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How to Plan an Engagement Session That Feels Like You

Your engagement session isn’t just a box to check — it’s a meaningful part of your wedding journey, and one of my favorite parts of the process. Whether you’re already booked or just beginning to plan, this guide is here to help you feel prepared and excited for what’s ahead

My approach to engagement sessions is rooted in intentionality. Yes, we’ll capture beautiful imagery — but more than that, it’s a space for you to slow down, connect, and feel completely at ease in front of the camera before your wedding day arrives.

Think of this as your personal roadmap: what to expect, how to prepare, and how we’ll create something timeless together.

Scheduling With Intention

If your session is already on the calendar — perfect. But if you’re still deciding, here’s what I usually recommend couples consider:

1. What kind of vibe do you want?

Are you dreaming of golden hour by the lake, cozy downtown streets, or something lush and green? Your location and overall aesthetic will often influence the season and timing of the shoot.

2. How far out is your wedding — and do you need the photos for anything?

If you’re planning to use your engagement photos for save the dates, invitations, or a guest book, we’ll want to schedule your session at least 2–3 months ahead of when you need them printed.

Seasonality also plays a role — winter sessions feel very different from late summer or early fall. If you’re unsure, I’m always happy to offer guidance based on your timeline and vision.

Choosing a Location

Where we take your engagement photos matters just as much as what you wear — and choosing a meaningful location can bring so much more depth and emotion to your session.

I always encourage couples to first think about places that are special to them. Maybe you…


– Just bought your first home together
– Had your first date at a tucked-away beach
– Love walking through a certain park on slow weekends
– Have a go-to date night spot that feels like your thing

Choosing a place that holds meaning can make your photos feel less like a photoshoot and more like a reflection of your life together — the quiet rituals and little memories that make your story yours.

That said, if you have a location in mind but aren’t sure how it will photograph, I’m always happy to take a look and share my thoughts on lighting, logistics, and overall feel.

And if there isn’t a specific spot that comes to mind? That’s totally okay. Once I know the vibe you’re drawn to — whether that’s romantic and soft, modern and architectural, or something in between — I’ll send over personalized location recommendations that align with your vision.

Styling Your Session

When it comes to choosing what to wear for your engagement session, my biggest piece of advice is simple: stay true to yourself. This isn’t the time to test-drive a totally new style — instead, wear something that feels authentically you. When you feel good, you look good. Confidence is always the best accessory.

I recommend starting with a color palette and building your outfits around it. Choosing tones that complement each other (rather than matching exactly) creates a more elevated, effortless look. Think: soft layering, interesting textures, and fabrics that move well.

As you’re narrowing down your options, keep the season and location in mind. What looks beautiful on the beach at golden hour might feel out of place in the woods during fall. When in doubt, neutrals tend to photograph beautifully — just be mindful that bright white can sometimes read a little blue on camera depending on the light.

A few other things to consider:
– Coordinate, don’t match
– Layer when possible (jackets, scarves, jewelry, etc.)
– Avoid logos or loud patterns that might distract from your connection
– Bring a second outfit if you’d like two different looks — one dressier, one more relaxed

If you’re feeling stuck, I’m always happy to help you piece together looks or offer feedback on outfit ideas. This session is about telling your story — and the way you show up should feel like a reflection of that.

What To Bring & How To Prepare

Props aren’t necessary — but if there’s something meaningful you’d love to include, I always say bring it! A bouquet from your local market, champagne to pop, your dog (yes, please), or even a picnic setup — small details like these can add a personal layer to your session and make the photos feel even more you.

If you’re not sure what to bring, don’t overthink it. The most important thing is that you show up feeling relaxed and comfortable.

Here are a few tips to help you prepare:

– Plan your outfits ahead of time and try them on a few days before
– Steam or iron your clothing the night before (especially linen or flowy fabrics)
– Pack a tote with touch-up essentials: hairbrush, lipstick, comfortable shoes, etc.
– Bring water and a snack, especially for longer sessions or warmer weather
– If we’re hiking or walking, wear comfy shoes to start and switch once we’re on location

And lastly, expect to ease in. I’ll guide you every step of the way with prompts and direction, but I promise — this is more about the two of you simply being yourselves than it is about posing. I want this session to feel fun, connected, and like a sweet little memory in itself.

Ask Me Anything

Have a question about what to wear? Not sure if a certain location will work well? Want help picking between two outfits? I’m always here. This session is about you, and I’m so honored to be part of this season in your lives.

Just shoot me a message — truly, nothing is too small to ask.

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BEHIND THE LENS

Hi, I'm        Alex.

As an internationally-lauded wedding photographer with decades of experience, Roselyn (Rose, for short) brings her signature timeless, editorial style and classic, romantic aesthetic to modern love stories. 

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Your engagement session isn’t just a box to check — it’s a meaningful part of your wedding journey, and one of my favorite parts of the process. Whether you’re already booked or just beginning to plan, this guide is here to help you feel prepared and excited for what’s ahead My approach to engagement sessions […]

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A classy, European-inspired engagement session at Villa Terrace in Milwaukee, filled with vintage charm, sunlit architecture, and timeless garden romance.

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Close-up editorial headshot of Alexia Rodriquez during her Milwaukee brand session at Studio North

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A minimal, editorial Milwaukee brand session marking a new chapter for Alexia Rodriquez — blending personal details, refined styling, and intentional storytelling.

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