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

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

You can make the date more stressful by not knowing what to wear. It doesn’t matter if you like it, but what you wear can have a big impact on how your date reacts to you. First impressions do count. If you aren’t dressed to impress then you are already behind the eight ball. We have put together this handy guide to help you look your best for date nights. 

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You want to look great while feeling comfortable in your 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. These small changes can help you look your best and impress your date. 

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

You can often determine how many dates it is by the clothes you wear on a first date. You want to impress your date if it is your first time meeting. You can be more relaxed on the second date, but still look your best. 

What to wear on a first date

This is the most important day. You want your potential love interest to be excited when you first meet her. You must present yourself in a way that grabs her attention and makes you feel comfortable. 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 about getting the basics right. A nice shirt, paired with jeans or casual chinos and some formal shoes, is a great way for a first impression. If you are feeling cold, layer your shirt with a jacket or denim. Keep it simple. Do not wear loud colors that draw too much attention. 

What to wear on a Second Date

You must have done enough to keep her interest the first time. It also means what you were wearing wasn’t overwhelming or off-putting. This means that she is comfortable with your style choices, and you can change things up. If you wore jeans on your first date, consider switching to chinos for the second. If you’re looking for something more casual, consider trading the shirt for a polo, or even a tee. Just be sure to wear a plain white tee or a neutral color that doesn’t overpower the rest of your outfit. You can also swap out your expensive shoes for a nice pair 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. You’re probably more into her style than you are about your clothes. Whatever you feel most comfortable in, depending on what date you have, such as a day at the beach, drinks at the bar, or dinner at a fine restaurant, is all that matters. and enjoy each other’s company. 

3 Great Date Night Outfit Styles To Try

There are hundreds of combinations for how to pair your trousers and shirt with shoes or shirts. There are literally endless combinations. There are some basic styles that work for all occasions. Here are three great options for date night outfits.


You should be going all out on your first date, taking her somewhere very formal or with a dress code. Chinos and shirt just won’t cut it. You don’t have to wear a suit if you want to look smart. However, you can pair a nice pair or trousers with a matching blazer and dress pants. A long-sleeve shirt and a leather belt go well with this suit. You can choose neutral colors such as blue, brown or grey, or black and white. These classic combinations never go out of fashion. Pair your outfit with brogues or Oxfords. 

Hot tip:Don’t tie the knot. You don’t want to overdo it. 

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This look falls somewhere between casual and formal. This look should be easy to wear and show that you can dress with the best. Jeans or chinos work well. Next, add a shirt or polo. If it is cold, a cardigan or sports jacket will be useful. Shoes can be worn in dress shoes but you can also wear boots. 

Hot tip:Chelsea boots look great paired with jeans and a top. 


Nightclub hopping 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 swap the shirt for a plain shirt. Graphics are fine, especially if it is a band shirt, just don’t go for anything too attention-grabbing. Jeans are your best friend when you’re wearing casual outfits. Blue or black jeans are the best options. Pair it with a lightweight, denim or bomber jacket with white trainers, Converse, or Vans casual footwear. 

Hot tip:Beanies or caps can be a great accessory. But save them for the second meeting. Your date should be able see your entire head and any hairs. 

What Kind of Date are You Going On?

We have provided three options for you to choose from. However, it is important to consider the date and the type of activity. You won’t be wearing a shirt and dress pants if you are having a picnic on the beach. Likewise, you wouldn’t be sporting a black tee and black skinny jeans when dining at a five-star restaurant. You need to understand the situation and dress accordingly. These are some of the most popular date ideas and what you can wear. 

Dinner Date


In the past, you might have put on your best suit and ironed a favorite shirt. However, dinner dates are now much more casual. That doesn’t mean you can dress like a slob. You can leave the jeans at home and opt for crisp chinos or nice pants. Choose a neutral-colored shirt. If it is cool, you can add a jacket or coat. Spider-Man is bringing back a great option thanks to his web design. Tom HollandThe turtleneck is a popular choice. Wear with nice shoes and a pair of slacks. You will be a true legend if you can pull it off. You will impress your date. You can finish with brogues or Oxfords. These versatile shoes will serve you well. 

  • Top:A turtleneck or collared shirt in neutral colors
  • Pants:Wear chinos or trousers
  • Outerwear:Blazer or coat
  • Shoes:Oxford or brogue. Chelsea boots are also available
  • Accessories: Watch, nice belt
  • Coffee Date

    couple having coffee

    Grab a coffee is one of the most popular date options. It allows you to give your date a second chance without having to commit to spending too much time together. Unless you are both adamant about getting along, it is unlikely that you will end up sharing a few cups of Joe. Even if it’s a short date, impressing is still important. A t-shirt or jeans is fine, but a collared top 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. If it is cold, layer with a lightweight jacket and sportscoat. Even though dress shoes are still appropriate, you can also wear loafers or white sneakers. 

