Fashion, Tips & Techniques

5 successful men on how to dress the part

4 key things to remember.

words by: Natasha Marsh
Mar 25, 2020

In 2018, I was way too comfortable at work. After two years at my company, dressing up became more of an afterthought. The culture got so lax that one day, when I wore tailored pants and a structured shirt, my coworkers asked if I had a date after work. Low point. So I decided it was time to hold myself – and those around me – to a higher standard. 

So I conducted an experiment. At least once a week for an entire year, I dressed as though it was my first day. The results were astounding. I felt more confident, and in a weird way, more capable

Curious to see what other professionals thought, ULTRA sat down with seven successful men working across fashion, law, government and art to see how they are dressing the part. 

Let’s start from the beginning, in this case, the interview. 


Know your audience 


You research a company beforehand to prepare for the interview, right? The same work should be done when deciding what to wear. Most companies are on social media, glancing over their profile to see what employees are wearing will give you some insight. If it isn’t obvious, scroll over to their tagged photos and see if you can at least get a vibe of their culture. Overdressing or underdressing could be a red flag for potential employers. 

Ten years ago, when Oscar was starting his career in Sacramento, slacks and white button downs filled his closet. His role: youth specialist for the government. His job was to help troubled youth find their way. Following the culture and nature of his company, Oscar was dressed daily in crisp black slacks and a white button down. 

When he moved to Los Angeles to pursue film, he took his wardrobe with him. “I felt so overdressed,” Oscar admitted, showing up in a tie, black slacks and an iron-pressed white shirt. His interviewer, meanwhile, was wearing light blue jeans, a white t-shirt and hat. “I felt almost embarrassed,” he admitted.



Research is crucial, echoes NYC-based stylist, Miguel. “If I’m going to Vogue, I’ll do Dr. Martens or Grenson boots. If I’m going to GQ or Office Mag, I’ll be in sneakers.” Working in fashion, it’s important for him to know the style of who he’ll interview with. It’s a cut throat industry and his biggest fear is offending a potential manager.

If your work involves client meetings, Landon, 31-year old marketing executive, recommends wearing a watch to interviews, “if you wear a watch, it suggests reliability and that punctuality is of great concern to you.” 


Preparation is key 


Remember that one Outkast song where Andree 3000 sings, “You can plan a pretty picnic / but you can’t predict the weather?” You can plan for every detail of your interview but you never know what drama or inconvenience lies ahead.  

For 28 year-old legislative director Trent, his two most important things are a haircut and shoe shine. “I never forget a shoe shine. I’ll either head to Nordstrom or a small place inside our building.” 

To streamline your morning routine, especially if you tend to sleep through your alarm, pick your outfit beforehand. Sam, a 28 year-old attorney, has a color coded closet, sectioned off for coat jackets, blazers, slacks, trousers, and different shirts. Majority of his wardrobe is dry cleaned to maintain prestigious quality. In the event that he washes his dress shirts at home, he will iron them out when they come out of the dryer. 



Now that you’ve got past the interview stage, how can you maintain your style?


Set boundaries


As your career progresses, the pressure to dress up can intensify. In some industries it becomes an expectation to dress the part. But do this with caution. Meaning, dress within your means. “When I was in school I shopped at Marshall a lot. Not to downgrade Marshalls, I just had to be smart with looking presentable while on a student budget” Sam said.

Of course, while on the clock, you want your manager and coworkers to respect you and you want to look like you know what you’re doing. But that’s not necessarily communicated through a pricey wardrobe.


Get personal


Society makes you believe dressing the part looks one way and one way only. But it’s OK to put your own twist on things. Depending on your industry this might take a bit more creativity. 

For Trent, the public sector doesn’t offer much leeway on colors or prints. “It’s definitely about the fit and tailoring. You can add in color and such with a tie or sock but your suit has to be clean colors,” he concludes. 

Working as an attorney, Sam experiences similar style restrictions. On the weekends, Sam likes to take risks in his apparel, often sporting blue shirts with gold pandas on it. But in an industry where things have to be quite clean and professional, he finds excitement playing with his cufflinks and socks. “I would get a matching blue cufflink, maybe even patterned, to match my shirt. To make it all blend in,” he says. “That’s my favorite part – doing the little things that no one would notice. Little secrets.” 




For many working men, fashion gets put on the back burner the longer they stay in a position. But no matter how busy you get, there’s always room to polish your professional style.