Most brides go into wedding dress shopping focused on what they want their dress to look like. You’ve probably saved necklines, silhouettes and sleeve details to Pinterest boards for months… but once you actually start to try dresses on, it will suddenly start to dawn on you that there are a lot of practical considerations too. A 20-foot train may look incredible on a mood board, but in reality, it will frustrate you before the ceremony is even over. A long sleeve gown may be the vison in your head, but if you’re getting married in the height of summer, think again. That basque waist may be stunning, but can you sit down and eat while wearing it?

Once you’ve starting trying dresses on and found one you like, ask yourself:

1. Can I move properly in this dress?

Sit down. Lift your arms up. Walk quickly. Dance a little. Try and walk up some stairs if you can. A dress can look incredible standing perfectly still on one of those weird plinth things boutique have, but it could be become a nightmare the second real life starts happening around it.

If you’re planning a wedding where you’ll be moving all day, comfort matters. Nobody wants to spend their reception guarding a thigh split or adjusting a slipping corset every seven minutes.

2. Can I wear this dress for 8+ hours?

Heavy beading, layered tulle and structured corsetry can feel very different after a long day of wear.

A lot of brides don’t realise how physically tiring some dresses are until fittings begin. If you’re getting married abroad, outdoors, during summer or at a festival-style wedding, fabric choice matters even more. Some dresses are designed more for photos than actually wearing for a long day.

Looking through different silhouettes and fabric options before your appointment can help narrow things down. Browsing collections like Terry Costa’s dresses for wedding can also give you a better sense of what styles actually match the kind of day you’re planning.

3. Is this dress designed with my body shape in mind?

Boutique samples are clipped, pinned and adjusted constantly during appointments. Sometimes heavily.

So, ask what size the sample is and how the actual ordered dress will fit compared to what you’re seeing in the mirror. Some fabrics drape very differently once properly fitted. A good bridal stylist will explain this honestly rather than relying entirely on imagination and optimism.

A lot of bridal brands will tell you a dress is available in a wide size range. That doesn’t automatically mean the design has been properly considered across those sizes. Some gowns scale beautifully. Others clearly started life with one body type in mind.

Delicate spaghetti straps might look great on a size 8 sample but feel completely different on a fuller bust. A corset with minimal structure may not offer enough support once scaled up. Certain necklines, fabrics and boning techniques behave very differently depending on sizing and proportions.

That doesn’t mean larger brides should avoid particular styles. It means it’s worth asking how the dress has been constructed and whether adjustments have been thoughtfully engineered rather than simply enlarged mathematically.

A good boutique should be able to talk honestly about support, fit and alterations without trying to squeeze every body into the exact same blueprint.

4. What are alterations going to cost?

Alterations are one of the biggest surprise wedding dress expenses. Depending on the construction of the gown, customisations and tailoring can easily add hundreds onto the final price.

Ask early:

What alterations will be needed?
Are alterations done in-house? (either is fine, but it’s good to know)
How many fittings should I expect?
What happens if my size changes?

A boutique being transparent about this from the beginning is usually a very good sign.

5. What underwear will I wear with this?

A deeply important question.

Some dresses require very specific bras, shapewear or tape setups. Others make underwear almost impossible altogether. It’s better to know upfront rather than panic-ordering five different backless bras at 1am three weeks before the wedding.

If comfort or a particular type of bra is important to you, say that clearly during appointments. A good stylist should work with your priorities. A lot of gowns have built-in cups, but if you have a large bust it’s important to ask if that’s going to be enough support for you.

6. Will I still like this in 6 – 9 months’ time?

Trend cycles are moving faster than ever. A dress that feels fresh right now might feel dated surprisingly quickly.

That doesn’t mean you should avoid trends entirely. It just means it’s worth asking yourself whether you genuinely love the dress or whether you’ve absorbed the same TikTok bridal aesthetic as everyone else.

Usually, the dresses people remember most fondly are the ones that felt recognisably like them.

7. Can this dress be customised?

A lot of brides don’t realise how much flexibility exists within bridal fashion. Straps can be added, sleeves removed, linings changed, slits lowered or raised. You can also change the look of a dress so much with gloves, capes, veils and detachable pieces.

If you love most of a dress but keep fixating on one detail, ask whether it can be changed before writing it off completely.

8. What kind of wedding is this dress actually for?

Some dresses belong in candlelit manor houses, some belong in a field with muddy boots and a live band, some are designed to let loose in Vegas at midnight. That’s not to say you have to follow these ‘rules’ but do think about the actual atmosphere of your wedding when choosing your gown. The best wedding outfits feel connected to the person wearing them and the environment around them.

9. Most importantly, ask yourself whether you feel good in it.

Not whether it looks “bridal enough”, not whether your mum likes it, not whether it photographs well from one specific angle, not if it will get likes on social media… You’re the one wearing it all day, you need to feel good in it. That’s the question that matters most.

