Going on a first date can feel like an intimidating experience, but with the right outfit, you can ensure that you look your best and give a great impression. Choosing what to wear can be tricky，so it’s important to find the perfect balance of style and comfort.
To help you out, we’ve put together a selection of classic and fashionable looks for men of all ages，from casual wear to semi-formal and creative styles.
As you scan through these options, don’t forget to groom yourself with confidence and to always think ahead to the type of occasion you’re trying to create.
With these tips in mind, you’ll be ready to dress to impress on your upcoming first date.
What to wear on a first date men casual outfits
Dark Denim Jeans
When it comes to what to wear on a first date, dark denim jeans are always a great option. This timeless piece of clothing is versatile enough to be dressed up with a fitted henley shirt or down with a simple t-shirt.
To really impress your date，make sure your jeans are fitted to help create an overall polished look.
For the ultimate first date outfit that exudes style and confidence, pair your dark denim jeans with a long-sleeved button-down shirt and your favorite leather jacket.
A Fitted Henley Shirt
- A fitted henley shirt is the perfect mix of casual and sophisticated，making it an ideal outfit choice for any first date.
- To make a statement, choose a patterned shirt in eye-catching colors.
- Alternatively，opt for a neutral-toned shirt and let your accessories do the talking.
Consider accessorizing with a bold watch, colorful pocket square, or one of the season’s newest trends for a look that’s all your own. With the right outfit, you’ll be sure to make a great impression and set the stage for a great night.
A Light Button-Down Shirt
When it comes to making a lasting impression, a light button-down shirt is a timeless choice for any special occasion，particularly a first date.
Opt for a tailored fit that flatters your physique，and select an easy-to-style classic in a neutral hue like white，gray, or navy. For an added splash of personality，choose a patterned shirt to really stand out in the crowd – just be sure to find the perfect balance of subtlety and flair.
To complete the look, accessorize with a bold watch or pair of statement shoes that will draw attention to the shirt and elevate your overall look. With this smart and polished ensemble, you’re sure to make a great first impression.
Smart Leather Shoes
First dates can be daunting，but making sure you look your best is key. A timeless leather shoe is a must-have for any man’s wardrobe.
Whether it’s loafers，brogues，or Oxfords, a well-fitted leather shoe will show that you take your look seriously.
Quality is also important – invest in a pair of leather shoes treated with a waterproof seal to ensure they stand up to whatever the night brings.
Finish off with a bold yet subtle pop of bright colored socks as the perfect accessory to your ensemble. With the right shoes, you’ll have the confidence to ace that first date.
Accessories to Spice Up Any Look
When it comes to date night，accessories are the perfect way to make your outfit reflect your personality and show off your individual style.
A well-chosen hat, belt, watch, or a bag can make all the difference when it comes to making the right impression. Choose something that speaks to your style and personality, like a cool fedora or a vintage watch. You can also add a pop of color with a stylish scarf that will make you look more polished.
For a more formal occasion, make sure to pick a statement leather bag that will upgrade your look and make you stand out from the crowd. Whatever you decide, accessories will make your outfit even more special and memorable.
A Slim-Fit Wool Suit
Whether you’re an old romantic dreaming of a beautiful evening or a young dude hoping to make good impression, a slim-fit wool suit is the perfect choice for a first date.
Not only is it effortlessly stylish and timeless，but it will also make you look sharp and smart.
The fitted cut gives a modern edge that elevates any look，and it’s easy to accessorize with a crisp white shirt and leather shoes. Make sure the color you choose is appropriate for the occasion – navy or charcoal are great options – and you’ll be ready to make a lasting impression.
Man in her 40s what to wear on a first date women
A Crisp White Shirt
A crisp white shirt is both timeless and sophisticated, creating an effortless but polished look on a first date.
Choose a slim-fit style and ensure it fits properly – avoid over-tight or wrinkled designs.
To avoid looking over-dressed，pair with subtle accessories and opt for a classic Oxford style for a timeless finish. A well-fitted white shirt will make sure you look as good as you feel on your first date.
Styling leather shoes for the right occasion can make all the difference on a first date. For a classic, dressed-up look, opt for a black Oxford or Derby.
The sleek silhouette will fit with any formal ensemble and will give off an air of sophistication.
