engagement sessions

How to Dress For Winter Engagement Photos in Chicago: Three Easy Tips to Make the Most of your Session.

November 12, 2022


engagement photos of a couple taken at north avenue beach in chicago

Winter is upon us. Want winter engagement photos in Chicago? Don’t know how people do it? I got you.

As I write this, I am sitting on my couch bundled in layers while it is 35 degrees and flurrying outside. (Cue tears about lack of sunshine, but hello Christmas decor bringing me serotonin season.) This summer was nothing short of spectacular, and while summer and fall are usually the most popular time of year for engagement photos, the winter is also a great time of year to shoot because it means less crowds at popular photo spots. Below are my three biggest tips to make the most of your winter engagement session in Chicago.

Let’s get into it.

1. Prepare to be cold. This goes without saying, but if you’re choosing to take photos in the winter months, there is a good chance you have already lived through a Midwest winter or two, so prepare accordingly. Bring extra layers, bring a blanket or two to use in between takes, and bring plenty of hand warmers. One of my clients bought me a rechargeable hand-warmer (linked here) and it is a GAME CHANGER. While our time shooting outside won’t be as long as it would be if it was June, these preparations will help you keep your mind off the cold weather during your photos.

2. Dress knowing you’re going to be outside. If you want to wear a formal dress for your engagement photos, I am going to recommend its best to shoot in warmer months (or peep #3 on this list), but to make it work in the winter you will need to be prepared (have a friend come with you to your session and have the car running type of stuff, as well as having a coat with you) — but here are clothing recommendations I have for winter sessions:

  • Winter coats. Here’s a link to mine that I love, but here are a few others I love that would photograph really well. Pair it with a neutral turtleneck or sweater and a scarf.
  • For men’s jackets, I’d recommend similar styles via Abercombie, H&M, Zara, Nordstrom and ASOS! A jacket can show as much of your personality and style as an outfit can, so keep that in mind while you’re styling your fits for your engagement session.
  • For tops, I am always going to recommend a good neutral turtleneck. Avoid busy patterns, super fine patterns, and neons. I have a handful of incredibly warm, soft and CUTE sweaters from Abercrombie (iykyk that they have overhauled and rebranded over the last few years!!), as well as One Quince and Nordstrom.
  • For bottoms, pants that you can wear long underwear under is key to staying warm. Whether it’s thermals under jeans or under dress pants, you can’t go wrong with an extra layer of warmth 🔥

3. Consider shooting at an indoor location or a studio instead. If you want to shoot in the winter without shooting in the cold, a studio session is the move. You don’t have to worry about the coats, the snow, the slush and the salt. While you’re limited to the backdrops available in the studio, shooting in one location allows for multiple, easy outfit changes, fun seating and props, and allows your photographer to get extra creative with posing and portraits. There are also plenty of beautiful indoor engagement photo locations in Chicago like Garfield Park Conservatory, the Art Institute of Chicago, and the Rookery Building, to name a few.

Garfield Park Conservatory for a January Engagement Session.

I know that shooting in the winter months is not ideal for most, but there are many pros to shooting engagement photos in the offseason. It can be unique, it makes popular spots like North Avenue Beach easier to park at without crowds, and you can finish your session with hot chocolate and donuts. It’s also an excuse to get extra close to your fiancé during your engagement session like in this photo below :’)

Have questions or need help planning your winter engagement photos (or wedding?! which I have two of next month!!) Click here to chat with me today.

To inquire with me for your 2023 wedding, click here.

  1. […] that blog post I made about what to wear for winter engagement sessions? That all gets tossed out the window when […]

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hi, i'm ARIELLE.

You can usually find me home with my golden retriever or day dreaming of my next trip to Italy.

I am a firm believer in living life with purpose and never missing the opportunity to experience something new. The Meyers-Briggs test says I am an INFJ with ESFJ qualities (an introverted extrovert, IYKYK), and my friends say I am the person they come to when they need comfort, advice, or fresh baked goods. I consider myself an empath, so special moments you share with your loved ones will likely get me all teary eyed and sentimental. I am not here to pretend life is picture perfect, but to capture genuine emotion and create timeless pieces of art to decorate your home. I’m constantly striving for perfection, but have a calming personality and am relatively easy going. 

When the camera is not around my neck, I am a big home body. I love hanging on the couch with my dog, making pasta, breads and desserts from scratch, squatting 400+ pounds in the gym, or plotting my next trip outside of the US. As a direct descendant of Italian immigrants, I feel most at home in Italy (and speak a bit of Italian, too.)



Arielle has photographed over 175 weddings across 12 states, 5 countries, and 3 continents. While her heart beats for coastal and countryside Italian weddings, she is willing to travel anywhere and everywhere to document your day.








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