Stephanie and Mason wanted their wedding to feel timeless and modern, but softened with unexpected details. Flowers became the biggest investment and the thing they focused on the most. As an avid gardener and tattoo artist, Stephanie spends plenty of time drawing florals, knew exactly where she wanted the budget to go. They worked with Ashton of The Spotted Poppy Floral who properly delivered on the visoin.

Instead of traditional arrangements, the couple wanted the flowers to be looser and more abstract. There were overgrown green florals throughout the day, from the ceremony arch to the Ikebana-inspired table arrangements, and they included fruit on the tables too. The bride’s bouquet was the only place colour appeared. Mason’s boutonniere echoed it with an orchid and rattlesnake grass, a nod to the location.

Finding the venue was one of their favourite parts of planning. “Driving around Texas Hill is so beautiful and we are spoiled for choice for venues in central Texas”, Stephanie explained. “But when we turned into Mae’s Ridge for the tour, one of our favourite Tyler Childer’s songs came on the radio. The ceremony site then sold it to us.”

There were no bridesmaids or groomsmen, instead friends and family were invited to play different roles. Their friend Brooke led the ceremony, which made it extra special. “She was also my make up artist and all around MVP of the day”, Stephanie explained. “It was SO windy that my veil got taken in the wind and my sister rescued it. Our guests said it looked very cinematic blowing in the wind. Our vows were filled with intimate stories, some inside jokes, and commitments to each other. Standing up at the altar with Mason time really stood still. The whole day can feel like a whirlwind, I felt the most present in that moment.”

Ultimately, they just wanted to make choices that felt natural for them, regardless of trends, which is why their day felt so authentic. “Looking back, the only thing I would change is that I would have preferred to do all photos before the ceremony and have spent the cocktail hour with our guests”. Stephanie admits. “But all in all we are so happy with the choices we made. The wedding industry is such a huge industry with so many amazing vendors to support. We skipped some of the trends like a stylist/ decorator, social media curator and videographer and here we are still being featured. Sometimes less is more, so our advice is just to do what feels right to you.”

Nostalgia feels good, so it’s no surprise it keeps finding its way back into weddings. What we loved in our younger days always resurfaces. Lately, there’s also been a clear move away from everything living online. An analogue response to a hyper-digital world where every moment is documented, filtered and uploaded before it’s even finished happening.

Couples are choosing tactile, sensory details for their weddings that feel slower and more personal. Things you can touch, hold, keep, or listen back to later. Not everything needs an app or a QR code. Some things are just better when they exist in the real world.

Here are a few analogue throwbacks we’ve noticed creeping back into weddings again:

Cigarette trays on tables or at the bar, left out for guests to help themselves. There’s nothing cool about sucking on a strawberry shortcake flavoured air. Health implications aside, the aesthetic callback of real cigs is very much part of the appeal.

Disposable film cameras dotted around tables for guests to use. Grainy, imperfect, unpredictable photos that won’t be seen for weeks. Yes there’s apps that can sort of recreate the aesthetic, but there’s nothing like the real thing.

Photographers offering film alongside digital, or instant shots worked into their galleries. Not as a gimmick, but as a way of capturing moments that feel different in tone and texture to the rest of the day.

Rotary phones used as guestbooks. Guests pick up the receiver and leave recorded messages instead of signing a book that rarely gets opened again.

Retro cocktails making a return. Manhattans, Old Fashioneds and Negronis served instead of prosecco. Maraschino cherries, paper umbrellas and all. What’s next, cider in plastic bottles or Budvar behind the bar? Absolutely here for it.

Cassette tapes and vinyl everywhere. Custom mixtapes as favours. Vinyl records repurposed as table markers or place names. DJs spinning actual records rather than playlists.

Retro entertainment that leans properly old-school. Arcade machines. Proper film photo booths that print real strips you can take home. Forget the slick digital versions with no soul. The real, bulky mid-century booths are where it’s at.

Printed newspapers and zines instead of wedding websites. Ceremony programmes laid out like mini publications, complete with interviews, timelines, in-jokes and quizzes. Yes, a website can give guests all the information they need but this is just so much cooler.

Monique and Jay’s London, Ontario wedding day began with a ceremony at Holy Diver where they actually got tattooed! They then moved to The Early Bird, a family owned restaurant and bar, where they had a second ceremony (with both their grandmothers as flower girls) and reception with their 35 guests. It was the very first wedding the venue had hosted, but the couple couldn’t have been happier with how it all turned out.

