I’m so excited for your portrait session! Whether I’m photographing your sweet family or doing a session to celebrate a special moment in your life, like your pregnancy or a newborn baby, I want you to know that I’m honored to be your photographer and humbled that you’ve trusted me with the responsibility of helping you create memories you’ll look back on and cherish for a lifetime. 

My goal is simple: for your session to be as fun and stress-free as possible! That’s why I’ve created this guide just for you! The following pages will help you get the absolute most out of your photos. By the time you’ve read through it, you'll have all of your questions answered and feel ready and prepared for your session!

This guide is packed with my best tips, tricks and insider secrets for scheduling and styling your portrait session –– and everything in between. Your only job is to be yourself, laugh a lot, have fun and let me do the rest! I can’t wait to get you in front of my camera and I’m so excited to see you soon! 

I photograph portrait sessions the way I like to be photographed myself: outdoors, in natural light, because I love images that are clean, bright, fresh and timeless. Images that look and feel like you! That’s why I begin all of my sessions 1-2 hours before the scheduled sunset (or at sunrise) –– during the magical “golden hour” –– when the light in the sky is the softest, dreamiest and most flattering.

You can use a sunset calculator online to determine the scheduled sunset for the date and location you’d like to do your session. Then, just subtract two hours to figure out your approximate session start time. If you’re wearing one outfit, we’ll start your session about 90 minutes before sunset. When scheduling your date, it’s important to remember that the sun sets much earlier during the colder months of the year and much later during the warmer months, so make sure to factor that in –– especially if you have small children with a specific eating or sleeping schedule, or if you (or your spouse) will need to leave work early to get ready for the session and arrive on time. If you don’t have plans after your session, I always recommend going out for a fun date night since you’re already dressed up!

My weekends fill up fast and far in advance, but my weekdays are much more flexible. So if you’d like to do your session sooner rather than later, scheduling mid-week is the way to go!

When you’re planning "getting ready" time before your session (scheduling your hair, makeup, etc.) please give yourself a lot more time than you think you'll need. Make sure to account for things like traffic, getting lost and parking, so you can prevent unnecessary stress, arrive a few minutes early to your session and be ready to start on time. I’m only able to shoot when light is still in the sky, so we’ll want to take advantage of every minute we have together before the sun goes down!

The location of your portrait session is completely up to you! As you’ll see throughout this guide, most of our clients love showcasing the natural beauty of our home state. For most of my sessions, outdoor, open-air environments are always my first choice. I love shooting in wide-open natural spaces because the light is divine, especially during golden hour. There are great options all around the state, so even if you've never seen me photograph in a specific place before, I’m always up for exploring a new spot together!

When it comes to choosing a location, don't be afraid to think outside the box! I encourage you to brainstorm unique places that you might have special access to that most people don’t. For example, maybe you (or someone you know) have access to an amazing location that would otherwise be off-limits, like a beautiful private estate, family ranch, exclusive country club or luxury resort. Spend a few minutes thinking about it and checking around with people in your personal and professional network. You’ll be surprised with what you come up with! If something seems out of reach, just remember: you never know until you ask! You can also consider Airbnb or other property rental sites!

Your portrait session includes my travel time anywhere in the Richmond Virginia area. If you’d like to go somewhere else in Virginia (or the surrounding area) I’m up for the adventure! If you’d like to shoot outside of the Richmond Virginia area, like in DC or the Mountains, for example, there will be a travel fee to account for the extra hours of drive time there and back, the time required beforehand for me to scout locations and the overall longer session time. For destination sessions, I allow three hours (instead of two) so we have enough time to drive to multiple scenic spots. 

If I’m already going to be in or near an area you’ve always dreamed of doing your photos, and we can coordinate our schedules, let’s set it up! I’d love to meet you somewhere beautiful and make it work! If you’d like me to meet you in a destination outside of Virginia for your portrait session where I don’t already have plans to visit, just let me know and I’ll send you a custom quote.

Wondering how many outfits you should plan? I’ve got you covered!

Changing outfits during a session always takes more time than my clients expect, so in order to maximize shooting time and give you the highest number of photos possible, I recommend the number of outfits (as follows) to keep stress low and the number of photos in your final gallery high:

Family Sessions - 1 Outfit

Maternity/Anniversary/Couples - 1 or 2 Outfits

Senior Sessions/Headshots - 2 or 3 Outfits

If you want your portrait session images to look and feel a little more editorial, I recommend bringing a few small, simple props with you, like fresh flowers to hold or a blanket to sit on. If you want to set up a picnic or incorporate another special element into your session, just let me know! Maybe you have access to some larger props that have a real “wow” factor, like a boat, classic car, vintage bicycle or hot air balloon. This is the time to dream a little bit and decide what really feels like you! Props aren’t a must by any means. Some of my clients love them and go all out. Some pick one or two items to bring. Others stick with just their outfits –– and that’s great, too! The most important things you need to bring to your session are love and laughter. I'll take care of the rest.

