Black and white engagement photo of a couple looking out at the Chicago skyline together

Booking your wedding date is such an exciting milestone — and for many couples, planning their engagement session is the very next step. This engagement session planning guide is designed to help you slow down, celebrate this season, and create images that feel intentional, refined, and deeply personal.

Your engagement photos aren’t just about getting comfortable in front of the camera. They’re an opportunity to connect, be present together, and create imagery that becomes part of your wedding story from the very beginning.

If you’re wondering when to schedule your engagement session, what to wear, or how to choose the perfect location, this guide will help you plan a session that feels effortless and meaningful.

Couple kissing in the water at Holland Beach as he holds her in his arms during their engagement session

Why Engagement Sessions Matter

An engagement session is often the first time we work together in a relaxed, unrushed setting. It allows you to experience my photography approach, feel confident in front of the camera, and understand how I guide couples into images that feel natural rather than posed.

Engagement photos are often used for:

  • Save-the-dates and wedding websites
  • Guest books and printed heirlooms
  • Framed artwork for your home

They become part of your wedding story — not just a planning task to check off.

Couple sharing a dip kiss at the Honeycomb structure in Lincoln Park Chicago

When to Schedule Your Engagement Session

Most couples schedule their engagement session 6–12 months before their wedding, though timing can vary based on how you plan to use your images.

When choosing a date, consider:

  • Seasonal preferences: Spring blooms, summer warmth, fall color, or a more editorial winter look
  • Wedding stationery timelines: If you plan to use photos for save-the-dates, earlier is better
  • Lighting: Golden hour (the hour before sunset) offers soft, flattering light and is always recommended

I help every couple select a session date that aligns with both their vision and the best photographic conditions.

Bride looking romantically at her fiancé while leading him through Cranbrook House and Gardens

Choosing the Right Engagement Session Location for Your Style

The best engagement session locations reflect who you are as a couple.

This could include:

  • Scenic outdoor locations with open light
  • Architectural or editorial-style venues
  • Meaningful places tied to your story
  • Minimal, neutral backdrops that feel timeless

You don’t need a crowded or trendy location. Often, quieter spaces with room to move result in the most authentic and refined images.

After booking, my couples receive personalized location recommendations based on their aesthetic, comfort level, and overall wedding vision.

Drone engagement photo of a couple walking together near a willow tree at Calvin Ecosystem Preserve

What to Wear for Engagement Photos

Choosing outfits doesn’t need to feel overwhelming. The goal is to feel confident, comfortable, and like yourselves — just slightly elevated.

Helpful tips include:

  • Wear clothing that allows you to move and interact naturally
  • Neutral tones, soft textures, and subtle patterns photograph beautifully
  • Consider one polished look and one more relaxed option
  • Avoid logos or overly bold graphics

When you feel good in what you’re wearing, it shows in your images.

Couple walking hand in hand through dune grass at Holland State Park during engagement photos

What to Expect During Your Engagement Session

If you’re worried about feeling awkward in front of the camera, you’re not alone — and you don’t need any experience.

My approach is guided and relaxed. I provide gentle direction, movement prompts, and natural interactions so you’re never left wondering what to do. The result is imagery that feels organic, connected, and timeless.

Many couples leave their engagement session feeling more confident and excited for their wedding day photography experience.

Couple cuddling together in the grass during golden hour in Lincoln Park Chicago

Making Your Engagement Session Personal

Your engagement session doesn’t need to follow a formula. It can be:

  • Romantic and understated
  • Editorial and fashion-inspired
  • Playful and candid
  • Quiet and intimate

The most meaningful sessions happen when couples trust the process and focus on being present together.

Drone photo of a couple laying together on a blanket in a flower-filled field during engagement session

For My Wedding Couples

After booking, my couples receive exclusive planning resources — including detailed engagement session guides, timeline considerations, and wedding day preparation tools — designed to ensure a seamless and elevated experience from start to finish.

This guide is just the beginning.

You Just Booked Your Date – Now It’s Time to Plan Your Engagement Session

Planning & Inspiration

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