First Date Fashion Ideas for Men

You know the adage that first impressions count? Well, there is no occasion on which they count more than a first date. Your smile, your features, and even your posture send out signals to your potential partner that you have no control over at all. However, when it comes to style, thankfully we are firmly in the driving seat.

Our choice of attire has a huge influence on how others perceive us, so it’s safe to say that we can control that visual first impression with the right look. But dressing for a first date is a veritable fashion minefield, so rather than leaving things to chance, here’s a list of a few fashion dos and don’ts followed by some tips for that first encounter.

Do dress to impress

A person will judge you and reach a conclusion on whether they like you or not within the first seven seconds of meeting. Pretty scary stuff, right? So give yourself the best chance of making it through the evening without an ‘emergency call/text’ situation by dressing to impress in those first seven seconds.

Your clothes must be clean and relatively new and not the usual attire that you wear every day. If you look like you made an effort by wearing a blazer or even a tie, this will impress the subconscious mind of your date, which is the perfect start.

Do plan your outfit

This could be the love of your life that you are about to meet so do yourself a favor and prepare yourself. Think about what you’d like to wear at least a few days before the date, so you have plenty of time should you need it.

Whether it’s a suit or jeans, flat cap, and a shirt, try everything on just to be sure it still fits. Last-minute realizations that your donut addiction has added a few inches to your waist are simply unthinkable.

Do have your ensemble pressed

Once you’ve chosen your outfit, get it pressed or iron it yourself. Nothing says ‘I am trying my best’ more than showing up in a neatly pressed shirt, so if you’re handy with an iron then go right ahead and knock yourself out.

On the other hand, if you don’t have the time then bring it to your local dry cleaners where they’ll have it back to you as good as new for just a few dollars. Money well spent if you ask me.

Do think about the location

Wherever you are going, you should dress accordingly. Consider the dress code at venues such as fine dining restaurants and the theater and if you’re not sure, call ahead. Some places require a jacket while others might also require a tie and there’s no excuse for turning up without one.

Then, of course, there’s the weather. Will you spend the evening outdoors? Do you need to walk anywhere? Is there even the remotest chance that you’ll end up wet?

Play it safe and plan for any meteorological possibility and whatever you do, don’t forget to tell your date.

Do ask for advice

There’s nothing better than the second pair of eyes (preferably of the same gender as your date) to run the rule over your outfit and give you their opinion. Make sure it’s someone you trust from a style point of view and who is prone to bouts of pure, unadulterated honesty.

A friend with an objective point of view might pick up on something that you missed or let you know what signals you are sending out with your choice of clothes.

But if you do ask, make sure that you take all constructive criticism, however painful it may be, on board.

Don’t do matchy-matchy

Try not to color coordinate your outfit or match up patterns. This will draw your date’s attention to your outfit when you want them to pay attention to you. A subtle approach to colors and patterns is preferable; remember you wear clothes, they don’t wear you.

Matching your shoes to your belt, or your pocket square to an element of your tie is perfectly acceptable, but an entire outfit in scarlet red is most certainly not.

Don’t wear branded clothes

So you have a penchant for athletic brands? That’s nice when you’re at the gym, but not when you’re on a date. Wearing branded clothing has its drawbacks.

Both originalities in style and individuality are quite attractive traits, but once you pull on a branded t-shirt, you’ve lost both.

You should also avoid sports jerseys and band/music hinted t-shirts. Who knows what team your date supports and maybe they just won’t get your devotion to One Direction.

Don’t wear new clothes

This might sound a bit strange because, after all, you want to look your best, right? Of course, you do, but you must think about the comfort aspect.

If you are wearing something new that itches or is a little too tight, then you will feel uncomfortable. This may lead to you fidgeting throughout the date (not a good thing) or losing your patience as you wonder how many blisters those new shoes are giving you.

While you may want to wear those shiny new oxfords, it makes more sense to break in your shoes. And the same goes for shirts, sweaters, and pants; you can do without that brand new itchiness or stiffness.

Fashion tips for first-time daters

The colors

You can have a lot of fun with colors in both casual and formal wear, but in this instance, you should play it safe and stick to subtle shades. Muted reds, blues, and browns are ideal while blacks and grays are acceptable but only as a complement to a lighter color.

Try not to draw too much attention to anyone aspect of your outfit by choosing understated shades of your favorite color. You don’t want your date to remember you as the guy in that tangerine jacket. Subtlety is everything.

The fit

It’s all in the fit.

