The Tip Jar #3: What to Wear to the Office in 2024: A Style Dilemma for Modern Professionals

From courtrooms to presentations, nail the modern office look with timeless, versatile pieces.

Last month, the Tip Jar helped a reader break free from their "dadcore" style by incorporating elements of a familiar look into a more versatile wardrobe. This month, we expand beyond just our male readers so that today’s tip will resonate with many people, so let’s dive right in.

Two readers recently reached out, sharing that many people in their fields (including themselves) feel stuck when figuring out what to wear to the office. One, a lawyer, is headed to court, while the other, an engineer, often gives big presentations to the NYC Department of Buildings (DOB). Both are grappling with the same conundrum: It’s 2024, the office looks different, and so do I — what’s the right look for today’s 9-to-5?

Before the pandemic, office life was a true five-day grind. In corporate life, it was all slacks and button-downs or blazers with pencil skirts—uninspired, a nod to the '80s, and stuck on repeat until the weekend set you free. A lot has changed since then, corporate America has done a 180. Some of us are new parents, others may run businesses from home, and many juggle hybrid or full-time schedules. Tossing in early workouts, new hobbies, meal prep, and getting dressed is trickier than ever. Plus, budgets have shifted—whether from career changes, layoffs, or rising childcare costs, we are all prioritizing our wallets differently.

Today, we'll tackle a mix of gender preferences, budgets, and styling needs, creating different outfits that capture the essence of versatile office staples — whether you're headed to the courthouse in your most polished look or dressing like a startup tech guru in more casual attire, dialing it down every step of the way. Not that anyone needs one more thing to buy, but I love that a classic 'power suit' look is versatility at its finest—taking you from the office to a date, meeting the parents, a weekend with friends, and beyond.

A Modern Twist on Professionalism: Redefining Womenswear

I’m drawn to timeless looks with modern twists when considering office wear. Pinstripes are no longer a print reserved for men. It’s the perfect choice, exuding professionalism while adding subtle sophistication. It’s the ideal balance for women who embrace classic style with a fresh, contemporary edge.

Corporate: The Updated ‘Power Suit’

For the ultimate corporate look with no budget limits, start with the updated ‘power suit’ - Paul Smith navy pinstripe blazer and matching wide-leg trousers updated with an elastic waistband for comfort and ease. Including a modernized DONNI wide pinstripe button-down, adds a contemporary twist to the classic ensemble. Plus, a bonus of stripe mixing elevates the entire ensemble. Pair with the sleek Harlow Pump in Nude by Dear Frances, enhancing elegance and stature. Finish with the understated sparkle of SHASHI's Andreia earrings and the minimalist charm of the Sterling Silver Cloud Bangles by Ring Concierge. This look effortlessly blends timeless professionalism with modern comfort and style.

Business Casual: A Chic Nod to Menswear

For a refined business casual look, start with the Paul Smith navy pinstripe wide-leg trousers and the DONNI. wide pinstripe button-down as your foundation. Swap the blazer for a Zara sweater vest, adding a cozy layer that keeps the outfit relaxed yet polished. For an even more laid-back refinement, consider wearing the sweater vest on its own. Ditch the heels and complete the look with sleek Rachel Espresso Leather Loafers by Loeffler Randall, blending sophistication with practicality. Finish off with SHASHI's Andreia earrings and the minimalist Sterling Silver Cloud Bangles by Ring Concierge, achieving the perfect balance of comfort and professional elegance.

Start-Up: The Perfect Casual Comfort Look

For the ultimate "start-up" guru vibe, keep it minimal yet effortlessly cool with a few standout pieces. Start with the Paul Smith navy pinstripe wide-leg trousers, and skip the button-down and vest in favor of the LESET Pointelle Long Sleeve, which still brings in stripes but with a modern textured twist. Ditch your traditional office footwear for the Onitsuka Tiger Tokuten Sneakers, offering chic, casual comfort. For accessories, keep it simple yet impactful with an Aurem Seraphine White Freshwater Pearl Necklace, adding a subtle but striking touch. This combination blends ease and style, creating a confident, approachable work-from-anywhere look.

Budget-Friendly and Still Fabulous: Style on Your Terms

Achieving the same look, but with some alternative more affordable options: Sezane Pinstripe Chelsea Jacket and Sezane Pinstripe Loulou Trousers and Zara Faux Patent Leather Sling-back Pumps and J.Crew Hinge Cuff Bangles

Contemporary Workwear: A Bold Take on Menswear

For menswear, I’m all about classic styles with a modern touch. Pinstripes are always in, but the key to updating the look is experimenting with unexpected color combinations. It’s a great way to keep the sophistication while adding a contemporary twist.

Corporate: The Upgraded ‘Power Suit’ 2.0

For a corporate look, where your wallet’s spending is endless, start with an upgraded ‘power suit’ but in an unexpected dark grey pinstripe color in this Suit Supply Dark Grey Striped Tailor Milano Suit, offering a sharp silhouette with a modern edge. A Todd Synder Twill Long Collar Dress Shirt, is perfect for creating a sharp, yet polished vibe. Add on a Tile Bar Pointed Tip Knit Black Tie to add a sleek, textured touch and Beckett Simonon Dean Oxfords for refined elegance and style. Complete the look with the Massimo Dutti Nappa Leather Belt, and Marcoliani Modal Cashmere Micro Polka Mid-Calf Socks for a touch of whimsical luxury.

Business Casual: A Modern Man on the Go

For a refined business casual look, keep only the blazer from Suit Supply Dark Grey Striped Tailor Milano Suit and add in Aurelien Cashwool® Extrafine Merino Polo Ivory as your top for a less serious but polished take. For the bottoms, look no further than the best-selling Rhone Commuter® Pant Slimter Pant Slim as they are multitasking marvels designed for your busy day. Ditch the tie but keep the balance of accessories to complete the ensemble - Beckett Simonon Dean Oxfords, Massimo Dutti Nappa Leather Belt, and Marcoliani Modal Cashmere Micro Polka Mid-Calf Socks.

Start-Up: Effortless Comfort with a Casual Edge

For the perfect 'start-up' visionary look, channel your inner Kendall Roy with a nod to the pinstripe suit, keeping it casual yet luxe with a Courrèges Gogo pinstripes Cap. Pair it with Everlane Premium-Weight Crew Uniform Heather Oatmeal and finish off with Marcoliani Modal Cashmere Micro Polka Mid-Calf Socks and Greats The Charlie White/White sneakers for a sleek, modern edge to close the deal.

Alternative Styles That Keep Your Wallet Happy

Replicating the Look with More Cost-Effective Choices: Madewell Pinstripe Baseball Hat and Clarks Whiddon Cap Oxfords and Everlane Long Sleeve Pique Polo and Tile Bar Lakeshore Chalk Stripe Charcoal Jacket and Banana Republic Factory Vegan Leather Sneakers.

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I don’t know about you, but I’m inspired by all the options and figuring out how to make them work, even with my office being more business casual. A well-fitted blazer, versatile trousers, and smart shoes can elevate your look without going overboard. The key is adaptability—keeping it sharp with knitwear or sleek sneakers to fit your exact office vibe. Whether you're in court or giving a presentation, it’s all about balancing style, comfort, and budget with versatile pieces that work for your day-to-day.

A warm welcome and shout-out to all the new readers joining in! I hope everyone found this month's edition of The Tip Jar helpful and insightful. If you’ve got more style questions or ideas for future topics, feel free to share your thoughts in the comments below.