We Asked a Hollywood Headshot Expert 20 Questions About Looking Hotter in Photos

When some of the world’s best looking people need to look even better, they call Marc Cartwright. As one of Hollywood’s leading headshot photographers, Cartwright has spent years photographing thousands of actors, models, and yes, even a few people not blessed with some of the best genetics on earth. In his 15-year career, Cartwright estimates he’s photographed more than 6,000 clients—ranging from A-listers to ordinary guys just looking to punch up their LinkedIn.

Cartwright also lends his expertise as a headshot authority with practical tips in his monthly column for Backstage magazine, which covers the nuances of looking better in front of the camera, addressing everything from what to wear to how to appear more relaxed during a shoot.

Whether or not those things come naturally to you, there are all kinds of tricks you can rely on to look stronger, more attractive, and more confident in photos, none of which require a Hollywood-tier hair and makeup department.

In this installment of 20 Questions, we asked Cartwright to share a few of the simplest ways that everyone can loosen up and look their best when a camera lens is pointed in your direction.

What are the biggest mistakes you see a lot of guys make on their dating app profile photos?

I always think it’s cheesy when people try too hard to be sexy. To me, it screams insecurity and that you have very little else going on. Of course, it depends what your intention is. If you’re trying to send a signal that you are only good for one night and have the brain power of a newt, sure, focus solely on the sex appeal. If your intention is to find a partner, then you want to be more authentic. Good photos show what you’re passionate about and show your potential date what life would be like if they were dating you.

They key is the photo needs to look like you. If you show up to a date and the photo doesn’t look like you, you’ve already started out lying to your potential mate, which is never a great first impression. That said, headshots should never be your profile photo on a dating website. The purpose of an actor headshot, for instance, is to represent the characters you could be considered for in the entertainment business. Dating profile pics should be somewhat candid—well lit, but natural.

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What about corporate headshots? How do you stand out in a sea of grey suits and ties without potentially looking immature or unprofessional?

First, find out if your company has a template or protocol for how they like images to look. Sometimes companies have a uniform look that they want for the branding of their operations. Besides that, when planning your corporate headshot, you need to have your customers and their lifestyle in mind. For instance, if your product is supposed to evoke fun and creativity, you want to have corporate shots with personality and that think outside of the box.

On the other hand, if for example you sell a financial product that could make or break the standing of your clients, you might want to have something that feels a little more serious and focused. Either way, I think it’s best to come across as trustworthy. You want to give your customers a feeling that you are going to take care of their needs, they’re not going feel intimidated when talking to you, and that by working with you they will move closer to whatever lifestyle they are going for through the purchase of your service or product. A lot of this is going to be in the performance in the shot but you can also use color, wardrobe, and atmosphere to set the tone.

If you can’t yet afford to hire a pro photographer, what are some secrets to taking a great headshot using your iPhone or laptop camera? Are there any filters, apps, or other tools that people should look into using?

I would never suggest taking a headshot with your phone. Your headshot is one of your most important tools and is many times a first impression. If you take your career seriously, take a few weekends off from buying drinks with friends, avoid the pricey coffees, etc., so that you can save up and hire a photographer that is capturing the vibe that you want.

There is bound to be a photographer that falls within your budget. When you are competing with other businesses, you don’t want yours to look like the one that is cutting corners or isn’t willing to invest in themselves. (Especially since you’re asking others to confidently invest in you.)

On the flip side, how much retouching is normal and how wary should men be of filtering away their flaws, especially now that it’s so easy to do so?

Retouching should always be kept to a minimum. Remove anything that isn’t permanent, color correct any skin issues and remove fly away hairs. Anything that involves changing your natural features, weight or skin-tone, really should be approached with caution. Furthermore, your photographer should be making sure to address these things at the photo session so there is little need for heavy retouching.

Also, remember that imperfections can sometimes be what make you unique, attractive or relatable. We all have negative thoughts about some aspect of ourselves. Nine times out of ten, ignore those thoughts. They aren’t your friend.

Any advice for helping someone who is selfie-shy to get more comfortable taking self-portraits?

The most powerful tool you have when taking photos is your mind. First, think about your intention. What do you want people to feel about you when they see your picture? People looking at your photograph will pick up what is in your mind. So, if you are looking at the camera like it’s the scariest thing you have ever seen, people will see fear and discomfort.

The eyes are the windows to the soul. You’d be surprised at how easily your facial expressions and appearance can be manipulated just using thought. When looking at the camera, pretend it is a person. For example, if you are wanting to come across as welcoming, pretend the camera is a person that you would like to charm, or someone that you are proud of. If you want to look powerful and resilient, think of someone that you would do anything to protect. Be specific. The more real you can make things for yourself, the more authentic your picture will be.

