What to Wear on a First Date – A Style Guide

Written by Stephanie Patterson

Stephanie Patterson

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Choosing what to wear to a first date can be a hard task because every man wants to make a great first impression. Don’t overthink it – be faithful to your style and add a few accessories if you feel like they will make you look better and feel more confident.

Confidence is everything when meeting someone new, so choosing a good outfit with a cool pair of socks or a beanie can help to make you more stylish.

Dates tend to be an occasion where people try to be looser, so learning what to wear on a casual first date and also on a more formal occasion is very helpful to make you feel calm and ready to focus on charming the other person.

A few things you are going to learn about and that will help create the perfect look for a date:

• What to wear in cold and warm weather
• Fun socks to add color and style to your look
• Tips on hairstyle and beanies
• Perfumes that are great for a first date
• What not to wear

What can men wear on a date?

This varies a lot based on weather, time and location, so if you are not sure about adding colors to your look, go with the basics that go well in any situation:

1. Black or white shirts
2. Jackets
3. Colorful shoes
4. Colorful pants

Shirt colors

Have you heard that less is more? This rule is great for those who enjoy wearing black and white, plus these colors allow you to be a bit of a daredevil and use colorful accessories such as red belts, yellow watches or bracelets for stylish men.

Jackets will make you look sexy

Men tend to always go for the jean jacket – which is a good option if you are trying to be on the safe side and keep your look low key. However, there are other colors and fabrics that go very well with black and white shirts and it is an upgrade that will make you look very handsome.

Black and brown shoes are not the only option

Black shoes go well with pretty much any color and it is easy to combine them with stylish pants and add a nice pair of men’s socks. There are many models, for casual or formal dates, and some can be worn on both occasions.

Check out models that go well at any time of the day and that match different crazy pair of socks.

If you choose to go with brown shoes, there are different shirt and socks combinations that will make you look modern and elegant. For example, you can match a pink shirt with brown shoes and also a pair of socks with brown shoes and a blue suit.

Both colors – black and brown – go well on any occasion and allow people to play a little bit with the look, but you can also be bold and go with colored shoes:

What color pants to wear on a date?

You might be asking yourself what color pants to wear with black shoes and other color variations so here are a few suggestions to help you prepare:

It’s all about adding details that will make you plain look a bit bolder and fun. No matter the shoe color, there is a pair of crazy socks to make you look stylish.

What to wear on cold and hot days?

It is not easy to think about matching layers and what to wear in 60-degree weather or lower, just like it is a challenge to find elegant looks for high temperatures, and this struggle is even worse for people who are not into fashion.

Since choosing the best look for a first date can be a hard task, our fashion specialists listed tips that can be followed according to the weather and mood.

Hot Weather

So, what to wear when it’s hot outside? Here are a few options:

1. Jean shorts and brown shoes
2. Black pants and white shirts
3. Shorts
4. Print shirts

Wear jean shorts, brown or black shoes for a more casual look and add accessories such as colored watches, glasses or male bracelets. During summer it is better to go with lightweight jeans and match light colored shirts with jeans shorts.

Black pants and grey or white shirts never go wrong or out of style. This classic James Dean combination looks good with different shoe styles and other accessories. This look goes better if your date is after sunset on a hot day.

Printed shirts are a good match for jeans, black or brown shorts. If you pick a long sleeve the look will be formal and it can be worn in the morning or late afternoon. Short sleeves are better for daytime dates.

Cold Weather

What about cold weather? Some of the options include:

1. A good pair of jeans
2. Suspenders and ties
3. Amazing sweaters
4. Layers 

You can not go wrong with a pair of jeans on cold days, you just have to find the best jeans for men that match your style. If you wish to add a little bit of color you can wear a leather jacket or opt for a light color T-shirt. Jean looks are also a great chance to pull off that pair of fun socks and show that you are a modern man with a strong personality.

For a date at a fancy location on the late afternoon it is safe to go with a tie and suspenders, plus this is a great chance to add a fun pair of socks to show personality and light up the formal mood. These are also amazing looks for weddings and other formal occasions.

Sweaters are like the joker: you can play them anywhere, anytime! For a date night on a chilly day, you can go with dark colors like maroon or black. If you feel like there is an opportunity to be bold, pick a pair of socks to add more style to it.

