How To Pick the Perfect Outfit for Your Engagement Session

Hi, fellow brides-to-be! It’s Ali from Love You, Mean It. I’m so excited to share our engagement photos with you today! Planning our e-sesh has been one of my favorite parts our engagement so far. We’ve used these beautiful images captured by Leslee Mitchell and Tarin Frantz on our wedding website and also printed a few for gifting to family. That said, it can also be stressful when deciding where to shoot and what to wear. So, I’ve put together a list of five tips to make the “what to wear” part a breeze.

1. Location

The first element to consider should be where you will be taking your photos. Will you be outside? What will the temperature be? Thinking through the locations will ensure you dress appropriately for the weather and will help inspire your outfits. If it will be chilly, you don’t want to be freezing the entire day. If you’re uncomfortable in your setting, you won’t be able to properly relax for the photos and be able to have fun. Will you be taking photos on a horse farm (like me!) or on grass? Don’t forget the appropriate footwear!

2. Number of Outfits

Once you have the location (or locations!) set with your photographer, it makes it easier to envision the appropriate outfits. Personally, I had two venues that I wanted different outfits for. I knew that I wanted to take more casual photos as well as dressier ones, and a few right in between. For me, it made sense to do the more casual photos when we were at home in Kentucky and take fancier ones in front of Perkins Chapel at SMU (just a few feet away from where we first met!). If you’re worried about coming off as “cheesy,” wear a typical Saturday outfit and it will make the photos look less staged and more real-life. On the other hand, I think it’s special to have photos that are a little more dressed-up to celebrate this exciting time. Ultimately, however, this is not the time to go completely out of your comfort zone when it comes to what you wear which leads me to my next point: deciding on the outfits!

3. Coordinate and Prepare Your Looks

It’s definitely necessary for both of you to think through and try-on your outfits before the day-of. You want to make sure you “match” each other when it comes to the level of dressiness. You also want to make sure you and your fiancé won’t clash and that everything is clean, pressed, and ready to go. If either of you have bought something new for the photos, make sure you give yourself plenty of time to receive the item and try it on so you can make any necessary alterations– you don’t want any surprises on the actual day! For our casual photos, I wore a solid color sweater and jeans and Ben wore a button down and jeans. Easy and comfortable! For the pictures we took in front of Perkins Chapel, I wore an ivory tulle skirt and embellished sweater from Jenny Yoo. My skirt felt bridal and super special. It’s actually from the same fabric that my bridesmaids dresses (also Jenny Yoo, of course!) will be made from which I thought was a special touch!

4. Test Your Wedding Hair/Make-up

If possible, engagement photos make a great occasion to test out your wedding hair and/or make-up. Luckily for me, I was able to meet with my wedding stylist when I was home in Kentucky for our photos. It allows you to get to know each other a little bit and, not to mention, your hair and make-up will be looking great in the photos! Because I wanted to look super natural, I asked for “my everyday look, just a little better!”

5. Be yourselves and have fun!

It’s a fact, staged photos can be AWKWARD. What you will wear should be the least of your worries! If you plan your outfits out ahead of time and feel good about them, it will be one less thing on your mind the day of the shoot. Also recommended: packing a cooler with snacks and champagne to celebrate as the day goes on!

I’ve also included a bunch of my favorite pieces for engagement sessions below, starting off with some beauties from Jenny Yoo!

How To Pick the Perfect Outfit for Your Engagement Session
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How To Pick the Perfect Outfit for Your Engagement Session
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Photography: Leslee Mitchell | Photography: Tarin Frantz | Church: Perkins Chapel | Embellished Sweater: Jenny Yoo | Tulle Skirt: Jenny Yoo

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Allison Hollins

Blogger Bride
Sweet Summer Garden Wedding

Why do I love these two? Because they love love loved their wedding, it’s obvious in every single pic by Nina & Wes Photography and throughout Bryan Starr Cinematography’s film. From the first look, when the Groom spontaneously twirled his beautiful Bride to this genuine JOY taking over as they walked down the aisle as newlyweds; these special images are what makes me smile all day long. Get in on all this goodness in our VAULT right this way!


From Nina & Wes Photography… Maddie and Austin got married at a beautiful park in Lexington, KY. There were so many unique and beautiful moments throughout their day. From the first look where Austin twirled his bride around in a moment of joy and fun… to Maddie’s first look with her father, where they both cried and embraced tightly… to the prayer before the ceremony where all of Maddie’s bridesmaids and family surrounded her… to the painting their friend created as the ceremony unfolded… and the music that guests were asked to join in during the ceremony… and every single look of joy throughout each moment of their wedding day was something beautiful to behold. The love Maddie and Austin have for one another is tangible and pure. We are so thankful we got to capture such an emotional and heartfelt day.

