Welcome

A NOTE ABOUT THIS GUIDE

I'm so excited to be working with you and we can’t wait for our time together during your engagement session! It’s normal to be a little nervous about your session. I always tell people that I still get nervous before having my photo 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. It takes time for most couples to warm up to being photographed and understand how I pose. Timelines can be pretty 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 so much better when couples do engagement sessions ahead of time. 

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

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

- Winterlyn

We 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. I look forward to it because it’s a great opportunity for us all to hang out a bit before the wedding day.

The Guys

A NOTE TO

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 I 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.

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. 

Is there a "good" time to take photos? 

TIME & LIGHT

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

A few things to keep in mind during each season:

Seasons

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Winter

snowfall, hot cocoa and cozy coats

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. 

Spring

fresh flowers and sunny days 

Even though Spring begins in March, I typically don’t begin shooting for another 6 weeks because the weather in Chicago is still pretty chilly. When I schedule spring dates, I typically schedule both a primary date and a backup rain date. 

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Summer

walks on the beach hand in hand

In spite of the heat, I'm a big fan of summer sessions! Because of the later sunset, sessions sometimes begin as late as 6pm. 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. 

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Fall

colorful leaves and snuggling close

Fall is one of the prettiest times of the year in the Midwest 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! 

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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, I 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

Locations

Illinois AND Chicago ENGAGEMENT LOCATIONS

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 downtown Chicago, while a local park or flower-filled fields may be more fitting for a couple planning a more rustic affair. The best session locations are often meaningful places to the couple; however, I'm also happy to make recommendations. From ski slopes to lavender fields to apple picking and college campuses, the options for engagement session locations are endless! 

Buckingham Fountain
Chicago Theater Sign & Alley 
The Chicago Art Institute –  Garden
Alfred Caldwell Lily Pool
Chicago Board of Trade 


CLASSIC & ELEGANT

Museum of Science and Industry
 Milton Lee Olive Park 
Adler Planetarium
Lake Katherine 
 

COASTAL

The Bean
 BP Pedestrian Bridge 
Jay Pritzker Pavilion 
Clark Street Bridge
Kinzie Street Railroad Bridge

URBAN

Montrose Beach 
North Ave Beach
Oak Street Beach
Lighthouse Beach

BEACH

A Vineyard
Lurie Garden 
Lincoln Park Zoo
Honeycomb at Lincoln Park Zoo
Chicago Botanic Garden 
Naperville Riverwalk

RUSTIC

Cooking class
 Hiking
 Sailing / Boating 

ADVENTURE

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

Destination Engagement Sessions

While I take most of my engagement sessions in the Chicago area, I love to travel and photograph in different areas. 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 take your engagement photos outside of my normal area.

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

My dog Red is a huge part of my family, which is why 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. I 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

Outfits

TIPS FOR LOOKING YOUR BEST

When picking outfits I recommend keeping in mind the word “complement” rather than “match.” For example, if the groom-to-be is wearing a blue and pink pastel plaid shirt, the bride-to-be 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.

 Generally couples pick two outfits for an engagement session: a more formal outfit and a casual outfit. I recommend saving 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 accessories! Statement necklaces, cute shoes and classic watches are great ways to add detail to outfits. 

FOR THE LADIES

FOR THE gENTS

on to the next

find it fast

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

I love the way larger patterns 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. 

Wardrobe Tips

ACCESSORIES

WHERE TO SHOP

HAIR & MAKEUP

MANICURE

Outfits

for the ladies

find it fast

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

And dresses with lace 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. Choose an outfit you feel comfortable in, but don’t be afraid to dress up!

Accessories

ACCESSORIES

WHERE TO SHOP

HAIR & MAKEUP

MANICURE

Outfits

for the ladies

find it fast

Rent the Runway
ASOS
Morning Lavender
J. Crew
Anthropologie
Free People
Francesca’s
Jessakae
ModCloth
Shop Ruche
Hazel & Olive

Favorite Shops

Lulu's 
H&M 
Shabby Apple
Vici Dolls
Nordstrom
One Loved Babe
Arden 
Filly Flair

ACCESSORIES

WHERE TO SHOP

HAIR & MAKEUP

MANICURE

Outfits

for the ladies

find it fast

Engagement sessions are the perfect time for a hair and makeup trial! Professionally done hair & makeup last longer than typical hair & makeup. They also tend to hold up better for humidity and wind.

I think it’s so important that you look and feel your best for your engagement photos - and if you’re planning to do a hair & makeup trial anyways, the engagement session is a great time to test how your hair & makeup look on camera.

Hair & Makeup

ACCESSORIES

WHERE TO SHOP

HAIR & MAKEUP

MANICURE

Outfits

for the ladies

find it fast

There will probably be times during your session when I'm shooting your hands holding or the engagement ring on your hand - which means it’s a good idea to clean up your nails before your session (this applies to the guys too!).

Manicure

ACCESSORIES

WHERE TO SHOP

HAIR & MAKEUP

MANICURE

Outfits

for the ladies

find it fast

You can’t go wrong with a suit and tie. Consider pulling out that suit you had to wear last time you were a groomsmen! Layer with a blazer and a fun tie - you can even wear jeans with this look. 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

WHERE TO SHOP

Outfits

for the gents

find it fast

Rent the Runway
ASOS
 Suit Supply
J. Crew
Zara
Leather & Cotton

Jack Threads 

Frank & Oak 

Nordstrom 
H&M
Urban Outfitters

Wardrobe

WHERE TO SHOP

Outfits

for the gents

Inclement Weather

what to do if it rains

It’s typical for me to schedule two engagement session dates. A primary date and a rain date. Having two dates helps me make sure that your photos happen in a timely manner. Coordinating schedules can be tough and I've found that the best way to make sure my couples get the look they have in mind for their photos is to schedule two dates at the same time.

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 it rain. 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. 

When I can, I always try to take a photo of your ring during your engagement session - so it’s a good idea to have it cleaned or clean it yourself before your shoot! 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.

Ring Cleaning

Props

champagne is always a good idea

If you’re planning to bring props to your engagement session, I recommend including them only if they’re meaningful to you. Shots of drinking coffee at a local coffee shop would be cute if that’s where you met; however, trying to fly a kite together when it’s not a part of your relationship may come off as contrived.

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"?

"What do I do
 with my hands"?

POSING

Date Night

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!

Unless I have a holiday closure, you can expect to receive your engagement photos between 2 and 3 weeks after your session. 

When to Expect Your Images

I know that this guide is long and hopefully it covers everything you need to know to prep for your engagement session! However if there is something I missed, or you need a recommendation feel free to email 
info@winterlynphotography.com

THANK YOU!