The Ultimate Engagement Session Planning Guide

Congratu-fucking-lations, you’re engaged! I know there are probably a million different things running through your head, but for now, it’s engagement session time! Before you start going into frantic wedding planning mode, let’s slow down, breathe, and take a second to soak it all in. This will be one of the most special times in your life, and you’re gonna want photos to document it. This resource will cover all the steps to take when planning your engagement session so you don’t have to worry about a thing! 

When should you schedule your engagement session?

First thing’s first – when should you schedule your engagement session? If you already have a date picked out, then you should aim to schedule your session for around 4-6 weeks before you need to send Save the Dates (allowing time to shoot, edit and get the photos back to you!). Same thing goes for holiday cards; I know tons of couples who want to use their photos for seasonal greetings! 

Going further, if you’re booking during the spring and summer, weekends may be a bit more limited than other times of the year. This is because the spring and summer months are usually peak wedding season, so most photographers are already booked and shooting! We can totally make a weekday work, just keep in mind that that might be the only availability for those seasons. And if you want golden hour or sunset photos, I highly recommend doing them on a weekday evening in the summer anyways! 

If you’re planning on booking your engagement session for the winter, keep in mind that daylight is gonna be pretttyyyy limited. The winter months are ideal for morning sessions, or even sessions that are completely indoors. If you want to see what an indoor-only engagement session would look like, check out Marianna + Rob’s blog! 

Last, but not least, certain locations do have seasonal hours or are simply better at different times of the day, so we’ll have to double-check well in advance. If your desired location doesn’t align with the timing of our session, then I’ll do my best to find a similar one that fits your vibe! 

Decide on a couple of locations for your engagement photos

It’s time to choose where you want the party to go down! The locations we decide on heavily depend on your inspiration/vision for your engagement photos. Do you want outdoor photos with tons of natural light, possibly at the beach or downtown area? Or do you prefer indoor photos with flash somewhere like a hotel or bar? If you have a Pinterest board, you can send it over to me and I’ll do my best to scout locations that match the vibe. We can usually fit 2 nearby locations during a full engagement session, so you’ll get lots of variety in your gallery! 

My favorite San Diego engagement photo locations

Don’t worry, I have an entire blog dedicated to the best engagement session location in San Diego! For now, we’ll just be briefly going over a few of my faves. Keep in mind that we’re absolutely NOT limited to San Diego – that’s my home base but travel is my passion. Wherever ya wanna go, I’m right there with you! 

PS – Don’t forget to check out my Top 10 San Diego Engagement Session Locations blog for even more ideas!

Downtown San Diego/Gaslamp Quarter

Where Becky and Marco took their EPIC paparazzi-vibes engagement photos! Very urban city vibes, which I’m finding more and more couples are gravitating towards. You can check out more photos of this location on their blog!

Balboa Park

Definitely a highlight of San Diego. You have a WIDE variety of locations within Balboa Park, including museums, gardens, restaurants, trails, and more. A great place to run around and experience lots of different scenery in close proximity!

Torrey Pines

For my couples who loooove all the nature vibes. You’ll actually feel like you’re in a national park here at Torrey Pines due to the amount of seclusion and greenery. Completely different from the previous two locations, but definitely suited to my outdoor lovers! 

What should you wear for your engagement session?

The age-old question: what the hell should you wear for your engagement session? My top rule for this is to wear what you’re comfortable in WHILE coordinating with your desired locations. Becky & Marco’s outfits totally fit the vibe of their downtown San Diego engagement session, so they’re a great example. Becky wore a modern suit dress for the outdoor photos, and a white, silk, fancier dress for their steamy indoor bar photos. She was comfortable, confident, and STYLISH AS FUCK. 

If you’re wanting to take engagement photos at the beach, I recommend wearing something light and flowy! And, of course, preferably something you don’t mind getting wet. For something like hotel room photos, try wearing a cute bralette or something more casual, but still fitting! I love when my couples have a casual and a dressy option so we can get two different looks during the same shoot. Don’t be afraid to incorporate your personal style into your look, as we want your photos to look and feel like you!! In fact, I encourage as much personality as possible 😉 

One last thing: when planning outfits with your partner, make sure you two coordinate without being overly-matchy. That was a trend for a different time! Try out different color combos (I share a list of my faves in my official Engagement Session Guide that all my couples get when booking with me!) to see what looks the best. Add in some movement with a flowy dress or cardigan, ‘cause I guarantee the more movement = better photos. And for the love of God, if you want to incorporate patterns, it should only be on ONE of you! We will not have clashing outfits that will make you think “What the hell was I thinking?” when looking back on your photos. Stay away from trendy patterns and stick to more minimal ones, if you must. Okay, I’ve said my piece! 

How to make your engagement photos unique 

Choose a location that’s meaningful to you

Remember, I travel all over the world to wherever your love story takes you! Think about where you had your first date, your first kiss, where you first met, or somewhere you visit often. It could even be a location that’s been on your bucket list for a hot minute! The “where” doesn’t have to be anywhere extravagant to get meaningful photos. We could visit the neighborhood where you grew up, your rooftop makeout spot, or your fave coffee shop! The world is your oyster. 

Add in some fun props!

The type of props you can include can be dependent on the location of your shoot, but I recommend going alllll out. If we’re shooting at the beach, think: surfboards, a cute lil’ picnic setup, rollerblades, or bikes for riding down the boardwalk. If we’re doing a rooftop sesh, think: vintage car rental (‘cause why the hell not), motorcycle vibes, or a skateboard! Always always always bring snacks and a bottle of champagne. These items are great for both casual or more dressed-up photos. Not EVERY place will allow a champagne pop, but if they do, your bet your ass we’re doing it. And last but not least, LLC is 420-friendly and heavily encouraged! 😉

Include your pets

As a very dedicated cat mom, I very much encourage bringing your pets to your engagement session! If that’s the plan, be sure to let me know in advance so I can make the necessary arrangements to make sure your session goes as smoothly as possible. We’ll choose a location with lots of open space to accommodate your little ones. Sometimes an in-home session is the best way to go for your pets, at least for the first location of the day! This is especially true if you want to include cats vs. dogs because… well, you know how cats are. 

The rule for Pinterest boards

As a photographer, I LOVE a good Pinterest board for outfit inspiration and color combinations. However, I advise that you don’t have the expectation that your photos will turn out exactly like the photos on Pinterest! Use your inspo board for exactly what it is – inspiration. Every photographer has their own unique style of photography and editing (duh, that’s why you picked them) so let them do their thang and your pics will turn out awesome. I will always try to match the vibe of your Pinterest board while still incorporating my unique style and flare as a photographer! You’re also more than welcome to scroll through my Instagram and pic out photos that you love <3

Your engagement session budget 

Along with the price of your actual photos, don’t forget to factor in things like hair, makeup, outfits, shoes, and accessories. You totally don’t have to buy two completely brand-new outfits if you already have stylish options in your closet. I’m a huge fan of thrifting, so you can also use this as an excuse to visit your favorite thrift shops to see what you can find! I do recommend treating yo’self and getting a blowout on the day of your session. A great tip for your makeup is to schedule a wedding makeup trial the same day as our sesh if possible – usually, a trial is either included in your makeup package OR offered at a lower price than the actual day-of wedding makeup. THANK ME LATER! 

You’re ready for your engagement session!

WOOHOO! You’re gonna kick ass at your engagement session. Now that you’re ready to book, you can fill out my contact form and I’ll get back to you with all the details!