Sometimes, a wedding comes along that sticks with me long after the camera clicks quiet down and the guests have made their way home. Kaley and Jack’s Chicago destination wedding at the St. Regis Hotel was a romantic production I’ll never forget—stylized yet personal, upscale yet deeply genuine.

 Refined Style Meets Personal Touches

This London-based couple envisioned something special—a destination wedding bursting with meaningful details, whimsical design, and extraordinary experiences. And oh, was it worth the journey. Chicago, with its diverse culture, iconic architecture, famous deep-dish pizza, and vibrant jazz and blues music scene, felt perfect for these two. (Jack’s shoes even quote Nietzsche’s sentiment that “without music, life would be a mistake.” It reiterates the idea that music touches our souls and sets the soundtrack to our lives. It certainly set the soundtrack for their wedding day!)

They chose the St. Regis Hotel as their canvas, a space known for its clean lines, contemporary sophistication, and beautifully abundant natural light—ideal for film photography (a detail that made my heart sing!).

If you’re planning a destination wedding or even a local celebration with a high-design feel, Kaley and Jack’s day is packed with inspiration. Let’s step into their story together.

A Relaxed Start to the Wedding Weekend

Since Kaley and Jack traveled from across the pond, we added a cozy engagement session the day before their wedding. We started with an intimate shoot inside a Chicago coffee shop. This relaxed moment allowed us to capture the couple’s easy-going personalities and offered a sweet contrast to their black-tie wedding the next day. (Speaking of contrast, I just loved their coffee shop session attire. They flipped their cream and black outfits so she wore a cream top while he wore black and vice versa for the pants. This couple has style!) Their laid-back mini shoot is a reminder to engaged couples everywhere: your wedding weekend doesn’t have to be all grandeur, all the time. Often, the simplest moments become the most treasured.

Personalization in Every Detail

When I walked into Kaley’s bridal suite, it became clear this wasn’t just another wedding. Thoughtful details seemed to be everywhere: bridesmaid boxes filled with goodies like chic reception sneakers and cozy shawls (perfect for the rooftop chill!). Even their invitation suite showcased adorable custom illustrations of each wedding party member. It’s these tiny personal touches that guests always remember.

Kaley took special care to style each bridesmaid uniquely. Each of the bridesmaids wore a different dress pattern and hairstyle, mirroring their personalities beautifully. The result? Wedding party photos that felt editorial—polished yet effortlessly authentic. If you’re craving something beyond traditional matching dresses, consider personalizing bridesmaid attire. It adds depth, visual interest, and personality to your wedding images.

Inspiration for Your Stylized Wedding

As I made my way into the ceremony space, my breath caught. Candlelight danced along the aisle, punctuated by abundant arrangements of whimsical florals. Overhead, glowing chandeliers illuminated bare branches woven with blooms, creating an installation that felt equal parts modern and romantic.

If you’re looking for ways to make your ceremony unforgettable, lighting is transformative. It influences mood, enhances decor, and elevates your photographs. Lighting sets the ambiance. Kaley and Jack’s thoughtful lighting choices truly made their ceremony feel warm, intimate, and stylized.

What Makes Your Heart Flutter?

One of my favorite things about this couple? How they incorporated their individual passions into their wedding day. Kaley’s love for whimsical florals shone throughout the decor. Soft petals cascaded over the ceremony altar and subtle petal appliqués adorned the table linens. Then, there was the most stunning four-tiered cake I’ve ever laid eyes on. Jack’s passion for music infused their celebration with spectacular energy. An orchestra serenaded the ceremony, a jazz band set the tone for cocktail hour, and, as a surprise, one bridesmaid performed a heartfelt guitar piece.

As you plan your special day, I encourage you to embrace your passions. Whether it’s music, art, or something altogether unconventional, weaving your interests into your wedding day creates genuine connection and lasting memories.

Stylish Wardrobe Changes & Unforgettable Moments

Kaley’s gown for the ceremony was lovely for their chic black-tie affair. But later, she surprised guests by changing into a dreamy, flowy dress—perfect for dancing and mingling. If you’re considering an outfit change, lean into your desire for comfort, movement, and personal style. It makes the celebration feel relaxed and frees you to dance the night away.

Throughout the night, Kaley’s love for film photography matched my own. Together, we documented their story on multiple film formats: romantic 35mm shots, lush medium-format portraits, and playful, spontaneous Polaroids. Mixing film formats is an artistic way to bring depth and texture to your visual narrative, allowing each moment to shine in its own unique way.

Kaley and Jack’s wedding is a powerful reminder that a highly stylized wedding can still be refreshingly approachable and deeply personal. From carefully curated bridesmaid dresses to personalized details infused throughout the day, their celebration combined sophisticated style with genuine heart.

Are you dreaming of your own thoughtfully designed wedding? What elements of your personality will you weave into your day, making it uniquely yours?

Whether you’re celebrating near or far, a wedding like Kaley and Jack’s proves that thoughtful planning, authentic details, and meaningful experiences create the richest memories—ones both you and your guests carry forever.

 

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Chicago Wedding Vendor Team

Venue: @stregischicago | @mirurestaurant⁠
Planning: @livenitup | @lizkriegs⁠
Floral + Decor: @kehoedesigns | @kehoedarling⁠
Lighting + Production: @blackoak.tech⁠
Band: @beatmixchicago⁠
Photography:@danielleheinsonphotography⁠
Videography: @banderafilms⁠
Photobooth: @fotioco⁠
Stationary: @mag.milestones⁠
Linens: @bbjlatavola⁠
Chairs: @nuagedesignsinc⁠
Rentals: @thefestivefrog | @hallsrental⁠
Wedding Cake: @pastrychefjuan⁠
Hair: @reneefeldmanweddings⁠
Makeup: @leesib⁠
Dresser: @theweddingdresser

 

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