101 Women Answer What a Man Should Wear On a First Date

This guest post is written by Peter Nguyen, a private personal stylist for successful men and founder of The Essential Man

On our first date, my girlfriend and I went to PDT (above), a really cool speakeasy bar here in NYC hidden behind a phone booth in a hot dog shop. They’re known for their amazing cocktails, which we gladly put to the test.

If you asked my girlfriend about our first date, she couldn’t tell you much, except for one thing — the shirt I was wearing. A striped tabbed collar dress shirt from Robert Geller.

“It’s my favorite shirt on you.” She says.

It made such an impression on her that it has survived a good 5 closet purges.

You’ve probably heard the saying “It only takes 7 seconds to make a first impression”.

What if I told you you actually had less time than that?

According to a study done by Princeton, it actually only takes the brain 1/10th of a second to make a snap judgment of someone.

So what does this mean for you my single, dating friend?

It means that before you’ve even opened your mouth, she’s already sized you up. So it’s in your best interest to use the only tool you got in that brief, 1/10th of a second: your style.

BUT WAIT, THAT’S SUPERFICIAL! LOOKS SHOULDN’T MATTER! SHE SHOULD LIKE ME FOR WHO I AM!

Whenever I’m at a party and I tell people that I’m a personal stylist for men, I get one of three reactions:

1. “THANK YOU!”
(This is the #1 response from women.)

2. “Oh man. How’s my outfit?”
(This is where I try to decide whether to give the polite answer or the real answer.)

3. “Cool man. I don’t focus so much on superficial stuff like that.”

Yes, someone said this to me at a party recently.

Here’s how it went down:

“Interesting. What do you mean by that?” I asked him.

“Oh, no offense,” he said.

(I love when people say “no offense”, or “not to sound racist”. It’s usually followed up by something offensive or racist.)

“I want people to like me for who I am, not whether I’m wearing a nice suit or whatever.”

“Totally. Hey, it was great to meet you.”

And then I walked away to pour myself a much-needed drink.

(Conversation tip: Sticking out your hand and saying “Hey, it was great to meet you.” is the best way to leave a conversation you don’t want to be in.)

You’d be surprised how often I get this kind of reaction, especially when I bring up that one of the best “dating hacks” is to improve your style.

“She should like me for who I am!” Guys say in response.

“Ok.” I’d say. “Describe to me your perfect girl.”

What do you think their answer always is?

Their perfect girl is always HOT.

“She should like me for who I am! Meanwhile, I want to date girls that look like this!”

Yeah, shocker, right?

This is what I call “The Perfect Girl Hypocrisy”. People think they’re exceptions. They want everyone else to change their standards instead of raising theirs for themselves.

Obese people want to change health and beauty standards instead of shedding the excess weight. Unqualified job hunters want companies to lower their requirements instead of getting more experience. Guys want hot girls but don’t want to work on and be judged by their looks.

Sorry, my friends, it isn’t happening. That’s not how the world works.

THE UNCOMFORTABLE TRUTH ABOUT OUR LOOKS

Here’s the uncomfortable truth about humans: We judge each other by how we look.

Yes, it’s superficial. Is it bad? Maybe.

The thing is, we’re superficial about almost everything.

You’re less likely to eat sad looking food in disposable tins because we associate sad looking food with unhealthy. Judging by its looks, It’s probably not as nutritious and is most likely going to make us sick. (Even though this might not be true.)

Vibrant, colorful food on clean white plates symbolize to us freshness, cleanliness, and that it’s healthy to eat.

This is called Thin slicing — it’s making snap judgments on something based on the information you have at hand. When you don’t know a lot about someone, all you can judge them on is what you see. Presentation matters, whether it’s a plate of pasta, or what you wear on a date.

It’s the reason why when surveyed, 76% of patients found doctors who wore white lab coats more trustworthy.

If your doctor came in wearing an oversized shirt, messy hair, sweatpants and dirty shoes, would you want him looking at your kid? NOPE.

GOOD NEWS: IMPROVING YOUR STYLE IS EASY

Before you curse the world, let’s take something else into account. Your style is one of the easiest things you can improve when it comes to dating.

If you’re an introvert, it’s going to take a lot of practice to improve your conversation skills.

Unsure of your career and life path? Good luck changing that in a week.

Bad style? No problem. You can head to a menswear shop and do a complete 180 in 15 minutes.

Of course, you’ll need to know what to get. Luckily, I got your back.

