Custom Men’s Underwear: Enticing Styles by Anderson/Chiles

Made-to-order. What images do those three words conjure up in your mind? Perhaps made-to-order pizza? Made-to-order suits? Or if you are a Seinfeld fan, maybe you remember the housekeeping company that sent Jerry a maid called Maid to Order (it’s a pun). What about custom men’s underwear?

One item that I never thought would be made-to-order is underwear. You read that correctly. Not mass-produced boxer briefs sewn in large textile factories, stuffed into smelly plastic bags, and then stocked by the hundreds at big-box/high street retailers. No, I mean tailor-made, fully-customized underwear for the highly sophisticated man (or woman!). And they are sewn by a woman who might just possibly be more passionate about men’s underwear than I am!

And with that passion, I kick off my inaugural Underwear Startup series by interviewing Bernadette Anderson-Chiles, founder and owner of Anderson/Chiles. While Ms. Anderson-Chiles designs and manufactures women’s and men’s underwear, I interviewed her only because she made custom men’s underwear. We had a fantastic time together for our hour interview over Zoom, and I felt her passion for ensuring men wear the best underwear on the planet. Yet, how did Ms. Anderson-Chiles, living in a conservative small town in Northern Ireland, become a bespoke underwear tailor for men? Well, let’s find out!

Custom Men’s Briefs by Anderson/Chiles

London: High Street High Fashion

Ms. Anderson-Chiles’ interest in underwear has been decades in the making. She embarked on her underwear path in life by earning her degree in Contour Fashion from De Montfort University, specializing in Swimwear and Lingerie. At the time, it was the only program in Europe and Ms. Anderson-Chiles lept at the opportunity. 

Yet, after Ms. Anderson-Chiles worked in the swimwear industry post-graduation and then freelanced for two years, she made the switch to teaching. “I really didn’t want to be a swimwear designer,” she notes. “I don’t know how I fell into teaching, but I became a teacher.”

Care about Men’s Underwear? Subscribe to my newsletter to receive my tips and reviews!

Favorite Underwear Style

She taught for 23 years at a public school near London – where she and her husband resided – teaching students textiles and art. With her husband, a freelance glass tradesman, Ms. Anderson-Chiles enjoyed her comfortable lifestyle in London. Yet, while Ms. Anderson-Chiles loved her students and loved teaching, she started losing her teaching flame. 

Looking for a creative outlet, Ms. Anderson-Chiles evoked her university days and side hustle as a freelance underwear designer. But as head of the Art Department at her school, and with the stressors of daily life, Ms. Anderson-Chiles didn’t have the time to dedicate to her underwear design business. And as she was approaching her 50th birthday, she knew she had to make adjustments to her life. 

“It isn’t that I don’t love teaching, but I was getting to the point, I just thought if I don’t do something now, I am going to be in my teaching post the rest of my life. Is this really what I want? Life is too short. One of my friends got seriously ill and unexpectedly passed away. I think that kind of catalyst, along with stuff happening at work, made me realize life is too short.”

– Ms. Anderson-Chiles

Approaching her 50th birthday and with the sudden passing of her friend, Ms. Anderson-Chiles felt the pressure to make a significant change in her life. With the support of her mom and her husband, she quit her job, packed up, and moved back to Northern Ireland to focus on her underwear business full-time. And with that, let’s dive into Anderson/Chiles custom men’s underwear.

Bespoke Underwear

Unlike mass-market brands, Ms. Anderson-Chiles prides herself on customizing each pair of underwear to her “clients,” as she calls her customers. Walking me through her process of onboarding a new client, she starts with an interview of her new client, asking them what they are looking for in a new set of underwear. For inspiration, she recommends new clients review the Anderson/Chiles website to see what models and colors inspire the client. After the website review, Ms. Anderson-Chiles may take her clients in two directions.

For more straightforward assignments, Ms. Anderson-Chiles can easily tweak designs found on her website. For example, a client may like a set of shorties (square-cut trunks to Americans), yet the client prefers a particular color palette. Ms. Anderson-Chiles can easily adjust the coloring to suit the client. After having the client send in their body measurements, Ms. Anderson-Chiles will create the customized men’s underwear pairs and send them off. An easy way to receive underwear precisely the way you want it!

