Dressing for a Date - A Man’s Ten Point Guide

How do you dress for a date? Do you wear casual clothes, do you like to look dapper or don’t you bother? What does a woman on a date expect of a man in terms of his appearance? 

A few years a friend of mine carried out a straw poll of her female friends at my request to see how men were getting on, from the woman’s viewpoint, in the dating world. The results were mixed, so I’ve put together a ten-point guide to help men look their best. 

I’m sure most of you won’t need this advice, but for those who are less confident here are some pointers:

1. 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 George Clooney — it's the effort and the thought that counts.

2. The same goes for the photo that you use online. I’ve seen profile photos where the man’s pint of beer is larger than his image, or where his dog has been given pride of place in the picture. Avoid 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. Avoid bare chests (or bare anything for that matter), however muscular, I can assure you that your unclothed body won’t plunge any woman into paroxysms of desire.

3. Wear smart, good quality, clean and, above all, well-fitting clothing — jackets, good quality knitwear. Go for smart casual with style.

4. Avoid busy, mismatching clothes. If in doubt, select plain, well-cut styles. 

5. Soft tactile fabrics go down well.

6. Wear good shoes. Poor or dirty/worn footwear will spoil any look. 

7. If you go for jeans, wear dark, raw denim that fits well and isn't artificially distressed. 

8. Good grooming is essential. Clean, scrubbed, smelling nice, minimal excess hair. 

9. Are your teeth well looked-after and clean? If your breath smells, visit a dentist, get advice, and use a breath-freshening mouthwash.  Chewing gum before a date, but not during, can be a help.

10. If in doubt, get style advice from a knowledgeable friend, a personal stylist (Sarah Gilfillan of Sartoria Lab, who specialises in helping men look their best, has always been a great help to me) or read a good men's style blog (like Grey Fox Blog!).  Alternatively follow the many stylish older men on Instagram who seem to be able to dress well with minimum fuss. 

I’ll be giving more detailed advice on some of these points in future features. Meanwhile, happy dating!

David Evans

Writer and Founder of Grey Fox Blog

David Evans (63) founded Grey Fox Blog in late 2011. As a man with little interest (then) in  fashion, he decided, for no particular reason, to set out on a search for style. The blog developed into a celebration of the best of menswear, cars, watches, food and drink. He also writes about the challenges and privileges of age and has addressed the subject of dating on many occasions on his blog.


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