

Which brands make bespoke and made to measure jeans?

Levi’s Bespoke jeans at Lot 1

Having any item of clothing made fully bespoke will be more of an experience. You will also always get a superior fit, along with the chance to really get stuck into the process and enjoy it. Once measured, there’s no need to constantly return, so you could effectively re-order to your hearts content once your style and fit has been perfected.

Levi’s have an exclusive bespoke jean option (which Simon Crompton of Permanent Style discusses in this post). Levi’s bespoke jeans are made by Lizzie at Lot 1 – this is a fashion destination spot in Great Marlborough Street where you will need to book. Launched five years ago, it has been a huge success. This isn’t a process they’ve taken lightly and have chosen only the best tailors to uphold their legendary name. The pricing isn’t clear on the website, and I suspect that it varies depending on the denim and amount of customisation requested

Based on reviews from our customers and friends, Lizzie at Levi’s has a great understanding of a customer’s fit requirements, so the process when started sounds relatively straight forward. If you love Levi’s, then this is a great way to have your ideal pair made and, given their heritage, I have no doubt that they’ll pass the test of time.

Spoke made to measure jeans online

If you’re a man with little time to spare, want a pair that fits well, a process that isn’t too arduous, and a guarantee the brand will remake them for you if your measurements end up a little squiffy, then this is a great option.

Spoke have a fit finder which will ask you a few simple questions such as height, weight, age, waist size, in-seam length, whether you ever size up with other brands, your preferred fit, body shape, and how tight you fasten your wrist watch (to cross-sell you with other brands, I suspect). The numbers are crunched and ‘hey voila’, your size is formulated for you. You’ll then be presented with a number of trouser styles to select from with transparent pricing. Spoke’s pricing starts from around £99 for a made to measure pair of chinos which is rather reasonable.

Spoke’s offering is made to measure rather than bespoke. It’s a hands-off experience so you won’t ever have someone measuring you, nor will they be cutting your jeans with their own bare hands.

A few of our customers who have used Spoke say the process is simple and the quality is good. Some people reported issues with the fit and needed to send them back to be re-made (with free postage and a 200-day no-questions returns guarantee), which is comforting, but a bit of a faff.

Alexandra Wood

We’re big advocates for men wearing smart jeans that fit well and our made to measure jeans ensure that they fit you like a glove. We’ll take into account where you want to wear your jeans – whether it’s to the office, out to lunch, or travelling and ensure the jeans fit in a way that is comfortable for those activities.

Each made to measure order is based on our exclusive design and can be made in dark blue, mid blue or bright blue.

While it takes a little longer and costs a little more, having your jeans made to measure with Alexandra Wood takes the pain out of shopping for the perfect pair. Actually – it’s fun!

The top jeans brands for men over 40

With so much choice in a heavily saturated jeans market, it can be tricky to choose a pair of jeans that fit both you and the purpose you’re buying them for – whether that’s pottering in the garden or going out to lunch. To make this easier, we’ve looked at the top brands and sort out which ones tick the boxes for comfort, style, value for money, casual wear and smart casual wear.

Levi’s Jeans

Levi’s iconic, sturdy designs are the ‘go to’ pair of jeans for millions of people. Deemed affordable, sturdy, classic and reliable, there’s no wonder why they’ve become a global favourite.

Why type of denim does Levi’s use to make their jeans? Levi’s typically make jeans that are sturdy and rigid. This means minimal, if any, stretch so you’ll always feel like you’re ‘wearing’ a pair.

What style of jeans do Lev’s make? Levi’s is known exclusively for jeans and their style offering is vast, with every cut available from skinny to boot cut. The difficulty is knowing which style will flatter you most. We suggest trying on a few pairs in store with their super helpful staff (I bought a pair, and they knew exactly what size I was – better than I did I hasten to add). They even have a helpful guide online which talks you through their styles.

What colour jeans do Levi’s make? Levi’s come in a huge variety of shades, which may can be confusing for some. Depending on the style of Levi’s, their colour offering also varies. You’ll find that their best-selling classics such as Levi 501’s have the most variety of shades.

