The Ultimate Guide to Planning Your Engagement Session

So you’re engaged! Now what?

You might have just gotten engaged yesterday or perhaps a few months or even over a year ago. Depending on the stage you are in with your wedding planning, this might be the time you’re starting to plan your engagement photo session, which is so exciting!

Brooklyn Bridge Park Engagement Session in Dumbo
Brooklyn Bridge Park Engagement Session in Dumbo

Here is why I love engagement sessions:

1. We Get to Know each other

Your wedding photographer is one of the only vendors your spend your entire wedding day with, so you NEED to have one you know, trust, and like! Choose someone who not only creates amazing work in the style that you love, but also someone who makes you feel comfortable and confident when you’re in front of the camera.

An engagement session gives us both time to get to know each other even more than our initial meeting. It helps me get a much better idea of what type of images you prefer which allows me to focus more on what makes you happy on your wedding day. Some couples want every photo to be perfectly posed and a piece of art. Others see perfection in the imperfect and cherish the candid moments full of laughter and emotions. If you’re like me, you want a variety of it all because that’s what your relationship is all about.

Getting to know each other means we’ll trust each other, and this is very important on your wedding day! You will know some of the poses I put you into might at times feel awkward but if you trust in the process, we’ll come away with some stunning images that bring out your best features.

It’s simply one less thing to worry about on your wedding day because you’ll know my team and I are always ready and prepared to capture those special moments.

New York City Oculus Engagement Session
New York City Oculus Engagement Session

2. Learn how to pose for the camera!

If you’re like most people, you may have never had professional photos taken before, or chances are your experience with them isn’t much more than the family sessions your parents forced you into when you were younger and now you pass by the canvas hanging on your living room wall every time you visit mom and dad.

This is an excellent opportunity to learn how to pose for the camera – where to look, what to do with your hands, how to walk (yes I have tricks for that too!) etc. All of this will come back to you on your wedding day which will make you feel so much more relaxed and that means you’ll look confident and stunning in your wedding day photos. It’s completely normal to feel weird in front of the camera and that goes away after some time working together when you start to trust the guidance and direction we give you.

Battery Park Engagement Session in New York City

You’ll also see how we work together. I never tell you to just look at the camera and smile. If we’re going for a casual, relaxed style and want to capture some authentic laughter and emotions I will give you and your fiance a real reason to laugh and smile by giving you games to play or silly things to whisper into each other’s ears (Sorry, I can’t give those away now!) At more formal sessions we’re generally a bit more serious, but still capture a large variety of images that can be just as fun and playful.

Just read through the testimonials past clients have left to see how much fun they have!

All we can say is WOW! My fiancé and I had our engagement session with Jakub yesterday and he is truly amazing!! We have never done a photo shoot and felt a bit strange posing for pictures but he made us feel so comfortable, making our experience so much fun, we didn’t want it to end!

Paulina and Giovanni

3. Wardrobe Options (and what to wear to your engagement session)

On your wedding day you’ll look absolutely stunning in your wedding gown and tuxedo, but an engagement session is the opportunity to dress up in one (or more!) of your favorite outfits.

Your wardrobe and personalities (which often go hand in hand) will determine so much about the direction the session will go in and my vision for how I want to capture you and your fiance.

There are essentially two directions we can go in – fun and casual, or elegant and formal.

If it’s a cool November day, the leaves have changed to yellow and orange and started to fall, you might want to consider dressing up in a cozy sweater and those new boots you got while we grab hot chocolate as a prop and walk around Central Park or head somewhere just outside the city like Storm King State Park.

Maybe even bring your dog?

autumn central park engagement session by the model sailboat pond
Autumn Central Park Engagement Session

Generally speaking, no matter how casual we are aiming for I highly recommend avoiding sneakers and shorts unless that is a very specific look we’re going for – such as a destination engagement session you can see below which makes it fitting to the story. I also recommend staying away from neon colors or ones that are very bright and/or reflective – we don’t want that to be the first thing you notice in every single image and sometimes clothing causes a color cast on our own or our partner’s skin which might not be possible to correct in post production.

Destination Engagement Session in Arraial Do Cabo, Brazil
Destination Engagement Session in Arraial Do Cabo, Brazil

On the other hand if we’re going more formal it’s a great opportunity to wear that newest evening gown and set of earrings you just bought, and definitely bring out the Louboutins 😉 Coordinate outfits with your fiance so the color pallets complement each other without being too matchy-matchy.

Guys can wear a nice suit or tuxedo and don’t be shy to get fancy with the accessories – a nice watch or set of cufflinks adds that extra detail to polish up the outfit. Leave the Apple watches at home – 10-20 years from now they will look dated whereas we’re looking to create images that are timeless. Don’t forget to shine your shoes and iron your shirt!

The fit of your clothing is very important – I am always very happy to go over outfits with you to make sure you not only look great in them together but also that they photograph well. Gentlemen – chances are high that if your suit jacket or sport coat is too big or too small it will make the point of wearing it moot…you’ll look better without a suit jacket than in one that doesn’t fit properly.