From the Bride… “I’ll never forget shortly after Austin and I decided to hold our ceremony outside at Waveland State Historic Site, we took a sunset stroll on the property—just dreaming together about our wedding day. About ten minutes into the walk,the grounds keeper approached us and asked if we were getting married here. His assumption of our romantic behavior was correct. Our conversation began so naturally as he humbly shared about the joys of marriage. The way he talked about his wife and his selfless, simple love for herafter 45 years brought euphoria to our souls. It was a moving moment, sharing a glimpse of our future together in an unanticipated exchange. He talked about how the grounds were a peaceful place—and they were indeed.

Austin and I reflected on that moment several times leading up to our wedding day. We couldn’t have been more satisfied sharing those special vows on Waveland’s overgrown, lush property. The woodland trails and rolling hills made our city-limits ceremony venue appear as the green, natural “heaven on earth” that we most wanted.
For us, it was all about sentiment. Many of our wedding decisions were made with sentimental attachments. From the reception venue to the tiniest details, the plans were made with more meaning than most of the guests would’ve ever known. But we liked it that way. We envisioned the experience for our friends and family by making every decision to create an atmosphere of love and joy. As people would be reunited with family and friends, we asked questions like how we could plan a seating chart or flow of events that would cause people to savor conversations, to laugh together, and enjoy celebrating the seasons of life. As everything culminated on August 14th, it was a true joy to look around and delight in all that it came to be. Unlike I’ve heard from so many other brides, Austin and I were able to enjoy our wedding day being fully present! It’s one of my favorite miracles about the day. Even if we had an unlimited budget to throw the most extravagant of celebrations, we couldn’t have imagined it any better. It was gloriously blessed and more than we could’ve dreamed. We are so thankful.

Peruse more rustic style weddings here!

Photography: Nina & Wes Photography | Floral Design: Hide And Seek Design | Wedding Dress: Coco Anais | Cake: Martine's Pastries | Ceremony Venue: Richard H. Lewis Lodge At Historic Cherokee State Park, Kenlake | Reception Venue: The Livery | Bride's Shoes: Charter Club | Rings: Sheila Bayes Fine Jewelry | Bridesmaids' Dresses: BHLDN | Catering: Karem Catering | Makeup: Simply Makeup | Hair: Hali B & Co | DJ: Bluegrass Beat | Groom's Attire: Men's Wearhouse | Ceremony Music: Curt Vernon & Julie Futch | Artist (Painting): Ember Canada | Centerpieces + Decor: Stems | Cinemetography: Bryan Starr Cinematography | Furniture Rentals: Goff Tents | Groom's Shoes: Bed Stu | Paper Goods: Melody Joy | Wedding Party Table: Louisville Farm Tables

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Romantic Winter Inspiration in Kentucky

Today is officially feeling like Fall making this cold-weathered inspiration all the more relevant. It’s a time to pull out your cozy sweaters, dust off those hot toddy recipes and settle in for the snow. And if winter is as pretty as this inspiration crafted by Lauren Chitwood, with flowers by Sarah Harris, invitations by Five Dot Design and photography by Amy Campbell, then we’re ready to embrace it

From Lauren ChitwoodThrough this long arduous winter we have all been experiencing , Lauren Chitwood, LBB Member, and her team decided to find the beauty in the cold with this sweet inspired photo shoot. Photographed by Amy Campbell, with a sparkling coat of ice over the Bluegrass the design team had a vision of warm luxury with a vintage mink, seasonal greenery, and vibrant shades of pomegranate and peach.

The bride wore a tailored lace gown with a detachable tulle skirt designed by Tara Keely. Earrings, headband, necklace and bracelets were sourced at Anthropologie and jeweled belt is from designer Kelly Faetaini graciously provided by Twirl Boutique. Ana Crane expertly crafted a convertible up-do that was easily taken down for a romantic but sexy half up- half down look. Highlighting our beautiful brides piercing eyes with lashes and smoky lid is a great dramatic look that transitioned from day to evening while photographing beautifully against the snow.

The sweet hear table was delicately crafted atop an antique leather top table with gold brushed tableware sliced pomegranates and full floral garland. The design team brought together the warm tones of pink Asiatic lilies, pink protea and peach Juliet garden roses and paired them with varieties eucalyptus, pine and spruce. The pussy willow stems added to the floral design were just enough to flirt with the suspicion that spring was seemingly just around the corner. Among the blooms and textured greenery, the team placed a cobalt blue Jim Beam bottle circa 1960 and a brass antique vanity stand to hold the bouquet thus creating a combination of perfect elements to carry through the essence vintage sophistication.

Five Dot Design, LBB member, created a striking invitation suite inspired by the warm gold tones and the deep plum hues. An elaborate crest monogram in gold complimented the regal table scape and a formal feeling that just feels so right in the snow.

This shoot make us just want to appreciate the crisp elegance of winter just a little bit longer.

Photography: Amy Campbell Photography | Event Designer: Lauren Chitwood Events | Floral Designer: Lauren Chitwood Events | Hair & Makeup: Applied Cosmetic Services | Venue: Wimbeldon Farm | Bridal Boutique: Twirl Boutique | Stationary Design: Five Dot Design