What sizes do Levi’s make their jeans in? Their waist sizes range from 26’’ waist through to 48’’ and offer leg lengths of 30’’, 32’’, 34’’ and 36’. They also cater for big and tall and create genderless jeans, making them pioneers in their dedication to making the best jeans available to everyone.

How much do Levi’s typically cost? Levi’s start from £80 a pair and the prices rise upwards for a full bespoke option. There are a limited number of stores who offer this service, along with their Levi’s tailor who can fix fallen studs or even embroider your name onto the pocket should you so desire.

Where can you wear Levi jeans? Our advice: wear casually for a cool off-duty look. Our preference would be to a dark denim pair which are a close enough fit that they’re comfortable but show that you indeed do have a pair of legs. Wear with T-shirts, sweatshirts, jeans and jumper and even a laid back, lumberjack style shirt or shacket. Never wear Levi’s with a sports jacket/shirt combination as it will look like you’ve tried to dress up your gardening jeans.

Armani Jeans

Armani make jeans under the Georgio Armani, Emporio Armani and A|X Armani Exchange brands.

Why type of denim does Armani use to make their jeans? Armani defy the rules  byusing a variety of materials for their jeans including standard denim, denim twill, 100% virgin wool, a wool-denim blend, selvedge denim and gaberdine cotton. The wool and wool-cotton blends offer a much softer overall appearance, with a brushed cotton like feel. Some blends are elasticated so have a little more stretch and may hug you more than a standard denim.

What style of jeans do Armani make? Armani primarily make slim and regular (straight) fit jeans. Their designs are true to brand: sleek, uncluttered and precise. This makes choosing a pair quite simple.

What colour jeans do Armani make? True to Armani’s house style, they stay relatively safe when it comes to colour with black, navy, blue and grey. Some pairs in the Emporio and Exchange lines offer a vintage washed or slightly ripped finish.

What sizes do Armani make their jeans in? Armani offer a 28” to 40” waist and 30” and 32” leg.

How much to Armani jeans cost? A pair of Emporio Armani branded jeans are around £160, with Georgio Armani pairs available around the £400 mark.

Where can you wear Armani jeans? A plain, dark pair from the Georgio Armani and Emporio Armani jeans lines would be suitable to wear for casual and smart casual events. The sleek, subtle designs make it easy to create outfits with knitwear, t-shirts, and casual button-down shirts.

Calvin Klein Jeans

Why type of denim do Calvin Klein use to make their jeans? Calvin Klein primarily uses standard denim with 98-99% cotton and 1-2% elastane for their slim jeans (the only ones really worth purchasing), with some pairs offering a higher percentage of recycled cotton.

What style of jeans do Calvin Klein make? Calvin Klein is a youthful, trend-led brand well-known for their jeans so expect a wide range of styles from skinny to slim, straight, tapered, relaxed and ‘dad’.  You’ll find a few pared-back styles which are worth looking at, but trend-led details like ripping, feathering, acid washing, and low rises abound so beware.

What colour jeans do Calvin Klein make? You’ll find the standard indigo, black, vintage blue together with a variety of greys, ice blue and even stone.

What sizes do Calvin Klein make their jeans in? Sizes lean toward the smaller end with jeans available in a 28” to 40” waist and 30”, 32” and 34” leg.

How much do Calvin Klein jeans cost? You’ll pay around £85 for a standard pair of slim jeans.

Where can you wear Calvin Klein jeans? Just like Levi’s, Calvin Klein jeans fall squarely into the casual wear category. Pair them with t-shirts, knitwear, and bomber jackets for a casual look with a bit of a street edge.

Hugo Boss

Why type of denim does Hugo Boss use to make their jeans? Given their small range, Hugo Boss make use of a variety of fabrics including standard denim, stretch and super-stretch denim varieties, a cosy brushed denim, and a micro structured denim made of 47% cotton, 33% polyester, 18% viscose and 2% elastane. As with other brands like Calvin Klein and Armani, Hugo Boss offer pairs using sustainable fabrics and recycled cotton.

What style of jeans do Hugo Boss make? In line with their brand, Hugo Boss jeans are simple and stylish with minimal detailing. Contrary to other trend-led brands, Hugo Boss offer classic shapes like regular (straight) fit, slim fit, tapered and relaxed. But honestly, even their relaxed style isn’t too baggy.

