Proposal Outfits

When it comes to proposing to the person you want to spend the rest of your life with, you can either wing it or you can prepare for it! If you’re here, chances are you’re ready to plan. 💍 Wondering what to wear for your proposal moment? We’ve got you covered with proposal outfit ideas for every couple, occasion and location you can imagine!

We easily connect people with trusted photographers for fun photo shoots and have captured over four million memories worldwide. The magic of Flytographer is both the experience and the photos. Explore the city with a fun, talented photographer and get wall-worthy photos to relive your trip, forever. Capturing this magical occasion with photos allows you to look back on the exact moment when you or your partner said “YES!” for years to come. 📸

TLDR

1. How to keep the surprise: You might be wondering how to dress up and keep the surprise!
2. Colours are key: Colour is the anchor of your outfits; play with some shades of warm and cool solid colours.
3. Formal attire ideas: Plan an occasion that warrants the glam without arousing suspicion.
4. Semi-formal attire ideas: You can still dress up for the proposal but with a more casual look.
5. Coordinating outfits: While some matching is good, too much matching turns into cheesy overkill.
6. Beach-appropriate outfits: Your proposal outfits should be as easy and breezy as your vacation!
7. Casual look: We encourage you to wear what you feel most comfortable and confident in.
8. Weather-appropriate outfits: It’s all about layering – especially in cooler climates or for fall and winter proposals.
9. Florals and patterns: Some patterns will lend themselves better to photos.
10. Proposal posing tips: We have a few tips to capture every precious emotion from your surprise proposal.

Photo: Marie in Maui for Flytographer. Emily and partner capture memories in Maui with a proposal photoshoot at Kapalua Ironwoods.

1. How to keep the surprise

Whether you are planning to propose in Paris, get engaged in London or pop the question on Maui, you might be wondering how to get your girlfriend to dress up for a proposal while keeping the surprise (or boyfriend!). 🤔 We have a few tactics up our sleeve to share with you! 

When it comes to planning how to propose, scheduling a fancy brunch, lunch or dinner at a favourite restaurant is by far the most common ploy. 🍽 This tactic is a sure-fire way to get you both dressed up and out the door avoiding any suspicion of the reason for getting dressed up. Oftentimes, we hear the question of “when” asked: “Should I propose before or after dinner?” We always recommend before! Before means 1) you can actually eat because those nerves are calmer post-proposal, 2) you avoid being bloated should you actually be able to eat, and 3) you have something planned to celebrate the occasion and can discuss all the antics that took place to make this exciting moment happen. Chances are you’ll both be full of emotion, so that time to just sit together, debrief, and share your love and enthusiasm is truly, truly special. 🥂

Make sure to check out our post on the 10 biggest mistakes to avoid when proposing for more helpful execution tips!

Photo: Shannon in Saint Martin for Flytographer. Joe and partner capture memories in Saint Martin with a proposal photoshoot at Indigo Bay Beach.

2. Colours are key

A proposal is an iconic moment where your and your partner’s love and emotions for each other are front and centre, so don’t let your proposal outfit become a distraction. When in doubt, our rule of thumb is to not overdo it. Colour is the anchor of your outfits, so aim to stick to two or three. 

Play with some shades of warm and cool colours and see what you prefer. Warm colours are reds, oranges and yellows, and they give a feeling of energy and brightness. Cool colours are blues, greens and purples, and they give a feeling of peace and serenity. 🔮

Once you’ve chosen your base colour, build the rest of your proposal outfit ideas with neutral colours such as grey, black, white, navy or taupe to tone it down and keep the focus on you!

Photo: Amanda in Chicago for Flytographer. Price and partner capture memories in Chicago with a proposal photoshoot.

3. Formal attire ideas

The streets of Paris … a rooftop restaurant in Barcelona … a private terrace for two. If your proposal is a formal occasion, we suggest leaving the flip-flops and t-shirts at home. What – a floor-length dress and fancy bowties don’t make regular appearances in your everyday wardrobe? Plan an occasion that warrants the glam without arousing suspicion, such as a fancy dinner reservation or brunch before the surprise proposal. Your partner will be dressed to the nines without thinking about what to wear when you think you’re getting engaged! ✨  

For women, long gowns, high heels and styled hair are classic proposal outfit ideas. For men, a well-fitted suit or blazer and tie paired with dress shoes will leave them feeling equally confident. (Pro tip: Treat your partner to a manicure the day before so their nails are picture-perfect and ready for their close-up.) There is nothing better than setting up the day with perfect proposal outfits for him and her.