Photographers often say it’s crucial to ‘loosen up’ before a photo shoot, but many people struggle to do that in front of a camera. What are some of the secrets you rely on to get people to relax?

I think the key to making someone comfortable is to invite as much of what they are already comfortable with into the space as possible. For instance, playing music they like, talking about their story or life path, asking questions. Every client is so different. As a photographer, you really have to quickly gauge who is walking into the studio and what type of communication they need.

Some clients need more of a soft approach, others want blunt communication, some have planned everything out while others need lots of advice. I think creating a great photoshoot is like putting a puzzle together and that is what I love about it.

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Most men who aren’t actors resist makeup at all costs. When should they reconsider and what will make the biggest difference?

It depends on what the photo is for, but generally I don’t personally like makeup in men’s photoshoots. I like a male groomer to make sure the hair looks great and maybe reduce discoloration in the skin if it’s there. But I like to see skin texture and find that when men wear makeup, it erases some of the character. It is much easier to remove simple blemishes in post than it is to make it look like someone isn’t wearing makeup.

Let’s talk about some common insecurities. What would you say to men who don’t think they have a great smile?

This goes back to the self-talk about our imperfections. Of course, it is case by case, but in my experience, when most people say they hate their smile, it is a personal insecurity and not something that other people actually notice.

Occasionally, you do get someone that is in the process of having work done on their teeth or maybe they have some other legitimate issue. For this we work through how large we want their smile to be and really try to get as much expression in the eyes without showcasing the element that the subject doesn’t feel comfortable with. There are many ways to smile and as we are photographing, we experiment with what looks best.

At the end of the day, a person being photographed wants to feel confident about the way they look, so the objective during a photo session is to translate the emotional value while maintaining the positive vision that the person being photographed has of themselves.

What about men who might have a weak jaw? Are there any tricks to make your jawline appear stronger?

Whatever element is closest to the camera will appear larger. So, depending on what type of weaker jaw they have, I may have the subject stick their chin out a little or I may bring the camera down a bit to make the lower part of the face more pronounced. Sometimes a straight on shot is better in this case.

Do most people really have a “good” side or is that just a myth? How do you figure out what your good side is?

The idea of a good side is not just a myth. Most people are asymmetrical. One eye might be larger than the other or one side might be rounder. I think which side is considered “good or bad” can be subjective, though. One person might like softer features and think their “good side” is their rounder side and feels less severe. Another person might want to use the side with sharper angles and their “good side” makes them feel square, grounded, and authoritative.

Figuring out the good side is trial and error. When having your photo taken, play around with both sides. I have had someone think their left side was their favorite, but we tried a shot on the right side, and they loved it.

What if you’re a heavier guy? Is there anything you can do to put less emphasis on your weight or appear slimmer?

Raising the camera higher or leaning into the camera, and pulling the chin slightly forward to erase any double chin.

How much of a factor is your skin tone? What are some things that more fair skinned guys might want to watch out for, versus men with darker complexions?

It’s mostly lighting and wardrobe contrast. You want to increase light as the skin tones get darker. If you have a fair complexion, you don’t want to wear clothing that is going to wash you out. For darker complexions, you want to choose wardrobe that allows you exposing for proper skin tone while not creating a situation where you are overexposing the clothing.

If you do hire a makeup artist for your photo session, make sure they are proficient at matching all types of skin tones. There is nothing worse than gray looking makeup on darker skin or washed-out tones on lighter complexions.

What if you have thinning hair or no hair at all? Do you have any advice for balding (or completely bald) men?

As always, you never want to misrepresent yourself. There are, however, ways to help the situation. Sometimes going for a shorter hair style or repositioning a part can give the illusion of thicker hair. You don’t want to use too much product which can weigh hair down or appear to thin the hair.

This could also be a great time to hire a male groomer who might have quick tricks. I have seen my hair artists use hair fibers. Also, makeup in the hairline when done correctly can give the illusion of fuller hair. This must be done carefully, as you don’t want any hairline volumizers to show on camera. You are just trying to present an illusion.

For completely bald men, shave any stray hairs that may be growing and be sure to de-shine the head. A little loose powder or even (if your complexion allows), baby powder applied sparingly can reduce the shine.

Are there any common facial hair traps you should avoid?

How groomed your facial hair is, really, depends on what you are going for in the photo. I believe all facial hair needs a little grooming, and certainly you want to make sure your facial hair is clean for your photoshoot.

If you are going for something casual or edgy, the facial hair can be more natural and less structured, but don’t just let it grow without some attention. If you are taking a corporate shot, I do suggest making the facial hair more streamlined, but try to avoid lines that are too severe. I even think that sometimes, depending on how quickly your hair grows, a day to let the shave settle is a good idea. If your hair grows quickly, this isn’t a good choice, but even then, you don’t want the facial hair to feel too boxy or drawn on.