What colour jeans do Hugo Boss make? They stand by the classics – indigo, black, and blue, but do offer pairs in paler and vintage blues and greys. They also offer a small variety in finishes – primary a washed look and feathering.

What sizes do Hugo Boss make their jeans in?  Hugo Boss jeans are available in a 29” to 40” waist and 30”, 32”, 34” and 36” leg, so there are ample options for taller gents.

How much to Hugo Boss jeans cost? A top quality slim fit or regular fit pair will set you back around £120 – £140.

Where can you wear Hugo Boss jeans?  Hugo Boss jeans are a go-to for smart casual. With deep rich colours, sharp cuts and minimal detailing, their dark slim fit and regular jeans work well with shirts and blazers for casual office days and nights at the pub.

Hiut jeans – the newcomer

Hiut jeans are one of the newest jean companies on the block yet are already making their mark in the industry. Jeans is all they make and all they will ever make. Their jeans are made in their own workshops in Wales where they’re passionate about creating sturdy, stylish jeans that last.

Why type of denim do Hiut use to make their jeans? Study jeans need sturdy fabric so Hiut favour 100% Japanese selvedge denim, raw organic denim. You’ll feel like you’re wearing a pair of jeans in these.

What style of jeans do Hiut make? Solid, bullet proof jeans that will last you a century or two. They’re made to be a true classic jean that are robust and a nod to the original style of jean. 

What colour jeans do Hiut make? Hiut keep it simple offering only dark indigo jeans. They do offer a fashion printed pair, but we won’t talk about those…

What sizes do Hiut make their jeans in? They offer jeans in a 26” to 40” waist and 30”, 32” and 34” leg.

How much to Hiut jeans cost? Prices range from £185 to £245. Yes, they’re expensive, but a pair of Hiut jeans will last you for decades.

Where can you wear Hiut jeans?  Their regular and slim fit jeans (which aren’t too slim) have minimal detailing so you can’t go wrong when creating an outfit whether casual or smart casual.

Alexandra Wood

What type of denim does Alexandra Wood use?
We have found the lightest, most comfortable pure Italian cotton denim. At 98% denim cotton and 2% stretch and weighing only 500grams, they’re perfect for all seasons.

What style of jeans does Alexandra Wood make?Our jeans range evolved from a customer’s request for the perfect made to measure jeans and were so good that we just had to make them into a full range. We offer a straight fit that is slim enough to be flattering, but not so tight they need to be rolled on. We’ve kept the cut streamlined and use minimal detailing to make the jeans as versatile as possible.

What colour jeans do Alexandra Wood make? We live for dark denim so only offer jeans in dark blue, mid blue and bright blue. Our range of chinos make a good alternative if you’re looking to add a bit of colour to your casual/smart-casual wardrobe.

What sizes does Alexandra Wood make?  Our ready-to-wear jeans are made in a 32” to 38” waist and a 32” and 36” leg. We also do made to measure so you’ll always get the perfect fit.

How much does a pair of Alexandra Wood jeans cost? Our jeans are 175. They are made to last, and when cared for well, will be your go to pair for years.

Where can you wear Alexandra Wood jeans? Our jeans are a perfect combination of style and comfort. They’re the ideal piece to create a smart tailored look that will successfully take you from a shopping trip to a Michelin starred restaurant.

How to care for your Alexandra Wood jeans The reality is that jeans don’t need to be washed as much as you think and are designed to be left alone and simply spot cleaned as required (Just a little dab with a sponge). You can wash conventional jeans at 30-40 degrees but will shrink and then give again when they’re worn.

However, with our jeans, we advise that you dry clean them. You may think this is too much work, but our customers have confirmed that it hasn’t been a problem.


A round up of our jeans debate

Which jeans are best for casualwear? Levi’s

Which jeans are best for smart wear? Armani

Which jeans are best for comfort? Alexandra Wood

Which jeans offer the best quality for money? Alexandra Wood or Hugo Boss

Which jeans offer the best style for men over 40? Alexandra Wood or Hugo Boss

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