Photo: Mattia in Lake Como for Flytographer. Manjot and partner celebrate a proposal in Lake Como with a surprise proposal photoshoot in Bellagio.

4. Semi-formal attire ideas

If you still want to dress up for the proposal without the gusto of a gown, semi-formal attire feels a touch more relaxed for the dress code. A proposal outfit for her might be a flowy skirt or a midi cocktail-style dress. For a men’s proposal outfit, opt for a button-up shirt, pants and a jacket. This proposal outfit idea approach will also allow for the engagement ring to pop in those engagement photos.

Photo: Claudia in Sintra for Flytographer. Mark and partner celebrate a proposal in Sintra with a surprise proposal photoshoot at Monserrate Palace and Gardens.

5. Coordinating outfits

Repeat after us – coordinating outfits does not mean matching outfits! 🙅 While some matching is good, too much matching turns into cheesy overkill for the special occasion. When thinking about what to wear when you get engaged, your coordinating outfits should be partners, not twins, and a little planning goes a long way.

To craft the perfect proposal outfit for men, consider the setting and atmosphere you want to create. And even for ladies searching for dreamy dresses to get engaged in, keep your location and weather in mind. For example, Italy’s array of pastel-coloured houses pairs well with a neutral palette or even a white dress, while a natural background offers the chance for a pop of colour. The season can also influence your proposal outfit ideas. A fall wardrobe is full of earthy tones like rust, mustard and olive. A summer wardrobe is perfect for whites, blues, yellows or bright pink. A winter wardrobe is best for neutral pieces, as you’ll be layering up to keep warm! ❤️

Photo: Alyse in Napa-Sonoma for Flytographer. Neil and partner capture memories in Napa-Sonoma with a proposal photoshoot.

6. Beach-appropriate outfits

Whisking your love story away to a romantic beach destination? 🌴 Your proposal outfit ideas should be as easy and breezy as your vacation. If you like a pop of colour, we recommend bright pinks, teals, purples and shades of blue. If you prefer more neutral pastels, opt for light blues, greens, corals and other light colours. If you are wearing light or bright colours, your partner should wear light or bright colours too.  

There’s no better feeling than your toes in the sand, so leave your shoes behind and keep those feet bare! For beach proposal outfits for men, rolled-up pants are a dressier choice, while nice shorts are more casual. We’re fans of a comfortable t-shirt, but choose one that is logo-free and in a solid colour. For ladies, a beach proposal dress is as airy as your location (maxi dresses are perfect for the flowy effect). Choose a breathable fabric like cotton or linen that can get a little wet when you dip your toes in the ocean. Talk about a romantic proposal dress that flows in the ocean breeze! 🌊

Photo: Allie in Los Angeles for Flytographer. Manraj and partner capture memories in Las Angeles with a proposal photoshoot at Manhattan Beach Pier.

7. Casual looks

Our most important rule is … to forget the rules! 😎 We encourage you to wear what you feel most comfortable and confident in, and you likely have the perfect proposal outfit ideas in your wardrobe already. 

If you’re keeping your photo shoot outfits casual but still feel overwhelmed by the choices, we have some proposal outfit ideas for him and her that are a bit more on the casual side.

• Start with a palette of no more than two to three colours max. For example, a neutral combination of cream, grey and tan always does well together. Then, add pink for a light and airy look, or go for a bold look by adding orange or navy. 
• Another option is to start with a statement piece in a pattern or variety of colours and work off those colours for the rest of your outfit. For example, bold floral proposal dresses would coordinate well with an olive-green shirt and neutral pants. 
• Find inspiration from your location: the Mediterranean blues of Santorini, the bold colours of Tokyo, the warm pinks of Venice or the soft green palm trees of Maui. Every destination tells a colour story that can continue in your engagement outfit.

If this starts to feel complicated or overwhelming, remember our two favourite words: simple and clean. 👏 When you’re looking back on your photos years from now, a timeless outfit with simple pieces won’t feel dated. 

Photo: Natalia in Barcelona for Flytographer. Silvia and partner capture memories in Barcelona with a proposal photoshoot at El Born and Parc de la Ciutadella.

