You know what? I’m going to start with my biggest wedding guest fashion disaster because honestly, it was so spectacularly bad that it’s become legendary in my family. This was back in 2019, before kids completely rewired my brain and my priorities. My college friend Sarah was getting married at this gorgeous venue in Wisconsin, and I… well, I completely overthought everything.
I spent weeks agonizing over what to wear. WEEKS. Like I was preparing for the Met Gala instead of a Saturday afternoon wedding in Madison. I bought this midi dress from Anthropologie – you know the kind, all romantic florals and awkward sleeve situation – that looked amazing on the model but made me look like I was cosplaying as a prairie wife. Then I paired it with these strappy heels that were clearly designed by someone who’d never actually walked anywhere, and topped the whole thing off with this fascinator-adjacent headpiece that my mom insisted was “very elegant.”
The headpiece. Oh my god. It was this weird beaded thing with feathers that kept tickling my ear, and every time I turned my head too quickly, I was basically weaponized. I nearly took out the maid of honor during cocktail hour. The photographer – bless him – gently suggested I might want to “adjust my hair accessory” for the group shots, which was his polite way of saying “that thing on your head looks insane.”
But here’s the worst part: I was so uncomfortable in everything I’d chosen that I spent the entire reception worried about whether I looked appropriate instead of actually celebrating with my friend. I kept checking mirrors, adjusting the dress, walking weird because of the shoes. By the time they cut the cake, I’d basically given up and borrowed someone’s cardigan because I was freezing and my “elegant” dress had zero practical warmth.
That was my wake-up call about wedding guest dressing. Not just for my own sanity, but because I realized I’d completely missed the point. Sarah later told me she barely noticed what anyone was wearing – she was too busy being happy and overwhelmed and trying to talk to 150 people in one day. Meanwhile, I’d stressed myself out for months over an outfit that literally no one cared about except me.
Fast-forward to now, when I’m 35 with two kids and exactly zero patience for clothing that doesn’t work in real life, and my approach to wedding guest outfits has completely changed. I’ve been to maybe eight weddings since having kids – which is fewer than my twenties but each one required way more strategic planning because hello, babysitters cost money and I’m not wasting my rare nights out being uncomfortable.
The biggest shift for me has been realizing that “dressy” doesn’t have to mean “completely different from how I normally dress.” Like, revolutionary concept, right? But seriously, I spent so many years thinking I needed to transform into some other version of myself for weddings, when really I just needed to be a slightly more polished version of regular me.
My go-to now is honestly pretty simple: a really good jumpsuit. I know, I know – jumpsuits at weddings used to be controversial or whatever. But hear me out. I have this navy one from Everlane that I’ve worn to three different weddings (sue me, I’m not buying a new outfit every time someone gets married when I can barely afford the gift). It’s comfortable enough that I can chase my kids around at family-friendly ceremonies, but it looks put-together enough that other people’s moms don’t give me side-eye.
The best part? I can actually move in it. I can sit normally during the ceremony without worrying about my hem riding up. I can dance without adjusting anything. I can eat dinner without feeling like I’m going to burst out of something. These seem like basic requirements for clothing, but apparently formal wear designers didn’t get that memo.
I pair it with whatever blazer I’m currently obsessing over – right now it’s this camel-colored one from Madewell that I bought for school pickup but works for basically everything – and comfortable block heels that I can actually walk in. Block heels were a game-changer, by the way. All those years I thought I needed stilettos to look formal, when really I just needed shoes that didn’t require advanced engineering degrees to navigate.
For accessories, I’ve completely abandoned the idea of matching sets or anything too precious. Statement earrings from Target or those fun ones I see on Instagram ads, a bag that’s actually big enough to hold my phone and lipstick and emergency snacks (because mom life means always being prepared for hunger emergencies), and that’s pretty much it. No fancy clutches that I’ll lose or forget in the bathroom, no delicate jewelry that’ll break if I hug someone too enthusiastically.
The color thing used to stress me out too. All those rules about what you can and can’t wear to weddings, avoiding white obviously but then also avoiding anything too bright or too dark or too anything. Now I just wear colors I actually like and look good in. Shocking, I know. Navy works on me, so I wear navy. Black makes me feel confident, so sometimes I wear black. I’m not showing up in a wedding dress or funeral attire, and beyond that, I figure adults can handle seeing me in whatever color makes me feel good.
My friend Emma got married last fall, and I wore this rust-colored midi skirt from & Other Stories with a cream sweater and ankle boots. Not groundbreaking fashion or anything, just clothes that I felt good in and could actually wear again. Which I have, multiple times, because that’s how clothing is supposed to work. Revolutionary concept in the wedding guest world, apparently.
The whole thing about buying special “occasion wear” that sits in your closet forever makes no sense to me anymore. Like, I have exactly zero space in my life or my budget for clothes I’ll wear once. Everything needs to earn its keep now. That navy jumpsuit has been to weddings, work events back when I worked, dinner dates with my husband, even school concerts where I wanted to look slightly more pulled together than my usual mom uniform.
Same with shoes – I’m done with the torture devices masquerading as formal footwear. Those block heels I mentioned? I wear them everywhere. They’re comfortable enough for walking around Target but nice enough for fancy dinners. The strappy death traps from my twenties are long gone, and I don’t miss them even a little bit.
What’s funny is that other moms at these weddings always compliment the practical choices. We’re all figuring out how to look like adults while also being functional humans with real responsibilities. Nobody has time for clothing that requires special underwear or walking techniques or cannot get wet if someone spills something.
I went to my cousin’s wedding last spring – outdoor ceremony, reception in a barn, very casual Midwest affair – and I wore jeans. Nice jeans, dark wash, with a silk camisole and blazer, but still jeans. Five years ago I would have been mortified. Now? I looked appropriate for the venue, I was comfortable, and I could actually enjoy the day instead of worrying about grass stains or sitting on hay bales in a dress.
The bride specifically told people to dress casually because she knew half the family would be traveling with kids and she didn’t want anyone stressed about clothing. More brides should do this, honestly. The whole formal dress code thing feels outdated when people are dealing with real life logistics.
Don’t get me wrong – I still put effort into wedding guest outfits. But now it’s effort toward looking like myself instead of effort toward looking like someone else’s idea of formal. I’ll do my makeup a little more carefully, maybe curl my hair instead of throwing it in my usual mom bun, choose my nicest accessories. But the foundation is still clothes that make sense for my actual life and body and comfort level.
The pandemic kind of accelerated this whole thing too. When weddings started happening again, everyone was just so happy to celebrate that the clothing rules felt less important. People wore what they had, what made them comfortable, what they could afford after a year of financial uncertainty. And you know what? The weddings were still beautiful. The important part was never really the outfits anyway.
So if you’re stressing about what to wear to someone’s wedding, here’s my mom-who-learned-the-hard-way advice: start with what makes you feel good and work from there. Don’t buy anything you can’t imagine wearing again. Prioritize comfort without sacrificing style – they’re not mutually exclusive, whatever the formal wear industry wants you to believe. And remember that literally no one will remember what you wore except maybe you, so you might as well wear something that lets you actually enjoy the party.
That fascinator from Sarah’s wedding? It’s somewhere in my closet, probably tangled up with old Halloween costume accessories. I keep meaning to donate it, but honestly, it serves as a good reminder of how much simpler things can be when you stop overthinking them.
Taylor’s a Minneapolis mom rediscovering her style between school runs and snack time. She writes about fashion that survives real life—affordable, comfortable, and still cute. Her posts are for moms who want to feel good without pretending motherhood is effortless.
