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I recently found myself thinking a lot about repeating outfits at work. After half a decade of remote and hybrid workdays, I’m being asked to show up four, sometimes five, days a week to the office. But as much as I like to banter with my coworkers in between meetings, there are more in-office days than there are shirts, pants, and dresses in my closet. It’s forced me to think long and hard about how to discreetly become an outfit repeater without it being noticed, a challenge that is especially difficult when you work in the fashion industry.
If I were my fully functioning best self every day, being able to whip up five to six creative summer office outfits with a single item is easy. But the truth is, I lack time and energy after spending nine hours at my desk, plus the commute, to then think about new ways to style a button-down shirt or blazer on a random Thursday at 7:20 a.m. So, I’ve resorted to planning all my outfits in advance. I take a single garment like, say, these new bermuda shorts I got from Aritzia last Sunday, and make a mess of my bedroom playing dress-up. Over time, I’ve learned just how many ways there are to style one item of clothing, camouflaging it to look like something new every single time.
It becomes a fun game once you get started. A dress can be turned into a skirt if you wear a cardigan over it, and a button-down layers beautifully under a crewneck when you let the collars pop out from under. In the two examples pictured below, for instance, I transformed a simple skirt and a pair of long shorts by mixing and matching them with other wardrobe staples.
Three ways to style a skirt for work:
How to style long shorts for work in three different ways:
Okay, I’ll stop gate-keeping my tricks: Here’s the secret to repeating outfits in the office without anyone catching on.
The Item: A Knee-Length Skirt
It’s not a mini-, maxi-, or midiskirt that’s been on heavy rotation this summer, but a classic corporate knee-length skirt. Celebrities like Zendaya, Kendall Jenner, and Zoe Kravitz have provided us with endless styling inspiration on how to put the silhouette to the test. Some days call for a preppy striped cardigan with a headband; others require an elegant top with heels. For the office, I like to tie my sweater around my shoulders as a visual focal point. Here are three looks I’d wear to the office in a heartbeat.
The Styling:
Look 1:
Separates in neutral colors don't have to be boring if you style them with intention. Wearing a cardigan over your shoulders one day, then tie it around your waist the next for a totally different vibe. Little details like adding socks to your loafers can also shake up a silhouette.
Look 2:
The next time you wear your favorite knee-length skirt, go a little dressier to subtly signal that this is a completely new look. Pieces with elegant shapes like pointed-toe mules or a structured bag always look put together.
Look 3:
Casual Friday? Lean into your personal style with pieces that are less stuffy than a black skirt suit but no less appropriate for the office.
The Item: The Bermuda shorts
I love the boyish silhouette of tailored Bermuda shorts. They’re trendy, yes, but they’re also an appropriate length to wear to the office and better for summer than classic black trousers. You can dress them up with a satin cami and luxurious cardigan tied around the shoulders, or go the sporty-chic route with some sneakers and a button-down.
Look 1:
Tailored shorts are great because you can so easily mix and match with different shoe styles. Slingback kitten heels have become a workwear favorite in 2026…
Look 2:
…while sneakers have become totally office appropriate at most workplaces these days. If you're going to wear them, just make sure to go with more elevated work uniform staples like a button-down shirt and/or a nice watch.
Look 3:
Pops of color instantly change the mood of an outfit and will draw the eye away from anyone the hero piece you're rewearing. Luckily, red shoes are having a moment.
The item: The button-up shirt
If you’re wondering how to repeat an outfit like a true pro, then you need to know the layering tricks editors have been using for decades. For example, a collared button-down can be worn under a crewneck for added dimension. I recommend switching up your classic button-up shirt for one with elbow-length sleeves because it offers a breezy summer silhouette that still feels professional. I style mine with a fun bubble skirt and statement earrings, or black jeans and high-vamp mules. A white button-up shirt is chic blank canvas that can be worn under crewnecks, over trousers, or layered on top of a spaghetti-strapped black dress.
Look 1:
Self-conscious about repeating outfits? Don't overthink it. A simple white button-down shirt and black skirt are timeless for a reason—you could get away with wearing this outfit every week, and nobody would bat an eye. It's always that good.
Look 2:
When in doubt, layer! Adding a blazer on top of a shirt, for example, transforms the hero piece with very little effort.
Look 3:
Accessories can do a lot of heavy lifting, too. If you tend to stick to black leather basics for the office, consider switching it up with brown suede one day. You'll be amazed at the subtle yet effective shift.
The Item: The short-sleeve dress
When I don’t know what to wear, I reach for a black dress. They require little to no brain power to throw on when you’re feeling groggy in the mornings, but still look streamlined. That also means they’re the trickiest to repeatedly wear without coworkers getting suspicious. I like to add a crewneck sweater over my work dresses and pretend I’m wearing a skirt-and-top combo. Or, take the attention away from the dress with an eye-catching bag or accessory.
Look 1:
Colorful statement earrings will draw the eye upward and away from your dress—an intentional move that'll allow you to wear it again soon without anyone noticing.
Look 2:
Next time you wear your favorite dress, cinch the waist in with a belt: It creates a totally new silhouette.
Look 3:
Another easy styling trick: Wear a sweater on top to create the illusion of a skirt.
The Item: The wide-leg trousers
Breezy linen pants are a lifesaver on hot summer office days, so much so that I’m sure you’re tempted to wear them daily. If that feels too casual for your workplace, you can't go wrong with wide-leg trousers. I recommend styling them with exciting personality pieces that divert the gaze from the pants and onto your red shoe, diamond earring, or cool sunglasses.
Look 1:
An open button-down shirt over a tank top is one stylish way to keep your workwear basics from feeling overly stuffy, and it allows you to add a little color to an otherwise neutral outfit.
Look 2:
I said it before: The red shoe trend is a game changer for those of us who need to repeat outfits. It pulls so much focus, you won't need to spend much time overthinking the rest of the look.
Look 3:
Prints are another way to subtly change up a look. Polka dots are big this summer, and not so out-there that you'd feel silly wearing them to the workplace.