Dress It Up



Have you been eyeing a gorgeous dress, but just never had an occasion for it? This is your chance to do it up! Remember: there’s no such thing as “too dressed up” when it comes to your portrait session, so don’t be afraid to have some fun! If you don’t want to spend a ton of money adding a new permanent piece to your wardrobe, a lot of my clients love Rent the Runway for their portrait photos because you don’t have to spend a lot to feel like a million bucks. Plus, you can send the outfits back when the session is over! Some of my clients love having an excuse to go shopping and purchase a new permanent piece (or two!) for their wardrobe –– and that’s okay, too! Whatever works for you!

Say Yes to the Dress

There's nothing more romantic than a long, flowy dress. Dresses and skirts tend to look most stunning on camera because they really flatter the female body — which is probably why the red carpet is always full of so many dresses and not very many pantsuits! I recommend choosing long, flowy dresses or skirts because they’re flattering on all body types, look amazing on camera and bring extra movement and dimension to your photos. Maxi (or floor length) skirts and dresses will give us the best “twirl factor,” add more romance to your walking photos and look especially gorgeous when juxtaposed with nature, like the desert, forest, fields or beach. Cute, shorter cocktail-length dresses or midi skirts photograph beautifully as well. My clients who choose to bring two dresses will sometimes choose one of each! I recommend avoiding pants and shorts for your session, and saying yes to a dress (or skirt!) or two! You won't regret it!

Flattering Your Features

In my experience, every woman (regardless of her size or shape) has an area of her body that she’s self conscious about. Recognizing the areas you’re self conscious about when selecting your outfits is key. Choosing flattering silhouettes and colors that complement your natural features is the best way to ensure you’ll love the way you look in your photos. Three-quarter length sleeves create an awesome slimming effect on all arms, so be on the lookout for an option with a longer length sleeve. If your dress has shorter sleeves (or no sleeves) consider bringing a cute jacket, blazer, cardigan or pashmina to incorporate into your look. Skinny straps or strapless dresses have the opposite effect on arms on camera. For most women, skinny straps actually make arms look BIGGER. So I recommend avoiding those whenever possible if your goal is slimmer-looking arms. If it’s colder outside, I suggest bringing a warm coat (the longer, the better!) to wear when we’re not shooting so you don’t freeze in your dress.

For shoes, keep in mind that heels elongate women’s legs and force constant tension in the calves –– which makes them look more toned. Closed-toed heels, in particular, look great on camera because they carry out the line of your leg all the way down to your toe. You can never go wrong with a pair of neutral pumps! If your toes are showing in a peep-toe heel, you might want to schedule a pedicure before your session so you don’t regret letting your toes show. If your shoes don’t show at all in the dress you’ve selected, you could always choose neutral ballet flats to make your session more comfortable. Lastly, make sure to bring a pair of flats/flip flops to wear when moving from place to place. Your feet will thank you later!

Make a Statement

Pairing an accessory or two with your outfit can really help bring some extra dimension to your images. Whether it’s a necklace, belt, bracelet, earrings, hat, or scarf, bringing an accessory or two can bring great visual interest to your photos, so choose one or two that don’t compete for attention when paired together. For example, if you go with bolder earnings, you might want to choose a more humble necklace, or maybe even no necklace at all. Fresh florals in a crown or bouquet can be a really romantic touch as well!

Go Pro: Hair & Makeup

Professional hair and makeup is on the top of most of my clients’ portrait session checklists because it looks amazing on camera and removes the stress of getting ready on your own. You’ll have these photos forever, so this is the time to pamper yourself! Whether it’s lash extensions or blown-out hair, professional hair and makeup will give you an extra boost of confidence in front of the camera, and it always photographs like a dream. If you’re working with a makeup artist, have her apply your makeup in natural light (if possible) so that it looks fresh and not too heavy. Plus, that’s the type of light we’ll be shooting in, so it’ll give you the best expectation of how it will translate on camera. Most of my clients feel like their makeup is “too much” at first, since it’s more than they would wear on a normal day, so if you feel that way at the beginning, don’t worry! Good makeup artists know how to get it just right for the camera — and my clients always love the final result. If you need a recommendation for hair and makeup, I work with the best in the business and have a go-to team! They’re sweet as pie, talented as heck, unbelievable professionals and wonderful people. You’ll LOVE them! Just let me know and I’ll send you their information. I know they’ll take good care of you!

