Men’s Guide To Date Night Outfits for Any Occasion

Knowing what to wear on a date can cause you more stress than the actual date itself. Whether you like it or not, what you wear has a huge impact on how your date goes. First impressions do count. If you aren’t dressed to impress then you are already behind the eight ball. So to make sure you are looking fly, we have come up with this handy guide for you to follow so you have date night outfits sorted for any occasion. 

You want to look good while still feeling comfortable in your own skin. This might mean you have to wear clothes you don’t normally wear often. We aren’t suggesting you need to reinvent your wardrobe, but if you’re more of a t-shirt guy than a collared shirt guy, this might need to change if you are meeting in a classy bar for a drink. Small changes like this might need to be made to make sure you are at your best and impress your date from the get-go. 

A Men’s Guide To Date Night Outfits for Any Occasion

What you wear on a date can often be chalked up to what number date it is. If it is the first time you are meeting you want to impress her by wearing something that will catch her eye. If it is the second date you can take a more chill vibe while still looking your best. 

What To Wear on a First Date

This is the most important date. When you first meet your prospective love interest you want her to be excited. You need to present yourself in a way that catches her eye and puts you at ease. Wearing a skate tee with shorts and an old pair of Vans probably isn’t going to get her motor running. 

The first date is all about getting the basics right. A nice shirt paired with jeans or chinos and some dress shoes is a great way to make a first impression. Layer with a denim or bomber jacket if cold. Keep things simple. Stay away from loud colors that draw too much attention to your outfit. 

What To Wear on a Second Date

If you have managed to make it to a second date, you must have done enough to keep her interested the first time around. It also means what you were wearing wasn’t overwhelming or off-putting. This means she is fine with your style choices and allows you to change things up a little. If you wore chinos on the first date, swap them for jeans the second time around. If your next catch-up is a little more low-key, trade the shirt for a polo or even a t-shirt. Just be sure to wear a plain white tee or a neutral color that doesn’t overpower the rest of your outfit. This is also where you can trade the fancy shoes for a nice pair of trainers.

What To Wear Going Forward

If you have got to date three then you don’t really have to worry too much about your dress sense. She is obviously cool with your style and is most likely more into your personality than what you wear anyway. Just wear whatever feels comfortable based on the type of date (day at the beach, drinks at a bar, dinner at a classy restaurant, etc.) and enjoy each other’s company. 

3 Great Date Night Outfit Styles To Try

There are literally hundreds of combinations when it comes to how you pair your trousers with a shirt or shoes. The options are almost endless. But there are a few staples that work for most occasions. Here are three of the best types of date night outfit styles you can try.

Formal

If you are going all out on the first date and taking her someplace super nice and formal or that has a dress code, you need to up your game. Chinos and shirt just won’t cut it. While a suit is going over the top, you can wear a nice pair of trousers or dress pants with a matching blazer. Pair with a long sleeve shirt and leather belt. Go for neutral colors like blue, brown, grey, black, or white. These are classic combinations that never go out of style. Finish your outfit with a pair of Oxfords or brogues. 

Hot tip: Leave the tie at home. You don’t want to overdo it. 

Sophisticated

This look falls somewhere in between formal and casual. You want to show you can dress with the best of them while still showcasing your personality and not looking like you are trying too hard. Jeans or chinos are a good start. Then throw on a shirt or polo. If the weather is a little chilly, a sports jacket or cardigan works well. For shoes, you can still go dress shoes, but a pair of boots also work well. 

Hot tip: Chelsea boots are a great look with jeans and a shirt. 

Casual

Bar hopping for the night? Bowling and beers? These types of dates don’t require you to overdo it when it comes to your outfit choices. That’s not to say you can’t look good. You can ditch the shirt for a plain tee. Graphics are fine, especially if it is a band shirt, just don’t go for anything too attention-grabbing. Casual outfits are where jeans become your best friend, with blue or black denim the best choices. Pair with a denim, lightweight, or bomber jacket and some white trainers or casual footwear like Converse or Vans. 

Hot tip: While beanies or caps are a great accessory, maybe save for the second catch-up. You want your date to be able to see your whole head and whether you have any hair. 

What Kind of Date Are You Going On?

So we have given you three main styles to choose from, but when it comes to the actual date, the type of activity or the location also makes a difference. If you are having a picnic at the beach you are probably not going to be wearing dress pants and a shirt. Likewise, you wouldn’t be sporting a black tee and black skinny jeans when dining at a five-star restaurant. Understand the situation and dress accordingly. To help you out, here are some of the more popular date ideas you might encounter and what to wear. 

Dinner Date

Once upon a time you might have got out your best suit and ironed your favorite shirt, but these days dinner dates are a lot more casual. That doesn’t mean you can dress like a slob. Leave the jeans at home and go for a crisp pair of chinos or nice dress pants. Then pick a neutral-colored shirt. Add a blazer or coat if the weather is cool. Another great option that is back in fashion thanks to Spider-Man himself, Tom Holland, is the turtleneck. Wear with pair of slacks and nice shoes. If you can pull it off you will look like an absolute legend that exudes style and sophistication. Your date will be impressed. Finish with Oxfords or brogues. These are nice, versatile dress shoes that will serve you well. 

• Top: Collared shirt or turtleneck in neutral colors
• Pants: Chinos or trousers
• Outerwear: Blazer or coat
• Shoes: Oxford or brogue. Chelsea boots also work
• Accessories: Watch, nice belt

Coffee Date

One of the most popular date options, grabbing a coffee enables you to give your date the once over without being committed to spending too much time with them. Unless you both get on like a house on fire and end up knocking back a few cups of Joe. That said, you still want to impress, even if it is only a short date. Chinos or jeans are fine, while a collared shirt of some sort is recommended. A t-shirt also works, but creates a much more casual vibe and could give your date the impression you didn’t give much thought to your outfit. Layer with a lightweight jacket or sportscoat if chilly. While dress shoes still work, a pair of loafers or white sneakers will also suffice. 

