Expert Guide to Finding the Perfect Fit of Jeans for People Over 50 – I Tried on Over 60 So You Don’t Have to and These Are the Best

You might not wear jeans to a wedding, but apart from that, there are jeans for every occasion these days.

You can wear loose, baggy jeans with a turtleneck to the office, or with sleek, tailored flared shoes and a velvet jacket you’re ready for a cocktail party.

These days, the average woman is expected to own as many pairs of jeans as she does earrings – one for every conceivable event in her life, from walking the dog to a job interview – and, frankly, we’re spoiled for choice.

Marks & Spencer offers eight denim styles, and John Lewis’s total is ten. But we need to know our way around these many jeans styles to maximise their potential.

With that in mind, I tried on 60 pairs of jeans from the best stores in the season’s four key styles.

After much gyration in front of the mirror—some panting and eye-rolling and a lot of grimacing—I’ve narrowed it down to ten of the most wearable and versatile wide-leg, flare, bootcut, and straight styles. (If you want skinnies or cigarettes, they’re available, but they’re not at the top of my list for fall.)

Generally, most brands offer their popular models in six color variations, including black and gray and sometimes leopard. However, I am talking about a blue mid-tone, unless otherwise stated.

THE WIDE BUNCH

On the catwalk at the Gucci Cruise 2025 show

Pinstripe Bag, £50, gap.co.uk

Gap’s ‘high rise stride’, £55, gap.co.uk

Baggy jeans, £35, johnlewis.com

The easiest way to upgrade your jeans is to add volume. It’s that simple. We’ve reached the point where your 20-something cousin is walking around in jeans that from a distance look like a slouchy A-line maxi skirt. But how do we pull this look off?

First of all, don’t assume that loose legs will make your thighs look bigger (often the opposite is true). Aim for the middle, which is usually described as ‘wide legs’ rather than ‘barrel’, ‘baggy’ or ‘palazzo’.

I tried on a few barrel styles – roomy and tapered at the bottom – and felt like I’d left the house in an emergency and grabbed a pair of 19-year-old jeans. I’m of the opinion that anything wide in the thighs and narrow at the bottom is not going to do you any favors, so that rules out carrot cuts and mom jeans.

I also say no to cargos, another wide leg style but with pockets on the legs. Tailored cargos can look smart, but it’s hard to find a flattering cargo jean style (I tried). And palazzo styles, the very wide swooshy ones, only work if you have narrow hips and are tall.

So I would go for wide legs and flared shoes – and these are the best ones you can find on the high street.

First up, the high rise wide jeans from M&S (£35, marksandspencer.com). To be honest, I’d never tried on a pair of M&S jeans before. I’ve always assumed you get what you pay for with jeans, so I’m surprised to report that these are spot on.

High rise – like the waistband knot that covers your belly button – is the most flattering and what we should all be wearing right now. These are well cut, flowy from the hip, in a good quality denim – firm but not heavy with just the right amount of stretch to give you comfort plus a bit of a corset effect.

I would buy them in black, for extra elegance in the office and evening.

Length matters: cropped is not the look of the moment. M&S offers its top denim styles in small, regular and long. I am nearly 5ft 9in and take a regular.

Other wide-leg jeans worth mentioning include the indigo straight leg jeans from John Lewis (£59, johnlewis.com). They are called ‘straight’, but they have about the same shape as the wide jeans from M&S, only in my size they are a lot roomier.

I like them because of the starchy material and the yellow stitching, which makes them stylish enough to wear to the office with a blazer.

Gap’s ‘high rise stride’ in a stretch denim (£55, gap.co.uk) are fitted through the waist and hips with a relaxed wide leg. Don’t be put off by the detachable denim belt. These are flattering at the bottom with good sized pockets, although the raw hems – designed to look like you’ve taken them off a few times – do make them a little more casual.

Gap’s baggy pinstripe style (£50) is looser and has a mid-rise (not high) but is still flattering.

There’s a fine line between dad jeans and baggy jeans. The Richmond baggy jeans from John Lewis (£35, johnlewis.com) don’t sit high enough on the hips. River Island’s wide leg (£50, riverisland.com) with two front pockets that were too tight.

Marks & Spencer’s high rise wide jeans, £35, marksandspencer.com

Dark indigo straight leg jeans from John Lewis, £59, johnlewis.com

River Island’s wide leg style, £50, riverisland.com

FLARES AND BOOTCUTS

A word about flares. When they fit well, they can look very smart and smart, especially when worn with a cropped or waist-length coat. They should never be tight – forget the seventies and wear your flares slouchy and looser on your leg.

Bootcuts or slim flares can be a neater fit and are always flattering. M&S is first again with its high-waisted crease-front slim flare (£39.50).

I am beginning to see why M&S are the market leaders in women’s jeans; you get great value for money and I would happily choose these over most designer brands. These are also worth getting in black.

For a different bootcut style, try Zara (£29.99, zara.com). They have a looser fit and a longer leg. They may be less formal, but they are cooler and look better with boots with a mid-height heel.

As for roomier flares, I’ve gotten more compliments on my old, sloppy Me+Em flares with contrast denim panels (not for everyone) than on anything I’ve worn below the waist. The current Me+Em flared style is a side-fastening with plenty of stretch (£175, meandem.com ) and, like all Me+Em trousers, they look good on your bum and legs. However, I miss the front fly and they look a little too stretchy and therefore lack the naughty glamour that flares need.

I would go for the subtle flare with two front patch pockets (£175) from Me+Em instead. As the name suggests, these shoes won’t scare you off and still look tip top.

With all of these wider styles, it’s important to keep your outerwear neat and fitted, otherwise you’ll quickly look overstuffed.

Flared jeans, £39.50, marksand spencer.com

Bootcut mid-rise, £29.99, zara.com

Slim flare with front crease, £39.50, marksand spencer.com

Subtle Flare, £175, meandem.com

RIGHTS OR COLUMNS

Some people will always love a straight fit jean, and the classic vintage style, loose around the hips and thighs Levi’s 501 ’90s’ (£100, levi.com) are still a safe choice and have the praise label, although I don’t find it does much for me.

I would go for the relaxed fit high waist jeans from Zara instead (£29.99). This particular straight style has a neat little turn-up with red detailing on the seams. Normally I wouldn’t recommend a turn-up (they do make deep ones for autumn) but these look smart.

There’s always a place for a pair of black straight leg jeans in your wardrobe. They have the advantage of showing off your boots or shoes (patent or red) and can double as a smart casual tuxedo. And Next’s column jeans (£32, next.co.uk) fit well and are affordable.

In general, be careful with high-rise, straight fit, rigid ankle jeans (as they’re called), because they can look like don’t-really-care, any-old jeans. And our fall jeans are all about looking like we know exactly what we’re doing.

Column jeans, £32, next.co.uk

Relaxed fit straight jeans, £29.99, zara.com

501 90’S jeans, £100, levi.com