Custom Couples’ Matching Underwear Pair by Anderson/Chiles

For truly custom men’s underwear, the process is more complicated yet necessary to create truly one-of-a-kind designs. After discussing in depth what the client is desiring, and after the client sends in their body measurements, Ms. Anderson-Chiles creates a trial design and sends that to the client to wear, along with additional fabric samples. The trial ensures that the client is happy with the fit, design, and fabric. After wearing the trial pair, Ms. Anderson-Chiles solicits feedback from the client to make adjustments. With these adjustments in place, she will make the final set, and additional pairs, for the client. 

Blog post continues after these brief announcements…

Watch my most popular YouTube shorts!

Haut Underwear banner
Claim your 15% discount at Haut Underwear by using coupon code MUG15

Custom Men’s Underwear Challenges

And Ms. Anderson-Chiles relishes the challenge of creating truly customized men’s underwear. She retold a fun story of creating her first jockstrap for a friend in London. Ms. Anderson-Chiles previously made two bespoke sets of a vest and shorties for this client. Appreciating her fine eye for design, he returned for the third time, but this time with a different request: a one-of-a-kind jockstrap.

Ms. Anderson-Chiles had never made a jockstrap previously. The challenge of a new design sparked her creativity. She chose fabrics and colors that she felt really spoke to her friend and studied jockstrap design. After sending him the trial pair and soliciting feedback, Ms. Anderson-Chiles crafted a unique jockstrap the client loved. And for Ms. Anderson-Chiles, it added yet another style of men’s underwear to her repertoire.

While making custom men’s underwear may seem to be a luxury – I certainly thought so! – Ms. Anderson-Chiles showed me otherwise. She also recounted a female client that had large breasts. So much so that the client couldn’t find a bra that gave her support and comfort, a real-life problem! Ms. Anderson-Chiles again took on the challenge head-on, despite not truly knowing if Ms. Anderson-Chiles could do it. As her husband – who works in construction – told her, “you have to put in a massive structure to support the weight.” After six trial pairs and a “massive learning curve,” as Ms. Anderson-Chiles describes the process, the client found the bra right for her.

Yet, the iterative design process didn’t stop there. The client returned to Ms. Anderson-Chiles, asking her to design front bra clasps instead of rear bra clasps. Front clasps would assist the client with her arthritis. Ms. Anderson-Chiles not only rose to the challenge again but also felt pleasure in being able to provide genuinely life-changing custom underwear to this client. I thought this was a fantastic story and shows there is a real need for custom underwear!

“There’s something about menswear.”

Throughout my interview with Ms. Anderson-Chiles, I could tell she has a real passion for men’s underwear. I found this passion intriguing since I (wrongly) held the stereotype that a female designer would gravitate towards designing women’s lingerie. From her university days, Ms. Anderson-Chiles has always had an eye towards men’s fashion. But why choose men’s underwear as her business?

As Ms. Anderson-Chiles notes, women for centuries have had the finest fashions to choose from when dressing up. The choice includes fine underwear for women, for which we even have a fancy French term: lingerie. Yet, for men, the selection of fine underwear available had been minimal until quite recently. Ms. Anderson-Chiles notes that men have started to pay more attention to their fashion and their grooming. And as guys will know, during the past few years, many companies have caught on that there is real money to be made in men’s fashion and grooming.

Part of the reason for this boom in men’s products is educating men in their increasing choices. Ms. Anderson-Chiles opines that if you never offer men options, men “won’t know it is there and they won’t want it because they don’t know they want it.” I completely agree! I’m reminded of the saying that you don’t know what you don’t know. If men aren’t aware of fabrics other than cotton for their underwear, or complex pouch designs to cradle their balls, men won’t know those options exist. 

And for Ms. Anderson-Chiles, men haven’t realized that they too can wear nice underwear until recently. Getting personal, she mentions her husband has always “loved fashion.” He likes “Barker shoes, really beautiful jeans…he dresses up smart and wears good quality clothes.” Yet while he wore “decent underwear,” his underwear collection previously was just mainly “black boxer shorts, or white [boxer shorts], or Calvin Kleins.” How many guys do you know that can relate? Maybe you…?

