Rustic Manor 1848, Wisconsin
Milwaukee, Wisconsin
Timeless,Intentional Photography
Romantic wedding photography and portrait sessions that capture your authentic story with elegance and care.
Nice to Meet You
Hi, I'm Bailey
Hi, I'm Bailey — the photographer behind Bailey Bryn Photography, based in Milwaukee and serving Wisconsin + Illinois.
I believe your photos should feel like a memory you can step back into — the quiet hand squeeze before "I do," the way your partner looks at you when no one else is watching, the soft in-between moments that make your story yours.
My style is warm, candid, and timeless, with natural tones and true-to-life color that never feels trendy or over-edited. I'll guide you gently when you need it, and step back when the moments speak for themselves — so your images feel effortless, emotional, and elevated.
I specialize in weddings, engagements, maternity, family, and intimate motherhood sessions — documenting seasons that deserve to be remembered beautifully.
I photograph weddings throughout Southeast Wisconsin, including Milwaukee, Lake Geneva, and surrounding areas. If you're drawn to romantic imagery, honest connection, and photos that feel both refined and real, I would love to tell your story.
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Services & Pricing
My Offerings
My approach is timeless, romantic, and experience-led — from inquiry to gallery delivery. Each session is crafted to capture your authentic moments and bring your story to life. Serving Milwaukee, Wisconsin and Illinois.
Weddings
As a Milwaukee wedding photographer, I specialize in candid, documentary-style coverage with a touch of guided portraits. From vows to dance floor moments, I preserve your day with timeless, heartfelt imagery.
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Engagement Sessions
Capture your love story with romantic, natural engagement photography in Milwaukee and across Wisconsin. These sessions highlight your genuine connection, giving you timeless images that feel true to you.
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Sessions
Whether in my natural light Milwaukee studio or outdoors, I create a relaxed space for families, couples, and maternity sessions. Your photos will feel authentic, timeless, and filled with genuine emotion.
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Newborn & Milestones
Capture those fleeting first days and special milestones at Studio 11:11 in Bay View, Milwaukee. From newborn sessions to first birthday cake smashes, I document every precious stage.
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Ready to Book?
Sessions from $400 | Weddings from $2,100
Wedding collections tailored to your day.
Get Your Custom QuoteRecent Work
Featured Images
Browse my recent wedding, engagement, family, maternity, and newborn photography sessions from Milwaukee, Waukesha, and throughout Wisconsin.
Rustic Manor 1848, Wisconsin
Couple Golden Hour Portrait
Rustic Manor 1848, Wisconsin
Wedding Ceremony Details
Rustic Manor 1848, Wisconsin
Bridal Preparations
Rustic Manor 1848, Wisconsin
Reception Details
Rustic Manor 1848, Wisconsin
Dance Floor Moments
Wisconsin Wedding
Bride & Groom Portraits
Wisconsin Wedding
Intimate Couple Moment
Serving Milwaukee, Waukesha, Lake Geneva, and surrounding Wisconsin areas
Book Your SessionFeatured Wedding
Rustic Manor 1848 Wedding
A stunning rustic celebration featuring dramatic barn architecture and natural beauty.
Don't Wait to Preserve Your Memories
Limited availability for 2026 & 2027 weddings. Newborn sessions book up fast!
Check AvailabilityClient Love
Kind Words
"Bailey captured our wedding day perfectly. Every photo tells a story and brings back all the emotions from that special day. She made us feel so comfortable and the results exceeded our expectations."
Working Together
The Experience
Personalized Consultation
Let's talk about your love story—your vision, your style, the moments that matter most. Together, we'll craft a custom session that feels authentically you.
Relaxed Photo Session
You'll forget the camera is there. I guide you through gentle moments while capturing the real connection, the stolen glances, the laughter that comes naturally.
Careful Curation
Every image is thoughtfully edited with warmth and intention. Each photo tells a part of your story—timeless, romantic, and uniquely beautiful.
Gallery Delivery
Your photos arrive beautifully edited and ready to share within 2-3 weeks, so you can relive those precious moments sooner.
Common Questions
Frequently Asked Questions
I recommend booking 12-18 months in advance for peak wedding season (May-October). For off-season weddings, 6-9 months is typically sufficient. Popular dates book up quickly, so the earlier you reach out, the better chance of securing your date.
Yes! While I'm based in Milwaukee, Wisconsin, I travel throughout the state and beyond. Travel within 50 miles of Milwaukee is included. For destinations further away, travel fees may apply. I've photographed weddings across Wisconsin, Chicago, and destination locations.
The ideal window for newborn photography is within the first 5-14 days after birth. During this time, babies are sleepier and more flexible, allowing for those precious curled-up poses. I recommend booking your session during your second trimester to ensure availability.
I recommend coordinating colors rather than matching outfits. Neutral tones, soft pastels, and earth tones photograph beautifully. Avoid busy patterns, logos, and neon colors. I provide a detailed style guide after booking to help you plan the perfect outfits.
Wedding galleries are delivered within 6-8 weeks. Engagement, family, and portrait sessions are delivered within 2-3 weeks. Newborn sessions are delivered within 2 weeks. You'll receive a beautiful online gallery where you can view, download, and share your images.
Yes. I offer flexible payment plans for all packages. A retainer is due at booking to secure your date, with the remaining balance due before your session or wedding day.
Have another question? Get in touch
Get in Touch
Let's Create Together
Ready to capture your special moments? I'd love to hear about your vision. Fill out the form or reach out directly—I respond to all inquiries within 24 hours.
Location
Milwaukee, Wisconsin
Response Time
Within 24 hours, M-F 9AM-5PM CST
Ready to Book Your Session?
Click below to open my contact form and tell me about your vision for your wedding, family session, or portrait. I can't wait to hear from you!
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