De-stress from the Dress
Dress codes like "cocktail" and "evening" turn me into a ball of anxiety. But there are non-obvious ways to feel good in what we wear.
This is just a note to everyone out there who doesn’t wear make-up, heels or jewellery, and feels stressed every time they need to attend a fancier than usual event—hello there, I feel you. I am you.
A dear friend of mine got married last week. I flew to Singapore to attend the wedding, excited about seeing her in her all bridal glory and celebrating the occasion with friends, good food, music and dancing.
And it was fun—a good, proper party where we got extremely festive with the cocktails and dancing, and went home with armloads of lilies that the hotel was going to throw out (the waste!).
Less fun was the agony of wondering what to wear in the lead-up. To be clear, I know how to do “normal dress-up”, like Christmas parties, office parties etc—I’ll combine something simple with something that has a texture or a detail that says “refined”, and call it a day. Easy.
Events that call for actual glamour—not so easy. Especially when the invite specifies dressy cocktail or semi-formal. To show up in anything less feels like a declaration: I did not dress up for this. I know this is just in my head and my friends don’t care what I wear (that’s why we are friends). But I want to make the effort. You might even say I want to fit in, and , why not, if it simply means to I want to respect the occasion and channel the mood.
But how do I that and still feel “me”? Since I don’t wear make-up and avoid heels or jewellery, styling tips like a strappy sandal, a red lip, or statement jewellery don’t work for me (or suit me), and these elements are arguably what elevates a simple outfit.
For a couple of weeks, I felt uncertain about what to wear, even though I knew it was silly to fuss over an occasion where I’m just the supporting act. I felt compelled to try and “glam up” my usual look, and I didn’t really know why. Although I drew the line at buying a whole new outfit, I nearly ordered a pair of Dries Van Noten mesh opera gloves with a floral print. (I didn’t but they are so nice and would totally suit someone with the pizazz to pull them off.)
In the end, I decided the best action was no action, and I stuck to my fail-safe fallbacks—I packed a long navy silk dress from Filippa K that has seen at least three weddings, and my white glove flats. My sister, whom I was staying with, lent me a shiny ivory mesh purse with gold accents that had belonged to our grandmother, and I wore a little tiny gold and steel watch (inherited from my mum) for extra shine.
For the church ceremony and luncheon earlier in the day, I wore a vintage waistcoat and tailored trousers.
And of course it turned out fine. No one will look at a photo of me and think “glam”, but it doesn’t matter. I stuck to my uniform and it held up. The dress is simple but the length gives it drama and the swishy volumes of fabric swing very satisfyingly when I move. My flat shoes were perfect for a whole night of dancing. The bag and watch twinkled just enough to make me feel festive.
On hindsight, I feel silly for fretting, but I’m probably not alone experiencing the moments of doubt whenever we venture into a space outside our comfort zone, filled with prescribed ideas of what we’re supposed to look like. In these moments, I am vulnerable to caring about what other think, and I compare myself with others. Inevitably, I am tempted to shop for something new as an easy way out, to settle the nerves.
Sometimes, it is true that we have nothing to wear—bodies change, needs change—and shopping is actually the solution. And sometimes, we want to push our style a little bit and that’s ok too. But on this occasion, I really needed to just cool off and think about what I really want (and need) from my clothes, and give my nerves the space to relax.
For inspiration, I turned to my favourite red carpet role models: female film directors—think Sofia Coppola, Chloe Zhao, and more recently, Celine Song and Justine Triet. Obviously, the stakes are much higher for them; they’re dressing for a moment where not only their work is being scrutinised, but also their physical selves and their identities as female directors. Their clothes aren’t just about what they like, they’re also a message to whoever’s looking.
And by and large, I think they’ve done a great job telegraphing themselves as women behind the camera, not in front, while staying true to their personal tastes (Coppola and Zhao incorporate more delicate flourishes and softer colours, while Triet and Song prefer tailoring. I look at Zhao wearing Hermes with barely a trace of make-up at the Oscars, and I’m inspired by how she’s giving the world who she is, not who she isn’t.
This gave me much needed perspective—I may love seeing glamour in action, but my objective for attending the wedding is to celebrate a joyful moment in a friend’s life. I reconciled with the fact that glamour is not something I need to channel through my clothes—my clothes just need to bridge the gap enough for me to cross over and join in the fun. And in that regard, the things I already had were enough.
So, here’s what I’ve learnt from fretting about dressing up.
If you already have a go-to outfit, wear it (again and again)
Since dressing up is already outside my comfort zone, I find that wearing something tried and tested gives me more confidence than wearing a new thing. It’s tempting to imagine that a new outfit will finally transform me into something “better” (whatever that is), but a surer bet is wearing a piece you know you feel good in.
