What do I wear if I don't want to look boring in a casual blazer?
Sometimes the greatest antidote is exactly what you want to resist -- lean into the snooze
One question that recently came up was how to wear a blazer without looking boring. I answered the question indirectly in part through this dispatch on how to dress for work, which you can revisit here. The alternative solutions are vast.
On the one hand, you can resolve that even though you’re not a bride, you sure as shit want to feel like one.
…The kind who knows offhand the difference between a GAAP and a non-GAAP measure. (Disclaimer: I did not know the difference between these units until I googled, just 2 minutes ago, “common terms in finance”).
Theoretically, you could wear this to look professional (though I’m not sure it hits the right note to wear to work de facto; maybe more like an after-hours gathering in, say, a carpeted hotel ballroom) but also to act chill (puka shell shoes!). It says, “I know what I’m doing with my life, and I’m bringing turquoise beads with me.”
Another direction you could take: counter the initial question (what do I wear if I don't want to look boring in a blazer?) with another.
Why not instead wear a blazer that is categorically not boring?
But this advice isn’t scalable. It requires that you own a blazer that’s not boring, which maybe you do — in which case, I suggest pairing it with knee cap leggings and slingback sandals. I recently bought these sandals and walked 37 blocks while wearing them for the first time which I mention only to illustrate how comfortable they are. So that’s that — if you have a non-boring black blazer, just wear that. But don’t go out and get one if you don’t, there’s another solution and this is the one I’m going to spend the most time on because:
Sometimes the greatest antidote to not looking boring is actually to first make yourself look even more boring.
Let me explain by first highlighting what goes on under the blazer.
Here is a pretty typical pairing — a t-shirt and jeans, which I am confident many of us can cobble together from within the depths of our respective wardrobes. My choice rendering for the “typical pairing” includes:
A boat neck cotton shirt that is long sleeve and striped (La Ligne). Plain gray works too (I like Kule or Gap for these). So would something graphic (Jessica Biales makes cool seashell t-shirts).
Doesn’t matter if the shirt is long or short sleeve although my preference is long for when we add the blazer (sleeve scrunching — I’ll demonstrate below).
The jeans are a light wash bootcut style. They’re midrise, which you can’t see, and hit just above the bone on the arch of my foot. If you have a pair of straight-leg jeans, those work too. So would a trouser style or wide leg. I might stay away from skinnies for this exercise because proportions are the unsung hero of making boring clothes look less boring and right now, we’re pairing a straighter leg with a bigger jacket.
Jewelry
We’ll add the blazer, sure, but also a strand of pearls. They don’t have to be pearls — it’s my preference because of the way they contrast the mariner stripes, the latter of which have become as informal a marker of casualwear as, say, ripped jeans or an army jacket. So the pearls add some polish — the “stick up” to your “ass,” but in a good way. Honestly, though, opals, a gold chain, a silver chain, or some warm-colored (red, orange, even yellow) beads will do.
In the second to last Man Repeller office we occupied, I kept a jar of neon beads with string next to them in the middle of a table in the conference room for the exact purpose of making necklaces to wear with plain old t-shirts.
I often don’t like to wear a necklace over a boat neck collar, but when I put the blazer on, the neckline starts to slouch, which makes it look kind of like a necklace itself, and that creates a sort of layering effect over the pearls. It’s messy, but not — the “stick up” to your “ass,” magnifying just how anal the beads (pearls) really are.
That escalated quickly!
Added some bracelets too. My preference is to load up one wrist and keep one either bare or boasting just like, the one delicate cuff or chain. Asymmetry adds one more point of action within the parameters of an outfit so basic. If you don’t have many bracelets, I might suggest wrapping a chunky necklace around your wrist several times; if you’re in the market for new jewelry, I might suggest subscribing to this newsletter because next week, I’ll bring you a guide to great small brands.
By now you also see we’re dealing in the currency of a double breast blazer, as boxy as the t-shirt (though if your preference is one that is more fitted, you can just as easily wear that and tuck it in), loose fit as the jeans. This is the style I tend towards but if you’re working with another type — single breast or fitted, I suggest a tank top (love this one by Doen) tucked into wide-leg jeans or kneecap leggings (these from the Gap should do the trick and are 40% off) and the jacket button closed (like in photo no.1), respectively speaking. If you’re shorter, you’re going to want to wear a blazer that either crops right on your ass cheeks or just above them (this one from Zimmermann on The Real Real is pretty good).
Footwear
There’s a connotation about wearing a blazer — it’s formal, it’s professional, it’s stiff, it’s stuffy. But — and not to be dramatic here — you don’t have to fulfill that narrative if you prefer to use yours some other way.
So what are the most expected shoes you might think to pair with a blazer — loafers? Pumps? Structured ballet flats? Wear none! Often I have a hard time with blazers before it gets warm enough to either wear sandals or something short. With jeans, it’s all too same-on-same. You’re wearing all your basics together. Your go-tos have been gone to.
Boots, meanwhile, are too polished (unless they’re knee-high and your pants are loose-fit — sweatpants or otherwise — and tucked into the boots), sneakers are too obviously not polished (and therefore no longer unexpected at all).
When you’re wearing a mini dress or skirt or shorts, though, the stakes are different, so there’s more flexing room. It’s like, you put a blazer over running shorts, or pajama pants, or a beach dress and suddenly, you’re asserting something different completely in your marriage of disparate scenarios coming together unconventionally. That puts less pressure on the shoes to perform. Loafers or flats or even pumps if you want make much more sense when you’re not wearing them with the prototypical pants and a blazer. They become an unconventional talking point. Add a pair of socks and suddenly, you’re an agent of surprises!
We can talk about this in another installment, just tap reply and tell me you want to — but for now, because I am wearing reg pants with the blazer, I’m also wearing what I consider to be a great solution: ugly sandals.
I chose flip flops — these ones are by Neous (here in black), but you might choose some other pair — it seems most forms of flip flops would actually work pretty well (I like these, these, these, and I actually really think these are about to happen) but Birkenstock-style chunkers could be good too. Why do they work? They’re an unexpected enough option to make you wonder whether the outfit truly does makes sense, but as part of the complete constellation, they’re also basic enough to give you enough confidence to take the small risk of leaving your home wearing something you’re yet to feel sure in. Worst case scenario, you go home and change. Best case, you just learned something new about your style.
In sum: sometimes the greatest antidote is exactly what you want to resist -- lean into the snooze.
How was this for you?
The first subscriber-only open thread is next week! And another dispatch may or may not be hitting you up later today or sometime tomorrow. Hope to see you at both. Signing off yours truly,
Leandra