I spent the last 5 months asking women around the world a question: What should a guy wear on the first date?

In total, I gathered 101 responses from women of all backgrounds, jobs, ages, and locations. Women from as close as New York City, to as far away as Tokyo, Sydney, and Tehran.

Here’s a brief overview of the women I spoke with:

Average Age: 28
Single: 42%
Relationship (Less than 3 years) 29%
Married: 29%

And here’s what they said:

#1. EFFORT IS THE MOST IMPORTANT THING

Does it matter if you’re wearing expensive designer clothes on a first date? No. In fact, of the 101 women surveyed, not one mentioned designer clothes.

However, the most common theme in the written portion of the survey? Above all else, effort (e.g. trying to look nice) was the most important quality of a man’s style on a first date.

Our style is a symbol of who and what we are. It represents choices that we’ve made in life.

Getting dressed is an action. And, as the saying goes, actions speak louder than words.

Does it matter what kind of car a father drives to pick up his kids? Of course not. What’s more important is that he shows up. It symbolizes that he’s responsible and cares for his kids.

“As a woman, I will make an effort to look nice and pretty for my date because I want to respect his company and effort for asking me out — and I would like the person to feel proud to be with me. When a guy dresses like a teenage boy and it looks like he didn’t care at all, it is distracting and really kills the first impression.” – Morganna, 27

WHAT YOU CAN DO TODAY: If you’re new to improving your style, check out my post “A Beginner’s Guide: 16 Essential Style Tips For Guys Who Want to Dress Better”

#2. THE RIGHT FIT IS MORE IMPORTANT THAN EXPENSIVE CLOTHES

Any clothing that doesn’t fit well is an instant put off. – Jennifer, 27

I’ve preached many times that getting clothes that fit will solve 90% of your style problems.

In my experience, men often wear clothes that are too big for them because:

1. They grew up (like me) in a time where wearing baggy clothes was cool and never learned any better.
2. They feel that it’s more comfortable.

Ill-fitting clothes wrecks havoc on your attractiveness. It makes you look fatter, shorter, and sloppy. Wearing clothes that fit properly not only makes you look better, it allows you to look good even when you’re dressed in something as simple as a t-shirt and jeans. (See: Ryan Gosling, above left)

If that doesn’t persuade you to wear clothes that fit properly, maybe this will:

Loose fitting [pants] remind me of my dad. – R, 24

There’s nothing that’s going to kill sexual attraction faster than that.

WHAT YOU CAN DO TODAY: Download my free “Style Starter Triple Pack”. It’s a combination of my 3 best guides, including my “How clothes should fit” cheat sheets that’ll help you master fit in 10 minutes.

#3. STYLE HACK: SWAP IN A BUTTON-UP SHIRT IN PLACE OF A T-SHIRT

60.2% of the women surveyed loved to see their date show up in a button-up collared shirt, while just 14.8% of women said they wouldn’t mind seeing their date in a t-shirt.

T-shirts are often associated with “casual” dressing. Swapping in a collared shirt signals that you’re putting an effort to go beyond “casual”.

Instant upgrade.

WHAT CAN YOU DO TODAY: Not sure what kind of button-up shirt to get? Read my post on my favorite button-up shirt of all time “Essentails: The Chambray Shirt”

#4. SHOES? NOT AS IMPORTANT AS YOU MIGHT HAVE THOUGHT

This part of the survey surprised me the most, as I’ve heard time and time again that women will judge you based on your shoes.

Yet, when I asked women what kind of shoes they loved to see their date wear, the results were all pretty even.

A nice pair of boots won overall, but just barely, gaining 34% of the votes. The rest was split evenly between clean white sneakers, dress shoes, and “Other”, with the write-in answers consisting mostly of “it doesn’t matter”.

My recommendation? It’s hard to beat a solid pair of boots, as they can work with jeans or dress pants. My current favorite boots are from Thursday Boot Company, shown above.

And whatever you do, just don’t show up to your date wearing Vibram five finger shoes.

On behalf of all men, I apologize to these poor women.

#5. WOMEN LOVE A MAN IN A NICE LEATHER JACKET

When asked what single piece of clothing would a woman love seeing her date wear, the clear winner was a perfectly fitted leather jacket.

A perfectly fitted leather jacket (50% of votes) beat a tailored suit (24.3%) by a little more than double, and completely crushed hoodies (2.8% of the votes, sorry readers in Silicon Valley).

