The Professional Touch: Design Your Work Wardrobe with Ryan Newman of Wilfred Newman

by Kate Jacobsen | March 28th, 2012   

By Kate Jacobsen

As the hour closes in on 5 o’clock, the nostalgia associated with the end of another work day begins to build. Whether it be watching Derrick Rose lead the Bulls to yet another Playoff game or attending the hottest new restaurant opening, 5 o’clock serves as a cattle call for working professionals all over the city to head to their favorite after-work spots. However, one question still remains: What outfit do you wear to the office that will segue from day-to-night?

After reading (and writing) countless articles about day-to-night fashion for women, I decided it was time to get a man’s perspective on the subject – and on men’s fashion in general. As a stylish man himself who dresses the top business professionals and athletes in the city, Ryan Newman, President of Wilfred Newman Clothing, was the ideal candidate to sit down with and have a candid conversation about the men’s fashion industry. I asked Newman to pick one of his many favorite after-work spots. After choosing the Pump Room library, we met where he revealed the best spots for dates, where to watch sports, and where to conduct client dinner meetings. He also disclosed how to dress for all of the aforementioned occasions and forecasted future men’s fashion trends. We also discussed the business of tailoring and Newman provided essential styling tips every guy should know. Read the full interview below.

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Ryan Newman, President of Wilfred Newman

Ryan Newman grew up in Columbus, Ohio, home to some of the biggest retail brands in the United States, including Abercrombie & Fitch, Express, and Victoria’s Secret. As Newman was exposed to industry execs such as Michael Weiss, President of Express, and Les Wexner, Founder of Limited Brands, he became fascinated by the sense of style exhibited by these men. Newman moved to Chicago embarking on a journey to help others look their best. Propelled by his entrepreneurial spirit and a keen eye for fashion, Newman has been the driving force behind the success of his company and the Wilfred Newman brand.

TheWorkingWardrobe: Tell me more extensively about your background and how you ended up in men’s tailoring?

Ryan Newman: I love that question. I get asked that all the time. I always had an interest in fashion. I never really knew how I was going to get into it because I never wanted to work retail. I didn’t have any intention of getting involved with [men’s tailoring] until I moved to Chicago. A friend of mine who I grew up with was working for a company in men’s tailoring. He hired me and I apprenticed with him, learning the industry. I worked for [the company] for about 4 years getting a good grasp on the business. Afterwards, I did a stint with another really large clothing manufacturer where I was the Vice President of Sales Development. Hiring and training people forced me to really hone my skills. In between that job and starting Wilfred Newman, I traveled somewhat extensively all over the place building relationships with manufacturers so I could start my business.

TWW: When did you start it?

RN: I started [Wilfred Newman] in the Fall of 2009 with a very limited budget and the lack of an in-depth business plan. I just had a desire to start the company. I felt like I could accomplish a lot by doing it. I have faced a lot of challenges and adversity along the way, but things are finally starting to come to fruition.

TWW: How do you think your background in sales and marketing helped you?

RN: I think [sales and marketing] helps a lot. It appeals to people. I’m social, very observant and read people well. I know what people gravitate towards. I have a knack for that sort of thing. It’s just more my personality, I guess.

TWW: How would you instruct your clients to effectively translate their office attire from day-to-night for after-work get togethers?

RN: I would tell them not to think too hard. Men need to keep it classic and simple. For instance, a nice alternative to a tie would be to wear a pocket square. It’s also nice to have a good selection of blazers and sport coats that you can wear with jeans or slacks. It’s not quite as formal as a suit but still looks professional and mature. Office outfits also depend on what season it is. In fall/winter you can do a layered look by wearing a sweater over a button-down shirt. In the summer time you can wear a v-neck shirt with a blazer. This particular ensemble looks cool and really fresh. Just have everything well-fitted. That’s very important. As long as it fits you right, it will look good.

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TWW: Do you follow men’s street style fashion blogs, men’s fashion week shows, trends, etc very closely? If so, which ones and why? How important, if at all, is it to the success of your business and men’s tailoring?