The best socks to wear on a date

Forget plain socks! A pair of socks might be the key to make your look a success, especially if you choose to wear a monochromatic look, but that is not the only combination that allows fun socks, so if you don’t know what to wear on the first date check out the suggestions below based on different situations:

• Fancy dinner date
• Daytime date
• Late afternoon drinks
• Casual nights out
• Outdoor dates

Fancy Dinner Date

Choose a dress shirt as this is definitely not the time or place to wear a t-shirt or polo shirts. The pants can either be black dress pants or any fabric as long as you choose dark colors and then match them with beautiful shoes and socks.

The shoes don’t need to be dark and you are free to wear any shoe color, as long the socks match them and the rest of the look.

Daytime date

For a day time date, you can go with white or light brown pants or jeans. Pick socks that have bright colors on them such as yellow, orange and pink.

It is not a problem to match striped shirts with polka dot socks, as long as the shoes and pants are plain colors.

Late afternoon drinks

This might be the hardest look to come up with because it is in between casual and formal, so you are allowed to go either for a dark or light pair of pants. This situation is all about the shoes and socks combination.

Most of the time is a good idea to choose dark color socks, but depending on the shoe color the socks can be bright colors. Stripes and funny designs are also an option for this occasion.

Casual nights out

Casual nights out are the perfect occasion for geometric shapes such as rectangles, triangles, stars, hearts and even stripes. The colors can vary and the shades too, but it is a good idea to consider light-colored shoes and also matching the watch or the belt to the socks, for example.

Dark shoes also work for a casual look and the crazy socks go very well with them as well:

Outdoor dates

If your date is in a park or anywhere outdoors the polka dot and other fun prints are the perfect match. This look is usually based on tennis shoes so it is quite casual and highly appropriate to wear funny socks and T-shirts.

Outdoor dates are usually more laid back so you can play with the style a bit and wear socks with crazy prints too, like foodie prints or holiday prints, like Christmas and Halloween.

Don’t be afraid to show that you are fun and enjoy a good laugh. After all everybody loves someone with a good sense of humor.

What hairstyle should I wear on a first date?

Getting a haircut before a first date is a great idea and it gives you a chance to change and improve your style a little bit. Go for something new, elegant and easy to take care of. 

Although most men still prefer the short hairstyle, long haircuts are very charming. Learning how to wear a beanie or a hat can be a trick up your sleeve when it comes to building an attractive look. Check out a few of the favorite male haircuts:

1. Short hair with a fade
2. Medium length hair
3. The Pompadour
4. Man bun
5. Dreads 
6. Super short or shaved hair

Fade

Short hair with a progressive fade, from top to bottom, never goes out of style. This is a classy haircut for men and it has become a very popular one because it blends well with the beard. Some hairdressers even have signature cuts, such as adding a shape to the haircut.

Medium length hair

Medium length hair is a bit harder to take care of because it needs to be moisturized and frequently combed in order to show its healthy glow. It is also important to own a few hair products for hairstyling before leaving for the date.

The Pompadour

The Pompadour was popularized by Elvis, and has since become a great hairstyle for any occasion. Plus, if your hair is long enough to be successfully “pompadoured”, you can probably play around a bit and use other hairstyles such as a combed option for a formal event.

Man bun

Man bun has been popular among men who love long hairs and enjoy a Thor-like look. There are a few variations to the hairstyle such as pony bun, the top knot, and low bun and the best part about this hairstyle is that it doesn’t require a lot of work, you just need to tie your hair up.

Dreads

Dreadlocks are a great option because any hair length can have dreads and the styles can vary a lot. Some men even dye part of their dreads or/and add the undercut. It is a chance to have a unique look that will definitely not go unnoticed.

Short or shaved hair

Short and shaved hairstyles are the most common ones and hairdressers all over the world have improved their skills and found a way to turn boring plain cuts into beautiful hair designs. Most short haircuts nowadays have a mix of shaved and designs on the side, like a navy style. 

If you have a hairstylist of your preference and who knows your hair well, ask them for suggestions.

Hats and beanies on a first date? Sign us up!

