Select Page
Subscribe to Podcast

Subscribe on iTunes
Subscribe on Stitcher
Subscribe on Google Play
Subscribe on Spotify

<script><!-- [et_pb_line_break_holder] -->var readingBar = document.getElementById("ds-reading-bar");<!-- [et_pb_line_break_holder] -->addEventListener("scroll", function (event) {<!-- [et_pb_line_break_holder] --> var total = document.body.scrollHeight - window.innerHeight;<!-- [et_pb_line_break_holder] --> console.log(total);<!-- [et_pb_line_break_holder] --> console.log(scrollY);<!-- [et_pb_line_break_holder] --> var percent = (window.scrollY / total) * 105;<!-- [et_pb_line_break_holder] --> if (percent > 4) = percent + "%";<!-- [et_pb_line_break_holder] --> if (percent == 100) readingBar.className = "finished";<!-- [et_pb_line_break_holder] --> else readingBar.className = "";<!-- [et_pb_line_break_holder] -->});<!-- [et_pb_line_break_holder] --></script>


Dear Henry, I am a young man in my early twenties and I have been on the dating scene for a little while and have dated girls my own age. I recently met a lady, who is quite a bit older than me. She is very stylish and sophisticated. I asked her out on a date and she accepted.

I am now in a panic as I don’t know what to wear. My usual outfit of T-shirt and jeans is not going to cut it.  What shall I wear?

Hopelessly Confused, C. C.  Chicago, USA


Dear Mr C.

The charms of an older woman. Those were the days, when I was a young rapscallion dashing around the world and I was always seduced by the allure of the Older Woman. I remember watching ‘Mrs Robinson’ as a young man enthralled by the whole escapade, little did I know it was going to happen to me, many times over.

Damn it, there I go reminiscing again and not answering the question! The first date dressing dilemma is usually the prerogative of the Lady, but it is increasingly becoming an issue for men. As we now don’t have to dress for dinner (damn shame that, maybe we can bring it back) and that used to take the pressure off. Now, we gentlemen need to put a little bit more effort in it.

I am in total agreement with you that your usual uniform is certainly not suitable! Can I assume that you have taken our general advice about dating and you have invited the lady to dinner at a proper restaurant. If that is the case then I suggest a smart casual outfit.

You want a good pair of trousers, preferably a dark colour. I would suggest a collared shirt, in a nice plain colour. If you are a chap with a bit of zest, then perhaps a good pink works well and I suggest a nice blue blazer or casual jacket. Dark shoes, that are polished, you can wear loafers or more casual shoes. Jazz up the jacket with a pocket square that matches the shirt.

If that doesn’t work then I am not Uncle Henry!  Good luck Mr Collins and have a fantastic date.

Now, where did I put my copy of ‘The Graduate’.

Toodle Pip,

Uncle Henry

If you have a question for Uncle Henry email or #askhenry on Twitter @ThePgentlemen

Get My Free Cheatsheet

Get My Free Cheatsheet

15 sure-fire ways to triple the size of your email list in 30 days

You have Successfully Subscribed!

Pin It on Pinterest