If this doesn’t convince you to get yourself that perfect leather jacket, I don’t know what will.

WHAT YOU CAN DO TODAY: For those looking to add this essential into their wardrobe, check out my Ultimate Guide to Buying A Leather Jacket here.

#6. WHEREVER YOU GO, MAKE SURE THERE’S SOME ALCOHOL

While many women agreed that you don’t need alcohol to have a great first date (a few even said bar dates were uncreative and cliché) the data still showed they all wanted the option to drink. (Relax the first date nerves, perhaps?)

When asked what was their favorite place for a first date was, 65.8% of the votes went to places that had alcohol.

A nice cocktail bar received 27.8% of votes, a great dinner captured 25% of the votes, and a fun dive bar got 13% of the votes.

The remaining votes were split between coffee (19.4%), and “Other” (14.8%), which included write-in answers ranging from “it depends on the guy”, “a nice walk in the park”, and “a museum”.

OK, NOW WHAT?

Not sure what to do with this advice yet? Not to worry.

To help you out, I’m sharing with you some date and outfit idea combos based on this data to get your first date off to a great start.

THE MUSEUM DATE

Eyeglasses: Watts Eyeglasses by Warby Parker – $95, Wool Scarf: Acne Studios – $180, Blue Suede Bomber Jacket: Valstar – $1,135, Mandarin Collared Strip Shirt: FOLK – $185, Slim Fit Stretch Chinos: NN07 – $160, Socks: The Workers Club – $40, Boots: Thursday Boot Co. – $199

The Date: Museum dates are a great way to break up the monotony of meeting up a bar, but it requires a bit of strategy.

The biggest mistake you can make on a museum date? Spending a lot of time looking at the art and reading the text! I know, it doesn’t make sense, but hear me out. First dates are all about getting to know each other. When you’re examining the art and reading at a museum, you have a tendency to be quiet. The real focus of your date isn’t the art, it’s your company. Think of the museum like a beautiful backdrop, just the same as if you were strolling through a park.

Here’s a better strategy, thanks to my friend Nick Gray, founder and CEO of Museum Hack:

1. Grab a map for you and your date.
2. Next, walk and talk, glance at the art, but don’t stop, especially to read the text. That takes away from precious time to get to know each other.
3. After the initial walk through, take a break at the museum café, order some food, talk some more, then pick parts of the museum you want to have a second look at together on the map.
4. Go back to the spots you chose and enjoy the art.
5. Don’t forget to stop at the gift shop and pick up something nice. (Like the wallet from the MoMA above.)

The Outfit: The key items in this look are the collared shirt and boots. Wearing a suit on a first date, especially something like a museum, can feel like overkill. You want to communicate that you’re putting a little effort into it, and this is why instead of a t-shirt and sneakers we swap in a button-up shirt and boots. Blues and browns are a great color combination that help you stand out, especially if you’re visiting a museum in NYC where everyone loves to wear black. Give it a pop of color with a bordeaux colored scarf.

THE NON-CLICHÉ COCKTAIL BAR

Leather Jacket: Hugo Boss – $745, Grosgrain-trim collared polo: Lanvin – $375, Wool dress pants: Suit Supply – $189, Socks: FALKE – $28, Suede slip-on sneakers: Common Projects – $420

The Date: I love a date at a cool speakeasy, but securing a spot at one can be stressful, especially on a first date. There are plenty of cocktail places with great stories that don’t require you to search for a hidden, unmarked door – like Bar Goto, a Japanese bar opened by ex-Pegu club alum Kenta Goto. Order his signature Sakura martini – a blend of gin, sake, maraschino liqueur finished with a beautiful sakura blossom. (Photo above)

The Outfit: The polo is the happy medium between a t-shirt and button-up shirt. The key to not looking like your dad is picking one that’s slimmer cut in a non-traditional color, like this sleek Lanvin number. Slip on sneakers can sound like an odd choice at first, but like the polo, we’ve elevated it. This suede model from Common Projects isn’t your 16-year-old brother’s Vans, and gives a nice casual contrast to the formal dress pants. Bordeaux and charcoal gray is my all time favorite color combination. It’s warm and romantic, paired with a sleek black leather racer jacket, you’ll be hard to forget.

