The cream-colored invitation has been haunting my coffee table for weeks now, and honestly, I’m starting to think my friend Emma did this on purpose. Right there, in that fancy calligraphy font that probably cost more than my monthly coffee budget, are the three most terrifying words in wedding guest vocabulary: “Dress comfortably.”
I mean, what does that even mean? Comfortable like my ratty pajama pants that I’ve worn so many times the elastic waistband has given up all pretense of actually holding anything up? Or comfortable like that one dress I own that doesn’t make me feel like I’m being slowly strangled by fabric after two hours of sitting? Because let me tell you, those are very different levels of comfortable.
When I texted Emma for clarification – because obviously I did, within about twelve seconds of opening the invitation – her response was peak Emma: “Oh, just wear whatever feels right! It’s going to be super chill!” This from someone who showed up to my “casual backyard barbecue” birthday party wearing what I’m pretty sure was a vintage Diane von Furstenberg wrap dress. Her definition of chill exists in an alternate reality where everyone naturally looks effortlessly put-together.
You know what “dress comfortably” really is? It’s a trap. Too casual and you look like you rolled out of bed and couldn’t be bothered to care about someone’s wedding day. Too formal and everyone’s staring at you like you fundamentally misunderstood the assignment. And here in Britain, where wedding traditions change completely depending on whether the couple met at university or through their local cricket club, it’s basically impossible to get right.
I learned this lesson the hard way at my colleague James’s wedding two years ago. The invitation said “dress comfortably” for a summer ceremony in the Peak District, so I went with what I thought was a safe choice – floral midi dress, cardigan, sensible sandals. Perfect for an outdoor wedding, right? Wrong. I showed up to find half the guests in full-on morning dress with proper hats, while the other half looked like they were headed to Glastonbury. The bride’s grandmother was wearing pearls and a fascinator. The groom’s best mate was in cargo shorts. I spent the entire day feeling like I was either wildly overdressed or completely underdressed depending on who I happened to be standing next to.
Since then, I’ve become something of a detective when it comes to decoding wedding dress codes. It’s all about reading between the lines and considering about fifteen different factors that the couple probably didn’t even think about when they wrote “dress comfortably” on their invitations.
Location is everything. Emma’s wedding is at some converted barn in Gloucestershire, which immediately tells me several things. One, there will definitely be uneven ground, probably gravel or grass that will eat stilettos alive. Two, British weather being what it is, I need to prepare for everything from blazing sunshine to sideways rain, possibly within the same hour. Three, barn venues are notorious for having either arctic air conditioning or no ventilation whatsoever – there’s no middle ground.
For this kind of venue, I’m thinking about comfort in very practical terms. Block heels that won’t sink into grass, layers I can add or remove when the temperature inevitably fluctuates by twenty degrees throughout the day, and fabrics that won’t look completely destroyed after six hours of sitting, standing, and pretending to enjoy small talk with distant relatives.
I’ve got my eye on this forest green jumpsuit I bought last month – it’s made from some kind of stretchy crepe that doesn’t wrinkle, which passed the crucial “sit in your car for three hours” test when I wore it to visit my parents. The wide legs make it feel formal enough for a wedding, but it’s basically structured pajamas, which is my personal sweet spot for event dressing. I’m planning to pair it with these leather ankle boots that have maybe a two-inch heel – high enough to look intentional, low enough that I won’t be hobbling by the time we get to the dancing portion of the evening.
But here’s where it gets complicated – this is a June wedding, which means I’m dressing for the theoretical possibility of actual warm weather. British summer weddings exist in this weird meteorological limbo where you could be shivering under a patio heater or quietly melting in a stuffy marquee, sometimes during the same event.
My strategy is always layers, but like, sneaky layers that don’t make you look like you’re prepared for an Arctic expedition. I’m bringing a blazer that I can lose if the sun decides to make an appearance, plus one of those lightweight scarves that takes up no space in your bag but can save your life when the evening temperature drops fifteen degrees the moment the sun sets.