Roxy Hotel Engagement Session in NYC
Roxy Hotel Engagement Session

These formal, elegant types of sessions are my personal favorite, but of course we can find a middle ground that falls somewhere between black-tie and a casual date out, like the photo below:

Columbia University Autumn Engagement Session
Columbia University Autumn Engagement Session

What if it’s cold? I recommend dressing in layers and staying warm, however still keeping style in mind and avoiding jackets that are meant for the great outdoors or skiing. They also often have very prominent logos which should be avoided for a more timeless look.

Can you see a difference between the wardrobes below?

On the left we see longer coats that fit properly to their bodies – this was a planned engagement session where we had time to prepare and coordinate.

On the right was a proposal I captured which was coordinated last minute and there was no way for me to control what the clients were going to wear. Let’s be honest – the jackets are poofy and don’t flatter their bodies.

Colder weather doesn’t have to stop us and extra layers don’t have to be a bad thing!

4. Hair and Makeup Trials!

While hair and make-up may seem like a frivolous extra, it’s an essential part for some ladies to feel confident in front of the camera. A professional makeup artist has the ability to enhance your natural features and hide any blemishes you might not want to attract extra attention to.

Getting a hair and makeup trial before your wedding day is a great idea to make sure it turns out just the way you want it on your big day and you’re not stressing over any significant changes.

This is the perfect opportunity to use that trial! And here’s a bonus tip: you’re already going to be dressed up and looking amazing so why not make a night of it? Plan a fancy dinner with your fiance right after we finish up!

If you’re doing your own hair and makeup, I recommend staying away from glossy/glitter makeup as it usually does not photograph well. Powder foundations work well for photos and help avoid that “shiny look”. If it’s looking to be a hot day, consider investing in some oil absorbing wipes before your session.

In the end, the goal is to capture images you love yourself in, and pampering yourself before your session will certainly help with that. Not only will you look amazing, you will also feel amazing– and that is most important!

5. Location

The engagement session location we choose will be heavily influenced by your wardrobe choices, and vice versa. So think of what style you’re drawn more to (casual or formal) and then think of what location will allow those wardrobes to fit into perfectly.

There are also many locations where both formal and casual styles would work, such as a beach.

Destination Engagement Session in Iceland - Reynisfjara Black Sand Beach
Destination Engagement Session in Iceland – Reynisfjara Black Sand Beach

Locations with beautiful and more elaborate architecture work better for something more formal like the photo below which almost has a magical vibe. The location, wardrobe, and lighting really lined up perfectly here and it was all thanks to proper planning.

Fire Island Lighthouse Engagement Session
Fire Island Lighthouse Engagement Session

Do you need help choosing a location? Contact me and I would love to help you in deciding! There are some spots throughout New York City that are incredibly popular for engagement sessions – mainly Central Park and Brooklyn Bridge Park. Literally hundreds of engagement sessions happen every week at these spots so I try to steer my clients to exploring new ideas so we can create images which are completely unique to you and not just a cookie cutter approach of the same places everyone else does their photos in.

Think of unique locations you might have access to – maybe a rooftop or beautiful loft in the heart of midtown manhattan, or a farm with a barn just outside the city, or maybe you (or one of your friends!) has a boat or there’s a vineyard you two visit frequently that would be a perfect spot for a session. Is your old college campus super picturesque like the one at Princeton or Columbia University? Think outside the box!

Let’s get lost on the streets of SoHo, visit the Bronx Zoo or Brooklyn Botanical Garden, venture out of the city for a hot air balloon ride, go horse back riding in Jamaica Bay, or maybe pay a little extra (~150-200) for a permit at a stunning location like the Vanderbilt Museum or Mill Neck Manor. I am always looking for new locations to photograph in so ask me what I can currently recommend or if you have your own special place I would love to hear about it!

If you’re super adventurous and want to do your engagement session somewhere else in the world, I’m all ears and always open to travel!

6. Enjoying the Images!

Well now we finished the session and it’s time to decide how you would like to enjoy them!

Engagement Session Wall Art Collection

There are so many things you can do with your engagement session images. One of the most popular choices is of course to print them for your walls or in a wedding reception guestbook your friends and family can sign on your wedding day.

Another popular option is creating save the dates using your engagement images. These are typically sent out to your guests about 6 months before the wedding before the formal invitations go out.

detail shot of invitations and save the date

Bonus Tips

  • Less is more! Textures and prints can be fun, but often distracting in photographs and some can cause a moire pattern. If you’re not sure, just ask me!
  • Wear clothing that is awesome, and comfortable!
  • Consider bringing a change of shoes if you think we’ll be walking a bit
  • Hot day? Bring some water 🙂
  • Your fiance spent more than a little on that engagement ring, so consider getting it cleaned if it’s been a while and definitely get your nails done as we’ll be getting close ups of it!
  • Guys: Get a haircut about a week before so it grows in just a little and looks natural. Everyone’s skin is different, so you should know when to shave to avoid redness and irritation in your photos.
Little Red Lighthouse Engagement Session
Little Red Lighthouse Engagement Session

Are you ready to start planning?

All of this advice and suggestions are very general since I still have no idea who you are or what you’re looking for!

Contact me today and we will get to know each other, find out what style suits you and your fiance perfectly, and take things from there!

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