Skip the Spray Tan

Although it might seem counter-intuitive, I recommend that you do not get a spray tan before your session (even a few days prior) because it tends to photograph orange even when it’s applied subtly and by a professional. Your actual skin tone will photograph most beautifully.

Choosing Colors

When choosing colors for your outfits, I recommend selecting lighter, neutral tones and more muted shades. Bright, bold or neon colors are distracting and take the focus away from where it should be: YOU! And how much you love each other :) You can never go wrong with light neutral colors like cream, taupe, camel or light gray. The camera loves shades of soft pinks and muted blues, mixed with sophisticated light-colored neutrals. That softer, more pastel-leaning color palette fits beautifully into almost all natural outdoor environments!

The goal for coordinating a family’s outfits is to visually break up the colors and shades so that you’re not all wearing the same color on top and bottom (like everyone in blue jeans with white shirts). The more you can mix it up, the better! I encourage you to think about planning each outfit with “dominant colors” and “accent colors” in mind. A dominant color is the color that you see the most in an outfit, while an accent has a smaller piece of visual real estate. When you’re planning each family member’s outfit, if you can aim for each person to have a different dominant color, and then tie in and vary the accent colors, it’ll look great all together.

For example, if you’re wearing a blush dress, soft blue earrings and nude heels (blush being your dominant color), then your spouse could wear a navy coat with a white button-down and gray pants, paired with brown leather shoes and maybe even a blush pocket square (making navy his dominant color). Your daughter could wear a soft blue top with a white tulle skirt (making a soft blue her dominant color) while your son could wear light beige pants with navy suspenders and a white button down (making white his dominant color). Now each person has their own dominant color while still incorporating a few touches of the other colors that will pull all the looks together. This will visually break up all the colors and highlight each person and their individual personality. Most of my moms choose their dress first, and then build the rest of the family’s outfits based on that.

Coordinating the Looks

As you’re coordinating your outfit with your family, keep in mind that your outfits will look the most cohesive on camera when the color palette and wardrobe pieces coordinate, but don’t actually “match.” In fact, I recommend that you avoid thinking about “matching,” and instead think about what “fits” together. This will create more visual interest, and allow each personality to shine through.

Mixing Up the Pieces

If you have multiple children, don’t feel like you need to put them all in the same type of outfit. For example, if one of your daughters wears a dress and flats, the other can wear a skirt and boots, if that’s more of her style. If one of your sons wears a bowtie, the other can wear suspenders. Mixing up the wardrobe pieces will bring even more visual interest to the photos.

For Examples Visit My: Wardrobe Inspiration Guide or Wardrobe Inspiration Board

Tops & Bottoms



The same way that a dress is the most flattering silhouette for the female body, a blazer, sport coat or jacket has the same flattering effect for men. You can’t go wrong with a dress shirt, slacks and a blazer.

Long sleeves are more flattering than short sleeves on men, so we’d recommend steering clear of t-shirts or polos, and instead opting for a long-sleeve button-down. The other benefit to long sleeves is we can roll the sleeves up for a slightly more casual look, which gives you two looks with one shirt.

For colors, I recommend neutrals and soft. When selecting your pieces, I recommend choosing a different “weight” for the pants and coat. So for example, navy pants (darker) and a heather gray blazer (lighter). Or gray pants (darker) with a soft powder blue shirt (lighter).

When selecting an outfit for photos, the most important part isn’t the price. It’s the fit. For men, it’s important to have a jacket that fits snugly (but not too tight), and pants that are the correct length and don’t have too many breaks. Just like high heels make women look taller than they are, bunched up fabric stacked on top of a man’s shoes makes him look physically shorter than he really is.

Solid colors will help keep the attention where it belongs, whereas pinstripes or plaid patterns tend to distract the eye, so stay away from too strong of prints, avoid logos and opt for solids instead.

Layered Looks

The next time you walk by a store like J. Crew or Banana Republic, you’ll notice the male mannequins and models are always wearing several layers at once. Layers on men look great on camera, so even when it’s hot outside, it’s worth an hour or two of discomfort for photos that will last you a lifetime. Adding extra layers will bring additional dimension and visual interest to your photos. If the temperature permits, you could even consider adding a v-neck sweater with a pop of color from a long-sleeved collared shirt and tie underneath, or bringing a leather or denim jacket with you. Don’t be afraid to get a little creative with layers!

It’s All in the Details

Long pants with closed-toed shoes is the most sophisticated and masculine look for a man. They draw attention away from your legs and feet, and place it where you want it: on your face! So, for your session, it’s best to leave the shorts and sandals at home. Dress pants, colored pants or nice dark-washed jeans work best. Brown leather dress shoes complement almost every look, whether you’re wearing slacks, colored pants or dark-washed jeans. As opposed to athletic shoes, dress shoes, help elevate your photos and will give them a more editorial look.

