From Downtown Dates to Tree Farm Snuggles: How to Choose the Perfect Location and Outfits for Your Engagement Session: From Naperville Wedding Photographer
- rkruegerphoto
- Jan 1
- 4 min read
Updated: Jan 20
From Downtown Dates to Tree Farm Snuggles: How to Choose the Perfect Location and Outfits for Your Engagement Session: From Naperville Wedding Photographer Selecting a location and outfits for your engagement session becomes a lot easier when you think first about the story you want your photos to tell. Your budget of $400–$800 can absolutely cover a meaningful, well-planned engagement session that feels like the two of you, whether that’s downtown Naperville at sunset or wandering through a quiet tree farm in the fall.
Start With Your Session “Vibe”
Before you worry about outfits or exact spots, pick the overall vibe you want: urban, nature, cozy, or something seasonal and unique. Urban sessions in places like downtown Naperville or downtown Chicago are great if you love city energy, coffee dates, and date nights out; parks, barns, and orchards are perfect if you’re more laid-back and outdoorsy.
Ask yourselves: Would we rather look back on photos of us dressed up on a city street, or snuggled into sweaters under some trees with boots crunching on leaves? Your answer will start to point you toward the right location and style.
Urban: Downtown Naperville to Downtown Chicago
For couples who love a modern, city feel, an urban engagement session can be really fun and romantic. Downtown Naperville’s Riverwalk mixes charming brick paths, bridges, and water views with chic storefronts and cafes, so you can get both “city” and “nature” in one spot.
If you want to go full-city, heading into downtown Chicago gives you options like skyline views, bridges, riverwalks, and classic architecture all within walking distance, which is perfect for a 60–90 minute session in the $400–$800 range. Plan one or two main routes instead of lots of tiny stops so you can relax, enjoy each other, and still end up with a big variety of images.
Outfit ideas for urban sessions:
Dressier looks photograph beautifully: a fitted dress or jumpsuit for her, a blazer or sport coat with dark jeans or chinos for him.
Think in layers—jackets, scarves, or a long coat add movement and give you quick “mini outfit changes” without losing shooting time.
Rustic: Barns, Fields, and Hidden Gems
If you picture golden fields, tall grasses, and a wind-swept dress instead of skyscrapers, a rustic or barn location might fit better. Local preserves and farmstead-style locations around the Naperville area offer open fields, barns, and river views that feel private and relaxed without a long drive.
These spots are perfect if you want that warm, glowing, sun-on-your-shoulders feeling at sunset, especially in late summer and early fall when the light and colors are soft. You’ll get space to move, laugh, and explore together, and your engagement photos will feel cozy and timeless rather than overly posed.
Outfit ideas for rustic sessions:
For her: a flowy midi or maxi dress, boots or block heels, and soft neutrals or earthy tones (cream, rust, olive, burgundy).
For him: a well-fitted button-down or Henley with jeans and boots; avoid big logos so the focus stays on you.
Unique & Seasonal: Tree Farms and Apple Orchards
Tree farms and apple orchards are amazing if you want something that feels a little bit different but still very “Midwest romantic.” In fall, apple orchards bring warm colors and hands-on moments—picking apples, walking through rows of trees, cozy blankets, and maybe a mug of cider.
In winter or early holiday season, Christmas tree farms offer perfect rows of evergreens, twinkle light vibes, and a natural backdrop that looks beautiful with more bundled-up outfits. These locations are especially great in a $400–$800 engagement range because you can get a ton of variety in one spot without driving between locations.
Outfit ideas for unique/seasonal sessions:
Lean into texture: sweaters, scarves, knits, flannels, and coats in rich jewel tones photograph beautifully among trees.
Coordinate colors with the environment—think deep greens, burgundy, cream, and tan for tree farms, or warm earth tones for orchards.
How to Choose Outfits That Photograph Well
Once you know your location, it’s much easier to finalize what to wear. A few simple guidelines go a long way, especially when you’re investing in professional photography and want your images to feel elevated.
Coordinate, don’t match: Choose 2–3 complementary colors instead of everyone in the same shade.
Avoid tiny patterns and neon tones: they can distract the eye and reflect onto skin; soft, solid colors or larger prints are more forgiving.
Bring one “elevated” look and one more casual option if your session length and budget allow—often a quick jacket change or swapping shoes is enough.
Think about movement: dresses and layers that catch the wind add interest to your photos without any extra posing.
Making the Most of Your $400–$800 Engagement Session
A well-planned engagement session does more than give you pretty photos—it lets you get comfortable in front of the camera before the wedding day. Use this time to test hair and makeup, see how different outfits photograph, and get used to how your photographer poses and directs you.
Within a $400–$800 budget, you can usually choose a location that feels special to you (downtown Naperville, a favorite Chicago neighborhood, a barn or orchard), have enough time for one outfit change, and walk away with a gallery full of images for your save-the-dates, wedding website, and prints at home. When in doubt, pick the location that feels like “a perfect date night” for the two of you—and let the session tell that story.
Rob Krueger Photography
