Valentine’s Day is a very special holiday that many people celebrate and is a day dedicated to love and showing those we care about how much we love them. The holiday originated as a celebratory feast during the third century and was established by Pope Gelasius I in AD 496 in honour of Saint Valentine of Rome, who died on February 14, AD 269.
During the 14th and 15th centuries, the celebration became associated with romantic love, when ideas of courtly love flourished, and during the 18th century, the day grew into an occasion where people would express their love for one another through flowers, confectionery and sending greeting cards – called valentines.
How to Dress for Date Night
While Valentine’s Day is a special occasion, date nights can occur at any time of the year, so it’s important to have a range of outfit options for all kinds of dates.
- Casual Date Night Outfits
A casual outfit is a great option for a low-key location, like a picnic or coffee date, however, don’t be fooled by the use of the word ‘casual’ in the name – you still want to look put together.
This kind of outfit should integrate relaxed elements, like a rugby jumper and a pair of jeans, that allow you to relax and enjoy the date but still have a sense of style in your outfit. For accessories, add a simple leather belt and a watch to elevate your look.
- Refined Date Night Outfits
A refined date night outfit is a little more dressed up than a casual look but still not as formal as a suit and tie. For dates like dinner and a movie or having drinks at a bar, you want to be comfortable yet also wear items that have more of a classic, elevated appeal.
Instead of jeans, opt for a pair of dark wash casual pants or chinos – these will help you stay comfortable while sitting, while also elevating your look thanks to the darker colour. For the top, a long-sleeve button-down and a sports jacket or blazer is a great option and helps to keep the look fashionable without looking overdressed. Make sure to add a nice watch to add an extra sense of sophistication to your outfit.
- Formal Date Night Outfit
For dates at a fancy restaurant or special occasion dates, like a proposal, birthday dinner or celebratory event, you want to look your very best. Stick to clothing items with neutral, block colours. For pants, opt for stylish business or dress pants paired with a white button-down. Make sure to add a blazer or dress coat and a clean pair of dress shoes to keep the outfit on point. For accessories, add a tie or pocket square, a watch with a metal band and a classy belt to tie the outfit all together.
Common Date Types and What to Wear
When it comes to choosing the location for your date night, there are a few options that always work well and means that everyone can have a fun and romantic time.
Watching a movie at the cinema is a fun way to get to spend the evening with someone. You can relax and enjoy the movie without having to think of things to say, especially if it’s a first date. For your outfit, it can be more on the casual/ refined side, so opt for a pair of chinos or jeans and long sleeve shirt. Bring along a cardigan or sports jacket, as the cinema can get cold, especially if it’s a long movie.
For dates on the adventurous side, like walks, hikes, or dates with an activity involved, you want to opt for a casual outfit, that is cool and comfortable but will keep you looking stylish. Depending on the weather and the type of activity, will depend upon the type of clothing. For cooler days, you can opt for jeans, a crew neck jumper, a vest, sneakers and a cap. For warmer days, a linen shirt paired with some casual shorts and a leather belt will keep you feeling active and stylish.
A dinner date is one of the more traditional kinds of date nights, but they’re a staple for a reason. Eating out is a fun way to try new cuisines and spend some quality time with your favourite person, so don’t be afraid to go fancy with it, especially on Valentine’s Day. For a fancy dinner date, make sure you look the part with a sophisticated outfit. A blazer and matching coloured dress pants, ironed button-down, dress shoes and for very fancy places, a matching tie.
First dates can be tricky because you want to impress the person you’re going on a date with but not look overdressed if only going for coffee. For first dates, opt for a smart-casual outfit, that allows you to appear well presented without going over the top. A pair of chinos and a long sleeve shirt for cooler days works well together, while for warmer days a pair of chinos and a linen shirt provide a comfortable outfit with a laid back but stylish aesthetic. Make sure to add a watch and a nice smelling cologne to make that all-important good first impression.
A concert is a fun idea for a date night, especially if both parties share similar music tastes and is a great way to create lasting, shared memories. Concerts that are more on the formal side, like an opera or classical music ensemble, dress pants and a button-down work well to hit the dress code. For outdoor concerts or concerts that are more casual, a pair of jeans and a basic tee help you stay cool and comfortable and enjoy the music with your special someone. Make sure to bring along a jacket or rugby jumper, especially for cooler weather and a scarf if particularly cold.
What to Consider When Selecting a Date Night Outfit
First and foremost, deciding what to wear on a date should never be completely random. Sure, there are some go-to looks that will come in handy in a wide variety of situations (more on that in a minute), but you also need to make sure you’re dressing appropriately for the type of date you’re attending. And in order to make crafting a men’s date outfit as easy as possible for your next outing, here are a few factors to keep in mind while searching through your closet or hitting the mall.
Time of Day
Is your date in the morning or in the evening? Morning dates, like grabbing coffee or brunch, tend to fall on the casual side, therefore casual attire is best suited for these types of dates. (Simply put, do not wear dress pants and a button-down shirt for a daytime lunch.) Evening dates, on the other hand, typically call for more dressed-up looks, although it ultimately depends on where you’re going.
The venue and location of your date are two factors that are extremely important when figuring out what to wear. For instance, if you’re going to a fancy restaurant, you should opt for a more dressed-up look and leave the jeans and sneakers at home. A walk in the park? Nice jeans and a shirt will suffice. And if you’re going to an event or a country club, be sure to research if there’s a dress code so there are no surprises upon arrival.
You never want to wear something that feels completely inauthentic to who you are. That said, you should also pay attention to the type of person your date is when selecting an outfit. “Try to compliment who your date is,” suggests Barrett. “If your date is very [elegant] in all his or her profile images, then you should be too. If not, then you can afford to go more casual.”
How Neat Your Clothes Look
You could be wearing a gorgeous button-down shirt in the perfect color, but if it’s wrinkled and/or stained, the effect is pretty much gone. “Make sure the clothes are clean and pressed,” Barrett says. “There is looking casual and then there is looking unkempt.”
Date Night Style Tips and Advice
As mentioned above, finding a good men’s date outfit can easily leave you feeling overwhelmed, especially if you are a fashion rookie. To make things more manageable, though, keep these general tips in mind before heading out on your next outing.
Get Advice from a Friend
Barrett recommends getting style advice from a friend you can trust, if possible (or maybe a sibling or cousin). “A good friend will look at you from the perspective of your date,” she says. They can tell you honestly what they think of your outfit or they can help you put one together.