For a more casual date night, choose a brown pair of brogues – the texture and detailing will add some character to your look.
Whatever you choose，make sure it fits perfectly and offers breathability for the evening. Invest in a quality leather pair and you’ll never go wrong!
A Solid-Colored Tie
Whether you’re heading out on a first date or attending an important business meeting, a solid-colored tie can provide the perfect finishing touch to your look.
Choose a hue that will match your outfit, such as a navy or black for a timeless look, or opt for a bolder color, like burgundy or teal，to make a statement.
When selecting a tie，make sure it’s the appropriate size and length for your body type, and don’t forget to tuck in the edges for a polished look.
For a little extra flair, add a pocket square for an effortless pop of color.
H2：Classic Accessories for Finishing Touches
When it comes to choosing the perfect accessories for a first date look，it pays to stick with the classics. A slim black leather belt with a silver or gold buckle will finish off a suit perfectly，and also adds a subtle touch of elegance. For a more traditional look, a pocket watch and cufflinks can add a touch of sophistication. To keep your look timeless and modern, choose a classic wristwatch with features that fit your lifestyle. Finally, round off your look with a pair of timeless sunglasses. Remember，the key to making a lasting impression on a first date is striking the right balance between classic and modern.
If you’re looking to make a good impression on your first date, it’s essential to choose the right outfit. Smart streetwear is a great option that allows you to show off your unique style without looking too over the top.
Start with a bomber jacket and dark jeans for the foundation and pair it up with a crisp white shirt and trainers for a sharp, timeless look that is never out of style.
Top off the look with a statement hat or an eye-catching backpack to add a touch of personality and show that you take fashion seriously but know how to keep it fun and relaxed.
With this perfect blend of style and comfort，you’ll be sure to make a lasting impression on your date.
Matching the Occasion
For men, dressing for a first date doesn’t have to be a challenge.
The key is to be mindful of the occasion and choose an outfit that reflects the tone of the evening.
If you’re going for a fancy dinner date, make sure to dress smartly and opt for something classic like a stylish blazer，tailored trousers，and a crisp shirt. Alternatively，if you’re going out for something more casual，you can never go wrong with a pair of dark wash jeans, a polo shirt，and some stylish sneakers.
Whatever you choose, make sure it’s comfortable and that you feel confident in it.
A Well-Fitted Statement Shirt
- A well-fitted statement shirt is the perfect way to make a memorable first impression.
- Choose one that is tailored to your body and made from quality fabrics, such as a crisp cotton or lightweight linen.
- Select a shirt in a bold shade or print，like a checkered pattern，to draw attention without being too loud.
For a complete look，pair the shirt with neutral bottoms and add subtle details，such as interesting buttons and a stylish collar, for a hint of personality. With the right statement shirt，you’ll be dressing for success for date night.
When it comes to first dates, accessories are a quick and easy way of expressing your style.
From a vibrant pocket square to an eye-catching enamel pin, these details can help you stand out while ensuring you look your best.
Don’t forget the old classics，either-a timeless leather belt，watch, or wallet are sure to make a statement. With the right accessories, you’ll be glowing with confidence on any date night.
Break the Rules
When it comes to dressing for a first date，it’s important to strike the perfect balance between putting your best self forward and having fun with fashion.
A tailored blazer and T-shirt is always a classic look, but if you’re feeling bold，you can make a statement with a bright-colored suit or printed blazer.
Add a unique touch with accessories like a bright pocket square or a patterned belt.
Don’t forget the shoes either – go for something eye-catching but still comfortable. With the right pieces，you can make a great first impression and show off your unique style.
Dark Denim Jeans
When it comes to fashion for a first date, dark denim jeans can be the perfect choice for a timeless, classic look.
Opt for a slim-fit pair for a handsome silhouette that flatters any body type. Choose your other pieces to complement the jeans，like a fitted Henley that adds depth to a look or an Oxford for a more polished outfit.
For a touch of edge，a navy blazer can complete the ensemble. Finish off your outfit with a stylish pair of leather shoes to add a luxe touch.
Smart Polo Shirt
When it comes to first dates, it’s best to err on the side of formal but not over-the-top.
A polo shirt is the perfect compromise, offering a smart but comfortable look that’s sure to make a great impression.
