Photography sessions are perfect for engagement images and family portraits. These sessions are done on-location and there are many choices of prints, products, and digital image collections for you to choose after the session.

Click here or use the contact link to the left to inquire about working with Kristen Wynn Photography for your engagement session or wedding day!


If you don’t see the answer to your question, email me at!

1. How much does a session cost with Kristen Wynn Photography? How much can I expect to pay total?

I like to keep things simple.

For your convenience, we have two types of sessions – the Simple Session and the Signature Session.

The Simple Session is perfect for those couples/families that are seeking “just a few” images. Simple Sessions are one hour, one outfit sessions held in White Oak/McKeesport Monday through Thursdays. The session includes ten fully edited photographer selected digital images and a reprint release for $500+tax.

The Signature Session is perfect for those couples/families seeking a custom portrait experience. This multiple outfit, multiple location session is two hours, held on location in Allegheny County, and available seven days a week. This session includes forty fully edited photographed selected digital images and a reprint release for $800+tax.

My session fees are non-refundable and non-transferable.

After the session, you are able to view your images and make additional purchases if desired. Please see the “Pricing” guide for more information.

2. Can I have my images on a USB drive for printing and sharing?

Yes, high resolution images are provided in both the Simple and Signature Sessions.

3. What’s the booking process?

In order to book, simply email me and we can talk about your session as far as locations and possible dates. I’ll ask you to choose a main date and a rain date (if the session is to be outside). If I’m available and we’re a good fit, I will email you a contract and invoice. In order to reserve the time and date, simply sign and mail back the portrait contract and your session fee plus sales tax and any applicable fees, such as travel. Once I receive the contract and session fee, you are booked. I will confirm with you via email and we can begin planning your session!

In rare cases of last minute bookings where there isn’t time for snail mail, you may be able to reserve my time with both a signed contract delivered electronically and a credit card payment for the deposit. Contact me for further details.

4. If I want the photos for a certain date, such as engagement portraits to display at the wedding, how far in advance does the session need to be held?

If purchasing only digital images, please allow at least six to eight weeks prior to your deadline, as editing alone will take up to one month. You may want to leave yourself additional time in case we would need to reschedule for rain, etc. Albums and products can take six weeks to arrive, so please order early and schedule your session even earlier. If you have a specific question about the timeline for delivery of a product, let me know. Please let me know upon initial contact if you have a deadline looming.

5. What’s your rescheduling policy?

Rescheduling is at my discretion due to weather. For all other circumstances, please provide at least three hours of notice. In case of a last-minute emergency, contact me as soon as possible. You may be responsible for reimbursement of permit fees or travel. I will transfer your deposit to another available date within one month of the original session (if there is another portrait slot open) one time, after which no further rescheduling is possible, and another non-refundable, non-transferable deposit must be placed.

When scheduling, we ask you to choose both a main date and a rain date. It’s Pittsburgh, after all!

6. When is the best time for photos?

To keep you cool in the heat and provide the best light, the best session start times are right at sunrise and two hours before sunset. For maternity sessions, the best time is when you are very pregnant, but not yet uncomfortable!

7. What kind of lifestyle sessions are available?

The most popular sessions at Kristen Wynn Photography are engagement sessions and family portraits. Other portrait sessions are possible subject to availability.

8. What’s the justification behind the cost?

The short answer-there is a lot of overhead in running a photography business, even a small one operated frugally.

I know the investment can be a little surprising if you’ve never hired a photographer before – it sure was for me when I got my first wedding photography job as an assistant. The investment in photography goes to pay for equipment, licensing, software, insurance, travel, professional dues, products, shipping, education, taxes, marketing, utilities/studio space, and the photographer’s time for planning, photographing, and editing.

9. Do you offer any deals or specials?

I don’t offer unadvertised discounts or asked-for discounts out of fairness to all customers. From time to time, I may offer specials, so please follow Kristen Wynn Photography on social media to stay abreast of any sales.

10. I have a place in mind that requires a photography permit-do you get it?

If a permit is required, the client must obtain and pay for the permit. Please ask me about some locations — I hold permits for some of the most popular locations already.

Before the Session

11. After I’m booked, what happens next?

After you are booked, we can get more into the planning for your session and discuss the specifics! I can help you with clothing choices and specific locations if you’d like, and I welcome your input as to what you are looking for from your session. We will confirm a few days prior to the session all of the details.

12. Do you honor special requests?

Yes, please let me know if you are looking for a certain pose or an image for a specific purpose, such as for a special spot in the home.

13. Where are sessions held?

Simple Sessions are held in White Oak or McKeesport, Pennsylvania.

Signature Sessions are primarily held on-locations in Pittsburgh, Pennsylvania and the surrounding areas, but may be available in other locations as well (travel fees may apply and subject to my availability). I have some great ideas for locations, and I’d love to hear your ideas as well.


14. Do you have any suggestions for on-location portraits?

I’m always open to new locations, but here are some of my previous portrait locations. Let’s talk about what would work best for you.