The guest list is another crucial piece of the puzzle. Emma’s friendship group is this mix of artsy London types who think vintage band t-shirts count as formal wear, and her family, who I’m pretty sure still believe you shouldn’t leave the house without proper shoes and a coordinating handbag. This tells me the interpretation of “comfortable” is going to be all over the place, so I need to aim for somewhere in the middle – special enough that I don’t look like I’m running errands next to the relatives who will inevitably ignore the casual dress code, but not so formal that I look stiff next to her friends who consider ironic vintage the height of sophistication.
Time of day matters too. This is a 2 PM ceremony, which generally skews more casual than evening events, but it’s followed by dinner and dancing, so it can’t be too casual. I went to a similar timeline wedding last year where most people interpreted “comfortable” as cocktail attire in fabrics that didn’t restrict movement – lots of wrap dresses and jumpsuits, men in suits without ties or blazers with nice jeans.
There’s also the question of your relationship to the couple. I’m not immediate family or in the wedding party, so I don’t need to worry about photographs or representing anyone but myself, which gives me more flexibility. When my cousin got married and used the same dress code, my aunt still showed up in a proper coordinated outfit with a hat because, as mother of the bride, her version of “comfortable” needed to be more elevated than everyone else’s.
But honestly, the most important factor is knowing what actually makes you feel comfortable. I have friends who are only truly relaxed in dresses with pockets and flat shoes. Others who feel most themselves in tailored trousers and button-downs. Some who need substantial stretch in their clothes to feel human.
For me, comfort has very specific requirements. I need to be able to sit for hours without fabric cutting into my waist, I need shoes I can wear from ceremony through late-night dancing without wanting to set them on fire, and I need to be prepared for temperature changes because I’m one of those people who’s either freezing or overheating with no comfortable middle ground.
This means no new shoes – I learned that lesson at my friend Lucy’s wedding when I thought “comfortable” meant I could break in those gorgeous nude heels that matched my dress perfectly. Three hours in, I was barefoot under the dinner table, and those shoes are still sitting unworn in my closet because they’re now forever associated with foot torture.
The most successful “comfortable” wedding outfit I’ve ever worn was to my university friend Tom’s celebration last summer. After way too much deliberation, I went with wide-leg black trousers in this fabric with enough structure to look formal but enough stretch to allow for enthusiastic dancing, a silk blouse in deep blue that I could push the sleeves up if needed, and these mary jane style shoes with a chunky heel. Statement earrings made the whole thing feel more special.
That outfit passed my ultimate test for wedding guest attire – I completely forgot I was wearing it about an hour into the event. No adjusting, no regretting shoe choices, no wishing I’d brought a different layer. Just enjoying the celebration without my clothes demanding any of my mental energy.
For Emma’s wedding, I think I’ve finally cracked the code of her particular brand of “comfortable.” The green jumpsuit feels appropriately special but practical for a barn setting, the ankle boots can handle whatever surface situation we encounter, and I’m bringing contingency plans – flat sandals in my car for when my feet inevitably rebel during dancing, and a lightweight wrap that can handle evening temperature drops.
This might seem like excessive planning for something described as “comfortable,” but it’s the only way to actually achieve comfort when you’re dealing with British weather, mixed guest lists, and the general chaos of wedding celebrations.
The truth is, “dress comfortably” might be the most honest dress code couples can put on their invitations. They want guests who feel good in what they’re wearing, who aren’t distracted by pinching shoes or restrictive waistbands, who can fully participate in celebrating without spending the day adjusting their outfits.
It’s just that achieving that comfort requires way more strategic thinking than the phrase suggests. You need to consider the venue, the weather, the guest list, the timeline, and your own personal comfort requirements. Then choose something that makes you feel like the best version of yourself – special enough to honor the occasion, practical enough for whatever the day throws at you, and comfortable enough that you can focus on the celebration rather than your clothing choices.
And always, always have a backup plan for your shoes. Trust me on this one – your feet will thank you when you’re still dancing at midnight instead of limping to your car at 9 PM.
Riley’s an environmental consultant in Seattle with strong opinions on greenwashing and fast fashion. She writes about sustainability without the guilt trip—realistic tips, honest brand talk, and a reminder that progress beats perfection.