How to Prep Your Man

Even though taking photos might not be his favorite thing... YOU ARE! Most men aren’t overly excited to take photos for two hours, mostly because they don’t have an expectation of what’s to come and why it’s so important to you, which is why I recommend sitting down together for fifteen minutes to educate and empower your man. Tell him why you chose me and my style of photography. Show him your three favorite sessions that I’ve done, explain why you love the photos so much and express to him how much this session means to you. Trust me, he’ll bring his A-game and light up the camera for you! The most common thing I hear from guys before portrait sessions is this: because of a bad experience in the past, they don’t like taking photos or don’t feel like they’ll be good at it. By the time the session is over, though, most guys can’t believe how fast it went and just how much fun they had!

Setting expectations before your session is the key to great photos and happy kids.

Before your session, pack a bag with water and your kids’ favorite snacks. If they’re too young to follow directions, bring any objects that you think might help me get their attention (like small toys or stuffed animals) when it’s time for them to look at the camera.

If your little ones are old enough to understand you, it’s a good idea to prepare them for what’s to come before the session starts. Explain how much the photos mean to you so they know to be on their best behavior. A lot of families pick something fun to do –– as a treat after the session –– if their kiddos are good listeners. Like dinner at their favorite pizza place or an ice cream cone!

It also helps if your kids' bellies are full and they’ve had some good rest before the session. After you do your best to prepare them, give yourself (and them) some grace! I have a lot of experience working with kids, so if they’re “in a mood” or aren’t cooperating perfectly for some reason, rest assured that we’re not judging you (or them). I’ve seen it all and know how to get great photos no matter what! My goal is to make this as fun and stress-free as it possibly can be for you and your family! This season of life feels long right now, but in the grand scheme of things, it's short. So even if things don't go exactly as planned or as you'd hoped in terms of your kids’ behavior, one day, you’ll be so glad you took these photos.  

When seasons change and temperatures drop, sometimes it’s just too cold for a dress and heels by themselves (no matter how warm your coverup overcoat is). So I have some suggestions for late fall and winter that will still help you be fashion-forward and keep your color tones camera friendly.

First, let’s talk about color palettes. Just like in warmer weather, I recommend muted hues over bold, primary colors. During fall, warm neutrals like camel, taupe, cream, champagne, and gray are still going to look great. If you’d like to incorporate color, choose sophisticated jewel-toned versions of bright primary colors. Here are some examples: mustard over yellow, crimson or burgundy over red, camel over orange, sage or emerald over green, and powder blue or navy over blue. These jewel tones will photograph beautifully in any season.

Cold Weather Tips:

Add a pea coat, tights, scarves and heeled booties to a form-fitting cocktail dress.

Snow Session:

Statement coat with a beanie, scarf and gloves or a warm, oversized, snuggly sweater with tall boots and a hat. The great thing about snow is it creates a beautiful white backdrop, so even though it might seem counterintuitive, soft pastel, muted colors like soft pinks and powder blues still look great! And, remember, regardless of the setting, you can never go wrong with neutrals!

1 Week - Sneak Peek

In the week following your session, I’ll post a sneak peek of one of my favorite photos from our time together on my Facebook page and Instagram account –– so keep an eye out for that! I’m so excited for you to see how beautiful you look through my eyes.

2 Weeks - Blog Post

About two weeks after your session, I’ll post a blog with some of my favorite highlights at www.leahfillmorephotography.com/blog

4 Weeks - Full Gallery

Four weeks after your session, I’ll send you a link to your online gallery with all of your final, retouched, high-resolution images. You can share the link with your family and friends, post to social media and more! I recommend changing the lock screen on your phone first :) 

I know I just gave you A LOT to think about! Don’t panic :) Just take it one step at a time. If you have any questions at any point, please know I’m here for you! If you’re deciding between two dresses and can’t commit, no problem! I’m here. If you love two locations but can’t make up your mind, no worries! I can help with that, too. If you need a recommendation of any kind, I’m on it! Remember, I’m just one email away :)

At the end of the day, though, the location you choose and the outfits you wear won’t matter nearly as much as the fun we have together and the memories you make. The style choices you make will definitely enhance your photos, but the most important accessory to bring with you is joyfulness –– which is the one that makes the biggest difference in your photos anyways. You don’t need to have prior experience in front of the camera. Just show up with a smile and I’ll take care of the rest :)

I’m so excited! See you soon!

- Leah Fillmore