A Gentleman’s Guide to First-Date Fashion


Tips for the Modern Man.

So, you’ve plucked up the courage to ask her out, finally! What took you so long? The good news is she said “yes”. The bad news is, that was the easy part. Now you have to follow through and make it a night to remember – possibly for the rest your lives. For this reason, the way you dress is vital. It’s a clear way for the woman to see that you are serious about her, and the possibility of developing a relationship. Here is a short guide on how to make the right statements about yourself by focusing on what you wear.

1. Informal/Active Dates
Many men make the mistake of assuming that they don’t need to make an effort when going on an informal date. I’m not saying that you have to wear your 3 piece suit to go to the cinema, or bowling, but you should still make sure that your clothes accentuate your best bits and give off a good vibe.

• Don’t wear your oldest pair of jeans. Wear the new ones that don’t have holes in.
• Wear a collared shirt and make sure it’s ironed and, of course, clean.
• Planning something sporty? Don’t wear the tatty old t-shirt you’d normally wear to the gym/tennis court – wear your “best t-shirt” and match it with a pair of smart shorts and your best trainers.

2. Formal/Dinner Dates
Formal doesn't necessarily mean that you need to wear black-tie. What’s important is that you dress suitably for where you are planning to go.

• Restaurants
A nice pair of trousers and a well-tailored jacket should be enough to create a good impression. But it’s important that you wear a well-matched shirt, and tuck it in! However, if you’ve really gone overboard and booked a very formal venue, make sure you wear a dinner suit. The last thing you want is to look under, or over, dressed. Not only will you stand out for all the wrong reasons, you’ll also make your date feel uncomfortable.

• Theatre
Theatres are great first-date venues because it is difficult to over or under dress for the occasion. Some men dress in elaborate suits, complete with top-hats and frilly shirts. Other men wear modest outfits; jeans and t-shirts. For this reason you can wear a full suit, with freshly-pressed shirt and tie, safe in the knowledge that you won’t make a fool of yourself. If you do go out for drinks or dinner after you can take of you tie and unbutton your top button to create a more relaxed look. This is good because it shows your date two different sides of your personality. She may very well imagine seeing you in the morning, before work, and greeting you at home at the end of a hard day.

3. Blind Dates
What if you don’t know exactly where you are going, or even what type of place you’ll end up in? Many make the mistake of dressing in their most expensive suit, in an effort to be prepared “just in case” they end up in some swanky restaurant. But the real key to dressing well for a blind date is to wear something versatile. Versatile? Like a boiler suit? Hiking shoes? No, no, no. Versatile means that you could wear your outfit to a high-end, rooftop cocktail lounge, or a builders’ cafe, and still fit in. The right outfit will accentuate your good points, without making you stand out like a sore thumb. Wear a pair of your best, dark jeans, with a pair of good, clean shoes, a pastel-coloured shirt and a simple jacket. You may not look as smart as people wearing dinner suits if you go to an upmarket place, but you will still blend in. Likewise, you won’t look over-dressed if you end up in a casual diner or cinema venue.

4. Grooming and Accessories
Wherever you go and whatever you decide to wear, make sure you are well groomed, clean and fresh. Don’t try new or fancy hairstyles, stick to what works best for you. Brush your teeth and chew mints or gum (before meeting your date) to keep your breath fresh – you may even get a kiss out of it! Make sure your clothes and shoes are clean and polished. Accessories, such as your belt, should also match your outfit and shoes. Don’t wear overly flamboyant jewellery unless you want to look like some kind of pimp (regardless of what you may here in popular music, most girls do not like pimps). Much as a woman can tell a lot about a man by looking at his shoes – watches, necklaces and bracelets also say a lot about your personality. You may think you look like some kind of rock star but it could quite easily give off the wrong impression.

5. Finished Touches
There’s no point dressing like a gentleman unless you are going to follow through and act like one too. Greet your date with a smile and a compliment; give her confidence about how she looks, but never fish for compliments about your attire. Where possible make sure to let your date know the plans of the evening. You may get excited about surprises but it’s unlikely that a lady in heels would be excited about a surprise hike to the top of a nearby mountain, regardless of our romantic the views are.

Once you’ve got the outfit sorted, focus on showing her a great time. Not just by being fun, but also by displaying characteristics that most young women look for ain a potential partner. Be kind, considerate, and attentive – listen to her and ask her questions. Be interested and most of all - be a gentleman.