choosing the perfect time, location, outfit & more!

Engagement Session

planning your

to the HILLARY SHEDD PHOTO website

Second, you can showcase your personalities in a more casual setting that is signficant 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. 

We’ll cover what to wear, whether to bring pets & how to manage them, location ideas and more! 

The engagement season is my favorite life season to document. For now, it feels like normal life, but you will look back on this time and be thankful for the space to build the foundation of your marriage. "Babies" you will think while looking at your engagement photos 50 years from now. For this is just the beginning!

It’s normal to be a little nervous about your session. I always share 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. Timelines can be tight on weddings days and 30 minutes may be all we have for portraits - which is why I’ve found that wedding day portraits turn out much better when couples do engagement session ahead of time. 

Welcome

A photo from our engagement session in 2018 taken by Anna Peters.

I get it. Having your picture taken for 1-2 hours might not be in your top-10 favorite things to do during your downtime. And 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! These photos will be timeless and document such a special time in your life that will be over before you know it. I also look forward to these sessions because it’s a great opportunity for us all to get to know each other before your wedding day. My goal is to feel like more than your wedding photographer. I also want to be your friend, confidante, and trusted supporter. 

reluctant 

if you're

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 and a half and when when we can—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 to get gorgeous golden light like this photo.

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. 

"GOOD" TIME TO TAKE PHOTOS? 

Time & Light: is there a

While I shoot most of my engagement sessions between June and late October, sessions can take place all year. Most of our couples choose a season based on the location where they want to shoot. 

A few things to keep in mind during each season:

Seasons

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. 

snowfall, hot cocoa and cozy coats

Winter

Even though Spring begins in March, I typically don’t begin shooting spring sessions until late May because the snow in Colorado tends to stick around or turn into mud. When I schedule spring dates, I sometimes schedule both a primary date and a backup rain date, just in case. 

mystery weather and sunny days 

Spring

I love summer sessions! Yes, summer is busier for weddings, but weekday engagement sessions are always beautiful. Because of the later sunset, sessions sometimes begin as late as 7pm. If you’re taking your engagement photos during the summer, I recommend bringing extra makeup and a few towels to make sure you stay fresh throughout your session. 

mountain tops and glowy light

Summer

Fall is one of the prettiest times of the year in Colorado and because of the perfect weather, my schedules typically book up quickly! If you have your heart set on a fall engagement session, I recommend scheduling it as soon as you book! 

colorful leaves and snuggling close

Fall

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, we 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

Cooking class
 Your Favorite Hike
Date Night
Cozy at Home

Personalizzed

Moraine Park
Devils Lake
Trail Ridge Road
Lilly Lake


Rocky Mountain National Park

The above locations are all beautiful but I love exploring meaningful locations with my couples the most!

Brainard Lake
Horsetooth Reservoir
Piney River Ranch
Clinton Gulch Dam Resevoir

Water & mountains

Oldtown Fort Collins
Downtown Denver
Pearl Street, Boulder

URBAN

Chautauqua Park
Lost Gulch Overlook
Devil's Backbone

Classic colorado

Cheesman Park
Denver Botanic Gardens
Your Favorite Winery
College Campuses

CLASSIC & ELEGANT

I love when couples choose a location for their session that complements their wedding. For example if you’re planning a chic, elegant wedding, it may be fitting to take your engagement portraits among the classic architecture in Denver, while Rocky Mountain National Park may be more fitting for a couple planning a more outdoorsy affair.

The best session locations are often meaningful places to the couple; however, I'm also happy to make recommendations. From ski slopes to apple picking and college campuses, the options for engagement session locations are endless! 

colorado ENGAGEMENT LOCATIONS

Locations

While I take most of our engagement sessions in Colorado,  I’ve photographed sessions everywhere from Chicago to Las Vegas to New York City. 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 photograph your engagement photos outside of  Colorado.

Travel fees may apply depending on the location and my availability.

Engagement sessions

destination

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 pets 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 

When picking outfits I recommend keeping in mind the word “complement” rather than “match.” For example, if one of you is wearing a blue and pink pastel plaid shirt, the other may want to choose a long, soft blue dress. It can also be a great idea to choose “color-families,” such as pastels or jewel tones.

I recommend couples pick two outfits for an engagement session: a more formal outfit and a casual everyday outfit.  Save your favorite outfit for later in the session, when couples usually feel more comfortable in front of the camera. And don’t forget to bring a few favorite accessories. Classic necklaces, cute shoes and special watches are great ways to add details to any outfit. 