Choose one in a deep，neutral hue like navy，midnight blue or charcoal gray，and team it with a pair of dark，slim-fit jeans. Add a belt and watch to finish things off，and you’ve got one stylish yet understated look.
Here are the best ideas on what to wear on a first date for men
A Chunky Knit Cardigan
When deciding what to wear on a first date, a chunky knit cardigan is a great way to add a touch of sophistication and style to your outfit.
For a classic and timeless look, choose one in a neutral color like grey，navy, or black，and layer it over a crisp white dress shirt and a pair of leather dress shoes.
For something a bit more daring, opt for a navy cardigan paired with a printed dress shirt and a pair of desert boots. Accessorize to your heart’s content with a pocket square or watch, and you’ll be prepared to make a great impression on your date.
For men looking to make a lasting impression on a first date，the gingham shirt is an ideal choice. Its classic cut，subtle print，and light color palette combine traditional appeal with a modern touch, for a style that stands out without being too over-the-top.
When wearing a gingham shirt，opt for slim-fitting chinos and complete the look with a few sophisticated accessories like a watch or pocket square.
This timeless look will ensure you make a great impression on your first date and beyond.
Smart Leather Shoes
When it comes to a first date，it’s often the small details that make the biggest impression. The right pair of leather shoes can make all the difference, instantly transforming a casual or semi-formal outfit into one that oozes sophistication and style.
Opt for a plain，timeless style that speaks volumes without dominating your look – and make sure to choose shoes made from genuine leather for a luxurious finish.
Finally，don’t forget a pair of dark socks – they can really pull the whole look together. With these tips in mind, you’re sure to make an unforgettable impression on your date.
Think of the Occasion
If you want to make a lasting impression on a first date，your outfit is an essential part of that. Start by considering the kind of date you’re going on，as this can help guide what kind of look you should go for.
For instance，if you’re planning a dinner date in a formal setting，then you should opt for a semi-formal look with polished pieces like tailored trousers，a smart shirt, and a slim fit blazer.
However, if you’re going for a morning coffee，then a smart casual look with chinos and a comfortable sweater may fit the bill.
Don’t forget to accessorize properly，as your accessories can add an extra layer of detail to your look and make you stand out.
Whenever you’re getting dressed for a date，think about what sort of impression you want to give and then find an outfit that reflects that.
Choosing the right colors for a first date is key to making a great impression. You don’t need to be a fashion expert to coordinate colors that work well together, but there are a few tips and tricks to keep in mind.
Neutral colors like beige，grey，and navy are always a safe bet and work great together. Alternatively, try pairing a classic color combination such as black and white or burgundy and olive.
If you want to add a pop of color while still looking put-together，a bold statement piece paired with neutrals can be a great option. No matter what colors you choose，make sure they coordinate seamlessly and bring out the best in your outfit.
Choose Quality Fabrics
Quality fabrics are the foundation of a great first date look. Natural fibers like cotton, wool, and linen are great options that not only look great and drape nicely, but are also breathable and comfortable.
When shopping for fabrics，look for tight weaves that won’t wrinkle easily and avoid overly glossy textures.
Invest in quality fabrics to ensure your look is both flattering and long-lasting. And don’t forget, comfort and confidence are key when it comes to a first date look. With the right fabric，you can show off your style and stand out from the crowd.
Make sure Your Shoes Match Your Outfit
When it comes to your date outfit，don’t forget about the details like your shoes.
While most men are familiar with the standard dress shoes for formal occasions，there are plenty of stylish options that can work for a variety of looks.
Invest in a pair of smart leather shoes or loafers that can dress up a casual outfit，or go for a pair of dress shoes that you can dress down with the right accessories.
When it comes to colors, consider matching hues across your entire look for a pulled-together look.
Also, take your height into consideration and opt for shoes with a low heel or thicker sole if you’re on the shorter side. With the right shoes, you can make a great impression while staying comfortable and stylish.
Being well-dressed for a first date can be daunting, but it doesn’t have to be. As long as you find the balance between formal and casual，stick to wardrobe classics, and pay attention to the little details that make a big difference，you can make a great impression.
A tailored suit and crisp dress shirt creates a sharp, sophisticated look that shows you’re confident, while adding a touch of personality with a brightly colored pocket square and bold watch adds distinction.
Ultimately, your goal is to look and feel your best, so don’t be afraid to experiment and have fun with it.