What are you gonna wear?
Outfits for a night out.
This post was inspired by that one question we text our friends before a night out to gauge the overall style mood for the occasion: What are you gonna wear? In Substack world, an iteration of this question gets posed a lot: What is everyone wearing for going-out tops? Recs for what to wear for [girls’ night/drinks/a birthday dinner, etc.]?
It seems to be a common dilemma, especially for us older millennials. I suspect it has to do with the fact that our tastes have changed, our bodies have changed, and let’s face it, our version of going out has also probably changed. Many of us may still enjoy getting dressed up but are no longer dressing for bars and clubs like we used to.
Dressing up to go out in my university days and early 20s was easy… and expensive. I would throw on whatever new flashy, low-cut (going-out) top or form-fitting mini dress I bought with my employee discount working part-time at Marciano (the older, sexier sister to Guess.) I’d get a few wears out of each piece, and then replace it with something else shiny and new because they weren’t really built for versatility or longevity. I hardly put any thought into my going-out outfits—my choices mostly revolved around showing some a lot of skin. Everything was too tight, too short, too revealing.
Nowadays, my version of going out is usually a nice, early-ish dinner with my husband and/or friends. Maybe some drinks. And a concert thrown in here and there. I only have a few pieces in my closet I purposely collected for special occasions, which I re-wear because they’re quite simple and I can get away with wearing them over and over again without it feeling overdone (read: I don’t spend a lot of money on going-out clothes anymore.) I’m not opposed to showing skin, but I like to think I’m a little more methodical about it (more on this below.) My style is a lot more pared back, and I’m continuously trying to find the balance between what I think looks good and what I feel comfortable in (because I feel like I look better the more comfortable I am.)
My birthday is coming up this month, and while I’m not exactly sure what our plans are, I know I’ll end up re-wearing something I already own. Here’s a look at some of the going-out pieces in my closet, how I approach dressing up at my age (I’m turning 38, btw), and finally, some recommendations.
I’ll start by saying that, what’s worked for me, was buying a few special pieces I loved even though I didn’t necessarily have an upcoming occasion to wear them for. Buying something you don’t need isn’t something I always recommend. But it’s worked for me to have a few pieces already in my closet that I can wear for a night out, this way, I’m not scrambling last-minute, feeling like I have nothing to wear and panic buying something I don’t really love. Just having a few pieces you can rely on makes a difference.
Case in point: this red satin slip dress I bought from Oak + Fort last spring. I was immediately drawn to it when I saw it (the colour!) but hesitated because I didn’t have anything to wear it for, and I was worried about wasting my money. It sat in my closet for a few months before I actually got to wear it, but it’s something I’ve reached for multiple times now. I wore it with a black blazer and heels for my birthday last year but think I’ll go for something a little more toned-down next time, and wear it with a black cardigan and flats (inspired by this photo of @gabrigofis wearing cute flats with her dress). Also excited to top it with a long coat when the weather gets cooler because the contrast of a slip dress and heavy coat seems so chic. I find wearing something satin, or better yet, silk is an easy way to feel dressed up, and if you don’t want to do a dress, you can always do a top, skirt or pair of pants instead.
Two other pieces I rely on heavily for going out are a pair of trousers and a blazer. I think the key is to find the styles that don’t feel like just regular office wear and for me, that usually means something looser and less tailored. In a pinch, my go-to outfit for dinner is either jeans + a tank/tee + oversized blazer or trousers + a turtleneck (a mix of dressy and casual pieces.) But sometimes, I’ll wear the blazer and trousers together, like I did for my brother’s birthday this past summer. I wore it with this Sculpt Knit Sweetheart Tube top to balance out the proportions with something a bit more slim-fitted. In the warmer seasons, I wear this exact outfit but switch up the blazer for a white open button-up.
Like I mentioned above, I’m not opposed to showing some skin. I think my style will always lean a little bit on the sexier side when I’m going out but I don’t want to feel exposed, so I’m more intentional about which parts I show. After breastfeeding two babies, I tend to feel self-conscious in low-cut tops, so instead I’ll wear something with a higher neckline and open back. I’m naturally drawn to pieces with details that expose a hint of skin, whether it’s a dress with a cut-out or something subtler, like a top with an asymmetrical neckline that shows off my collarbone and shoulders.
Up until recently, my going-out look tended to be all done up, complete with layers of makeup and curly hair (which never turned out to be the loose waves I was actually going for.) Looking back at pictures, it was all too much. Too primped and polished. As I get older, I find myself gravitating towards a more natural, less-is-more look, especially if I’m wearing something already dressy. I’ll do less with my makeup and even more so with my hair, leaving it straight down or putting it up in a simple pony (I know, I know, it’s a privilege to have low-maintenance hair.) Instead of putting in the effort to create a perfect look, I try to be more conscious of how to keep it looking relaxed and a bit undone. I’ll drape my blazer over my shoulder, instead of wearing it. I’ll tuck my hair into my coat or jacket.
Going out edit
A mix of pieces, in varying price points, for getting dressed up.
If a going-out top is what you’re looking for, let’s start with Aritzia because they seem to have plenty right now (and all at decent price points). These are all options I would wear to dinner, depending on the vibe of the restaurant, from less coverage to more (1 / 2 / 3 / 4 / 5)
Another off-the-shoulder top I really want.
I’d wear this DISSH fitted ruched midi dress (on sale) with boots and a blazer.
I like Zara for going out dresses that don’t break the bank. The one I’m wearing in the pic above is a Zara off-white, asymmetrical, cut-out midi dress that I’ve worn for two past anniversary dinners and have brought with me on trips. Here are a few dresses from this season’s collection that have caught my eye: 1. This romantic option with a sheer overlay 2. Satin slip dresses (burgundy / chocolate / beige) that you can wear under your long coat when it gets too cold 3. A similar cut-out style to mine but in fall colours and textured fabric 4. This contrasting knit halter dress has repeat-wear written all over it.
Sheer skirts (this splurge-y but special one or this more affordable one) that you can pair with a cozy sweater.
Going-out options for colder weather: 1. One of my husband’s favourites is this high neck top I wear with trousers or under a blazer with jeans 2. Love the colour of this long-sleeve, asymmetrical knit 3. This sweater dress feels very Sofia Richie-esque.
I’ve been using the same Saint Laurent Kate bag for going out for years now to get my money’s worth. I’m now starting to get the itch to buy something new and a little more subtle in style. This Freja one is at the top of my list. Also secretly praying that COS restocks their Cavatelli clutch in Bordeaux (this Mansur Gavriel Oversized Cloud Clutch in the colour Pomegranate is pricier but the closest thing I could find to it.)
Last but not least, here are a few quick jewelry picks. I’m fairly simple when it comes to accessorizing for a night out and usually just wear earrings. I have these Mejuri Mega Dome earrings I wear all the time, but there’s also these Charlotte Bold Hoops that I find so chic (fyi, they’re currently having a sale of 15% off of $200 in case you’re eyeing anything.)
also mentioned in a recent send how she wears these Heaven Mayhem earrings to girls’ night and now I can’t stop thinking about them in silver.
Do you have a go-to outfit for a night out? Let me know in the comments. x
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Love all of this! I often have a hard time with “going out” clothes!
That red dress on you! 🔥