“The venue team played such a huge role in making our wedding day what it was”, Monique said. “From the cute signage out front, to the incredible food, to the genuinely helpful staff and management – it all came together so seamlessly. From our very first walkthrough, we could tell they were excited and fully on board with what we were planning, and they absolutely delivered. Not once were we told that an idea wasn’t possible, and they even offered to keep some disco balls up from their New Year’s Eve setup because they knew it fit our vibe perfectly. After our experience, we’d definitely recommend that other couples look into their favourite local bars and restaurants as potential venues. You might be surprised at just how perfect it can be!”

And the theme? “Tats, cats, fast cars and love!” she said. “I’ve always loved tattoos and tattoo culture, and it’s something that’s meaningful in our relationship too; Jay and I actually got matching tattoos just a few months into dating. We also share our sweet feline daughter, Chicken, who is truly the love of our lives. And of course, there’s the racing – Jay (and his family) are deeply involved in the Ontario racing scene, which keeps us busy every year. Our goal was for people to be having a great time while also thinking, ‘this is so them’.”

The couple hired a wedding planner, With Love Events, who handled a lot of the logistics, flowers and additional décor for them. Guests enjoyed a taco bar, cocktails, temporary tattoos and race and cat-themed details. Chicken the cat appeared everywhere from signage to décor and an old race car door became the guestbook. They had word searches as place setting with references to their relationship hidden throughout.

“Our planner, Christina, absolutely went above and beyond spending hours on a ton of DIYs. When I say the day wouldn’t have been possible without her, I truly mean it! Every little detail tied perfectly into our colour palette and aesthetic, and seeing them come to life was such a joy to see throughout the day.”

As evening hit, the wedding relocated again. More than 60 people packed into Jay’s garage for the afterparty. NASCAR played on TVs overhead and they served pizza straight from the boxes which were stacked up next to coolers full of drinks. Karaoke took over at some point during the night and they partied way into the early hours.

Even with the unconventional structure, Monique said the hardest part of planning had nothing to do with logistics. “One thing I hadn’t really considered when planning a non-traditional wedding was that there wouldn’t be a clear reference point,” she said. “For my friends, my family, or even myself. Trusting that everything would come together and flow the way I imagined, without me or anyone I knew having experienced anything like it before, was definitely a challenge. I didn’t feel the need to explain or justify our choices, since I felt confident in the decisions we’d made, but there was still a quiet undertone of ‘just trust me’ when sharing our plans with others – even as I worked through my own small moments of uncertainty leading up to the day.”

Still, the couple never felt pressure to pull the day into something else. They planned the wedding in six months and found that working outside traditional wedding structures actually made the process a lot easier. “There were no scheduling conflicts, no sense of competing with other couples,” Monique concluded. “Just set the date and do the damn thing. As someone who is anti copy-and-paste wedding approach, I really think your energy should best spent creating a day that feels like you. Nothing is more timeless than staying true to yourselves and filling the space with the people, colours, and details you genuinely love.”

When Madeline booked a trip to Cabo for spring break 2014, she had no plans beyond a week away with friends. But she met Eliot, who had grown up in Los Cabos, who spent the week showing the group around. By the time Madeline flew home, they were already figuring out how to make long distance work.

“Seven days of snorkelling, beach camping, hiking, and late-night hammock talks later, what started as a vacation turned into something undeniable”, she said, “Long-distance quickly became daily Skype calls, road trips, and eventually a leap of faith that brought me to Los Cabos for good.”

They were married at Flora Farms in Baja California Sur, in November. Their overall vision leaned into the atmosphere and aesthetic they already live in. They used vintage references, wore relaxed tailoring, and included handmade details with and a mix of desert textures and garden-style florals.

Eliot plays drums in The Shamans, a band known throughout Cabo and Mexico’s music scene, so music and entertainment was a big consideration too. They had multiple bands and DJs – all of them friends – performing throughout the day and night.

Madeline’s dress was also designed by her friend Alexia Guzmán of Hoseu while her earrings came another. The custom stationery and signage were created collaboratively with friends, alongside hand-painted lanterns that later lit up the reception space.

The ceremony took place surrounded by mountains, palms and desert plants. Instead of building a traditional floral installation, they sourced potted desert plants from a local nursery and arranged them around the ceremony space before later replanting them at home. Bougainvillea blooms were scattered loosely along the aisle. “We wanted our ceremony to feel simple but elevated”, Madeline explained, “allowing the surrounding mountains, palms, and desert landscape to take centre stage.” Eliot’s best friend officiated while Madeline’s friend stepped in as flower boy.

Dinner was served beneath mango trees with long candlelit tables layered in beige chiffon linens, striped details and single stem florals in peach and green tones. Later, the party moved to an industrial open-air space tied. Guests crowded around the DJ booth while the night carried on into the early hours. Madeline and Eliot even did a surprise DJ set together

“Trust each other, make decisions together, and don’t be afraid to do things your own way”, they advise. “Start the planning process earlier than you think and give yourself time to be truly involved. People often say a wedding is for everyone else, but we believe it should first and foremost feel true to you.”