THE LOW-KEY DINNER DATE

Cashmere Coat: Suit Supply – $699, Brushed twill shirt: J.crew – $39, Watch: IWC – $3,950, Wool Drawstring Pants: Acne Studios – $350, Embroidered wool scarf: Paul Smith – $225, Socks: FALKE – $28, Derbys: A.P.C. – $455

The Date: Dinner on a first date can sometimes feel like a trap. What if you realize you two aren’t really into each other and your entrees just came? Instead of a proper dinner for a first date, I recommend getting some wine and tapas.

Tapas are small plates of appetizers and snacks that you share over drinks. I love it because the tapas themselves become a conversation point. Decide on ordering things you’d never normally try, get adventurous. Start with a few plates and see how things go. If it’s going well, you two can order more and keep the date going. Not feeling it? No worries, you share a few bites and don’t have to commit to a conversation over an entire entree. Grab the check and part ways.

Some recommendations for you first-time tapas eaters: Dátiles con beicon (dates stuffed with almonds and cheese, wrapped in bacon) and patatas bravas (crispy potatoes with an aioli) are easy crowd pleasers. My all time favorite: Jamon Iberico, slices of ham from pigs fed acorns then aged for 36 months. Fatty, nutty, and worth the (very expensive) price.

The Outfit: Suits on first dates is a little too much. Subtle style substitute – wear a tailored topcoat. It gives the same feeling that you “dressed up” without going full blown suit.

When I think tapas, I think sharing food, drinking wine, having an amazing conversation. So take off your coat and relax a little bit. You’re going to be moving plates around and passing food to her, so don’t be afraid to unbutton and partially roll up your sleeves. This is a great opportunity to show off a nice watch. My pick: IWC’s refined entry Mark XVIII. It’s a watch that says “I have really good taste and I don’t need to be flashy”.

GET THAT SECOND DATE

First dates are like movie trailers, a preview to get her interested and excited and make her want to see more.

While I’ve armed you with some style tips to make sure you look your best, remember that clothes don’t make the man, they just enhance him.

To make sure you kill it on your first date and get her asking when can she see you again, I’ve put together a free bonus guide for Linx with some of the best first date tips.

8 Things Gentlemen Do on First Dates

The point of the first date is to discover if there’s real compatibility beyond initial interest. If she’s already said yes, consider yourself off to a good start. If you want to give yourself the best chances of romantic connection—or even a second date—consider the chivalrous route. Here are 8 things gentleman do on first dates that prove chivalry is not dead.

Suggest a first date in a place convenient for her.

Instead of suggesting the restaurant or bar closest to you, you ask what is most convenient for her. Your asking demonstrates consideration and shows that you are willing and able to make her life easier—a feeling that will ultimately make her feel more relaxed during the first date. Same logic applies when you ask about any food allergies or preferences she has. Any research you do before the date will benefit you exponentially_.

Observe the 4 p.m. deadline.

If you have plans tonight, text or call to confirm your date by 4 p.m. Many women start wondering if the date is still on, especially if a few days pass between the ask and the event. A short text to the effect of, “Looking forward to seeing you tonight. Let me know if we need to adjust the timing” will keep everyone on the same page.

Mind your (table) manners.

Follow behind as you make your way to the table; she should not be walking in your wake. When you get to the table, ask if you can help her check her coat. At the table, let her order first. Letting her take the lead shows that you are want to make sure her needs are met before yours. This simple gesture is another way you can ensure she is comfortable. Lastly, always encourage a glance at the dessert menu. There’s nothing more sexy than indulging in the senses and enjoying the rich decadence of chocolate.  Even if you’re not a dessert guy, order one to share.

Introduce her.

Should you run into friends on your date, be sure to introduce your date without saying “my friend”. There is no need for an extensive introduction, but you must acknowledge your date if a friend says hello. You could say, “I’d like you to meet [date’s name]. We were both excited to try this place.”

Mind the Drinking.

Pay attention to what she orders and offer a refill when the glass is empty- same principal goes for her water glass. Even though your nerves may want to order a third drink, stick to a two-drink maximum. Slurring your words is not classy.

Pay the bill.

That’s right. Let’s keep this equation simple. Be prepared to foot the bill and keep any conversation surrounding this transaction to a minimum. If she offers to pay, politely decline and change the subject. Paying for her is a sign of interest and shows that you are happily willing to invest when you have feelings. If you both continue to date, it’s very appropriate for her to reciprocate at some point but definitely not on date one.

Offer to get an Uber for her.

When a simple gesture that takes 2 minutes can make all the difference, you should do it. Let her know that you’re interested in getting her home safely, whether that means you ping Uber or offer to drive her yourself.