No matter how smart your outfit is, it all counts for naught if it doesn’t fit right. Make sure that your pants are the correct length (no socks showing please) and that the shoulder seams on your shirts sit right on the edge of your shoulder.

You should also take care that you don’t wear anything too tight as you may feel uncomfortable and end up sitting or walking in an odd position throughout your date. On the other hand, you can’t go too big either. Loose-fitting clothing is so 80s and 90s and makes you look like a twelve-year-old in his father’s suit. Something to avoid when looking to impress your date.

The style

Each person has their particular taste when it comes to clothing and while being adventurous has its benefits, on a first date, it’s best to stick with what you know.

The chances are that at this stage of your life you have a personal style nailed down and provided that it doesn’t consist of vests and board shorts, you should try to stay true to yourself.

However, as mentioned earlier, this is where a friend’s opinion is worth its weight in gold. It could be that your taste in clothes isn’t all that flattering or perhaps you’re stuck in a check shirt rut that just doesn’t suit you.

Ask for that honest opinion and if you need some improvement then act on it. You can’t miss out on the potential love of your life because of a clothing mishap. Yes, it could happen.

Three outfits for three first dates

Assuming that you aren’t taking your date deep-sea diving or paragliding (great date ideas by the way), your attire should fit into one of three categories; casual, smart casual, and formal. And while there’s plenty of room for adjustment, here are a few ideas for an outfit to suit the vast majority of first dates.

The casual look

Perfect for – The movies, drinks at a bar, picnic in the park, a concert

People often get confused with the whole casual category thinking that it’s an ‘anything goes’ style. Unfortunately, it’s not. You simply won’t get away with a tracksuit or your favorite high school hoodie on any date, never mind a first one.

The casual look is based on simplicity and comfort.

• Pants – Jeans or chinos in a contrasting color to your sweater or shirt. You will most likely choose a lighter color for your top half so stick with dark colors in the bottom half.

• Shirt – A plain or check shirt in a subtle tone. If patterned, make sure that it’s not overly complicated. Remember simple is always best.

• Sweater – An essential piece of your dating arsenal especially in the colder months. You can take it off if there are any food spillages or offer it to your date if it gets a bit chilly. Avoid patterns and stick with a solid color such as blue or red in a soft hue.

• Shoes – You can stick to your tennis shoe if you like, but to truly impress, dress up ever so slightly with a pair of brogues (definitely the best option). A freshly shined pair of shoes gives the impression of maturity and security which are traits that many single people are on the lookout for.

The smart casual

Perfect for – Dinner, the races, semi-formal social events

Another misunderstood style that many dismiss as being too formal, the smart casual outfit is an ideal way to impress a date.

It’s just a slight change from casual, but it makes all the difference.

• Pants – As with casual you want a pair of chinos or jeans that contrast with the other main elements of your ensemble.

• Shirt – A solid color such as pale blue or even white is ideal.

• Sport Coat – And this is what makes the look. The sport coat or blazer is the ideal way to take your casual look up a notch. It’s suave, it’s sophisticated, and it’s incredibly easy to pull off as a look. And you can even use your suit jacket if you don’t fancy splashing out on a new one.

• Shoes – It’s got to be a good old-fashioned pair of oxfords that are preferably brown with a slightly weathered look.

The formal

Perfect for – A night at the theater, fine dining

And for those very special dates, there’s a formal look. There aren’t many that will take this option on a first date, but to those brave few, I tip my hat.

When choosing formal wear, it’s worth investing (should your budget allow) in a custom made suit. Not only will it look the part but it should last you a lifetime.

• Suit – Everyone is wearing navy these days and with good reason. It’s the color that goes with everything, and as a bonus, you can use the jacket as a blazer for that smart casual look.

• Shirt – Again it’s best to stick to a plain color and keep your look simple. Lighter colors are the obvious choice to go with your navy suit, and white is the best of the bunch.

• Tie – Forget the usual suspects and go for a slim black Yes, you may remember that navy and black cannot go together, but this is a style myth that you are about to bust again.

• Shoes – Black oxfords. Yes, you read that right, you are going to wear black shoes with a navy suit. A black shoe brings your suit to a level of formality fit for a theater or the most exclusive of restaurants, and that black-tie finishes off the look perfectly.

So now that you have the know-how, it’s time to get out there and there and make that first date a great one and hopefully a prelude to life’s biggest adventure. And don’t worry, I’m sure that your data will give you a little more than seven seconds to leave an impression.