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ENGAGEMENT SESSION
PLANNING YOUR
choosing the perfect time, location, outfit & More!
Welcome
A NOTE ABOUT THIS GUIDE
I'm so excited to be working with you, and I can’t wait for our time together during your engagement session! It’s normal to be a little nervous about your session. I always tell people that I still get nervous before having my photos taken - and I do this for a living!
I'm a big fan of engagement sessions for a few reasons. First, they allow you to get comfortable in front of the camera. It takes time for most couples to warm up to being photographed. Timelines can be pretty tight on wedding days, and thirty minutes may be all we have for portraits, which is why I've found that wedding day portraits turn out so much better when couples do engagement sessions ahead of time.
Secondly, you can showcase your personalities in a more casual setting that is significant to the two of you (and even include pets!). While they’re great for save-the-dates, I've taken engagement photos anywhere from 18 months in advance to a few days before the wedding.
There is a lot to think about when it comes to planning a session and since I get asked the same things over and over again, I thought it would be the most beneficial if I put together a guide that walks you through everything you need to know.
I'll cover what to wear, whether to bring pets & how to manage them, location ideas and more!
- Ellen
I get it. Having your picture taken for an hour or so might not be in your top ten favorite things to do during your downtime. At first, you might feel sort of awkward being in front of the camera. But I think you’ll find that by the end of the session, it’s a lot easier than you thought, and you even had a little fun. I look forward to it because it’s a great opportunity for us all to hang out a bit before the wedding day.
Hey, Guys
A quick note
Engagement sessions can take place anywhere from immediately following a proposal to just a few days before the wedding. I've found that there isn’t a “good” or “bad” time to take your photos. I normally plan sessions based on a particular “look” a couple has in mind, spring flowers for example, or based on schedules.
Sessions typically last about an hour to an hour and a half, and I love to begin sessions about two hours before sunset. I prefer to shoot when the sun is lower in the sky to avoid harsh shadows and bright sun patches. The first two hours after sunrise is also an ideal time to shoot. While sunrise sessions haven't always been popular, definitely consider an early-morning session because very few people will be around!
I schedule sessions during what I believe will be the best light of the day - which means that it’s super important to be on time. If you’re late to an evening session, we could run out of light before we’ve finished shooting and if your session takes place in the morning, the sun gets more harsh as it rises.
Is there a "good" time to take photos?
TIME & LIGHT
While I shoot most engagement sessions between April and late October, sessions can take place all year. Most of my couples choose a season based on the location where they want to shoot.
A few things to keep in mind during each season:
Seasons
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Winter
snowfall, hot cocoa, and cozy coats
If you’re planning to take your engagement photos during the winter, keep in mind that if your session takes place in the evening, we could begin shooting as early as 2:30pm to catch the sunset. I recommend dressing in layers so that in between photos you can warm up. Make sure you bring a little extra makeup and tissues in case your nose begins running.
Spring
fresh flowers and sunny days
Even though Spring begins in March, I typically don’t begin shooting for another 6 weeks because the weather in New England is still pretty chilly. Spring weather can be unpredictable, so be prepared to likely need to use our backup date. The flowers typically start blooming by late April in Boston, and I suggest waiting until mid-May to shoot in Vermont (because: mud season!)
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Summer
walks on the beach hand in hand
In spite of the heat, I'm a big fan of summer sessions! Because of the later sunset, sessions sometimes begin as late as 7 pm. If you’re taking your engagement photos during the summer, I recommend bringing extra makeup and a hair brush to make sure you stay fresh throughout your session.
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Fall
colorful leaves and cider donuts
Fall is one of the prettiest times of the year in New England and because of the perfect weather and beautiful foliage, my calendar typically books up quickly! If you have your heart set on a fall engagement session, I recommend scheduling it as soon as you book. Peak foliage is hard to pinpoint, but if we aim for the first half of October, we should have some gorgeous backdrops!
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If your wedding is local, save the dates should be sent between 6 and 8 months before the wedding. For a destination wedding, you’ll want to send them out 8 to 10 months before the wedding.
If you’re hoping to use your engagement photos for your save the dates, I recommend scheduling your session at least two months before you plan to send out your save-the-dates. Between inclement weather, editing, designing your save-the-dates and printing, two months is generally a safe amount of time to make sure your images and cards are ready.
Save-the-dates
Locations
Boston + vermont
ENGAGEMENT LOCATIONS
New England offers countless photogenic locations, and many of them are just steps from our homes.
