How to Actually "Dress for Success," According to a Career Expert

Working in a creative space is a blessing and a curse when it comes to getting dressed in the morning. While we rejoice at the opportunity to embrace our personal style, a lax dress code can be a bit confusing: Will my boss think I take my job less seriously if I forgo a button-down in favor of a comfy T-shirt ? Does HR really approve of jeans?

To help answer these questions and quash your worries, we sat down with career expert Lauren McGoodwin, founder and creator of Career Contessa, to learn her thoughts on how to dress for a professional environment without sacrificing your personal style. Scroll to read her advice (and feel free to treat yourself to a few new HR-approved pieces in the process).


(Image credit: Career Contessa)

Tell us a bit about your business.

Career Contessa is a comprehensive resource for women that provides online tools, advice, courses, and the direction they may need to navigate, enhance, or change their careers. I wanted to ensure women felt supported.


(Image credit: Style Du Monde)

What exactly does dressing for success mean to you?

I used to reply to this by saying "Dress for the job you want,” but after interviewing plenty of great women for my podcast, The Femails, I realize that dressing for your authentic self is best. If that means a great pair of heels, great, but it might also mean sneakers with a dress. However you need to dress to show up and perform at your optimal level is how you should build your look. If that means being more comfortable and casual so you’re not shifting around at your desk all day getting distracted, opt for that.


(Image credit: The Style Stalker )

Speaking of dressing for the job you want, not the job you have, do you think upper management notices how employees dress?

All people experience unconscious bias, so you might have a boss who associates your appearance with how much you care about work. A good way to decide how important your put-together appearance matters to your boss is by looking at how they dress for their day-to-day. It’s not a great reality, but it’s the truth. That being said, putting in extra effort should not mean changing your look. Just because your boss wears a blazer and slacks doesn’t mean you need to change your personal taste to impress them. Find a way to look polished that feels true to you. And you can make sure when you’re a boss one day to only promote/reward based on merit.


(Image credit: The Style Stalker )

Creative offices with no dress code can feel like a bit of a gray area. Are there any pieces you believe should be avoided despite not necessarily being inappropriate?

I think "polished” and "practicality” are a good filters to run gray-area items through. For example, do flip-flops look polished? Are they practical if you need to walk around the office with clients? Probably not. Are ripped jeans polished? Not necessarily, but they may look polished as long as you pair them with the right top and shoes.

If your pieces aren’t stained, worn-through, and or impractical for your job, they pass the test. I’ve found that investing in wardrobe essentials is key. Some items I invested in that I still use all the time are flattering dark skinny jeans, leather flats, a black blazer in a less-formal material, and a "grown-up” backpack that feels practical (but a bit more exciting that a tote or briefcase).


(Image credit: Style du Monde )

What if your office does have a strict business dress code? Any tips for still making the style your own?

My first job had a strict business dress code, and most of the things I wore were black, white, and gray. To mix it up, I’d wear brighter jewelry, paint my nails a bold red, or wear a printed shirt under my jacket. It’s important to inject a bit of personality into your look when you can.

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