Dressing well would be easy, they said.

There are two voices in the men’s style world. One is that fashion is really hard and it takes dedication and a passion for the art form to get it right. The other is that dressing well is incredibly easy, all you have to know is the basics and you’ll be the best dressed man in the room.

But any guy who has, well, ever worn clothing, knows there’s another, frustrating aspect: Practicality.

You’re doing your best, you bought the thing that people said was good. But either because of your line of work, lifestyle, or unique body, something about your style is obstructing instead of doing its job—make you look and feel damn good, then be out of the way as you get on with your day.

You’re not alone, in fact, based on all the talking about men’s style I do with guys, it’s more the norm than the outlier.

So today I’m running down some specific style picks that address common frustrations Primer readers and friends have reached out about. These include struggling to look presentable in a job that requires a lot of moving around, options for sizes outside of the frustratingly narrow scale found at most stores, and more.

Nice-ish Business Casual Work Pants for Guys Who Move A Lot for Their Job, Get Hot, But Don’t Want to Wear Shorts or Hiking Pants

Take for example, my friend Eric who had an issue I’ve heard multiple times from Primer readers. Eric was wrestling with finding work attire that was practical and kept him presentable. Eric is the co-founder of a business that builds testing equipment for the aerospace industry. On any given day, he could be in a 90 degree airplane hanger wrestling heavy gear, running cables, troubleshooting over here and over there – and then have to give a presentation to the client in a boardroom an hour later.

“I need to work and not overheat, have some stretch, but have a fit that is intentional enough that I can still throw it on with a button down and not look like I’m wearing hiking pants,” he told me.

The find he’s been most happy with is the Free Radikl pant from Khul, which are technical pants offering stretch, reinforced construction, lightweight and quick-drying – and come in a modern, tailored fit without the zippers and pockets of many similar options on the market.

Stylish Pants for Guys with Inseams Longer Than 34

Men who wear larger sizes have always struggled to find options. But our tall, slim brethren perhaps have had it harder than most.

It’s true that common stores like J.Crew and Banana Republic offer an inseam length as long as 36 in some styles but only for larger waist sizes.

For guys like me who prefer an awkward 29-29.5 inseam, it’s annoying, but at least I can pay someone to remove fabric. If you need anything in an inseam longer than 34 that isn’t also accommodating a higher waist size, you can’t just pay a tailor to sew on extra denim to the bottom. (I mean, I guess they’d take your money, but I wouldn’t recommend the outcome.)

Stillman Brown is the perfect example of this. At 6’7”, Stillman’s 36 inseam makes one of the foundational requirements of participating in society – wearing pants – a significant challenge. “Levi’s has it for some, but it ruined pants shopping for me for a long time,” he told me.

Fortunately, in the last couple of years there have been more options than ever for taller guys. Recently when we were hanging out he told me about some new brands he’s come across. One is American Tall – it’s essentially a Banana Republic aesthetic and price but for guys 6’ to 7’1” (and women up to 6’6”).

So If you need a smart casual pair of stretch chinos in a 32×40 or a budget-friendly $129 pair of suede boots in size 16, now there’s a place to look.

PRIMER PARTNER

Underwear That Actually DOES Something

If you’re a guy that has to move a lot, the struggle of heat and chafing is real. From sweat to irritation to honest-to-goodness medical problems – the external male anatomy wasn’t designed for an extended lifespan cooped up in pants.

And while every iteration of the modern under garment, from boxers to briefs to boxer briefs, has been an attempt to silo those parts of the body from the legs, all were half measures with flaws of their own.

If there’s one type of guy that would know this alarmingly well, it’s a US Army veteran doing two tours in Iraq in 2007:

“I was under extremely hot conditions and all I wanted was a pair of underwear with a pouch or pocket to separate my balls to keep them from sticking to my legs. The male groin generates more heat than any other part of the body. Similar to the skull and the armpits. I had a hat and sleeves but my balls were out of control,” Robert Patton told Primer in 2017.

The undefeatable temperatures, heavy gear, and inherent stress meant life was a sweaty, chafed disaster. The soldier-turned-inventor got to work with the supplies he had on hand in the desert, fashioning his first prototype of the pouch underwear that would be the foundation of his eventual raving success, Sheath:

Now 17 years later, Sheath is the official underwear of the UFC, relied upon by world-class fighters, Olympians, and law enforcement; and Inc. Magazine labeled the company one of the 100 fastest growing veteran-owned businesses in the United States. From that initial makeshift prototype, Patton’s Sheath brand now offers 5 versions, including single or dual pouches, differing lengths, material options like modal or bamboo, and a palette of colors and patterns.

