What to wear: On a Date

Fieldy’s top five:

• Important are the shirt and the shoes.
• Iron the shirt, not just the collar.
• One shirt button is reserved, two buttons is relaxed, and three is awful.
• Wear colours that suit and you enjoy.
• Shoes, shoes and shoes.

Job interviews, weddings, parties. What to wear for these occasions are all a walk in the park compared to deciding what to wear on a date. Rest assured both of you will be as anxious as each other to pitch it right. Easy. Right?

First dates are notoriously tricky for this very reason. She’ll want to see that you’ve made some effort, and you’ll want her to think that you haven’t gone to too much trouble. The cool, calm and collected man that you are.

It’s all about striking the balance between smart but attainable, and being stylish without going overboard.

Taking for granted the fact that a shower beforehand does reap a host of benefits, there are two items that will be clocked and judged by the time you’ve asked your second question. They are your shirt and your shoes.


The shirt is always an indication of you and your character. Even if you’re wearing a white shirt, it’s all about how you wear it. Whether you’ve got one button undone or two. Whether you’ve bothered to iron it. For the record, two buttons undone is fine on a good shirt, as long as you don’t team this up with a pair of dark shades. “The Sleezy Italian” look will be a non starter for the majority. Three or four buttons and one wonders what the point of wearing the shirt is at all.

Guys, you know how the right girls never have everything out on display all at once – because it’s all about creating the allure of what might lie beneath? Well guess what, same goes for us. Below, you may envy his money, but don’t envy the shirt. It doesn’t have enough buttons.

X Factor

Simon Cowell

By the time we’ve all hit the age for dating, we all have a fairly good idea what colours suit us. So wear one that does. And for this occasion don’t shy away from wearing a pink shirt if it suits you. It’s a colour that radiates confidence and compassion. Two massive points that she’ll be looking out for. (Starting to feel like Will Smith in the film ‘Hitch’ now.)


“Keep them clean to keep them keen”. Why are they so important? After all they’re right at the bottom? Think of it like writing a press release without “Dotting the I’s” and “Crossing the T’s”. Attention to detail is important. Guys get lazy with shoes, and it’s always a shame if you’ve gone to a lot of effort with what lies above. I see it time and time again.

Shoes can be classic or quirky (if that’s you), but make sure they are clean!

One final thing….

Too many men never develop a sense of outerwear embarrassment. There are a host of us who somehow think it’s ok to dress like we did when we were children. Anoraks away please. Wear a good structured coat.

It’s a shame really, because outerwear on a man can be a truly transforming thing. A coat can help your figure flaws and add gravitas to your frame.


…in case you’re wondering, I’m likely to go for a good tailored shirt, sports jacket or blazer and dark jeans. Not forgetting my Cleverley shoes of course!

Cleverley Shoes

Follow James at: www.twitter.com/MrJamesField


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