8. Weather-appropriate outfits

Especially in colder climates, your favourite dresses or short-sleeved shirts might not be the best choice for proposal outfit ideas… unless goosebumps and red noses are your aesthetic. 🥶

Fall Proposal Outfit 

Autumn might be one of our favourite seasons for fashion. Bust out the knee-high boots, scarves and your favourite trench. For her, we recommend a flattering wrap dress in a dark colour, paired with neutral knee-high boots and a coordinating wool coat – an ensemble that photographs beautifully against fall foliage. 🍂

For him, ditch the fleece and consider a well-fitted dark-coloured blazer layered over a neutral cable-knit sweater, paired with dark jeans and leather boots. This polished yet relaxed look works perfectly for an “impromptu” photoshoot that won’t raise suspicions about the upcoming proposal. This proposal outfit for him strikes that sweet spot between casual and dressy, ensuring you’ll look timeless in those surprise engagement photos.

Winter Proposal Outfit 

Winter proposals create a magical atmosphere, especially with fresh snow as your backdrop. Layer up in style with cozy yet camera-ready pieces that’ll keep you warm during those special moments. For her, we suggest a classic cream sweater dress paired with thick knit tights and knee-high leather boots, topped with a sophisticated long wool coat in camel or soft grey. ❄️

For him, ditch the puffer jacket and opt for a charcoal wool peacoat over a burgundy merino sweater, paired with well-fitted dark trousers and leather Chelsea boots. See! Mens’ proposal outfits can be as simple as 1, 2, 3! Don’t forget a coordinating scarf – it’ll not only keep you warm but also add sophisticated detail to your engagement photos.

Photo: Flytographer in Banff. Joseph and partner capture memories in Banff with a proposal photoshoot at Lake Minnewanka.

9. Florals and patterns

Choosing the perfect floral pattern can feel impossible with so many options available. While we’ve never seen a flower we didn’t like, some patterns will lend themselves better to photos. Let’s talk about the patterns of our favourite dresses to get proposed in. 🌺

Consider going with a more neutral pattern with your florals, so you still have the benefit of adding texture and interest in a subtle way. For example, a small print will be less distracting than a large print, as will a print with similar colours rather than one with a large and bright variety of colours. Build the rest of your proposal outfits around the floral print by pulling your accent colours from the pattern itself for your partner’s wardrobe. Mix solids and patterns to add visual interest, or keep patterns to a minimum and add interest through varying textures and fabrics for proposal outfit ideas. 

If your partner has chosen a strong pattern to wear, we would recommend choosing a solid colour that coordinates with the pattern. Or if they chose a solid colour, then there is your opportunity to add a pattern into your outfit. 🎨

Photo: Spyros in Santorini for Flytographer. Peter and partner celebrate a proposal in Santorini with a surprise proposal photoshoot at Imerovigli Village.

10. Proposal Posing Tips 

The proposal shot is iconic and one you’ll treasure for a lifetime. To capture the shot, we have a few tips for you to keep in mind to help your Flytographer capture every precious emotion that you and your (very, very excited) partner will experience. 

1. Hire a professional Flytographer. We’ve captured thousands of proposals across the world, so we’ve truly perfected the proposal process. Our local photographers have recommendations for the best times and locations in your destination to make the proposal everything you’ve dreamed of. Check out our tips on how to plan the perfect destination proposal for location inspo!
2. Practice kneeling. Whether you’re getting down on one knee in pants, shorts or a dress, this probably isn’t a pose you get into every day. Make sure your clothing is kneeling-friendly (that the back of your pants doesn’t gape or pull down, for example), the ring is easily accessible and you feel comfortable. 
3. Act natural. As you ask your partner to marry you, nothing is more important than just being in the moment! Tears, laughter, a Breakfast Club-style celebratory fist in the air – feel free to let your joy take over.
4. Stay on your knee longer than you think you need to. While you’ve probably been thinking about this moment for what feels like forever, the moment itself is fleeting. We invite you to savour every second by staying down on one knee as you ask the big question, get the “Yes!” and slide the ring onto your now-fiancée’s finger. 💍 This also gives your photographer the opportunity to capture as many shots as possible of you and your loved one. 

Photo: Flytographer in Honolulu. Paul and partner celebrate a proposal in Honolulu with a surprise proposal photoshoot at Makapuu Lookout.

Capturing your Surprise Proposal

The proposal outfit ideas are flowing, the proposal plan is ready to go and all that’s left to do is pop the big question! Are you now inspired and full of romantic engagement ideas to surprise your partner? Don’t forget to book your proposal Flytographer to capture the magic of it all! ✨