The best session locations are often meaningful places to my couples; however, I'm also happy to make recommendations. I absolutely love shooting in Boston, especially in Charlestown and the Seaport. In Vermont, my favorite spots are Shelburne Farms and Trapp Family Lodge.
Beacon Hill
Charlestown
Navy Yard
Seaport - Fan Pier Park
Public Garden
Back Bay
Christopher Columbus Park
The Esplanade
South End
North End
Boston
Trapp Family Lodge - Stowe
Shelburne Farms
Stowe Bike Path
Oakledge Park - BTV
All Souls - Shelburne, VT
vermont
Cooking class
Hiking
(Stowe Pinnacle or Mount Philo
are perfect!)
Sailing / Boating
(Charlestown Ferry is an easy way to capture the Boston skyline from the water!)
ADVENTURE
The above locations are all beautiful but I also love exploring meaningful locations with my couples!
Destination Engagement Sessions
While I take most of our engagement sessions in the Boston and northern Vermont area, I've photographed sessions everywhere from Atlanta to Brooklyn to Maine. If you have a location in mind that is significant to the two of you, let me know because if our schedules align, I might be able to take your engagement photos outside of my normal area.
Travel fees may apply depending on the location and my availability.
I'm a huge dog lover and wannabe dog owner, which is why I love when couples choose to incorporate pets into their session. Keep in mind that bringing a pet along often means that we’ll need to choose a pet friendly location.
I recommend planning for your pet to be at the first part of your session and then either dropping them off or having a friend take them home. We won’t use the pet in every single photo so it’s also nice to have a friend available to hold him or her in between shots.
If you’re going to bring a pet, I recommend exercising your pet before the session and bringing your pet's favorite toy or treats! Depending on your pet’s fur type, it might also be a good idea to groom them before the shoot.
Pets
Outfits
TIPS FOR LOOKING YOUR BEST
When planning your looks, aim for outfits that feel like you, just a slightly elevated version. Think timeless and comfortable rather than trendy or stiff. If you feel great in what you’re wearing, that confidence will shine through in every photo.
Most couples choose two outfits for their engagement session—one a bit more dressed up, and one more casual. I recommend saving your favorite look for the second half of the session, when you’ll naturally feel more relaxed and confident in front of the camera.
find it fast
When it comes to colors, neutrals and softer tones almost always photograph beautifully. Creams, taupes, grays, blues, sage greens, and warm earthy hues tend to complement each other (and your surroundings) without competing for attention. You don’t need to match exactly—coordinating tones and textures will make your photos feel cohesive and natural.
Patterns can be beautiful in photos — they add personality and texture — but they can also steal the spotlight if they’re too bold or busy. When choosing outfits for your engagement session, aim for subtle, timeless prints like small florals, soft plaids, or delicate textures. These photograph beautifully without overwhelming your faces or the connection between you. If one of you wears a pattern, have the other stick to a solid color that complements it so your looks feel cohesive, not competing.
Wardrobe Tips
dresses
You do you
HAIR & MAKEUP
MANICURE
Outfits
for the ladies
find it fast
Don’t be afraid to dress up a little! Engagement photos are such a fun excuse to wear something that makes you feel amazing — think flowy dresses, movement, and fabrics that catch the light. That said, comfort is key. The best outfit is one you can move in, sit in, laugh in — something that feels like you. When you feel good, it always shows on camera.
Dresses
dresses
you do you
HAIR & MAKEUP
MANICURE
Outfits
for the ladies
find it fast
I know that choosing outfits for your engagement photos can feel overwhelming—I totally get it! While this guide is full of tips and inspiration, the most important thing is to wear something that makes you feel amazing, even if it bends the “rules.” Confidence always photographs beautifully, and if you’re not feeling great in what you’re wearing, it’ll show in the final images.
I’m here to help however you need! Want to text me photos of outfit options laid out on your bed? Go for it. Thinking about bringing a few choices to your session so we can decide together? Love that idea.
You Do You!
dresses
you do you
HAIR & MAKEUP
MANICURE
Outfits
for the ladies
find it fast
Your engagement session is the perfect opportunity for a hair and makeup trial! Professionally styled hair and makeup tend to last longer, photograph beautifully, and hold up better against humidity, wind, or a little extra movement.
That said, it’s by no means a requirement. The goal is for you to feel like the best version of yourself—whether that means a professional glam session or doing your own makeup at home. If you’re already planning a hair and makeup trial for your wedding day, your engagement session is the perfect time to see how your look translates on camera.
