How To Dress Well As A Plus-Size Man: Expert Tailoring Tips From Designers & Customers

For men often overlooked by fashion’s narrow size range, a quiet revolution in menswear is tailoring confidence, one fit at a time.

Men’s fashion can sometimes feel like it’s designed for one type of man – standard-sized with simple, unassuming taste. Yet some local designers are reshaping what menswear can be. They’re cutting different silhouettes, experimenting with colour palettes and proving that style has never belonged to one body type.

At the centre of that movement is Wellington’s Mandatory, a menswear institution that’s spent nearly three decades championing unique offerings, custom fits and local craftsmanship.

“There’s no correlation between taste and shape,” says founder Clare Bowden, who established the brand in 1997. “We want people to come in and find the things they really like but it’s long odds that every piece will be sitting there in their exact size and colourway. That’s why we make to fit.”

For Bowden, who still spends most days on the shop floor of her Ghuznee St atelier, it’s a philosophy born of both pragmatism and respect.

“Menswear is inherently tailored,” she explains. “Better fabrics and more structured lines mean it’s expensive to produce, so you have to be smart about waste. Holding back fabric lets us create what each person actually needs without over-making or discounting what doesn’t sell.”

Mandatory’s clientele is as diverse as our country itself: heights from 4’10” (1.5m) to 6’11” (2.10m), lean to solid, round to sporty builds.

“We’ve got a huge ethnic diversity in a small population,” Bowden says. “Plenty of Dutch clients that are never under 6’ 3″, and Pasifika corporates who’ve struggled to find anything off the rack that fits or flatters. You can’t solve those challenges with one pattern.”

“It’s what an atelier should be,” Bowden says. “You can see the craft, and we’re helping people see the value in that.”

Her commitment to customisation for all body sizes goes beyond fit; it’s about identity.

“It’s easy enough to fix fit issues,” she says. “But if you end up looking tidy and appropriate yet not like yourself, that’s limiting. Whether it’s a wedding suit or workwear, it still has to express who you are.”

Creating what the client has in mind comes with some interesting requests, like the rugby player who surprised Bowden by asking for the daintiest cotton shirting.

“You’d never have guessed it, but he loved those fabrics. That’s why we do what we do. Taste doesn’t come in a size and everyone should be able to choose to wear what makes them feel most like themselves.”

Architect and DJ Ben Stevens, better known to Wellington’s music scene as Longboss, stands at 6’8”. For him, Mandatory has been a lifeline.

“If it wasn’t for Clare, I’d have nowhere to buy clothes,” he says. “I’m constantly astounded by how little there is for men in general, let alone tall men. We oscillate between Kmart level and tailored suits. There’s nothing much in between.”

Stevens discovered Mandatory decades ago through the city’s creative scene, and Bowden has been making his shirts and trousers ever since, adding 16cm to the length and shifting the knee position so the proportions make architectural sense.

“What Clare does isn’t just about fit,” he says. “It’s about how clothing hangs and responds to your physique and your persona.”

He remembers his first fitting vividly.

“She measured my chest and must’ve seen me flinch because she said, ‘You feel a bit sensitive about that, we’ll give you a little more room to breathe there.’ That moment really stayed with me. Clothing isn’t just functional; it’s psychological. It’s your outer skin.”

As an architect, he recognises the shared craft.

“Clare would never trumpet it, but she has this quiet understanding of structure, of how materials work, how seams carry tension. It’s the same discipline I apply in buildings: form following function, made personal.”

While Bowden has been holding the fort for years, another generation is pushing for change in menswear from a different perspective. Auckland designer John Tanuvasa, founder of OHN Clothing, built his bold label from his own experiences as a plus-size Pasifika man navigating a limited marketplace.

“Plus-size clothing is its own realm,” he says. “I started designing because I wanted pieces that felt like me that weren’t oversized streetwear or just basics.”

For Tanuvasa, everything about his colourful, intricate designs begins with construction.