Another great idea is to add a beanie or hat to the look, and there are a few styles that will go very well with the clothing options already mentioned in this blog post. Check out the beanies and hat suggestions for the modern and elegant man:

• Cuffed beanie
• Fisherman style beanie
• Bobble hat
• David Beckham beanie
• Baseball cap
• Flat cap
• Panama hat

Cuffed Beanie

This is probably the most common beanie because of its versatile look, especially if you pick a black or brown one. Grey beanies can also be a good fashion accessory.

Fisherman style

Most men will not try this one out because it seems hard to pull off, but it is a favorite among people who enjoy a hipster look. The fisherman beanie can be worn in casual and formal occasions.

Bobble hat beanie

Good for fancy and for formal occasions if matched with a sweater it will make any man look stylish. Choose dark tones such as maroon, dark green or dark blue. If possible, match the beanie to the shirt and socks color tones.

David Beckham style

Some people say this beanie should be avoided because it makes men look messy, but if you match it to the right shirt and socks, the beanie can be a perfect accessory for a chilly afternoon.

Baseball Caps 

Baseball Caps are definitely for casual moments and if worn it facing forward and matching the look, it will definitely be a home run on your look. For a date go with a plain color cap.

Flat caps

The Flat cap model makes people look smarter and it’s perfect for a brunch date or sunset watching with the crush.

Panama hat

Panama Hats are very sexy and great for formal occasions such as weddings and morning or late afternoon events.

How to take care of your beard before a date

Plan ahead and take good care of your beard and body just like you did with your hair and clothes.

If you choose to shave the beard remember to apply an aftershave, but in case you decide to pull off a cool beard, there are a few things that you can do to make it soft and with a great smell:

1. Wash it 2 to 3 times a week. If you use beard soap too many times a week the beard will get dry and unhealthy.
2. Use a beard conditioner to keep the beard soft. You may also try it out the so-called “beard softeners” that are silicon-based.
3. Apply oil to hydrate it and increase the conditioner results. The oils also add a good smell to the hair.
4. Brush it: always have a comb or brush in hand to keep the beard and mustache at their finest.
5. Disinfect it daily with antibacterial beard balm.

Ideally, you should find the best products to take care of your beard and maintain it weekly. It is also a good idea to have a trimmer and scissors at home to keep the beard healthy and also a styling balm to help during the date preparation.

Perfumes to wear on date

It’s date time and you need to smell good as well look good, so go over the fragrances and own and think about it: do they really show off your personality? Are the colognes seductive?

These are very important questions because people are drawn to smells. Our pheromones, for example, are our natural scent and some believe they are behind the attraction people feel for one another. But, how to wear a cologne?

Let’s be honest: we don’t want to play our chances and hope the pheromones exist or/and work, it’s better to play on the safe side and choose a fragrance to help you win that special person’s heart.

Our specialists made a list with a few suggestions for both men and women who are not sure about what to wear on a date as a perfume:

Outfit suggestions for women

The best outfit is always the one that makes you feel comfortable so don’t think twice if you need to use an old pair of pants or that one shirt that you love so much. 

The first date is not only about trying to impress someone, but it is also about showing who you really are, so there is no reason to wear uncomfortable shoes or push up bras. Jeans and nude shoes will definitely work for either a daytime or nighttime date.

If your style is more casual and you enjoy adding color to the look there is always the option to use stripes and zig-zag designed socks, which are a great match for classic oxford shoes and will make you stand out.

For women who love tennis shoes the rage of options is wide and there is a pair for every personality. Choose a pair of socks that really show who you are and create a very personal and unique look. 

Feel free to show off, add as many accessories you wish and consider adding a fun pair of socks as well because it will add an extra charm to your look.

What to avoid on a first date

It is time to think about what not to do as this is your first chance to show a bit about yourself and first impressions are everything, especially if you met online. Avoid:

• Uncomfortable shoes
• Wearing too much perfume: you never know if the person will enjoy the scent or even worse if the person is allergic to anything
• Avoid brand new outfits, only new socks and are a-okay
• Wearing too much hair gel
• Eating something that will make your breath stink. 

If you follow the tips and stick to your personality you’ll feel comfortable, confident and the date has very high chances to be a success.