• Top: Collared shirt or polo in neutral colors. T-shirt can work
• Pants: Chinos or jeans
• Outerwear: Lightweight jacket or sportscoat
• Shoes: Sneakers or loafers over dress shoes, but both work
• Accessories: Watch

Bar Date

There isn’t a huge shift from a coffee date to a bar date. There are only a few small changes you can make that will help you update your outfit. A collard top, be it a shirt or polo works, but maybe get something with stripes or a small design to show off your personality. Tees are also an option but go for something solid like white or black. They are easier to match. Chinos and jeans both work too. Similar to a coffee date, you can wear dress shoes, but we recommend boots or trainers. A black pair of Vans also works. If you’re feeling the cold, a denim or bomber jacket is a good choice. 

• Top: Collared shirt, polo, or crisp white/black t-shirt
• Pants: Chinos or jeans
• Outerwear: Denim or bomber jacket
• Shoes: Trainers or Chelsea/combat boots
• Accessories: Watch

Day Date

When we say day date, we mean any type of meet-up during the day that doesn’t necessarily involve sitting in a coffee shop or a bar. You might go for a walk around the suburbs or take part in a picnic in the park. Whatever your choice, this gives you the chance for a more casual vibe. You can probably ditch the shirt and go for a polo (if you still want a collar) or t-shirt. Jeans or chinos are both suitable, as are sneakers as you will be outside. Also, rug up with some form of jacket or parka. Even a sweater can work well. 

• Top: Polo or tee
• Pants: Chinos or jeans
• Outerwear: Lightweight jacket, parka, or sweater
• Shoes: Sneakers

Cinema Date

Just because you are in the dark for two hours doesn’t mean you can’t wear something half decent. While style is still key, you want clothes that are comfortable. Skinny jeans aren’t really going to be ideal if you are stuck sitting down for an extended period of time. That’s why you should go for something tapered so you have room to move. Trade the shirt for a tee. Cinemas often get cold so bring a lightweight jacket or wear a sweater. Go for a pair of trainers when it comes to footwear. 

• Top: T-shirt
• Pants: Chinos or jeans
• Outerwear: Lightweight jacket or sweater
• Shoes: Sneakers

Outdoor Date

When we say ‘outdoor date,’ we mean something that involves an activity outside. This could be anything from a bike ride to a hike. For this type of date, you need to dress appropriately for the situation. A hike will require you to whip out a pair of shorts and some hiking boots. A bike ride might mean a waterproof jacket and sweatpants. This is one of the few times a cap or beanie is acceptable, depending on the weather conditions. 

• Top: T-shirt
• Pants: Any type of pant or short
• Outerwear: Lightweight/waterproof sports jacket or sweater
• Shoes: Sneakers or trainers. Hiking boots
• Accessories: Cap or beanie

Beach Date

This is as casual as you can get for a date. Boardshorts and a tee are all you need. You can even get away with a pair of slides or flip-flops. Just stay away from speedos unless you think you can pull them off. If you aren’t planning on swimming and it is more of a walk on the beach type scenario with the possibility of a drink at the closest pub, switch up the boardshorts to a pair of normal shorts. You might also want to whack on a polo for a touch of class. When it comes to footwear, a pair of boar shoes or loafers is a great option.

• Top: T-shirt or polo
• Pants: Boardshorts or any type of short
• Outerwear: Lightweight jacket
• Shoes: Slides, flip-flops, boat shoes, or loafers
• Accessories: Cap and sunscreen

Building a Date Night Wardrobe

So you know what to wear and when. Now it is time to make sure you have all the essentials covered. There are certain items that every man should have in his wardrobe. These essentials will cover all types of dates and are often interchangeable. Make sure you have at least one of each in your rotating selection of date night clothing options. 

• Long sleeve button up
• Polo shirt
• White t-shirt
• Jeans
• Chinos
• Blazer
• Lightweight jacket
• Sweater
• Dress shoes
• Sneakers/trainers
• Boots

Three Final Tips

You are almost ready to take the dating world by storm, but before you head out to meet your date, here are three final style tips to take into consideration. Follow these and you will be the envy of every guy.

Fit Is Important

There is nothing worse than a guy wearing clothes that aren’t made for his body. Your date will notice straight from the get-go. It looks sloppy and like you don’t really care what you look like. Your outfit should be made up of items that accentuate your body. If you have a barrel chest, tighter shirts work well, while if you had a little dad bod, you probably want something a little more loose around the tummy. This doesn’t mean you need to get all your clothes tailored, just make sure they fit your body type before picking them out. 

Grooming Is a Must

It can often be easy to focus so much on what you are wearing and forgot about the rest of your appearance. You need to look presentable all over as your date will be spending most of the evening looking at your face. Trim your beard and keep your hair styled. Make sure there are no unsightly nose hairs poking out. Bring breath mints with you to make sure you are minty fresh. These might only be small things but they can make a huge difference between getting a second date and no more dates. 

Accessories

You might not think it makes a big deal, but small details like a watch or leather belt can add a touch of difference. It can make you stand out without bringing too much attention to your outfit. Wear a nice dress watch when out for dinner and swap that for something more sporty during a day date. Even the addition of a ring or earring sets you apart from the average guy. There are plenty of options and ways you can go defining your look.