What to Wear on a First Date? (For Men)

One of the most nerve-wracking things a person can do, along with job interviews and public speaking engagements, is go on a first date.

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It’s essentially your one opportunity to demonstrate that you’re not only brilliant, but also kind, attentive, amusing, and, most importantly, well dressed.

You’re on your own for the first four attributes, but when it comes to dressing, my depth of men’s style knowledge comes in helpful.

I know it sounds superficial, but looking well is unquestionably important when it comes to establishing a good first impression in any setting.

This is why I put together a list of my favorite men’s first date outfits, which will cover you from casual coffee dates to extravagant dinners and everything in between.

Let’s get you looking great and feeling stylish about yourself.

Casual Daytime Date

For our first look, we’re looking for something casual and laid-back for a daytime date, such as meeting for coffee in a cafe or going for a stroll in the park.

I honestly believe that more and more women prefer something more casual for a first date, such as having coffee, because it feels like there is less pressure and time commitment for everyone interested.

You’ve undoubtedly formed a strong impression of the other person by the time you finish your cup of coffee. You can mention the idea of a second date if the vibes are positive.

So, what should a guy wear on such a low-key and laid-back date?

While I usually talk about how guys underestimate the power of a well-fitting t-shirt and dark wash jeans ensemble, you should take it a step further because this is your first date and you want to create a good impression.

Here’s what’s on my mind.

Let’s start with a traditional Oxford button-down shirt instead of a basic crew neck tee. The Oxford button-down is a clean and timeless men’s wardrobe staple that is more formal than a t-shirt but not as formal as a dress shirt.

I typically advise a man to have one in white and one in pale blue, but you may always go for something more seasonal, such as a darker hue in the winter and brighter colors in the spring and summer.

Also, roll up your sleeves and reveal a portion of your forearm. This appeals to women.

Combine the Oxford with dark wash denim or navy chinos and a pair of your favorite shoes for a style that’s both casual and stylish without seeming overly put-together.

You could easily replace the Oxford with a short sleeve button-up shirt in the summer, and if you want to show off your uniqueness even more, go for one with a stylish print.

Another option for a coffee date outfit is a bomber jacket with a crew neck sweater or t-shirt, dark wash jeans, and shoes, which is one of my favorite combinations.

The unzipped bomber vertically splits up your upper body, producing a slimming effect. This is a terrific look if you have a bit of weight in your waist.

Dressing for your body shape guarantees that you not only look well, but also feel good about yourself. And the bomber is one of those pieces that can be worn all year long by men of all shapes and sizes.

Casual Evening Date

Our second first date outfit is a little more flirty, fun, and perfect for a Friday night.

This time, we’re getting ready for an evening get-together, such as going out for drinks at a bar.

On a first date, meeting for a casual drink is similar to meeting for coffee in that there is less overall pressure and time commitment. You can always break up after one drink if you’re not feeling it.

Also, a little liquid bravery never hurts to take the edge off.

Remember that the goal of a first date isn’t to get wasted and tell the other person everything about your life, especially those uncomfortable adolescent years. It’s about getting to know the other person, having a good time, and always leaving the other person eager to learn more.

First up, a traditional polo shirt or crewneck sweater paired with a suave and stylish pair of chinos, which is one of my favorite outfit combinations.

You may believe that polo is not for you, but you simply haven’t discovered the ideal one. Try one on in a neutral color like black or navy, and I don’t think you’ll be surprised if you end up with one in every color.

Chinos are also a wonderful option for this outfit because they provide a more elevated vibe. They’re the ideal compromise between casual jeans and more formal wool pants. A pair of blue slacks may be surprisingly flexible.

Now let’s talk about your footwear. There are a few choices available here.

If you want something a little more laid-back, a pair of low-top shoes, especially in white, will lend some bounce to the deeper tones of the other pieces.

Choose a pair of brown lace-up dress shoes, such as Oxfords, if you want something more polished and dressier.

Finally, lace-up boots are the way to go if you’re looking for something that’s both dressy and casual.

Don’t be scared to finish off your ensemble with a watch or a metal cuff. A simple stylish accessory like this delivers the message that you’re self-assured and in command of your life.  Even if this isn’t always the case.

Let’s have a look at another date night dress as a variation on this one.

On top of that, we’ve got a casual yet stylish jacket to wear. Suede jackets are a personal favorite of mine. However, you can always opt for a wool or cotton bomber, or even a blue or black chore jacket.

In the evening, I like to suggest wearing darker coats to accentuate the sensual vibe that an evening date radiates.

Combine it with a sweater, t-shirt, and dark wash jeans for a seductively stylish ensemble that is sure to make a good first impression.

Dressy Evening Date

Our next first-day outfit suggestion is a little more dressy. It’s a dinner date outfit for the evening.

Dinner dates are a big thing for women, therefore you should constantly keep that in mind.

There are many emotions present, including excitement and anxiousness, as well as the underlying hope that it will be a success or, at the very least, not too unpleasant.

After all, unlike grabbing a coffee or a casual drink, you’ll be spending an hour or two getting to know one another, and it’ll be a far more intimate moment than grabbing a beer or coffee.

You can rest comfortable that she’s putting up the effort and time necessary to look her best, and you should as well. Otherwise, your lack of effort in your look would give the impression that you are uninterested in the date.

My go-to dress for a fantastic evening date is a tried-and-true ensemble that instantly communicates that you’re a capable man who cares about his appearance.

A sport coat, a button-down shirt, dark wash jeans, and a pair of sophisticated dress shoes make up the ensemble.

This outfit may appear simple at first glance, yet it is a master class in nailing the essentials, proving that the devil truly is in the details.

First and foremost, make sure that each component, especially the sports coat, fits you properly. When the jacket is buttoned, the sleeve should strike at the bend of your wrist, and the jacket should lightly hug your torso.

You’ll look like a kid who borrowed it from his father’s wardrobe if it’s too loose. As a result, having it customized to ensure a perfect fit.

If this is your first time purchasing a sports coat, choose one in a classic navy or charcoal color, as the darker hues will enhance the evening.

The dressiness of this type of jacket is offset by dark wash jeans and a shirt, resulting in a simple, clean, and stylish look.

Let’s talk about footwear for a moment.

Lace-up Oxford dress shoes are evidently the traditional go-to for a look like this. Alternatively, consider a pair of trendy loafers, such as leather penny loafers or suede driving mocs.

If this attire is a little too formal for your tastes, there are a number of ways to dress it down.

First and foremost, you can replace the formal shirt with a simple crewneck sweater; I think a merino wool version would look fantastic here.

If you’re searching for something a little more casual, a pair of simple lace-up sneakers is usually a good option.

Just make sure they’re clean and the laces are tucked in. Shoes, whether you like them or not, are one of the first things a lady observes about a man, so make sure they’re clean.

Another modification on this attire is if you don’t feel at ease wearing a sports coat.

If that’s the case, I completely understand. Sports coats have a preppy style to them that isn’t for everyone, but the most important thing is that you show up for your first date looking and feeling your best.

If you’re worried, it’ll show in your body language, and there’s nothing more ugly than a man fidgeting or feeling uncomfortable in his clothes.

If you’re in doubt, get out your go-to bomber jacket and pair it with a white, navy, or black Oxford or polo shirt. Wear your lace-up boots with a pair of dressy wool trousers.

This ensemble nearly feels casual, but the collared shirt and wool pants give it a more professional, put-together vibe that’s excellent for a dinner date.

If you want to convey that you’re looking for a more elevated look, tuck your shirt in the front and wear a belt that matches the color of your boots.

This may appear to be overly meticulous, but those small details can help you secure a second date.