For My Sister
E2: Office style lessons from The Masters
Alright, folks, it’s that time again—another episode of For My Sister that no one asked for... except for, you guessed it, my sister. This time, we’re talking office clothes and making sure you're still not secretly resenting them. One of us is heading to a work conference soon, so I promised I’d throw together something helpful—because nothing says “professional” like unsolicited fashion advice. right?
Full disclosure: I can’t guarantee HR won’t be sending you a stern email about some of these outfits. But hey, just tell them to take a deep breath and live a little.
Now, I totally get it. Work clothes often feel like a necessary evil—something we have to buy because, well, the office demands it, but it doesn’t mean we have to settle for drab, uninspired pieces that sit at the back of our closet gathering dust. We've all been there: staring at that grey blazer or those stiff dress pants, just wondering how in the world you got stuck with them. It’s almost like they’re mocking you, hanging there with their dull promise of “professionalism” while offering zero excitement.
But here’s the truth. You spend a huge chunk of your life in these clothes, so why not make them something that actually makes you feel good? Your work wardrobe shouldn’t have to reflect your boredom or the monotony of office life.
Instead, it can be an extension of your personality, your style, and your mood—while still adhering to that fine line of "professional." So, let’s get rid of those soul-sucking clothes that don't inspire us and invest in items that are an upgrade for your day-to-day—clothes that make you feel confident, happy, and just a little bit adventurous.
Because, spoiler alert: You’re not boring, and neither are your work clothes.
So, let’s start on top and take a look at some pieces I’ve picked out that are perfect for the office, a work conference, or dinner with the crew—because these tops eat. We're talking about those versatile pieces that seamlessly transition from the boardroom to the bar without skipping a beat. No more settling for boring, stiff, one-dimensional workwear that just collects dust in your closet. These pieces are designed to turn heads and get the job done—especially this red Proenza Schouler silk shirt.
Nothing says I’m the boss quite like this one.
When it comes to turning heads, we can't overlook the masters who have perfected the art of style and design before us. I’m constantly drawing inspiration from iconic runway shows and fashion legends whose work has stood the test of time.
Take Miuccia Prada, for example. She has this rare talent for making structured pieces feel effortlessly fresh and dynamic. Her designs are so bold and well-crafted that they command attention on their own, without the need for any extra accessories.
But it’s not just the runways that teach us about timeless style—Princess Diana, the people’s princess, is another endless source of inspiration. She had an incredible ability to make classic, professional clothing look effortless—even in the sweltering heat of Egypt. She knew how to wear pieces that were perfectly tailored yet still looked light and breezy, as if she were casually strolling down a desert runway.
It’s a powerful reminder that you don’t need to chase trends to be iconic—you just need a killer outfit and a whole lot of poise (and maybe some air conditioning).
A few more tops I’m loving and would wear on repeat—paired with oversized trousers or dressed down with jeans. PS get yourself on the waitlist for this Khaite blouse.
Très chic.
Moving on to bottoms. What’s the saying, The wider the pants, the closer to God? Or is that about hair? Anyway, we’re officially in an era where trousers are back, and I’m all for it. Seriously, what’s more comfortable than pants that aren’t glued to your legs?
Let’s be real—nothing beats the freedom of movement when your pants actually move with you. Plus, there’s something so satisfying about a wide-leg silhouette—it’s like strutting around in your own personal wind tunnel, full of swagger.
Bring on the drama.
I’ll be the first to say it—jeans 👏🏻 work 👏🏻 for 👏🏻 work. But for now, let’s talk about a few pairs that feel just a little more elevated. I’m a huge, and I mean HUGE, fan of Nili Lotan’s pants (the Megan style, in particular, is a workhorse in my closet). That being said, I’m also loving these wide-leg Françoise pants, or maybe the navy pinstripe ones, just to add a touch of I’m-in-charge to the mix. Because let’s face it, who doesn’t want to add a dash of bossy to their look—without having to send any emails?
The Fall 2025 shows were a masterclass in structured jackets and wide-leg pants. Let’s all take a moment to observe and appreciate one of my favorite brands, Sportmax.
Don’t go yet, things are just getting good…
Next, let’s talk about the icon First Wife of suits, blazers, and timeless style: Diane Keaton. Trust me, there’s a lot we can learn from her. She’s a woman who knows exactly what she likes—and yes, that’s usually a suit.
But let’s be honest, when has Diane ever worn something boring?
She’s Nina Banks, the matriarch of America’s favorite family, and when I think of a matriarch, I think boss lady. Diane Keaton has elevated the suit to an art form, mixing dramatic details with elegance. Even in her uniform of a turtleneck and slacks, she’s the ultimate example that being chic doesn’t require sacrificing personality.
And without further ado, let’s dive into my picks from The RealReal—one of my go-to spots for workwear that won’t put you to sleep or drain your bank account. P.S. These pieces are hot, hot, hot, so you better act fast before they vanish. First up, a timeless classic that will never go out of style: a pleated Issey Miyake top.
Or how about a printed Kallmeyer piece that will make you look like a gift to your co-workers? I’ve also been on the hunt for a Gucci cashmere sweater, this one is perfect.
Consider it an investment in both your comfort and your office reputation.
And finally, let’s not forget our leading men. As we slip into our own suits, we can’t help but be reminded that sometimes they just do it better. Take Edward Lewis, for example—AKA my husband, AKA the love of my life, etc., etc.
Men’s style has some serious heavy hitters, and Richard Gere is basically the professor of How to Look Good in a Suit. The man is a master and is aging like the finest wine.
Speaking of The Masters (see what I did there?)…
There are certain cultural and historic moments that have shaped fashion as we know it. Take, for example, the weekends when our husbands and boyfriends settle in front of the TV to watch The Masters, the most prestigious golf event of the year, held in Augusta, Georgia. It’s that time when the lucky winner is gifted the legendary green jacket. Sure, it’s not a Miuccia Prada or Ralph Lauren tailored masterpiece, but it’s iconic in its own right.
That green jacket? It’s like the blazer equivalent of I’m the boss now.
It may not be crafted from Italian silk or custom-designed by a famous tailor, but when you slip it on, you instantly feel accomplished.
Sure, the color might be a little bold, but it definitely gets the job done—and if that doesn’t scream I’m owning this, I don’t know what does. Now, imagine if we wore our work clothes with that same energy. Maybe your office blazer isn’t green, but it can still give you that same sense of pride and confidence.
It’s time to ditch the boring, stiff office wear and embrace pieces that make us feel like we’re in charge, whether we’re at a conference or just powering through the day.
Because, after all, a little confidence goes a long way.
More iconic blazers below.
I leave you with the one and only boss lady, the real Miranda Priestly.
Now go forth, conquer those closets—and take on the boardroom while you’re at it.
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