I'm Kristen with Kristen Wynn Photography - and I've been honored to be a wedding photographer for ten years and over 250 weddings! We describe our style as mainstream artistic and focus on comprehensive coverage and modern posed images as well as photojournalism.
Summer and fall are the most popular times for an engagement session in the northeast and mid-Atlantic regions of the United States, especially here in Pittsburgh where we're located. – With the busiest engagement season just around the corner, I wanted to share my best tips for a successful and fun engagement session!
I recommend doing an engagement session to get comfortable in front of the camera.
1. Consider doing your engagement session in the season opposite of your wedding. This will give you a nice variety of seasons here in the Mid-Atlantic region. We recommend having your session at least six months in advance of your wedding for save the date cards and to display images at the wedding itself.
2. The best time for portrait lighting is two hours before sunset and going through sunset. This gives softer shadows and a great glow, as well as allows us to incorporate some night shots!
3. Be prepared for your engagement session. Talk with your partner about what we do and show him/her my work. Plan to arrive early for parking/traffic as that can be a stressor! Don’t make time-sensitive plans immediately after the engagement session (such as firm dinner reservations or tickets to a ballgame) as we sometimes go a little long on the session time if we are feeling inspired!
4. As far as locations, think outside the box and make it personal! If you have a neighborhood where you had your first date, the college where you met on campus, or just a cool spot you saw on the side of the road driving to work, let me know! We of course have our favorite stand-bys and go-to’s like all photographers, but I love considering places and activities like a library, record shop, coffee shop, skiing, picnic, bike ride, your favorite bar, the fair, your home, Ikea, and more! Pro tip: Make sure the place you choose allows photography – we might need to grab a permit!
5. For outfits, you want to remember “fit, flatter, flare.” Let’s talk about fit!Fit: It’s important to feel confident during your session, so pick an outfit with the best possible fit – no gapping or bunching. Remember to match the undergarments to the outfit as far as style, color, support, etc. You might want to avoid those VPL’s – visible panty lines! Bralettes or bra straps showing are back in style, since the 90’s are back, but you might want to avoid a very functional bra or Spanx showing!
Many people want to camouflage their upper arms – if you have concern about this area, I recommend long sleeves. 
Remember that you will be sitting, walking, jumping, moving, and having fun, so you need freedom of movement. Skirts and dresses rise when sitting and necklines can plunge, so try on your outfits in front of the mirror before buying and make sure everything you want covered stays covered. If the outfit is great but you can’t sit in it, try a cami underneath, a cardigan over, or leggings with it.
Some empire-waisted gowns and tops have a tendency to make the wearer look bigger at the waist, so you may want to skip these or cinch with a belt.
6. The next key in an outfit is flatter – flattering your shape and your natural beauty.
Flatter: Don’t try to “match” your partner exactly. For example, both of you should not wear khaki pants and white shirts. Instead, come up with a color or two and coordinate around those selected colors.
Layers looks great and can help camouflage any perceived problem areas.
For many women, dresses and skirts photograph nicely.
Ladies, consider high heels if possible for a nice long line on the legs. If not heels, try boots, attractive flats, or dressy sandals or wedges. Both men and women should avoid inexpensive foam flip flops.
Avoid solid white or black shirts if possible, and choose a color that makes you feel wonderful!
Make sure your clothing is ironed if needed and avoid the sun in the days before the session. I ended up with a bad sunburn right before a portrait session once – yikes!
Avoid clothing with large logos across the front.
For men, make sure that your hair is neatly trimmed, especially around the neck and ears.
Flare: Many clients are using Rent the Runway or similar services now to get the look they’d like for an engagement session. Local wedding coordinators are even styling engagement sessions now!
Show your personality with great jewelry or accessories. Make sure to bring your engagement ring and if time allows, make sure it is clean and sparkly!
Layer, layer, layer! The outer layer should be a tighter layer – no bulky coats or loose sweaters. The fit should be snug on the top!
Consider architectural and structural details to pull the eye to your best features. A vintage headpiece can put more focus on the hairstyle and less on your upper arm or stomach.
Dress for the weather. Dressy and bright colored coats can look great in the winter while cute umbrellas and rain boots work great for overcast days!
7. Consider professional hair and makeup application for your engagement session! Ladies, wear more makeup than usual – false eyelashes can add a lot of drama.
Work with your hair, not against it! If you have wavy hair, don’t fight the curl in the humidity. If you have straight hair, trying to curl it can result in hair falling limp. Work with what nature gave you and enhance your beauty!
Avoid experimenting with a new-to-you hair color right before the session.
Make sure the nails on your fingers and toes are clean and neat – try to avoid chipped polish. Polish-free or gel manicures seems to work best!
8. Consider skipping sunglasses for a week prior or so prior to your session to avoid squinting in your images. If you plan to wear glasses and the session will be outside, avoid Transitions lenses that become sunglasses, as the camera won’t be able to see your eyes.
9. Get your gear together!
Try to get everything into one small bag. Consolidate phones, make up, spare shoes (bring comfy shoes for walking around!), down to one bag – leave larger bags with outfit changes in the car.
10. Furry friends are invited! We can incorporate your pets into your session – bring treats and a pretty and stylish leash. And also bring a friend to be the dog wrangler to take care of Fido after his portion of the session is up! Let us know if your pet is coming along for the session!
Bonus tip: We’d love to get a shot of your ring! Feel free to bring along a pretty vintage ring box or the card he/she gave you the night of the proposal – any little detail or item that will let us style that ring shot!
Planning on getting an engagement rather a pre-wedding photoshoot done? You have landed on the right page. Dear Kristen, your I appreciate you taking time from your busy schedules to educate readers who could also be future couples on some engagement photography tips. It is lovely to see how you being a photographer yourself talk highly about other wedding photographers.