My Style: Ross Whitfield

Name: Ross Whitfield
Residence: Traders Point
Occupation: Owner, Ross Whitfield State Farm (Located on Massachusetts Ave)

When it comes to style, Ross Whitfield is on point. Whether he is sporting the perfectly executed bow tie, or rocking an exquisitely tailored suit, Ross is no stranger to style. In fact, he is one of fashion’s biggest advocates. Believing whole-heartedly that what you wear defines you, his “classic with a hint of English flair” look is a testament to dressing up, not dressing down. Whether he is out and about on Mass Ave, heading to the theatre, or even grabbing a quick bite to eat with his wife, Whitfield busts out the fashion A Game. His look is consistent and curated flawlessly, encouraging us all to take inventory on how we want to be seen, how we want to feel, and how what we wear gives us a visual voice that’s louder than we realize.

Where are you from?
I was born in raised in Indianapolis on the Northwest side of town.

Tell me about yourself.
I own Ross Whitfield State Farm located in the 400 block of Mass Ave. I really love having a business downtown on such a wonderful artistic street. I have amazing neighbors and feel so supported in the community. That’s not something every downtown has, but ours definitely does.

Walking down Mass Ave is where I first spotted your impeccable taste in fashion. Whether it be your perfectly fitted suits, to your pocket squares. When did this sense of personal style ignite in you?
I can remember being very aware of my clothing and physical presentation as far back as kindergarten.  There is a funny story mother tells people about my first day of school.  I insisted on wearing my Sunday suit to school along with one of my father’s old briefcases filled with coloring books.  I saw him leave the house everyday dressed this way and I wanted to head off to my office looking the same way. I guess you can say it just continued to grow from there.

How would you describe your personal style?
I would say my style is a melding of Classic American/Prep and Traditional English.  I tend to be fairly conservative with an attention to detail.

Who or what inspires your style?
Again, my father had a major impact on my idea of how a gentleman dresses and carries himself.  In his heyday he was a larger than life figure with enormous stature. His personality and sense of style had a major impact on me, and how I saw myself.  He always shared with me the “rules” of dressing; how to appreciate good craftsmanship and what to look for in terms of quality. He educated me on all of it, from shoes to watches. Just as importantly, how to care for these items so that they lasted a long time.  They were an investment of sorts.

Do you have an interest in wearing independent labels?
I do own a few independent label pieces that are an important addition to my wardrobe. I would say they are my favorite pieces I own.  They are inherently unique and well made, so you really become quite fond of them and realize how important it is to find good quality products.

Where do you like to shop?
I tend to shop at Nordstrom and Raleigh Limited; when both stores have the periodic sales.

Favorite local business?
It’s funny, I don’t have one specific store that encompasses my sense of style.  You have to pick up items here and there that suit you and put the entire look together on your own.  Given my style, and my interest in wearing mostly classic pieces I don’t feel the need to continuously update and reinvent. I’m happy owning several nice pieces and just taking care of them. I replace items here and there as they wear out, but for the most part; I wear clothing I’ve had for over a decade.

Do you have a favorite local designer?
I don’t know if one considers Andrew Porter Fine Clothiers a designer, but I really like working with him. When I have an idea for a suit or sport coat I take my thoughts to him. The fact that I can share my vision and he will create exactly what I had in mind is incredible. It feels like creating your own piece of wearable art. It is one of the purest forms of self-expression and feels incredibly gratifying. He is truly an artist.

Describe your thoughts on the fashion scene here in Indy. What do you like and what do you think could be better?
The Indy fashion scene really has come quite a long way. It seems to me that more and more guys are paying attention to the way they dress.  Obviously, there will always be men who don’t really care what they wear and that’s fine; but increasingly I find myself complimenting gentlemen on items that they are wearing.  My office is downtown on Mass Ave and it isn’t uncommon for me to be walking past someone and say, “Nice jacket” or, “that’s a great pair of shoes” or “I dig your lid (hat)”.  I think the hipster scene has something to do with this as well as the fact that we are experiencing a migration of individuals relocating to our city from across the country and internationally.  This adds a bit of diversity to what is expected by way of men’s fashion here in the Midwest.  Its okay to give thought to what you put on your back.

Define fashion.
I am a firm believer that fashion and trends have nothing to do with one another.  Fashion is your own interpretation of style.  It’s what’s functional for your everyday activities. It’s what makes you, you. It’s an opportunity to voice exactly who you are without saying a single word. What a special thing, to express ourselves that way.

What is the one wardrobe essential you can’t live with out?
The sport coat. I love my jackets because they are so versatile, I can wear them with anything. I have a pretty big collection now.

Best fashionable moment?
When I was a year or two out of college I was invited to my first black tie event. I decided to purchase a tuxedo instead of renting one. I also went to Brooks Brothers and bought a real bow tie then proceeded to teach myself how to tie it. At the end of the event, opened my collar, untied the tie and allowed it to drape down my chest. I felt like a million bucks.

Favorite local event to get dressed up for
Indy Reads Alphabet Affair is an event my wife and I attend annually. We always have such a great time and it’s the perfect excuse to get dressed up and have fun. It’s also a great excuse to have fun with what you wear.

Worst fashion trend
Business casual and Crocs. I hate Crocs; they are foam shoes for goodness sake.

Best fashion trend
Best fashion trend…that’s a hard one as I don’t generally subscribe to trends.  Maybe the pull away from pleated pants to flat front trousers. That definitely needed to happen.

Favorite spot to get dressed up for a night on the town
My wife and I really enjoy going to the IRT. Once a month we will get cleaned up, but on our best and take in dinner and show.

Last but certainly not least, name your favorite fashion icon.
Easy. Ralph Lauren, Cary Grant and James Bond.

image by Aubrey Smith
image by Aubrey Smith
More from Laura Walters

My Style: Stacey Green

“The fashion scene here in Indianapolis is growing. People are finally not...
Read More