the best time of year

the best time of year


You may have a favorite season but is it the right one for your engagement photo shoot? I'll tell you my favorite time of year and why. Also the real life pros and cons of each season (hello red noses and rosy cheeks in the colder months)!

Getting married is one of the most exciting times of your life, but it isn’t just the big day that is important. Your engagement is something that should be celebrated, and what better way to do it than by having an engagement photo shoot?

There’s so much to think about when planning your photo shoot. What will you wear? Where will you be? You’re going to want everything – and everyone - to look perfect.

Here’s the thing though – the time of year can have a big effect on how your photos look. Typically, you might think summer is the perfect time, as it’s going to be full of sunshine.

But that’s not necessarily the case.

Seasons Change

Every place on earth has seasons. We are often acclimatized to having four seasons in a year: spring, summer, fall, and winter.

There are pros and cons to every season, and the trick is to decide what you want your photos to look like, and work with the weather to get the most out of it, even if it rains.

Being based in Chicago, I can tell you with confidence how to work with the four seasons we have. Hopefully you’ll find these ideas helpful no matter where in the world you live.

So, without further ado, let’s get started with some seasonal engagement photo shoot tips.

The Where & When

As the bride, you deserve the best of everything, so why not make the most of it? If your engagement photos look just like your wedding photos, you’ve missed an opportunity.

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Make sure you schedule your engagement photo shoot at a different time of year to your wedding. This will give both sets of photos a completely different look and feel, and will help remind you of the journey to your wedding day.

Think about it. If you’re going to have an outdoor summer wedding, how great are those photos going to look? Contrast them with a cozy fall engagement photo shoot!

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And how about the setting? Taking photos in a different location to your wedding day will again let you have some variety. Better yet, why not make it a destination photo shoot?

Sometimes you just have to find your happy place, so take a trip and find a photographer in the area. Nobody said you had to stay at home!

The Seasons


In Chicago, fall is the most popular time of year to have engagement photos taken. It’s a fair assumption that this is because of all the beautiful colors nature has to share at this time of year, but that’s not all.

Every couple wants to let the world know they are getting married, and for sending out save the dates, you’re going to need some photographs. There’s a natural deadline as you want to get the photos done before the snowy season comes in, and this leads to an interesting conundrum.

Fall is fantastic for taking photographs. Aside from the colors, the temperature is good – not so cold you need to wrap up, but not warm enough to make you sweat. You certainly don’t want to be rocking that look on your photos!

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But there’s a downside too. Fall is an exceptionally busy time for photographers, because everybody wants their photos taking at this time of year. Weddings, portraits, other couples who are newly engaged…you’re seriously going to have to book in advance if you want to stand any chance at all!

If you can get your photo shoot booked, you have so many ways to make it go well. You have numerous clothing options, and you’ll look great because the natural lighting in fall is amazing. It’s soft and warm, and the skies are a vibrant blue, a perfect contrast to the browns and oranges in nature.

That said, you have to time it right. At this time of year, flowers can be dead and burnt out, and you can never be quite certain of when the leaves will be the right color.

If you can catch it at the right time, I’m sure you will agree that a fall engagement photo shoot could provide some of the best photos you can imagine.


Chicago is well-known for snow in the winter, and if you’ve ever seen an engagement photo of a couple having fun in perfect, crisp, white snow, you’ll probably want to emulate it.

And you know what? When it works, it’s magical. Winter clothing can be fun and flattering, and your photos will be special.

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However…you’re probably over-romanticizing what snow it actually like! It’s cold. It’s wet. Perfect snowy days are very difficult to find, and even harder to schedule in advance. On most snowy days the sky is gray, and snow very quickly gets dirty and gray too.

This blandness leads to less variety in your photos, with less opportunity to experiment.

The temperature often shows through on the photos too. You’ll end up with a red nose, rosy cheeks, and watering eyes. You’ll be pulling your shoulders in for warmth, and let’s not even think about shivering.

Of course, you may still choose to go ahead with a winter photo shoot, but please remember that your photographer is human too. We get cold. We shiver. Our hands get so cold they stop working properly…it’s really hard to bring your ‘A’ game when you can’t press the buttons on the camera!


After the coldness of winter, spring comes as a relief to all in Chicago. Unfortunately, we might get a little too excited, as there’s no guarantee of warm weather and flowers until around the middle of May!

But this is the time that photographers are itching to get out there taking photos. Winter is so hard to work in. Spring, when it gets warmer, gives us chance to do what we love.

It feels fresh and bright. It looks so pretty as the flowers start to bloom. May is totally amazing for floral displays, far better than August for example. August is too hot, and all the flowers die in the heat.

If you want a garden setting, seriously – go for May.

But beware, as the weather in spring is far from settled. You know that saying about April showers bringing May flowers? Spring can be very rainy at times, and is very temperamental.

I like to think of spring as being the puppy of the seasons. It can be so sweet, so wonderful. But at a moment’s notice it can pee on your rug and tear up your shoes. Got to love it, right?


Something to keep in mind is that if you are planning a summer wedding, taking your engagement photos in spring is a little too late if you want to share or use them at your wedding. Give yourself plenty of time.


In Chicago, summer is the best. You can’t beat it. The question you need to be asking though is, “Is it suitable for my engagement photo shoot?”

Let me tell you how fantastic summer is for engagement photos. The weather is great. You get the best light out of the whole year, combined with the longest days. You have so many options for cute outfits. Sounds good, doesn’t it?

Well, wait, there’s more. You can have your photos taken at the beach. Yes! The beach! Don’t try that one in winter!

And then there are the sunsets…imagine it…a late evening stroll as the sun goes down, casting beautiful colors in the sky. You lean in to kiss, your noses touch, you giggle…

…as a drop of sweat runs down your forehead. Yes, sweat shows in a photo.

This is the major downside of summer, because everybody sweats. No, it’s not just you! Most of the brides I have photographed, and every single one of the grooms, have worried about sweating. We’re not on some TV show where everyone has a perfect life, we are real people in the real world, and real people sweat!

But that said, summer is a very busy time for photographers. Their weekends are almost always taken up with weddings, so you might need to have your photos taken on a weekday – but don’t forget you are likely to be busy too, as you’ll have all kinds of showers and events to attend.

Over to You

I know, it’s all just a little bit overwhelming. There’s so much to plan and arrange for a wedding, and you probably hadn’t even considered the seasons for your engagement photos before now. There are so many pros and cons for each season, but my guess is that one of these seasons stood out for you. There’s one that just resonated with you.

I often get asked which my favorite season is, and I feel that’s a horrible question. It’s like asking me to pick a favorite child.

But if I had to pick, I would say that right around Memorial Day is my favorite.

Downtown Chicago is so fresh and pretty! All the planters and downtown art is in, and the city is just so clean.

I love being able to wear a summer dress, but still being able to look good covering it with a cute jacket or a scarf. It’s a wonderful time of year.

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The couples I work with often go to dinner, or just grab a glass of wine along Michigan Avenue after the shoot. After the long Chicago winter, it’s really nice to be able to get outside, and doing this after the shoot makes it so much better.

Which season will you choose? What stands out for you? What do you really want to avoid?

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If you are still on the fence, check out the What to Wear Quiz and Location Finder Quiz in our other posts... sometimes you choose the outfit first, then decide on the season.