RN: Honestly, I don’t follow it a whole lot anymore. I used to. Men’s tailoring is a timeless look. I’m not really trying to reinvent the wheel or push the envelope. I respect people that do, but it’s not my style. Men’s tailoring will evolve a little bit here and there, but it doesn’t get too aggressive. We might see different vents or lapel styles, but in reality, men’s clothing is pretty straight forward. I usually like the [blogs] that incorporate more of a lifestyle as opposed to just fashion. I like TastingTable.com. I look at that all the time and UrbanDaddy.com, of course. I try to keep it local to Chicago. As far as strictly fashion, I probably prefer to look at the women’s stuff more so than the men’s.

TWW: What direction do you foresee men’s fashion going in the next five years?

RN: To me, it’s always going to take reference from history. Different eras becoming more popular here and there. Lately, we have seen a huge resurgence in the whole vintage 20’s sort of feel with Boardwalk Empire. I think two years before that we saw a big resurgence in the 60’s with the popularity of Mad Men. It will be interesting to see what direction it goes in. I hope not, but maybe the 70’s?! I have noticed Tom Ford doing a lot of wide lapels.  I am kind of a purist. I hope it doesn’t revolve back to bell-bottoms. or any loose-fitting clothing. I like things that are tailored and neat, real trim and cut properly. That is the direction I’ll be going in.

TWW: What are your thoughts on the coined term ‘business casual’ and its seeming growth in the workforce?

RN: Business casual is actually receding and people are starting to dress a bit more professional again. I have noticed that a lot, especially with my younger clients. Guys in the early stages of their careers want to dress better. I have also talked to older guys who are saying that their offices are getting more dressed up. Everything reciprocates and comes back around.

TWW: Why do you think that is?

RN: Honestly, I think a lot of it has to do with television shows, magazines, our culture and our society.

TWW: I feel like a lot of people are trying to do whatever they can to stand out, especially with the job market being so grim.

RN: The last thing guys want to do is stand out. They want to look sharp, be classic and well put-together, hence, the custom-tailored suit.  Granted, it may be a basic plain navy solid suit, but when it’s cut really well and tailored specifically towards them, then we focus on the details: different lapel styles,  different lapel widths, different side vents, functional working button holes, different colored linings inside the jackets. We might do something as subtle as putting a pocket on a slant to make it look more modern. Everyone is unique, everyone likes to wear their clothing a little bit different. The nice thing about Wilfred Newman is that we focus on each individual’s preference whether or not it’s how much shirt-sleeve he wants to show or how much break he wants on the pant bottom. Those are all details that we take into account.

TWW: What do men look for when they make purchases, especially when it comes to work wear?

RN: I think most guys gravitate towards the fabrics, then they really depend on me to make sure everything is fitted properly. Every guy that I work with wants everything to be trim and to be nicely tailored.

TWW: What about accessories?

RN: I think accessories are important. Right now, I am working on a whole line of cufflinks, neckwear, pocket squares. You can do a lot with accessories. It really makes the outfit. If you wear a pair of lousy shoes with a $10,000 suit, it’s going to look like crap. Just match your belt with your shoes.

TWW: What are three essential items that every man needs in order to have a successful working wardrobe?

RN: If he is a business professional, then a navy solid suit is a no-brainer as a foundation and the number one item. It’s the most business appropriate. You can wear it for any job interview or any business meeting. Navy suits can be worn with almost any shirt and tie combination and can be dressed up with black or brown shoes. Number two, as boring as it is, would be a nice crisp clean white dress shirt. It goes with everything. Trust me every guy needs it. For the final item, I would definitely recommend a nice classic blazer that you could wear more casually. It’s something you can wear with dark denim, wear out for drinks or cocktails. You can dress it up with a button down shirt or a V-neck sweater. It is very versatile.

