Wake Up Older Dating Men – how to get stylish!

6 mn read

So, she’s agreed to go out with you on a date and you’re well-groomed, dashingly well-dressed and generally ready to sweep her off her feet. Or are you? Internet dating is now big. But, despite its growth, I’ve been hearing a lot from woman friends of their disappointment at the poor efforts made by older men when dating.

I write a blog about my search for style as an older man so have more a passing interest in how we present ourselves to the world – and the picture, by some accounts, isn’t always good. What is the woman’s experience? Where are men going wrong? What are they doing right? What advice can be given to the older man looking to date successfully?

This e-mail is typical of the comments I’ve had from older women in the dating game:

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“At the ripe old age of 44 – and with three small children – I recently decided to dip my toe into the murky waters of internet dating. I was anxious and excited at the same time but there seemed to be a rather depressing recurring theme online. Most of the men I fancied were a good ten years younger than me. They were the ones who stood out from the crowd – presenting themselves with a decent haircut, a smart shirt or cool t-shirt, some kind of “style” that said they still cared about their appearance. I wasn’t specifically looking for someone who worked in fashion, or who was even particularly fashionable, but the men in my age bracket seemed to be stuck in some kind of sartorial rut.

So I chatted to my other single older woman friends about it and it seemed to be a common problem. Where are all the stylish single older men? How difficult can it be to purchase a decent pair of straight-leg jeans, decent trousers a grey or navy t-shirt or sweatshirt and a smart pair of shoes, jacket, tie or suit? This is not cutting edge fashion; it’s just a smart, simple, casual and classic look that should be easy to achieve by shopping on our high streets.

Do men reach a certain age and give up on looking after themselves? I would have thought most single men would be trying to make the most their looks especially as let’s face it, with internet dating, you have one chance to make a good first impression and whether you agree with it or not, it’s going to be based on your profile photos first and foremost.”

I discussed these matters with a well-known personal stylist, Sarah Gilfillan. Sarah occasionally helps me out on the blog and there is little she doesn’t know about dressing a man well. As a stylist, she works mainly with men, helping them select styles and buy clothes. To my delight she agreed to carry out an informal survey of women over 40 (contacted through Twitter, Facebook or social contacts) who’d tried internet dating.

We wanted to see what view they took of the men they met – were they trying hard enough? What could they do better? Is there any advice we can give to men who are finding it difficult to achieve a stylish look for a date?

This is Sarah’s report on the information she gathered:

“I sent out a short survey to find out how women liked to see guys over 40 dressed for dates. In general terms, when asked how they liked their man to dress, women want to see a man looking smart, groomed, and wearing good quality, well-fitting clothing. There seemed to be a slight leaning towards soft tactile fabrics – like cashmere sweaters, velvet jackets and soft brushed cotton shirts – all the better to cuddle up to!

It was pretty clear what they didn’t like on their guys over 40: baggy jeans, bright logo tees, trainers, and poorly fitting clothes. Men tend to wear over-large garments, which look sloppy. There were a few comments about mismatched items – either in terms of colour/pattern/fabric or the styles ie: walking trousers and a smart shirt.

No one thought guys over 40 should stop wearing jeans, as long as they’re dark, smart, fit well and are not too faded, ripped, skinny, or showing pants! Worn with a smart, plain t-shirt, polo shirt or casual shirt and perhaps a v-neck or half zip sweater, most felt that jeans are good weekend staples.

Many favoured boots for casual wear as an alternative to trainers – desert boots, Chelsea boots, Redwing boots all came up as ones they liked. The other favourite was the ever- popular pair of brogues.

For a smarter look – going out for dinner – nearly all said smart jeans again, or trousers/cords and a shirt, possibly with a smart jacket and worn again with brogues or smart shoes. Interestingly, only one person said a suit.

Nearly all of the women asked said that grooming was very important, but not overly groomed TOWIE style (which they found a complete turn off)! Most preferred clean-shaven, but some were happy with a beard as long as it was not too long or scruffy. All said regular haircuts were a must – even if there’s not much left, it needs to be neat round the edges.

Other aspects mentioned were tidying up nose and ear hair, and clean short nails – fingers and toes! There were mixed views on aftershave – one said “lots so it wafts” and some said it wasn’t important. It generally seemed that the ladies did like some sort of scent (I guess to denote that you’re fresh and clean) but not to go overboard.

One of the other things that cropped up was the importance of accessories, helping to make an outfit look groomed and smart and also contributing to a more modern, youthful look when chosen carefully. Colourful socks, good quality belts, bags and wallets plus hats – either flat caps/baker boy style/trilby (maybe as a distraction from thinning hair?) were items mentioned.

Every woman, bar one, said that it made their man more attractive to them when they were better dressed. Good advice! But if you are feeling intimidated by this or think it’s shallow, you might be cheered by the couple of girls who said; ‘he’s a bit of a scruff, but I love him’ and ‘I knew I was marrying a scruffy muppet so no problem!’ I would still argue though that you should get ahead in the dating game by not being a “scruffy muppet” but dressing well and giving yourself an edge over all the other men.

So, gentlemen, whatever you may think, the women’s perception is that older men entering the dating game aren’t trying their best. As one woman remarked, ‘We make all the effort only to find that the man hasn’t even tried to look presentable.’

The overall conclusion was that simple, smart, classy and well-fitted clothes work. You don’t need to try to be too young or fun, just find your own style and make sure it fits well. Update your look with interesting, quality accessories to keep it fresh and modern.

So, with Sarah’s report ringing in our ears, what advice can I give to you for dressing and preparing for a date? Here are a few fundamental points:

Show that you care by demonstrating that you’ve tried hard with your appearance. You may not always get it right – the woman won’t be expecting David Gandy – it’s the effort and the thought that counts.
The same goes for the photo that you use online. Don’t use an image of you in your budgie smugglers on the beach last year, from your employers’ website, or picking up your degree certificate 20 years ago – select a photo that shows you as you are now in smart but casual clothes in a neutral situation and certainly not trying to look sexy.
Wear smart, good quality, clean and, above all, well-fitting clothing – jackets, good quality knitwear. Go for smart casual with style. Proper fit is everything when it comes to selecting clothes.
Avoid busy, mismatching clothes. If in doubt, select plain, well-cut styles.
Accessories can add to a stylish look, showing that you’ve thought about your appearance.
Soft tactile fabrics go down well.
Wear good shoes. Poor or dirty/worn footwear will spoil any look.
If you go for jeans, wear dark raw denim that fits well and isn’t artificially distressed.
Good grooming is essential. Clean, scrubbed, smelling nice, minimal excess hair.
Are your teeth well looked-after and clean? If your breath smells, visit a dentist, get advice, use a breath-freshening mouthwash such as the excellent Ultra Dex.
If in doubt, get style advice from a knowledgeable friend, a stylist like our own Sarah Gilfillan of Sartoria Lab or read a good men’s style blog like Grey Fox Blog.
Make an effort; you can be sure that your date will have done. Show self-respect, and respect for her, by trying your best. It’s not my place to tell you how to behave during the date, but show interest, ask questions, don’t just talk about yourself.
Enjoy yourself!