Hair & Makeup
dresses
You do you
HAIR & MAKEUP
MANICURE
Outfits
for the ladies
find it fast
There will likely be moments during your session when I focus on those little details—your hands intertwined, your ring catching the light, or the way your fingers naturally rest together. Since your hands often make their way into photos more than you might expect, it’s worth giving your nails a little attention before your session. A simple manicure, a touch of lotion, or even just clean, trimmed nails can make those close-up shots feel polished and timeless.
Manicure
dresses
you do you
HAIR & MAKEUP
MANICURE
Outfits
for the ladies
find it fast
You don’t need a full suit to look sharp! Think layers and textures instead—like a button-up shirt with a casual blazer, a lightweight sweater over a collared shirt, or a crisp shirt with well-fitted jeans. For a more relaxed vibe, swap the blazer for a cozy cardigan or a nice pullover.
When it comes to patterns, keep them subtle—tiny prints can sometimes look busy on camera. Softer, neutral tones and pastels usually photograph best, and layering is a great way to stay comfortable and stylish in cooler months. Accessories like a watch or a scarf can add interest without stealing the spotlight.
Wardrobe
Why a blazer?
Outfits
for the guys
find it fast
Even if a blazer isn’t your everyday go-to, it’s a smart choice for engagement photos. The great thing about a blazer? It’s basically two outfits in one—we can capture shots with it on and off, giving you more variety in your final gallery.
Blazers also come with a built-in bonus: a perfect spot for your partner to rest her hands. “Where do I put my hands?” is the most common question during a session, and a blazer gives us an easy, natural option to play with. Trust me—it works!
Wardrobe
why a blazer?
Outfits
for the gents
Inclement Weather
what to do if it rains
It’s typical for me to schedule two engagement session dates. A primary date and a rain date. Having two dates helps us make sure that your photos happen in a timely manner. Coordinating schedules can be tough, and I've found that the best way to make sure my couples get the look they have in mind for their photos is to schedule two dates at the time of scheduling. Due to limited weekend availability from May through October thanks to peak wedding season, I'm currently scheduling engagement sessions on Wednesday evenings with the next day, Thursday, reserved as the rain date.
I'll check in the week of your engagement session to confirm the time & location we’re meeting and the weather. I know it takes a lot of time to get ready for an engagement session, and it’s the worst to get dressed up and drive out to your session only to have it rain. If the weather looks like it won’t be great, I typically try to make the call at least 24 hours in advance.
When I can, I always try to take a photo of your ring during your engagement session - so it’s a good idea to have it cleaned or clean it yourself before your shoot! To clean at home, soak your ring in warm water with dishwashing soap for 20 to 40 minutes. Then gently brush the stone with a soft toothbrush, rinse and repeat if needed.
Ring Cleaning
Props
champagne is always a good idea
If you’re planning to bring props to your engagement session, I recommend including them only if they’re meaningful to you. Photos of drinking coffee at a local coffee shop would be cute if that’s where you met; however, trying to fly a kite together when it’s not a part of your relationship may come off as contrived.
Alcohol is always encouraged (or not! I don't drink - so by no means do I intend to peer pressure you!) If you want, drink ahead of time, drink during the session, drink after the session! Whatever works for you works for me.
When it comes to posing for your engagement session, you don’t need to worry about a thing! I'll guide you through the entire process beginning with “poses” that are super easy and natural. If I tell you to do something that feels a little funny, it’s probably because I know it’s going to make the two of you laugh - and that’s the photo I'm actually looking for. While we'll take a few of the more "classically posed" shots, I strive to capture the candid, in between moments, which end up being some of my clients' favorite images. Throughout your session, I'll keep an eye on your hair, makeup and outfits to make sure things stay in place. I want you to feel as relaxed as possible and enjoy your time together!
"What do I do with
my hands"?
"What do I do
with my hands"?
POSING
Date Night
If you’re anything like me, you probably don’t get dressed up all that often. Which means that the day of your engagement session is the perfect occasion for a date night (or brunch if your session is in the morning!)
The engagement session is another part of celebrating your love and heading off to dinner is a great way to end the session!
As soon as possible after your session is complete, I'll upload your photos and share a sneak peek. Unless we have a holiday closure, you can expect to receive your edited gallery of images between 2 to 3 business weeks after your session.
When to Expect Your Images
I know that this guide is long and hopefully it covers everything you need to know to prep for your engagement session! If there is something I missed or you need a recommendation, feel free to shoot me an email - hello@ellensargentphotography.com