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Classic Wilfred Newman Blazer - #3 on Ryan's list of essential men's items

TWW: Men have many choices when it comes to tailoring. What do you think sets you apart from your competitors? Style, quality, competitive pricing, customer service?

RN: Actually it is everything. I have been in the industry for a while allowing me to truly build a strong foundation. I make cool, classic clothes that are well constructed. I can give guys great advice on what to wear and what looks good. I give impeccable customer service. For instance, I’ll meet with clients at 7:30 in the morning or at 9:00 at night. It’s a very customer-oriented type of service. Wilfred Newman is unique. I am not trying to copy all the other large custom-clothing companies out there who focus solely on direct sales and mass producing everything. Wilfred Newman is better style and in a league of its own.

TWW: What does it take to sustain a successful business in men’s wear? Any secrets?

RN: Positive mental attitude. I think that is something that resonates in any industry. If I could tell you all the obstacles I have had to overcome, you would laugh. You have to have a willingness to succeed and the drive to do it. You can’t get down on yourself or be negative and quit. I think there were a hundred times I could have easily given up, but I’m still trucking along, making things happen.

TWW: What can we expect from Wilfred Newman this coming year? The next five years?

RN: I’ve got a lot of stuff in the works, including cool new styles and concepts. We are going to be growing as a company and really make a mark here in Chicago and nationally as well. We will never be like one of those major companies who hire people left and right just to throw suits at their clients. We will always be small and unique. I am big on staying true to who I am and what I envision for Wilfred Newman. As long as we supply people with a great product that they really love, then I’m happy.

TWW: Do you feel that as a demographic men are overlooked in retail/fashion business? Do you think it makes it easier or harder for you when it comes to marketing your products? For example, are you able to capitalize off of the lack of it or do you have to work harder to gain business?

RN: I think it is difficult. A lot of guys don’t care enough. They don’t put enough thought and consideration into their appearance. I think that there is a misconception that if guys care too much about the way they look, then they are vain or metrosexual. Guys get afraid of that sort of thing when in actuality people respect guys that dress well and look good. I wish guys would care a little bit more. It would make my life a lot easier.  There’s a portion of my clients that have no clue how to dress and are in dire need of help, so they come to me.

TWW: You previously said that you pick after-work places depending on your mood. What was your mood today that inspired you to pick Pump Room? Why do you consider this one of your favorite spots in Chicago?

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Pump Room Library

RN: I like the fact that it is a Monday night and you can come in, sit down and relax. I love the atmosphere here. I love the fireplace. It’s a sexy vibe, and I like that. If it was a Friday or Saturday night, I might not come in. I might be better off cooped up in a dive bar somewhere.

TWW: I’m going to give you 3 scenarios for after-work spots. Please answer accordingly. What is your favorite after-work bar where you would go to watch sports? Why? Drink of choice? And of course, what would you wear?

RN: I live right down the street from Public House. It’s pretty convenient. I have so many favorite spots. For sports it’s kind of hard, I like Fireplace Inn, Benchmark in Old Town. Those are cool. There is always a new place opening up. I usually drink beer: Budweiser bottles and shots of Jameson. Jeans, Nikes and a shirt.

TWW: What is your favorite after-work date spot? Why? Drink of choice? What would you wear?

RN: Honestly, I really love Gilt Bar. I know I am keeping it real local because I live in River North, but it’s where I would go. I’m friends with a lot of the staff there. Sazerac. They make a really good one. I always end up wearing jeans and a blazer.

TWW: What is your favorite after-work place for a meeting? Why? Drink of choice? What would you wear?

RN: Joe’s Stone Crab. Suit it up.

Wilfred Newman Clothing is located at 161 W. Kinzie, Suite 2701. For an appointment, please call 312.854.1730. You can “Like” Wilfred Newman on Facebook or follow him on Twitter at @WilfredNewman.





@DesignDiction LOL well who WOULDN'T?! @wilfrednewman #fabinterview


@michellepavlack Thanks so much for the shout-out! @DesignDiction @wilfrednewman