Close out the evening with a text.

There is nothing gentlemanly about leaving a lady to wonder if she’ll hear from you again. Thank her for her time and company and, if you want to see her again, let her know. Be confident in your actions and consistent with your communications to the woman you’re interested in.

Dating Advice for Men and Women

We get many questions surrounding early stage dating and how to successfully get from date one, to date two, and beyond.

Simple advice for men: Keep it simple guys. Remember that chivalry is not dead. Women love when men are confident and have manners. I always tell guys who suffer some pre-date nerves to head to the restaurant ahead of time- this could mean even the day prior to your date to familiarize yourself with the setting, the menu, wine list, and start visualizing success. Here we see a Linx client confidently walking into the restaurant ahead of time to scope it out.

For a lady, chivalry means walking on the outside of the sidewalk, opening doors, paying for her dinner date (especially if the man is the one who asked her out), giving a genuine compliment, and actively listening. This is a perfect example of what a guy should do on a date. Our client is walking on the outside of the sidewalk- he is protecting his date from traffic and making her feel safe. The Linx team also loves how both our client and his date have dressed for the occasion. He looks dapper and well put-together and she is wearing a sexy maxi dress, paired with leather jacket, hair down….effortless and revealing *just* the right amount of skin.

When you sit down for your date, start with a little liquid courage. It’s fun to shake things up and order a cool cocktail instead of a standard glass of wine. If you both are feeling some sparks already, why not suggest your date has a sip of yours and vice versa? Now what to do if your date is a teetotaler? That is unfortunate for you. Kidding! Our advice if you or your date abstains from booze is to not make a big deal about it because that is a personal choice. If you want a glass of wine, order a drink but limit it to 2- especially if your date doesn’t drink. If you don’t drink as a result of sobriety, we have helped a handful of individuals develop techniques to combat anxiety and prepare themselves.

On your date, engage in the senses on your date- specifically touch. Body language is everything- from leaning in towards your date while you are deep in conversation, to even being in the moment and scooting chairs closer together. Our client felt that sitting across from one another would feel too formal and stuffy for this date. He responded quickly to being seated at a table for 4 and instead knew it could increase affinity if seated next to his date (while respecting personal boundaries). Definitely a smart move! Note this is a staged date and she is not a client of Linx. .

This couple also understands good body language and maintaining eye contact.

On the date, focus on your date! Don’t be Mr. “ADD” looking around the room or having shifty “crazy eyes.” Slow down, be in the moment, and block out all distractions around you (including distractions in your head about ‘what to do now’, ‘what to say’, ‘does she think I’m funny’, ‘does she find me attractive’ …) Try to stop that tape running in your mind- at least for now!

This couple is great at using body language to not be stiff…more so an example of her in this particular photo.

Express yourself, use arm gestures, laugh, smile, and most important have fun on your dates. Remember that the goal of the first date is not to get into a relationship. Instead it is to get to date two. Date two is to get to date three. If you apply this way of thinking you will immediately remove pressure on yourself.

Remember that your next date will be unpredictable- as is life! As much as you want the perfect outcome (if perfect really exists) there are inevitably going to be variables out of your control. What do I mean by this? Examples include: the waiter takes forever to take your order, it is noisier than you prefer, your date is not laughing at your jokes, the water you just sipped went down the wrong pipe and now you’re coughing like a maniac, you tripped on the way up the stairs to the table, your credit card just got declined even though there is plenty of cash in the reserve, your date is all of a sudden not hungry, your dish came out cold, you ran into an ex, your boss is seated next to you, your date just insulted you with profanity,…the list is frankly endless of hiccups that can happen and WILL happen!

Gain mastery over dating by being prepared (dating is a skill, repeat that over and over), being natural, being in the moment, and trying not to stress yourself out by the random invariables out of your control. The more you analyze things on your date, the higher probability of short circuiting the entire date!

Don’t be too quick to judge your date (maybe he/she has a bad work day). If you are stressed, you will come across as a stress-case and ‘Serious Sam’ or total ‘Debbie Downer.’

You gotta riff, embrace spontaneity, let the proverbial hair down so to speak, and STOP WORRYING SO MUCH ABOUT WHAT OTHERS THINK ABOUT YOU. If you “let go” and “go with the flow”, chances are you have just increased your chances of a next date. Case in point, our couple snapped on camera locked arm-in-arm leaving Nola’s last night!