“Seams can completely change how a garment fits and feels,” he explains. “I move them around, remove restrictive lines, create shapes that flatter all sizes. It’s not about hiding the body, it’s about showing confidence and personality, whatever your size.”

Representation, he says, is still miles behind.

“Plus-size men want to dress just like every other stylish guy out there. Brands often miss that. We need big men of all shapes and skin tones fronting campaigns and in fashion editorials, fragrance ads, everything. Representation matters.”

As a Pasifika designer, he draws as much from community as from cloth.

“My culture shows up through my models more than my prints. I find real people who are unfiltered and confident, and put them on the runway. That’s what my brand stands for: self-acceptance and the freedom to take up space unapologetically.”

For Benson Wilson, international opera singer, model and proud plus-size man, clothing has been both a source of frustration and joy.

“It’s a novelty to find my size in store,” he says. “And even when I do, most XL-plus garments are made for fat distribution, not for bigger builds. Being larger doesn’t always mean carrying more fat. Those assumptions can lead to ill-fitting clothes.”

Wilson, who spends as much time in tuxedos as he does in tees, has learned what works for him.

“Dropped-shoulder T-shirts flatter broad frames without adding bulk. When Levi’s released their ‘Athletic Cut’ jeans, I finally had a pair that fit my thighs without being baggy or skinny. Those small details matter.”

His go-to look?

“A good crew-neck tee, straight-cut jeans, a decent coat and trainers. Simple, comfortable and confident.”

On labels, he’s practical but loyal.

“Johnny Bigg and Hallensteins are great. They’re stylish, accessible and they carry larger shoe sizes, which is a huge plus for my wide-footed brothers.”

He’s also vocal about the deeper narrative.

“Fashion hasn’t caught up with body diversity,” he says. “We celebrate women’s curves, though not enough, but men are still left out of that conversation. I look forward to the day men of all shapes are celebrated the same way.”

For Wilson, confidence now outweighs what’s trending.

“My relationship with fashion has changed. I used to chase fast fashion and trends. Now it’s about wearing what makes me feel like a million bucks.”

Even with appealing options like Mandatory available, men can often feel less than enthusiastic about shopping, and Bowden sees the reluctance daily.

“Men are often occasional shoppers,” she says. “They come in under pressure for a wedding or a work event and hope something will just fit. Pants are the hardest. Everyone’s got a pair in their wardrobe that don’t quite work, but they bought them anyway. Our job is to fix that, to show there’s another way.”

Her business model, where custom-made costs the same as off-the-rack, removes one of the biggest barriers.

“It incentivises people to get something that truly fits instead of settling,” she explains. “We cut orders alongside new stock so it’s efficient. It’s called end-customisation, making just enough, right on time. Less waste, happier clients.”

That made-to-measure mindset also cultivates loyalty.

“We’ve got clients who’ve been with us 20 years,” Bowden says. “Seeing someone wear something you made for them until it’s threadbare – that’s pride.”

Tips for shopping for a bigger or taller frame

Start with fit, not label

As Clare Bowden points out, no two bodies or brands are alike. Focus on where seams sit and how fabric drapes rather than what the tag says. A good tailor can also adjust sleeve length, trouser rise or collar width to perfection.

Know your proportions

Ben Stevens swears by trousers with the knee positioned correctly for his 6’8” frame, a small tweak that changes everything. For bigger builds, athletic or relaxed cuts balance comfort with shape.

Look beyond size charts

Plus-size doesn’t always mean wider; sometimes it means taller, broader or more muscular. Try different cuts and don’t assume a larger size will automatically fit better.

Prioritise quality fabrics

Breathable cottons, linens and stretch wools move with the body and last longer, an investment echoed by Bowden’s decades of craftsmanship.

Find your trusted makers

Whether it’s a local atelier like Mandatory or a label that specialises in inclusive sizing, such as Johnny Bigg, forming a relationship with designers or retailers who understand fit pays dividends.

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