TIPS FOR LOOKING YOUR BEST

Outfits

on to the next

A good rule of thumb: pick 3 or so colors and spread them throughout your attire. Don't be afraid to mix a few subtle patterns or textures (different types of fabrics). 

Always pick your location first and then plan your outfit around it. If we're shooting in a green field, light green dresses might blend in too much with the surroundings. If we're shooting on a mountain top, looser clothes that can blow in the wind look incredible with the scenery. If we're shooting in downtown Denver, a form fitting outfit will be ideal in the urban surroundings. 

Choosing Outfits

for everyone

on to the next

Heels lengthen legs but if your heels aren’t comfortable for walking or we'll be in grass, bring an extra pair of shoes to slip into in between shots.

I love the way larger patterns and textures (like linen) photograph - just be careful not to choose a pattern that is too small - it may accidentally make your photo look a little too busy.

Softer, pastel colors tend to photograph better than bright colors - especially since bright colors could reflect on your skin. I love bright, neon dresses, but I don’t love the neon reflection they add to your complexion in photographs. 

Wardrobe Tips

for the ladies

For the Ladies

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Statement jewelry is a great way to add color or pattern to a simple dress. Lace and tulle look amazing in photographs.

Dresses with sleeves are a great way to help slim arms. Depending on your location, you might want to consider a fit and flare or a flowy dress. They look great in walking and photos with movement!

Most importantly, choose an outfit you feel comfortable in, and don’t be afraid to dress up!

Accessories

for the ladies

on to the next

Sunday Supply Co. 
Zara
Mango
Sezane
Hill House Home
Reformation
Nuuly
Ivy City
Shopbop
Everlane
Untuckit 
Veronica Beard
Banana Republic

Rent the Runway
Poshmark
J. Crew
Anthropologie
Free People
Jessakae
Baltic Born Clothing 
Madewell
Show Me Your Mumu
Perch Denver
Nordstrom Rack
REI
White House Black Market

Favorite Shops

Rent, purchase, invest

I think it’s so important that you look and feel your best for your photos. Investing in professional hair and makeup can go a long way towards creating photos you love for years. 

Professionally done hair & makeup last longer than typical hair & makeup. They also tend to hold up better in humidity and wind.

If you go this route, I recommend staying a bit “classic”. Now probably isn’t the best time to try out that new contouring technique you saw on TikTok. 

If you’re planning to do any spray tans or waxing, schedule those for a few days before the session to give your skin time to recover. 

Hair & Makeup

for the ladies

on to the next

You can’t go wrong with crisp button up or layering a blazer or sweater with jeans. Bowties are always a good idea!

Be careful not to choose a pattern that is too small - it may accidentally make your photo look a little too busy.

Softer, pastel colors tend to photograph better than bright colors - especially since bright colors could reflect on your skin. Cozy sweaters layered over button ups are a great way to stay warm and stylish during the cooler months.

Wardrobe

for the gents

on to the next

I always take a photo of your rings during your engagement session. If possible, try to have your engagement ring cleaned or clean it yourself.

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.

The Rings

There's an old saying that shares "If you don't like the weather, wait 10 minutes." I've found that afternoon rainstorms always happen in the summer, but they are also almost always short lived. If you're flexible with timing, we could wait it out. If you're ready to make some memories, all of my gear is water sealed!

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 engagement session and it’s the worst to get dressed up and drive out to your session only to have the weather not agree. Let me know what works best for the two of you - but if the weather looks like it won’t be great, I typically try to make the call at least 12 hours in advance. If you're not a fan of the windswept look, be sure to tell me so I can track the wind, too!

what to do if it rains

Inclement Weather

If you’re planning to bring props to your engagement session, I recommend including them only if they’re meaningful to you.

Shots drinking coffee at a local coffee shop would be cute if that’s where you met or coffee shops play a significant role in your relationship; however, trying to fly a kite together when it’s not a part of your relationship may come off as contrived.

props?

should we bring

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. 

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?"

posing

A note on

If you’re anything like my husband and I, 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!

Date Night

As soon as possible after your session is complete, I'll share a small sneak peek with you. It normally takes me about 3 weeks to edit your images. Unless I have a holiday closure, you can expect to receive your engagement photos between 2 and 3 weeks after your session. 

Images

When to Expect Your