Nick Roy has been a successful magician for years. Now he’s creating some real magic – helping men of all shapes and sizes look their best in custom-made garments that won’t break the budget with the Gentleman’s Cooperative. He’s selling them in a “clubby” atmosphere – John Allan’s (111West Jackson Blvd. South Loop, Chicago), a penthouse spa in Chicago where men can get a haircut, massage and manicure and then a shoe shine, a game of pool and a beer. Nick was recently seen on the latest season of “The Bachelorette.” While he didn’t get a rose that first night, his business is blooming.

Here’s a Q&A with Nick Roy about his concept and his (brief) time on the Bachelorette.

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 1. This may seem obvious, but what are some advantages to getting a custom-made suit?

There are several advantages to going the custom route. I would say the #1 reason guys go custom is for the proper fit. The obvious candidates for custom are the gentleman who are big, tall, short, or skinny, but there are plenty of guys in between. When most men say they are a “perfect fit” off the rack, there are usually a number of alterations that can be done to make it an even better fit that they just aren’t unaware of. If you are willing to spend at least $795 on a suit, there’s no reason to go to shop off the rack, and that’s not a sales pitch, it’s a fact. You can get a much better fit and a higher quality fabric by going custom, so long as you have the 4-6 weeks to wait for the turnaround time. Once you get your perfect fit down, reordering is such a breeze since our tailors keep your pattern on file. The other reason men go custom is for the customization options. Choices on pocket styles, pic stitching, contrasting thread, linings, and even a monogram, are non-existent in the off-the-rack world. Men also take more pride in their garments when they’ve had the luxury to design their own, since it has been made entirely for them.

2.What are some sizes and body types that particularly benefit from the service?

Tall guys have a hard time finding clothes to fit their arms, and pants that are not high-waters. Big guys have a hard time finding clothes that actually fit them and don’t make them look even bigger than they actually are. Most larger men have been told their whole life they can’t wear flat front pants because they need the added room from the pleats…not true in the custom world. Short guys have a really hard time finding a range of fabrics since the selections are very slim off the rack. Guys who work out a lot and have a big upper body but a slim waist have a very difficult time finding separates, and by the time the alter the pants that go with a jacket they’ve bought, their side pocket are almost in line with where their back pockets should be…not a good look. Another problem athletic men, and slim men have is finding shirts that don’t make them look like a kite billowing in the wind. Shirts here in America are made for overweight people generally, so a proper fit can really be a nightmare to find.

3. What inspired you to get into this line of work?

I have always been in sales, and always had a eye for fashion, so when Tom James had asked me to interview out of college, I checked it out. What I love about my job is that no day or client is the same, and you get to meet so many different walks of life. I’m definitely a people person, and everyday I get to outfit some of the most interesting people you could imagine. I also love the fact that at the end of the day, it’s just clothes. If your Northwestern Mutual guys screws up your account, it’s a lot more serious than me just having to let out a side seam. I’m a really easy-going down-to-earth kind of person, and this line of work fits perfectly with my personality.

4. Tell us about your space?

Our shop is located in the penthouse suite at 111 W Jackson in Chicago. We have partnered with a high-end men’s hair salon, so in addition to all of our custom outfitting, men can get a haircut, shoe shine, manicure, or even play a game of pool, relax in the lounge, or smoke a cigar on our rooftop patio. The space is really special.

5. What kind of experience are you trying to create?

Whenever I meet with a guy, it’s completely different than walking into a Nordstrom’s. I take the time to understand what each person does for work, who they see, and what image they try and portray, because as we all know, we only get 7 seconds to make our first impression. Going the extra mile is what distinguishes Gentleman’s Cooperative from our competition. Most retail stores don’t give men a reason to be loyal. We have created an environment where you will never have to worry about a pushy or incompetent salesperson. It’s a place where you feel at ease, and more like a member than a customer. Through our model of reciprocity, men quickly understand that it’s not just about the clothes with us…it’s about the lifestyle. After being in the industry for several years, it’s astonishing how much of a markup people will charge their customers. Granted those people will just say “it’s business”, but our philosophy is to give our guys a high-quality product we can stand beside and the epitome of customer-service, in exchange for their loyalty.

6. What did you learn about men’s fashion from your time on the Bachelorette?

Ah, the bachelorette. Well honestly I didn’t really learn anything about fashion from that experience, except that I had the best suit out of all the guys…which should be expected. I legally can’t speak to most of the behind the scenes stuff, let’s just say reality tv is not what you expect, as I’m sure most people are well aware of.

7. How does your own sense of style inform your work?

As in any field, it’s crucial to know your craft. I’ve never been one to follow fashion blogs, and stay on top of what’s trendy, but over the years I’ve read many publications on the do’s and don’ts of timeless fashion. I am definitely an outside the box thinker and have an intuition for what works. I would classify my sense of style as bold and timeless, because as we all know, fashion fades and style is forever. I love bright colors and loud patterns, which I would attribute to my personality, but my fashion sense has been more innate. A crucial rule for how I coordinate outfits is: Major Minor. What I mean by that is the minor color of a shirt should be the major color of a tie. The major color of a shirt could also be the minor color of the pinstripe in a suit. The major color of a pocket square could be a minor color of your shirt and tie. When your coordinate outfits according to this rule, things pop, they work together, and really turn an outfit into a wow-fit.

8. What’s your advice to clients on becoming one of the BestDressedMenOnThePlanet?

One rule I live by, is to be the best dressed man in the room by 10%. I’m very humble and not loud our boisterous, but you will certainly turn heads in a Gentleman Approved way if you shoot for dressing 10% better than your peers.


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Ties: $75+
Shirts: $99+
Pants: $249+
Shoes: $400+
Sport Coat: $625+
Suits $795+

Interview by Steve Oldfield

4 Responses to The Bachelorette’s Nick Roy Creates The Gentleman’s Cooperative: A space for Men to Shop, Drink, and Chill


  2. Fadell robinson says:

    very impressive website. i have yet to visit the store. it all sounds very exciting.

  3. James Christensen says:

    I am a loyal customer. don’t be foolish and spend $1500+ on an off the rack suit without coming here first. I treated myself to a navy blazer for my 60th birthday (~$1200) and it surpassed my expectations. I deal with Blake who is fantastic, but Nick keeps an ever present eye to make sure everything is a spot on fit. Please, I have shopped at Neiman, Saks, etc., come here first.

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