What to Wear on a First Date As A Guy

By Nicola Reynor

Posted 5 years agoOTHER

She has finally accepted your offer for a date! Now you are thinking what to wear to make a good impression on her (without looking like you’ve tried too hard). No idea how to achieve that? You’re not alone!
What to Wear on a First Date to Impress Her

Most guys feel nervous before their first date and mess up everything; but in order to make a solid first impression, you need to dress well. Women love clothes, so what you wear may be the first thing that she will notice about you. What to wear on a first date as a guy to impress her? You should dress in a manner that makes her feel, you care about her – Seriously!

A man with the great taste for style can make women go crazy about him. Surely your college hoodie will not save your day…neither will your formal suit. You need to tailor your look so that you can present yourself in the best way possible in front of the woman, who can well be your partner for life.

A lot depends on the kind of date you are planning to have. For instance, for a casual date you can choose something more casual such as jeans and a t-shirt or a dress shirt; but if you are planning to go on a dinner date in an urban setting, you should choose something more polished, such as a blazer jacket with a crisp and clean shirt.

What to Wear for the First Date as A Guy: 3 Outfit Ideas for Men

When it comes to matters of fashion, women seem to think that we guys have it easy. We just need to think about a top, put some jeans on, some shoes, and we’re alright. However, that’s not really the case. The lack of wardrobe choices is exactly the problem we constantly wrestle with. Because of this, we must heavily rely on two aspects: quality and curation. What to wear on a first date as a guy to impress her

While we really can’t help you with the aspect of quality, we certainly can assist you in putting together different outfits with finesse. This is what this article is going to be all about. We are going to share with you different outfit ideas that you can put together on your own and wear to set the best first impression on your first date.

Before we explain what to wear on a first date as a guy to impress her, you can check the current men’s street style trends to get the vibe. Now, let’s get started! Here is what to wear on a first date as a guy to impress her:

First Date Outfit Type1: The Casual Comfy Day Look

This is ideal if you’re going out during the day for coffee, lunch, or a movie and you want to set an impression of being a down-to-earth kind of guy. Here are the elements you’ll need to put the outfit together:

Crewneck Tee

Choose one at a color that complements your complexion and eyes. Since it is only a crewneck tee, investing in a high-quality one should not be too expensive. 

Comfortable Shoes

When choosing a pair of men’s comfortable shoes, white sneakers, or loafers will do. Just keep in mind that whatever you do, don’t choose an open-toed pair. No proper lady will appreciate seeing your toenails, no matter how freshly groomed they are. Also, make sure that your shoes are clean. It shows a lot about your character. You’re down-to-earth yes, with a pleasing and comfortable personality, but you’re not a slob. You care. 

Slim-Fit Chinos

This will go well with your tee. Plus, it’s not a baggy bottom that exudes that air of over-confidence. Get one that fits you just right. It shouldn’t be too tight.

Denim Jacket

Finally, to tie your look together, put a denim jacket on. It will look effortlessly stylish, while at the same time, it will give you something to put around her shoulders during a cold movie or breezy walk by the beach.

First Date Outfit Type 2: The Calm and Collected Day Look

If you want to set the first impression that you are a guy with proper taste, intellect, and confidence, then this is the look for you. 

Knit Polo

Hence, instead of just throwing a tee on, we recommend wearing a knit polo instead. As much as possible, we recommend something of good quality but don’t be in your face with the brand names of your pieces. 

Don’t Forget Men’s Accessories

Show your taste through your choice of accessories instead, favoring craftsmanship over high-end brands. The best way to show that is through proper accessories.

  • Leather Wallet. To the discerning eyes, your choice of a leather wallet will tell a lot about your knowledge and taste. There are different men’s leather wallets to choose from, but we recommend something that’s handcrafted by a master artisan, preferably from Florence, Italy.
  • Sunglasses. Being able to choose a pair that matches your facial aspects perfectly will tell the lady that you are very aware of who you are and you’re perfectly confident with your looks. Just don’t make the mistake of wearing them indoors.
  • A Casual Watch. There’s no need to wear an expensive piece, but if you do have a chance to inherit a valuable heirloom, then that’s the best route to go. Since you’re just sporting a casual look, a timepiece with a leather band will suit your outfit best. 

Chino Shorts

This will balance the look. It will send the message that you are concerned about your looks but you’re not too uptight.

Suede Loafers

Finally, add a touch of style to your look with a pair of suede loafers. Why suede? It shows that not only are you not too uptight, but you also know how to have fun. 

First Date Outfit Type 3: A Dressy Night Look

The big night is coming and you are wondering what to wear on a first date as a guy? Finally, if you want to take the lady out at night to a concert or a fancy dinner with drinks afterward, then this is the look for you:

Wrinkle-Free Dress Shirt

You’d want a top that’s more resilient to wrinkling so you won’t have to worry about your outfit all night and actually have a good time. 

Straight Leg Trousers

It’s formal enough to make you look smart but it’s not too tight to hinder your mobility if you somehow find yourself required to move and dance. 

Leather Bike Jacket

A dress shirt and trousers? Your lady might think you’re boring. We can’t have that, can we? Hence, throw on a leather jacket and give your outfit some edge. Plus, let’s not forget that it will give you something to warm her up should the night grow cold.

Leather Shoes

Of course, your leather jacket would require a pair of leather footwear to match. We’ll leave it up to you to choose which one you want. You can go with dress shoes, chelsea boots, or whatever you find suitable for your personal comfort.


