As a Chicago wedding photographer, I wear many hats, and thankfully, I love doing that! Engagement photography in this city isn't just about showing up and taking some photos—it's about knowing the best skyline views, hidden gems, and the way the city lights reflect off the river at golden hour. It’s about guiding couples through the process, helping them feel at ease in front of the camera, and even offering outfit recommendations that work well against the backdrop of iconic Chicago locations like Millennium Park, North Avenue Beach, or a cozy neighborhood café. Your engagement session is a celebration of your love and your story, set against the vibrant energy of Chicago, captured in timeless images you’ll cherish forever.
One of the biggest factors in achieving beautiful engagement photos is selecting the right outfits. From timeless classics to bold and creative choices, what you wear can elevate your engagement session and make it uniquely yours. So, let’s dive into some tried-and-true outfit ideas, styling tips, and common mistakes to avoid to ensure your photos turn out absolutely stunning.
Ten Outfits That Look Great for Engagement Photos
Finding the perfect engagement photo outfit can feel overwhelming, but here are ten outfit ideas that consistently look fantastic in engagement photos:
- A Classic White Dress – Timeless and Elegant
- A classic white dress is a foolproof option for engagement photos. It exudes timeless elegance and symbolizes new beginnings. Whether you opt for a chic midi dress, a flowy maxi, or a structured mini, white dresses photograph beautifully in both natural and urban settings. They also allow for easy accessorizing with statement jewelry or a soft bouquet.
- Casual Chic – Relaxed Yet Polished
- For a relaxed yet stylish look, opt for a smart-casual outfit. Think fitted dark jeans, a tailored blouse, or a cozy knit sweater paired with sleek boots. This look is perfect for couples who want a laid-back yet polished aesthetic. Consider adding a stylish hat or a structured jacket for added dimension.
- Flowy Long Dress – Movement and Romance
- Long, flowy dresses add a sense of movement and create breathtaking images, especially in outdoor settings. The way the fabric catches the wind can bring a dreamy, cinematic effect to your photos, making them look like something out of a fairy tale.
- Cozy and Intimate Loungewear – Authentic and Comfortable
- If you love the idea of an at-home engagement session, consider soft loungewear like cozy sweaters, knitwear, or even stylish sweatpants. This aesthetic works beautifully for intimate and natural-feeling photos, capturing genuine, candid moments of you and your partner in your element.
- Sporty & Personalized Jerseys – Show Your Team Spirit
- Are you both sports lovers? Why not incorporate jerseys from your favorite teams? This is a fun and unique way to add personality to your engagement session while celebrating a shared passion.
- Denim for a Cool and Laid-Back Look
- Denim-on-denim or a mix of denim with neutral tops can create an effortlessly cool and casual vibe. It’s an easy way to look put together without feeling too dressed up. Dark wash denim tends to look more refined, while lighter washes can create a fun, summery feel.
- Neutral Tones – A Soft, Harmonious Look
- Neutral colors—beige, ivory, soft grays, or pastels—blend well with most backgrounds and help keep the focus on you rather than the clothes. They create a soft and timeless look, making your images feel organic and natural.
- Statement Accessories and Sunglasses – Personality and Edge
- A bold accessory, such as a wide-brimmed hat, a stylish handbag, or unique boots, can add personality to your engagement photos. Sunglasses can also bring a cool, editorial feel to a few shots, making your engagement session look like a high-fashion moment.
- Vibrant Colors – Bold and Expressive
- If bold colors reflect your personality, embrace them! Deep jewel tones like emerald, sapphire, or burgundy look stunning on camera, especially against neutral or natural backdrops. Bright colors can create a striking contrast, making you stand out in any setting.
- Layered Looks – Versatile and Stylish
- Layering different textures (a knit sweater over a dress, a structured blazer with jeans) adds depth and visual interest to photos. Plus, layers give you the flexibility to switch up your look without a full outfit change, making your session more dynamic.



How to Choose What to Wear for Engagement Photos
- Consider the Location
- Your engagement session location heavily influences what you should wear. A ballgown may look out of place in a forest setting, while a casual outfit might not match the grandeur of a luxury venue. Think about the scenery, the season, and the colors that will complement your surroundings.
- Match Your Photoshoot Theme
- If your engagement shoot has a specific theme—vintage, bohemian, beachy, urban-chic—your outfits should enhance that aesthetic. Look for clothing that complements, rather than competes with, the overall vision.
- Bring Extra Outfits
- Variety is always a good idea! Bringing an extra outfit gives you more looks to choose from and ensures you’re prepared if something isn’t working on camera. Plus, it allows you to showcase different facets of your style.
- Don’t Forget the Accessories
- Accessories can elevate even the simplest outfit. A statement necklace, unique shoes, or a fun hat can add character to your engagement photos while making them feel more like you.
- Check the Weather Forecast
- Always check the weather before your shoot and dress accordingly. If it’s cold, layering is key. If it’s warm, opt for breathable fabrics to stay comfortable. Bring a backup outfit in case of sudden weather changes.
- Prioritize Comfort and Confidence
- You should feel comfortable and confident in your outfit. If you’re tugging at your clothes or constantly adjusting something, it will show in the photos. Wear something you love and feel great in!
- Coordinate with Your Wedding Theme
- If you’ve already chosen wedding colors or a specific aesthetic, consider subtly incorporating elements of that into your engagement outfits for a cohesive look across your wedding journey.



What to Be Careful Of for Engagement Photos
- 1. Avoid Uncomfortable Outfits
- If you don’t feel good in it, don’t wear it. Uncomfortable clothing will translate into awkward body language in photos.
- Beware of Overly Themed Outfits
- Themes can be fun, but if they’re too over-the-top, they can take away from the focus of the shoot—you and your love story.
- Watch Out for Clashing Patterns
- Patterns can work, but make sure they don’t clash between you and your partner. A loud pattern can overwhelm the image or clash with the scenery, making the photos feel too busy.
- Consider Your Skin Tone
- Choose colors that complement your skin tone. If you’re unsure, neutral colors or classic shades like navy, burgundy, and olive green tend to be universally flattering.
- 5. Choose Re-Wearable Outfits
- Invest in clothing that you can wear again beyond the photoshoot—whether it’s a dress you can wear to a future event or stylish separates that can be part of your everyday wardrobe.
Need Engagement Photos? Let’s Chat!
If you’re looking for a Chicago engagement photographer, I’d love to help you create timeless and romantic photos that capture your love story. Whether you're dreaming of a city skyline session, a cozy at-home shoot, or a dreamy outdoor engagement, I’ll guide you through the process to make your experience fun, relaxed, and memorable. Contact me today to book your session!