5 Wardrobe Fundamentals for Today’s Ambiguous Workplace

Intersectionalities of Image: The Red Hat + IBM Merger

Since IBM’s $34 billion acquisition of Red Hat was murmured, I’ve received emails from Red Hat executives and VP’s regarding the anticipated cultural shift. Now that it’s official, their questions center around, how should we dress now? Our cultures are so different. Should we dial back the casual dress code a bit? What are our clients going to expect?

IBM, also known as Big Blue, falls right into traditional Corporate American attire consisting of blue button-downs and extra-roomy khaki pants. As they join hands with the sexy new kid on the technology block, Red Hat, you can expect executives to step it up a notch, trading in their pleated khakis for bespoke sport jackets and skinny denim jeans.

Ginni Rometty talks with Jim Whitehurst. Courtesy of WRAL Techwire,    Rick Smith     Ginni Rometty, IBM CEO (left), dons the power color blue that communicates formality. Whitehurt (right), pairs red Italian loafers with well fitting trousers. The fundamental contrast in the company dress culture is on full display.

Ginni Rometty talks with Jim Whitehurst. Courtesy of WRAL Techwire, Rick Smith

Ginni Rometty, IBM CEO (left), dons the power color blue that communicates formality. Whitehurt (right), pairs red Italian loafers with well fitting trousers. The fundamental contrast in the company dress culture is on full display.

The Big Question

How do employees, in the midst of a company revamp, transition their internal brand authentically? It can be dicey transforming into a conservative presence, especially when merging a youthful, forward-thinking company with a traditional powerhouse corporation.

The Problem: ‘Flexible Work Dress Code’ is Subjective

The global investment firm, KKR, sent out a memo recently establishing a relaxed dress code company wide, citing the “changing nature of work places.” So, what’s the catch?

KKR’s memos, like many similar memos about a relaxed work dress code, didn’t specify what types of clothing are appropriate. Instead, the message is that employees get to decide what to wear: “We trust you all to strike the right balance and exercise good judgment.” Despite the easing of the rules, the memo goes on to say that employees are still required to have “business attire available,” particularly for client-facing encounters.

Unfortunately, when companies declare the dress code to be flexible without offering further guidance, what they are really saying to their employees is “you figure it out.”… at your peril.

The Five Fundamentals:

In my view, the flexible work dress code is a bit of a booby trap. Both IBM and Red Hat are comprised of client facing roles that require communicating to both prospective and current clients your understanding of their business needs and challenges. Initially, you accomplish this, nonverbally, with how you present yourself.

As a suiting and tailoring expert, I’m tasked with curating the wardrobes and personal brands for Raleigh’s top business leaders and young professionals rising through the ranks. Here are my top five wardrobe fundamentals to consider in today’s ambiguous workplace, especially in a merger environment:

1. Focus on Your Personal Brand

Regardless of a merger, never let your personal brand be overshadowed by a dress code. Dressing down in response to a company policy can come across as inauthentic. If you’re stylish, maintain it.

A well curated wardrobe will trigger profitable and meaningful conversations, which can be achieved by curating bespoke or applying the TossOrTailor™ method to your wardrobe. It doesn’t happen overnight — it takes time and discipline.

Pro Tip: If you can’t afford bespoke items straight away, invest in a classic suit jacket or a nice pair of dark trousers from a local retailer.

2. Align Your Personal Brand with Your Job Status

Something you’ll want to develop, regardless of your job title, is a “style signature,” which is a topic I will be covering in my forthcoming book. If you want to be respected and appear reliable, dress the part. Imagine a member of key leadership is suddenly unable to attend a pre-planned meeting. Chances are, your boss will ask the young woman known for her sharp trousers and leather trainers to stand in instead of the guy in tattered jeans and a pair of Vans.

3. Dressing Well Triggers Confidence

It’s time to look the part. What better way to communicate presence than having one? Clean up with a well fitting coat in the navy or khaki family in worsted woo, Super 120’s minimum. A well fitted coat can be stored at the office at all times and paired with a chino or a more casual pant, such as joggers.

Focus on dressing well, instead of dressing up, and you’ll come across as someone who cares about the details.

well fitted coat, dressing well .jpg

4. Focus on the Fit

When your garments are tailored and styled to fit your body, you look more put together. Before you invest in a bespoke garment, it’s helpful to gauge your fit preference. Your version of “tailored” might differ from mine.

Here’s your survival guide for the basics of office and lifestyle tailoring:

  • Shirt and Coat Sleeves: Your hands should be visible up to where the wrist flexes

  • Skirts: Aim for a hem that hits at the knee or 1” above the knee and splits no higher than mid quad. This will pass the “sit test”

  • Denim and Trousers: A medium break will be a mild gathering of fabric over the shoe. The Euro hem (above the ankles) should be used sparingly


Ginni Rommetty’s style is always elegant with a bit of bite. The fit helps exude confidence.

Ginni Rommetty’s style is always elegant with a bit of bite. The fit helps exude confidence.

5. Make Sure Your Garments Are in Good Repair

If you wear clothing that looks worn out or outdated, others will judge you accordingly. Toss any shirts that are soiled, worn, or faded — including collars and sleeve cuffs. Respect has to be earned and dressing well can help.

There you have it, five tips for figuring out how to navigate the Wild West of flexible work dress codes. As if you needed another reason to prove the importance of dressing well, there have been several psychological studieslinking how you dress at work to job performance. When you look polished, it affects your mood, your temperament, and your success at work. Being recognized by your coworkers and noticed by prospective clients is really just icing on the cake.

If you’re looking for a premier alterations, suiting, and personal styling experience, our team at Glenwood South Tailors and Alterations is ready to deliver. We are proud to introduce our Traveling Tailoring Club™️, a new subscription service accommodating the budgets of recent grads, young professionals, executives, and everyone in between. If you want to put your wardrobe refresh on 100% autopilot, get started here!

Allie Lochiatto