Don’t trim your beard into a point. Don’t shave the cheeks down too deep. Make sure you also shave the neck when going for a more structured look.

What are some common mistakes guys make when they’re trying to appear younger?

The first mistake guys make when trying to appear younger is that they aren’t embracing their true age. There are certainly ways to make yourself look younger without giving people the idea that you are holding on to your glory days. The goal is to find clothing that suits your age but is also modern and makes you feel current.

Some things that stand out to me are wearing backwards baseball caps as a casual accessory, wearing ill-fitting trendy clothing or dressing like a college student, wearing excessive colors or patterns, wearing haircuts that used to be fashionable, but are now outdated, and wearing graphic tees to look young.

Which style accessories will help you add personality without being distracting or goofy?

A nice watch. Sunglasses. Necktie. Bracelet. Socks.

Is there a basic, but classic go-to outfit that most guys can pull off? And how much does the tailoring matter?

I think the fit and tailoring of any outfit comes first when attempting to look fashionable. What is considered a go-to outfit is going to depend on individual style, but an outfit that doesn’t fit properly will never look great. You can wear a t-shirt and jeans, and have it look like a million dollars if the fit is right. When clothes don’t fit properly, they throw off your body proportions. Clothes that are too big make you not only look sloppy, but misshapen and shorter than you are.

What are some of the most tired, annoying, overused things you’re sick of seeing guys do in photos?

I think Instagram selfies have ruined how people take photos. Some of my pet peeves:

What if you can’t avoid having photos taken when you’re really tired? Say you’re a new parent. What are some quick ways to disguise the fact that you’re running on 2 hours of sleep?

If I know someone is tired, I don’t expect them to jump right into a personality filled shoot. I will first offer them coffee or matcha tea. I then have a conversation and try to determine what topics get their energy up. Everyone has thoughts or ideas that make them excited even when they are feeling rundown.

If you don’t have a photographer that is working with you in this way, I suggest doing quick spurts—10 frames where you push the emotion and then take a moment to regroup. This is easier for some, but when you have to get an important shot, you want to rally for even a few moments at a time.

Before going into a photo session, it might be a good idea to think about and write down things that make you feel the emotional value that you wish to portray in your photograph. During the session, revisit this list and talk about it with your photographer.

When I am tired, I take vitamin B or drink Matcha tea. Matcha is great because it gently picks you up and the energy coasts versus the quick crash that can happen with coffee.

What are some of the stupidest things that guys do when they’re trying to project confidence? What does true confidence really look like to you?

Again, it depends on what type of image you want to capture, but I think when someone is trying to look overly tough, it reads as douchey, inauthentic, and many times insecure. Confidence is quiet and observant. Confidence lets people come to it versus feeling the need to always announce its presence.

To me, true confidence is that person that doesn’t let their emotions control their actions. Confidence is being authentic and true to yourself, even when feeling vulnerable. The louder a person is, the more insecure they appear to me. They’re afraid that they aren’t being heard, taken seriously or that their needs will be met or considered important. Maybe they don’t know how to ask for what they need.

During sessions, when the goal of a shot is confidence, I like to explore what a person knows they are good at or feel powerful around. It’s also a fun exercise to learn more about the subject.

Some DMVs and passport services no longer allow you to smile. How do you make a more neutral expression look sexy—or at least not grumpy—when you’re taking a driver’s license or passport photo?

Think of your favorite food or drink. Think to yourself about how you are going to go buy that after your DMV experience (you’ll probably need it). Thoughts always factor into how we look in pictures. You can’t smile with teeth, but you can think of a person you would like to charm or a happy secret.

Do you have any advice for correcting poor posture?

If you are sitting down, push the lower back forward. That is usually enough to straighten up. If you are standing, try to touch your back shoulder blades together and then relax. You don’t want to look like you’re in the army.

Are there celebrities who photograph surprisingly well that guys can learn from? Who are your favorites?

When I think of a best photo subject, I look for someone that seems creative with their poses and performance, but isn’t trying too hard. Someone that isn’t a one trick pony or just standing there looking stoic. Before I photograph actors, I will ask for visual references of photos they like, so I know we’re on the same page. From these inspirations, I like to create vision boards for myself.

From the younger clients, the number one reference I get is Timothee Chalamet. He gives off an air of creative freedom that I think is appealing. He’s not just standing around looking bored. Another favorite is Ewan McGregor, who I find to be a bit of a chameleon. In one photo session, he can come across as artsy, trendy, and edgy, while in another he is classic and dignified. He’s masculine but doesn’t scream it at you and can be soft without seeming self-conscious or gimmicky.

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