I can personally vouch for them. I still have pairs from 2017(!) in my rotation because they’re in great condition. I was initially skeptical of how comfortable this could possibly be but they really do work as advertised. You completely forget you’re wearing anything different – except for the lack of swampiness and chafing. I didn’t recognize how beneficial the extra support was until I actually wore them.

Fortunately, you don’t have to take my word for it. Sheath offers a no-questions-asked 100% refund on your first pair, and a 6-month manufacturer warranty on defective items, plus Primer readers get an extra 20% off their first order.

Sunglasses for Low Nose Bridges

Stephen reached out to me frustrated about sunglasses. As he’s gotten more into developing his own personal style, he’s taken to the plastic sunglass frames common in a more refined aesthetic, but none of the ones he’s tried fit right.

“Every pair I’ve tried looks good for about 60 seconds but they always end up sliding down my face and sit on my cheeks,” he told me, “I’ve always been an aviator guy just because I can pinch the nose pads to force them to fit.”

The plastic acetate-style of sunglasses use the shape of the bridge, versus adjustable nose pads on metal styles like aviators, to hold them in place. So if you have a low nose bridge, there’s just no way these things are gonna stay up.

Fortunately, mainstream framemakers have started addressing this frustration. Brands like Warby Parker, Maui Jim, and Ray-Ban make acetate frames with wider, or in some cases, adjustable nose bridges so they stay put and don’t sit on your cheeks. Look for terms like “low nose bridge sunglasses” or “Asian fit sunglasses”.

Chinos for Guys Who Carry Things in Their Pockets (Everyone)

You know, we gave the old guys a hard time for their belt clip phone holders but at least they were doing something about a terribly annoying problem: Pants with side pockets like every pair of chinos, khakis, and dress pants cause your $1,000 smartphone to fall out CONSTANTLY.

We all smirked yet provided no alternative.

The Dockers Ultimate Chino is not only a budget-friendly, comfortable work pant that is widely available, it also features a sneaky hidden zip pocket right next to to the side pocket so you can keep your phone or keys or whatever else you want to haul without the risk of it sliding out every time you sit down.

It’s completely unnoticeable while zipped up and the pants can easily be worn dressed up or down.

Nicer Summer Shoes to Replace Boat Shoes

Connor messaged me with a plea more from his wife than him, “I grew up on the east coast but have lived with my wife in Ohio for 10 years. Every date night gets my go-to boat shoe treatment. She has been politely nudging me for years to get something a little less dock-ready.”

For some areas the boat shoe is akin to a white sneaker: It’s a perfectly acceptable uniform regardless of where you go. If you’re looking for something a little more refined, I’ve got just the thing, and for your part, you won’t even notice a difference.

Swapping your boat shoe for a suede loafer will give you the same summer comfort you’re used to but give off a little bit more of a dressy vibe. The right pair can still be worn with jeans and even in cooler temperatures, making them just as versatile as your go-to.

Dress Pants That Aren’t Dry Clean Only

Dress pants are usually made out of wool because of inherent temperature properties, ability to maintain shape, natural wrinkle resistance, and its ability to be woven in a variety of textures giving it a sophisticated look and feel.

Unfortunately, wool dress pants are typically labeled as “dry clean only” because the material can easily shrink, distort, or become felted if exposed to water and agitation. Linings and interfacing can also be damaged by regular machine washing.

“I have to wear dress pants almost every day of the week but I hate that I have to pay to have them cleaned so often,” Primer reader Jeremy lamented in a conversation we were having. My recommendation is textured cotton pants. The ones I’m wearing here are from Bonobos, and brands usually offer them in the fall. The benefit is since they’re cotton, they’re machine washable.

While not quite the same level of dressiness since they lack the fine, shiny weave of the dress pants, I’d argue they’re pretty interchangeable in a modern context for all but the dressiest situations. For a different option that’s currently available in a bunch of colors, check out the Weekday Warrior from Bonobos.

What are your solves for your clothing frustrations? Chat with me in the comments!