White Men’s Briefs with Mesh Paneling

by Anderson/Chiles

Yet, now her husband proudly wears nice underwear, and not just because Ms. Anderson-Chiles makes her husband’s underwear. Being a boxers/trunks guy, he knew that he preferred boxers and trunks because he didn’t like Y-fronts (briefs). Yet as Ms. Anderson-Chiles’ model, she introduced him to shorties (square-cut trunks). And he loves them! It is a perfect example of a guy not knowing he can wear better underwear because he didn’t realize it existed.

Furthermore, Ms. Anderson-Chiles notes that while her husband has his “everyday boring” underwear, he also has nicer pairs. Instead of only thinking of himself, on nights out on the town or special occasions, he will choose pairs that Ms. Anderson-Chiles likes on him. Perhaps that is the sexy mesh pair or the burgundy pair with velvet striping. Either way, a clear evolution from only wearing “black trunks from Marks & Spencers.” I feel this is true of many, many guys out there, and I support entirely guys stepping up their underwear collection. Not just for fashion, but comfort, for variety, for fun.

Care about Men’s Underwear? Subscribe to my newsletter to receive my tips and reviews!

Favorite Underwear Style

Looking towards the future of Men’s Underwear

Towards the end of our hour together, Ms. Anderson-Chiles and I chatted about the future of men’s underwear. We both agreed that more and more selection and options would come to men’s underwear, continuing the trend of the past few years. Of course, we are both very excited about this. 

However, a trend I hadn’t thought of is the growth of men’s lingerie. Ms. Anderson-Chiles sees men’s lingerie increasingly growing over the next few years. Not just briefs or jockstraps. Lacy underwear, satin underwear, underwear that is a mix of feminine style and masculine design. She notes several startup companies producing men’s lingerie, and she predicts more companies will jump into the field. 

Couples’ Matching Underwear Set by Anderson/Chiles

Nonetheless, she is quick to point out that it is a niche market. But not for the reason you may think – that men just may not care about the design. Instead, Ms. Anderson-Chiles notes that men’s underwear still has a negative connotation, especially outside of liberal, urban areas. 

For example, Ms. Anderson-Chiles tells me about the time she wanted to sell some of her bespoke men’s underwear at a local Artisan Market in Northern Ireland, where she lives.  She set up shop a couple of years ago – so still relatively recent – and sold some custom men’s underwear during her first couple of times. Yet, one week, management let her know that she could no longer display her garments on mannequins, as it was “inappropriate.” Feeling her brand disrespected, Ms. Anderson-Chiles pulled out of the market and hasn’t been back since.

Normalizing Men’s Underwear

Honestly, this story is reflective of my relationship with men’s underwear. I’m gay, and I had a fascination with men’s underwear for as long as I can remember (even before realizing I was gay!). Yet, despite having been openly gay for almost 15 years and being married for ten years, I recently felt comfortable to “come out” of the underwear drawer and create this blog. It took even more willpower to start making videos showing my face!

And my delayed “coming out” process is because of the general stigma I still feel is associated with men’s underwear. Yet, I now realize that instead of shying away from underwear, I need to use my blog to normalize discussion about men’s underwear and encourage open talk about it. Not just by gay guys with underwear fetishes, but by all guys. 

Nonetheless, I want to end this interview on a very positive note. Ms. Anderson-Chiles is creating beautiful custom men’s underwear, and I admire her openness and boldness. She – and other men’s underwear startup companies – are pushing niche men’s underwear designs further into the mainstream public. Beautiful designs. Luxury designs. Innovative designs. Men deserve fine underwear too. We must celebrate and champion their cause!

Haut Underwear banner
Claim your 15% discount at Haut Underwear by using coupon code MUG15

Care about Men’s Underwear? Subscribe to my newsletter to receive my tips and reviews!

Favorite Underwear Style

My Latest Blog Posts

Eric at

Eric is the creator and writer of He loves boxer briefs and trunks, exploring the new world of briefs, the soft feeling of modal and the lightness of mesh microfiber, and of course writing and researching the world of men's underwear.

Add Comment