  • Chatham University, Pittsburgh, PA
  • Allegheny Cemetery, Pittsburgh, PA
  • Kennywood Park, West Mifflin, PA
  • Lawrenceville, Pittsburgh, PA
  • Washington’s Landing, Pittsburgh, PA
  • Smithfield Street Bridge, Pittsburgh, PA
  • North Park, Wexford, PA
  • Seven Springs Resort, Champion, PA
  • Downtown McKeesport, PA
  • PNC Park, Pittsburgh, PA
  • Carnegie Mellon University, Pittsburgh, PA
  • Shadyside, Pittsburgh, PA
  • Downtown Pittsburgh, PA
  • David L. Lawrence Convention Center – Riverwalk, Pittsburgh, PA
  • Mount Washington Overlook, Pittsburgh, PA
  • Green Cove Yacht Club – Fredericktown, PA
  • High School Stadium – Fredericktown, PA
  • Randyland, Northside – Pittsburgh, PA
  • Highland Park, Pittsburgh, PA
  • Triangle Park, Sewickley, PA
  • Indian Lake Park, North Huntingdon, PA
  • White Oak Park, White Oak, PA
  • Camp Soles, PA
  • Schenley Park, Pittsburgh, PA
  • Phipps Conservatory Outdoor Garden, Pittsburgh, PA
  • Phipps Conservatory, Pittsburgh, PA
  • Point State Park, Pittsburgh, PA
  • Washington and Jefferson College, Washington, PA
  • Hartwood Acres Mansion, Gibsonia, PA
  • Mellon Park Walled Garden, Pittsburgh, PA
  • PPG Ice Rink, Pittsburgh, PA
  • Moon Park, Moon, PA
  • Carrie Furnace, Braddock, PA
  • Riverview Park, Pittsburgh, PA
  • White Oak Park, White Oak, PA
  • South Side, Pittsburgh, PA
  • Riverfront Park, Pittsburgh, PA
  • North Shore, Pittsburgh, PA
  • Par 2 Golf Course, Monroeville, PA
  • Strip District, Pittsburgh, Pennsylvania
  • Mexican War Streets, Pittsburgh, Pennsylvania
  • Allegheny Commons/Allegheny West Park, Pittsburgh, Pennsylvania
  • Robin Hill Park in Moon Township, Pennsylvania
  • Pittsburgh Zoo and Aquarium
  • Station Square in Pittsburgh, Pennsylvania
  • Private Homes
  • University of Pittsburgh
  • West End Overlook in Pittsburgh
  • Mellon Institute (commonly called “CMU Columns”)
  • Narcisi Winery
  • Robert Morris University
  • Renziehausen Park in McKeesport, Pennsylvania
  • Squaw Valley Park, Fox Chapel, Pennsylvania
  • Round Hill Park, Elizabeth, Pennsylvania
  • Cleveland Art Museum, Cleveland, Ohio
  • Catoma Street Overlook
  • Studio 618 in Point Breeze
  • Braddock, PA
  • Nova Place in Pittsburgh’s Northside
  • Candle Tree Farm, Washington, Pennsylvania
  • Highline, Southside, PittsburghProposals
  • Mount Washington Grandview Overlooks
  • PNC Park
  • The Point
  • At Home (or site of a new home build!)
  • West End Overlook
  • Succop Nature Park, Butler, Pennsylvania
  • Stables at Conquenessing, Renfrew, Pennsylvania
  • Clayton Home, Point Breeze, Pittsburgh, Pennsylvania
  • Bird Park, Mt. Lebanon
  • Bernard Dog Run, Lawrenceville, Pittsburgh, Pennsylvania


15. Can we do multiple locations? How about outfit changes?

Signature Sessions include multiple locations and outfit changes are possible as long as they fit comfortably in our two-hour session time.  In some public areas, it is difficult to find restroom facilities in which to change clothing, so I recommend the ladies wear a cami and simply switch the top, add another layer on top with a scarf or cardi, or wear leggings for easy, modest outfit changes in public locales.

16. What should we wear?

I say “fit, flatter, and flare.” Please take a look at the galleries here on the website under “Sessions” for ideas of outfits that worked well. As a very general guideline:

  • Consider skipping sunglasses for a week or so prior to your portrait session to avoid squinting in your images.
  • Ladies, wear much more makeup than usual. Mascara, concealer, blush/bronzer, and lip balm are musts. False eyelashes can add a lot of drama to your photos.
  • Consider having professional hair and makeup done if you aren’t as experienced with styling.
  • Work with your hair, not against it. If you have wavy hair like me, don’t fight the curl in the humidity. If you have straight hair, trying to curl it can result in the hair falling limp. So work with what nature gave you and enhance your beauty.
  • Ladies, consider high heels if possible for a nice long line on the legs. If not, boots, attractive flats, or dressy sandals/wedges can work well. Both men and women should avoid inexpensive foam flip flops.
  •  Make sure the nails on your fingers and toes are clean, neat, and manicured if you would like.
  • Don’t try to “match” your partner exactly, such as everyone in the group wearing khaki pants and white shirts. Instead, come up with a color or two, and everyone coordinate around those selected colors.
  • Avoid solid white or solid black shirts if possible, and choose a color that makes you feel wonderful!
  • It’s important to feel confident in your outfits, so pick something with the best possible fit – no gapping or bunching, and remember to match the undergarments to the outfit as far as style, color, support, etc.
  • Make sure your clothing is ironed if needed. Avoid the sun in the days before here in Florida – I ended up with a bad sunburn right before a portrait session once!
  • If you plan to wear glasses and the session will be outside, avoid the lenses that become sunglasses or shaded outdoors, as I will not be able to see your eyes.
  • For many women, dresses and skirts photograph very nicely.
  • Many people want to camouflage their upper arms, therefore, I recommend long sleeves if you have a concern about this area.
  • Remember that you will be sitting, walking, jumping, moving, picking up your children, kicking water in the ocean, and having fun, so you need freedom of movement. Skirts and dresses rise up when sitting and necklines can plunge, so try on your outfits in front of a mirror before buying and make sure everything you want covered stays covered! This is especially important with high school senior photography. If the outfit is great but you can’t sit in it, try a cami underneath, a cardi over, or leggings with it.
  • Avoid clothing with large logos across the front.
  •  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 them with a belt. These outfits do work wonderfully for maternity shoots to show off the bump!
  • Use diaper covers over disposable diapers for the youngest portrait subjects if not using cloth diapers.
  • For men, make sure that your hair is neatly trimmed, especially around the neck and ears.
  •  Show your personality with great jewelry or accessories!
  • Styling for engagement shoots is available (I’ll put you in touch with a great stylist) and I also recommend Rent the Runway too!

17. How long will the session be? Can we bring extended family? Can we bring pets to a family session?

Simple Sessions are one hour; Signature Sessions are up to two hours long. Extended family sessions are possible-please let me know prior to signing the contract. Pets are also possible; please let me know prior to signing the contract and have available a pet watcher while we do the rest of the non-pet photos.

18. What are some tips for best results?

Have fun! Try to have a really relaxing, smooth day before the session, make sure everyone is well-rested and well-fed, and no one’s arguing, cranky, or sick. Easier said than done, I know! 🙂 Make sure to arrive early because parking at some downtown spots can be tricky!

You might want to consider bringing some treats for any little ones or pets at family sessions and let me know if there’s a trick to getting your kids to smile! Lastly, adults, your job is to keep looking at me and smiling during posed images and I’ll worry about getting the kids to look at just the right second!

After the Session

19. What happens after the session?

After the session, all of your images are culled (I go through and select the absolute best for retouching and remove any outtakes) and retouching is completed. This may take up to thirty days. I will then contact you to let you know your gallery is ready or to set up an ordering session if you’d like some help.

20. How many images will be in the gallery?

For the Simple Session, you will see at least ten images in the gallery fully retouched. For the Signature Sessions, there will be at least forty images in the gallery.

21. Will all my images be retouched?

Yes, all gallery images have full retouching. Please let me know if there are any areas of concern. Body modification and the removal of braces may incur an additional charge if requested.

22. Will the images be cropped? Will it look like it looks on screen?

The images are shown at a 4:6 aspect ratio, and digital images will have this aspect ratio. If you select a different size for prints, the crop will appear on the photo for viewing. Some images work best at certain sizes. Please contact me if you have any concerns, and I will contact you if I have concerns about a certain size selected.

23. What kind of prints are your standard prints-are they shiny or matte?

My prints are from a professional lab and on matte paper. If you’d prefer a non-textured finish, please let me know. All 11×14″ prints and larger are mounted for easy framing and to support the print.

24. How do we pay for our prints and photo products?

Additional prints and products are purchased with credit or debit cards through the gallery. Special order products, seasonal items, and albums can be paid for via check or credit card, as these items are customized and not able to be ordered from the gallery.

25. Can family and friends place orders?

If you choose to share the gallery link with them, your family and friends are able to place orders.

26. How long are my images available for online to purchase?

Once the gallery is posted, your images will remain online for one year. If the gallery expires and you want it rehosted, one-time rehosting of the gallery is possible for a fee.

27. I have a special product in mind – do you offer it?

Customer service is my number one priority – let me know and I will see what I can do!

28. Can I choose black and white for color images? What about color images for black and white proofs?

You can order any image shown in color in black and white for a print. Any image shown in black and white can only be ordered as black and white.


29. If I need help selecting images, can you do in-person ordering?

Yes, I can if you would like some help, subject to availability. Let me know!

30. Can I make changes to my order after it is placed?

Once the order is placed, it is sent directly to the lab, so changes can’t be made. Please contact me if you have any problems and we can get them resolved for you.

31. What is the return policy?

Due to the custom nature of portraiture, no refunds are possible. However, I want you to be totally satisfied, so please contact me with any issues.

32. Can I order an album?

Absolutely, please see the “Albums” section to the left for more information.



33. How long are images saved?

After expiration of your gallery and delivery, I don’t guarantee storage of your images, so I recommend keeping digital copies of images in a safe place and making multiple archival copies. If you should lose images, please contact me and, if I still have a copy, we can discuss hosting another gallery for you.