  • Top: Collared shirt or polo in neutral colors. T-shirt can work
  • Pants:Jeans or chinos
  • Outerwear:Sportcoat or jacket lightweight
  • Shoes:Lone loafers or sneakers can be worn in lieu of dress shoes. But both can work.
  • Accessories:You can watch
  • Bar Date

    couple drinking cocktail at the bar

    There isn’t a huge shift from a coffee date to a bar date. You can make a few changes that will update your outfit. A collared top, whether it’s a shirt or polo, works well. But, you might consider a striped or small design to showcase your personality. Tees are another option, but you should choose something solid like black or white. They are easier for you to match. Both chinos and jeans work well. You can wear dress shoes for a coffee date but we recommend trainers or boots. You can also wear a black pair of Vans. 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:Jeans or chinos
  • Outerwear: Denim or bomber jacket
  • Shoes:Chelsea/combat boots or trainers
  • Accessories:You can 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 take a walk through the suburbs or enjoy a picnic at the park. This allows you to have a more casual atmosphere, no matter what your choice. If you don’t want a collar, you can wear a polo or a t-shirt. Jeans, chinos, and sneakers are all appropriate. You should also bring a jacket or a parka to cover your legs. Even a sweater works well. 

  • Top:Polo or tee
  • Pants:Jeans or chinos
  • Outerwear:Lightweight jackets, parkas, and sweater
  • Shoes:Sneakers
  • Cinema Date

    sweet couple having fun in movie theather

    Just because you are in the dark for two hours doesn’t mean you can’t wear something half decent. While style is important, comfortable clothes are also important. 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. You can swap the shirt for a tee. Bring a lightweight jacket or sweater to the cinema as it can get very cold. For footwear, choose a pair of trainers. 

  • Top: T-shirt
  • Pants:Jeans or chinos
  • Outerwear:Lightweight jackets and sweaters
  • Shoes:Sneakers
  • Outdoor Date

    lovely couple having great time outdoor

    When we say ‘outdoor date,’An activity that is outside is what we mean. This could include anything from a bike ride or a hike. This type of date requires you to dress appropriately. For a hike, you will need to wear shorts and hiking boots. For a bike ride, you might need a waterproof jacket and sweatpants. Depending on the weather, this is one of the few occasions a cap or beanie might be acceptable. 

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

    sweet couple with wine dating at the beach

    This is the most casual outfit you can wear on a date. All you need is a pair of boardshorts and a tee. You can even wear flip-flops and slides. If you aren’t sure if you can pull off speedos, you should avoid them. 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. For a touch more class, you might want to add a polo. A pair of loafers or boar shoes is a great choice for footwear.

  • Top:T-shirt or Polo
  • Pants:Boardshorts and any other type of short
  • Outerwear:Jacket of light weight
  • Shoes:Slides, flip-flops and boat shoes are all acceptable.
  • Accessories:Cap and sunscreen
  • Building a Date Night Wardrobe

    Now you know what to wear when. Now it is time for you to make sure that you have all the basics covered. There are certain items every man should have in his closet. These essentials are versatile and can be used on many occasions. You should have at least one of these essentials in your rotation of date night clothes options. 

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

    You are nearly ready to take on the dating world by storm. However, before you head out to meet up with your date, here are three style tips. These style tips will make you the envy and choice of every man.

    Fitness is important

    There is nothing worse than a guy wearing clothes that aren’t made for his body. It will be obvious to your date right away. It looks sloppy and like you don’t really care what you look like. You should choose items that highlight your body. Tighter shirts are best for someone with a large chest. However, if you have a smaller stomach, you might want something that is looser around your stomach. 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 is easy to be so focused on your clothes that you forget about the rest. As your date will be spending the majority of the evening looking at you, it is important that you look your best. Cut your beard and style your hair. Make sure your nose is free of unsightly hairs. To keep your breath fresh, bring some mints. Even though they may seem small, these little things can make all the difference between getting a second date or not. 


    Although it might not seem like a big deal to you, small details such as a watch or a leather belt can make a difference. It can make you stand apart without adding too much attention to the rest of your outfit. You can wear a nice dress to dinner and a more sporty one on a date. Even a ring or an earring can set you apart from the rest of the guys. There are many ways to define your look. 

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