An oft-worn piece also has something a new item doesn’t—emotional attachment. Every time I wear my “wedding guest” dress, I accumulate memories of moments I treasure. When I bring it out again, I remember the happy occasions of days past, and it gives me a bit of a lift when I put it on. These are clothes that will endure emotionally with repeat wearings.
And no one cares that you’re wearing the same thing to more than one occasion. If anyone does, it’s their problem, not yours.
If you’re buying something, buy with versatility in mind
One thing I like about my dress is that it works for a variety of occasions and seasons—garden weddings, beach resort weddings, ballroom weddings, vineyard weddings, you name it. It is plain, but it is this plainness that gives it its longevity. The dress stays constant, while my accessories evolved with my style (eg my dressy shoe of the moment is a high-vamp glove flat, but when I bought the dress in 2017, it was a flat gold sandal.)
Whenever I feel like I don’t quite have the right accessory, I borrow something from friends, and it is a blessing to have friends and family who are generous about this type of thing (and it really helps that my sisters and I have the same size feet).
Plan ahead
If something isn’t in your wheelhouse, don’t wing it; there’s no need to play it cool. Try on your go-to outfit well in advance to check whether it still fits, or whether you need to make small repairs or tweaks. And give yourself time in case you need to borrow or buy something; avoid panic shopping as much as possible.
Personally, a good haircut is what does it for me, so I get my hair trimmed a week or so before the event—plenty of time for the cut to “settle in”.
Get to know what “dressy” means to you
Find the thing that makes you feel polished and ready to face a dressy occasion. For me, it’s a fresh haircut, nice perfume, and a small purse, preferably something vintage-looking with a strap or handle of some kind. I wear glasses, so sometimes I swap my usual glasses for something more statement-ish.
But really, it can be anything, including yes, a red lip, a nice piece of jewellery or heels. It can be tailoring. It can be a pop of colour. It can be a specific fabric (silk and satin being obvious go-tos, or mesh). It can be showing a bit of skin.
It doesn’t matter if it looks ordinary to someone else, so long as it feels dressy to you.
Give yourself time and space to enjoy the process
I hate rushing, and I don’t like dressing up, so I always schedule a couple of hours for getting ready, even though I have no make-up or hair routine to speak off. I just like taking my time.
Because it’s often hot and humid in Singapore, I like taking a refreshing shower before getting dressed, and this is also the best time to break out the nice, luxe bath products.
I also remember the days of getting dressed with friends before hitting the clubs, so I still play music while getting dressed for a fun occasion—in honour of my friend, a devout fan of 2000s R&B and hip hop, I played a lot of Usher and Aaliyah.
This process also gives me lots of time to make last minute tweaks, like trying different shoes, or going with a different purse. After I’m dressed, I chill for about five minutes in the outfit to make sure I’m happy (I may make myself a nice cocktail or a cup of coffee) before I call an Uber.
Take photos with your friends that aren’t about the outfit
You know those photos where everyone is posing to show off their outfits and accessories? Nothing wrong with those if you enjoy them, but I feel so uncomfortable when I get dragged into one of those, and when I see the photos later I always wince. Not a great memory to associate with your clothes.
The photos that don’t make me cringe are the spontaneous ones that I snap for my loved ones while they’re enjoying themselves. So I always remind myself do this on special occasions, and once I start doing it, my friends do too. At the end of the night, we have lots of fun photos to trade, and the bonus is that it creates emotional attachment to whatever I happen to be wearing. I love the way clothes look when they are lived in and enjoyed, and these photos make me look forward to wearing the pieced again.
A sentimental postscript
There’s a photo of me and mum that sits on my desk. It was taken at sunset at my cousin’s very glamorous vineyard wedding in 2017, and I am wearing a long navy dress—the same one I wore to my friend’s wedding.
I can’t remember who took the photo, but I think it was one of my sisters. In the photo, I have a drink in one hand and my other arm is around my mum’s shoulders. We’re both wearing sunnies because the sun is in our eyes, and we’re looking at something just to right of the frame, and laughing. It’s magic hour and everything is golden.
A year later, my mum died. Whenever I see the photo of us, I am filled with sadness, but also grateful that we shared that moment of joy without reservations and worry.
Whenever I see the dress in my closet, I think of that moment. And there is no dress I can buy that would hit me the same way.
Such a beautiful post, it brought tears to my eyes. Thank you for writing it and sharing it x
What a beautiful post, Lin. The dress is gorgeous but the memories attached are everything. I feel the same way about so many of my clothes; the sentiment is irreplaceable.