Engagement & Style Guide
Your first date with The Montgomerys
Welcome — we’re so glad you’re here.
Your engagement session is more than just photos. It’s the first experience of your engagement season, and in many ways, it’s our first date together.
This time is meant to feel relaxed, fun, and natural — not like you’re checking something off a wedding to-do list. We want you to show up as yourselves, enjoy being together, and walk away thinking, “Wow… that was actually so much fun.”
This guide will walk you through what to expect, how to prepare, and how to make the most of your engagement experience — from choosing a location to planning outfits and everything in between. We encourage you to treat this like a date night: plan dinner after, grab a drink, make an evening of it.
This is the start of documenting your story — and we can’t wait to experience it with you.
What to expect
If this is your first time being professionally photographed together, you’re not alone — and you don’t need to have any experience for this to feel easy.
Our approach is relaxed, guided, and focused on connection. We’ll never leave you wondering what to do with your hands or how to stand, but nothing will feel stiff or forced. Think less “photoshoot” and more quality time together — with a little direction along the way.
This experience is designed to feel natural and enjoyable from start to finish. The more you lean into it and treat it like a date, the better it feels. Show up ready to be yourselves, have fun together, and trust that we’ve got the rest covered.
Before You Arrive
Preparation doesn’t need to be complicated — this is simply about showing up feeling confident and comfortable. When you feel good, it shows.
Since your hands naturally play a big role in engagement photos, we recommend clean, neutral nails and having your ring professionally cleaned a few days before your session. Most jewelers offer complimentary cleanings, and it makes a noticeable difference in close-up shots.
Hair and makeup are completely optional, but many couples choose to have them professionally done as a little extra boost of confidence. If you’re considering professional services for your wedding day, this is also a great opportunity to do a trial run.
If you plan on waxing, spray tanning, or trying something new, we suggest doing so a few days ahead of time to allow everything to settle and look its best. The goal is to feel like yourselves — just a little extra polished.
Choosing the right location
Location plays a big role in how your engagement experience feels. Rather than starting from scratch, we recommend choosing from our curated location gallery. These are spaces we know well — from lighting and timing to crowd flow and overall feel — which allows us to focus less on logistics and more on creating a relaxed, enjoyable experience for you.
Our gallery includes a variety of locations, from nature-forward spaces to urban settings and indoor studio options, so there’s something for every style and season. Choosing a familiar location helps us move seamlessly, anticipate the best light, and keep things feeling effortless rather than rushed or unpredictable.
If you have a specific location that holds special meaning — like a favorite bar, coffee shop, or personal space — we’re always happy to explore those options with you. In those cases, availability and any required rental or permit fees would be the responsibility of the couple.
Our goal is always the same: to create an experience that feels smooth, intentional, and fun. Starting with locations we know well allows us to do exactly that — so you can relax, be present, and enjoy the time together.
If you’re unsure about an outfit or want a second opinion, we’re always happy to help guide you.
What You Wear Sets the Tone
What you wear plays a big role in how your photos feel — not because it needs to be perfect, but because it helps set the overall tone of the experience.
The goal is to feel comfortable, confident, and like yourselves.
Rather than matching, we recommend coordinating.
Think complementary colors, textures, and tones that work together without competing. If one of you chooses a pattern or texture, let the other stay in something more neutral and solid to keep the look balanced and timeless.
Lighter, softer tones tend to photograph beautifully and keep the focus on connection rather than clothing. Accessories should feel intentional and classic — pieces you’ll still love looking back on years from now.
We recommend planning for one dressier look and, if you’d like, one more casual option. A dressy outfit adds variety and elevates the final gallery, while a casual look keeps things relaxed and natural. If you’re doing two outfits, reach out and ask us which one to arrive in first based on your chosen location.
For the dressier look, we especially love flowing dresses or skirts — pieces that feel feminine and allow for natural movement photograph beautifully.
Shoes matter more than most people expect. Heels or elevated footwear can help with posture and movement, but comfort always comes first. Clean, stylish sneakers are absolutely fine for casual outfits — just avoid athletic or running shoes, as they tend to stand out in photos.
Above all, choose pieces that allow you to move, sit, walk, and be close comfortably. When you feel good in what you’re wearing, it shows — and the experience naturally feels more effortless.
PUPS, PROPS & GUESTS
We love when couples choose to include their dogs — they’re part of your story, and they’re always welcome. If you plan to bring a pup along, we recommend bringing a friend to help hold a leash so we can easily transition between photos with and without them.
Pups
When it comes to props, simplicity goes a long way. Meaningful elements can be fun, but we recommend avoiding anything overly trendy or distracting. The focus of your engagement experience should always be the two of you — connection photographs best when it’s natural and unforced.
Props
While we adore your friends and family, we encourage keeping your engagement experience just for the two of you. Extra guests can unintentionally shift the energy or make things feel less relaxed. Think of this time as a date — playful, personal, and focused on each other.
Guests
Our goal is to create an experience that feels effortless and authentic, and a simpler approach helps us do exactly that.
NERVES & EXPECTATIONS
It’s Normal — We Promise
If you’re feeling a little nervous about being in front of the camera, you’re not alone. We hear this all the time — especially from couples who swear they’re “not photogenic” or worry one of them won’t enjoy the process.
Here’s the good news: you don’t need to know how to pose, perform, or act a certain way. Our role is to guide you just enough so things feel natural, relaxed, and easy. Nothing will be stiff or forced — we focus on movement, interaction, and real connection.
One of our favorite things to hear at the end of an engagement experience is, “That was actually so much fun.” And it happens more often than not.
This time together is meant to feel like a break from wedding planning — a chance to slow down, enjoy each other, and simply be present. Trust the process, lean into the experience, and let yourselves have fun. We’ve got you.
Right On Time
Timing plays an important role in how your engagement experience unfolds. We typically photograph during the best light of the day, and arriving on time allows us to make the most of it without feeling rushed.
Account for traffic and parking.
We recommend planning to arrive about 10 minutes early to allow time for parking, freshening up, and settling in. Starting on time keeps the experience relaxed and ensures we have plenty of space to create without watching the clock.
If possible, we encourage treating this like a date night — leave yourselves some margin, plan dinner or drinks afterward, and enjoy the evening together. When the experience flows naturally, everything feels better.
Let’s Do This
With love,
The Montgomerys
Photographers. Educators. Advocates.
You made it through the guide — and hopefully you’re feeling excited, not overwhelmed. Your engagement experience is meant to be fun, relaxed, and genuinely enjoyable,
and we’re here to guide you every step of the way.
This is the beginning of documenting your story — the first chance to slow down, be present with one another, and enjoy this season before the pace of wedding planning picks up. Show up ready to enjoy the time together, trust the process, and let yourselves have fun.
We can’t wait to photograph you and create something meaningful together. If any questions come up as you prepare, don’t hesitate to reach out — we’re always happy to help.