In the end, you just need to remember one thing when dressing up. It’s not the brands that you wear, but the pieces that you choose to wear. Each piece tells something about your personality. And whatever happens, don’t forget to groom yourself properly and wear a fresh pair of underwear just in case. Have fun!

What to Wear on a First Date As A Guy: THE GENERAL RULES

To make things easier for you, here is a simple guide that will increase the chances of impressing the pretty lady:

1. Stay Away From the Khakis

No matter how much you love wearing your khakis or you feel comfortable in them, avoid wearing them by all means. Khakis are just not perfect for the first date. According to the men’s fashion experts:

“Khakis scream ‘casual workplace,’” explains Bruce Pask, style director of the men’s fashion magazine Cargo. “They just don’t seem sexy.”

Jeans on the other hand is much more acceptable and sexy, contrary to what many men think. So if you don’t find anything better consider wearing a medium to dark jeans teamed with crisp cotton or linen shirt and a simple dark blazer. This accentuates your manliness unlike khakis.

2. Add a Hint of Color

Until and unless the woman you will be meeting is mad about ‘Men in Black’, avoid wearing all black attire. Remember, your first date is not a formal meeting, so you can consider adding some colors to make things look more cheerful.

Also avoid wearing beige or other neutral colors since they make you look boring. Instead consider some collared custom dress shirts in blue, maroon, etc. that can be paired with a light colored sweater or the other way round. This way you won’t look too flashy or too boring.

3. Don’t Wear a Suit, Try a Blazer Instead

You are not going to attend a meeting or appear for an interview, so you must avoid wearing suits on your first date. If you really want to look natural and charming, try a blazer instead. Blazers look cool and give you a little more casual mileage than suits.

Moreover you can pair blazers with jeans or trousers of your choice to make it look even more chic. Remember, the key to impress a woman is doing it right, not overdoing it. So save your suits for your wedding day.


4. Keep it Simple Silly

Love wearing casuals? Wearing casuals for the first date can be a good idea; but only if you stay away from your outlandish attire. Remember the theory of KISS (keep it simple, silly). Keep things simple and understated for the top half; that does not mean you have to get dressed in blue and grey. It is recommended to stay away from the neons. Save them for your beach party instead. The secret is to stay relaxed but avoid looking sloppy. Dress in a way that shows you’ve put in much effort to look well; being too much casual might send the wrong signal.

5. Highlight the Masculine Traits

Women get attracted to men who have a chiseled physique. If you have been blessed by a physique turn the heat on, then try wearing clothes that highlight the masculine traits such as broad shoulders, larger torso and the line of the face. For instance, sports jackets work great in highlighting the masculine features. The secret to impressing a woman on the very first date is to dress like a ‘man’ rather than dressing like a ‘boy. Don’t forget to wear the right attitude to create the right impression.


6. An Eye for Details

Wearing the right trouser and the right shirt or t-shirt is not enough. You need to have an eye for details. For instance, if you wearing a shirt with French cuffs, make sure you match it with good cuff-links.

Pay attention to the kind of shoes you are wearing. Good quality boots or trendy sneakers would be a good choice. Choose something that go perfectly with your attire – for instance boots look great with jeans, loafers look good with trousers, etc. Keep the climatic conditions in mind when choosing the shoes. Another piece of advice – avoid wearing jewelries on your first date, you might look tacky. Rather let your woman flaunt her jewelry and use your chance to praise her choice to sweep her off her feet.

Finally, wear a fragrance that increases her attraction towards you. But remember don’t use anything too strong that might make her feel like running away from you.If you overuse parfumes the undesired ‘I’ve tried too much effect’ is guaranteed.

7. Get a good hairstyle

The ultimate reason to style your hair? It’s attractive.

As mammals, we’re attracted to nice hair on a conscientious level, so play with hers natural instincts. Great haircut can make wonders. It’s definitely worth investing that 20$ more and make sure that you have a haircut which not only matches the trends of this decade, but also play up your best features and hide your flaws.

8. Don’t Break Your Bank

Men often think that they have to wear clothes from the best labels in order to impress the lady, but that’s far from true. The key is to carry yourself well (no matter what you wear) and be confident about yourself. So be smart when choosing clothes for the first date. Avoid spending a fortune on the clothes for the first date; rather choose clothes that will be suitable to wear all year long whether the lady gets impressed or not. Take time to choose clothes that will work with your existing wardrobe collection.

Investing in classic clothing is often better than spending money on a fashion piece that you can’t pair with the other clothes. Here’s one secret – you can make a blazer bought from the secondhand shop look like a million dollar blazer when paired correctly.

The secret to a successful first date is wearing clothes that make you feel comfortable. It is natural to feel nervous on your first date, but avoid going over the top. Choose your attire and accessories to send the right signal and shows off your personality.

Now, rules are meant for breaking, so you can also break the rules if you want. But that way you might be venturing into a risky territory. So if you want your first date to be successful, following the rules laid down above. Wear the right attire and the right attitude; you will be able to show off your best side!

About the author Nicola Reynor

Nicola Reynor is a passionate blogger who loves to blog about fashion, beauty, travel, health, fitness, wedding and lifestyle trends. When in leisure time, she prefers to spend time in traveling with friends and family. Connect with her on Google+ and Twitter.

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