When I was building my startups, I wasn't making any money. My mom was worried about my future and would often be quite dramatic. In fact, in front of our statue of Jesus in our home, she'd plead, "Please God, give my son a job where he has to dress nice". I ended up directing an entrepreneurship program at a Tier 1 research institution, and I definitely did not need to wear a suit to work. But I did. As soon as I got the gig, I ordered ten suits, none of them black.

Thanks, mom.

Now I work mostly with students, and most professors at the university do not wear a full suit. However, for me, given that I started this role extremely young, being sharply dressed has always worked in my favor. Reverse ageism certainly exists. More importantly, I always feel ready for anything once I step out of the door. This won't work for every career (and might even be inappropriate), and is simply what I do.

It's kinda funny because most people on campus assume I'm a student interviewing for a job. I’ve been ‘interviewing’ for years, I suppose.

Ananya Tiwari, founder of the nonprofit SwaTaleem

When I first started dressing more seriously, I had tremendous difficulty finding fashion advice for muscular and dark-skinned men. When I was on Pinterest searching 'Indian men style', I'd get a bunch of Bollywood and wedding outfits. If I searched 'black men style', I'd get images of white men dressed in black clothes. And if I Googled 'muscular men style', I'd get a whole nother list of useless tips. Here's what I learned about dressing up, and I’m sure I broke all the fashion ‘rules’.

I call it resort kick—from the time I misheard resort chic while on vacation. I can dress it down or dress it up, add accessories as needed, and most importantly, feel good.

Apologies in advance for the selfies taken in the Business College bathrooms.

Dr. Darnell Leatherwood, US Candidate for Congress

The most important rule is to create your own style. Take inspiration from everywhere, but blend it to mold to you. Experiment with different fabrics, colors, and styles. Experiment until the style gives you confidence. How do I want to look? You're not just using pieces of fabric to cover your body, you're trying to create an image for yourself. How appropriate or "good" this image is, depends entirely on the context it's inserted, and your objective.

Fit is everything. Buying clothes for muscular bodies is tough, but a fit body simultaneously will look really good in a variety of clothes (if you need motivation to workout). I love how James Bond fought crime effortlessly in a suit—tailoring and good material are essential. I, for one, bike to work in a suit and have done everything from playing frisbee with students to moving furniture in our office in a suit. Tailoring is key.

Rules are important, but not always necessary. Lots of online wardrobes tell you you must do things this way or that way. It misses the most important point—context. Getting fashion advice and inspiration from the internet may feel disconnected from reality. Fashion differs tremendously based on location, occasion, mood, intent, and author. Do you want to fit in? Do you want to stand out? Do you want to look professional? What do you want to signal to the world (and yourself)? Once you have that answered, you're on your way to creating your own style. The most important fashion advice is often internal.

You don't need a lot of clothes. 80/20. Have a few solid, versatile pieces. I own suits and workout tanks. I'm either working, working out, or sleeping. My white French cuff shirt is my go-to with my suits, for example, and my denim jacket works really well with all of my fall outfits. I’m picky because I truly want to love what I wear, and it shows. It also makes dressing very simple because I only have so many options.

Black and white are simple and go with everything. Unity can be a strong characteristic in outfits.

Furqan Hadi, owner of the NOW Massage & Clean Your Dirty Face

Cost doesn't guarantee fashion. Starting off, I didn't have much to splurge. My first suits were from retail malls and then tailored. Let me tell you, nobody knew the difference. You can go a long way with a bold tie, good shoes, and a little confidence. Dressing sharp doesn't need to break the bank if you're thoughtful.

Accessories - the cherry on the top. Socks, watches, cuff links, pocket squares, ties, shoes, and belts can add the finishing touches. Complete the outfit, don't make the outfit. Funky socks for the win. The outfit should be seen as a whole, not as a sum of individual parts. This applies to many elements in the outfit: fit, color, level of formality, style, etc. That is not to say that there can't be a hierarchy between different pieces of an outfit. It's ok to have one of the pieces as the focal point, as long as the outfit is designed to support it.

Some suit rules: unbutton the last button, unbutton when sitting down, dark suit -> light pocket square & vice versa, no white socks, waistcoat & tie should end at top of the belt, shirt cuffs shouldn't go over hands, tie knots shouldn't be too big or too small, tie should contrast with the suit, tie-bar shouldn't be wider than the tie, remove stitching and labels, the jacket should cover the zipper, and pocket square and tie should typically not match.

Lastly. These are just some guidelines I came up with. There are no rules for you, except the ones you create for yourself!