There’s a common myth in the men's style world.
Style is three-piece suits and perfectly creased trousers.
It’s silk ties and shoes polished until you can see your reflection.
In other words, style means dressed up.
This couldn’t be further from the truth.
Whether you’re dressing up or down, style is your message to the world. It shows your attitude towards what you do.
But let’s be real: if you’re a personal trainer, you’re not going to be wearing a suit.
Can you still be stylish? Yes!
The secret is to follow my style pyramid—Fit, Fabric, and Function.
Fit means even your gym shorts are the right size and shape to flatter your body.
Fabric means choosing hoodies and t-shirts based on the quality of their material, and function means you know when to dress down as well as you know when to dress up.
There are times when the dress code really is ultra-casual. That doesn’t mean you have to look like a slob. These five key items can make all the difference.
5 Ultra Casual Men’s Style Essentials
Dressing down doesn't have to mean looking like a mess. Here's how to style five low-key staples for high-key impact.
#1. Casual Men’s Outerwear – Track And Bomber Jackets
Casual jackets are one step above a hoodie and very easy to fit. You can gauge sizing the same way you would for a blazer or sports jacket.
Like a hoodie, however, this piece can look careless if you don’t consider the overall length, sleeve length, and shoulder points. The shoulder points should rest at the end of the shoulder joint, without sagging down onto the upper arm or pulling up the shoulder toward the neck.
A solid bomber will broaden the shoulders and taper in the midsection but allow your arms to move freely. Again, you should be able to have full mobility.
Elastane and cotton blends are a must for these jackets. Having a degree of stretch helps with mobility and looks more fitted to your body, giving a masculine silhouette.
A track jacket or bomber jacket that moves and breathes well can do double duty as a daily wear jacket or a workout piece for the cooler seasons. Good ones will simultaneously insulate from the cold and dry up sweat when your body heat rises.
#2. Casual Men’s Pants – All Day Everyday Track Pants (The Denim Alternative)
Track pants are go-to comfort clothes but don’t underestimate their versatility. The right pair can take you beyond the gym. It's all in the details and your attitude–wear them like a serious athlete would, and they won't be mistaken for the round-the-clock loungewear of a guy who's just giving up.
Look for comfortable, but not baggy. The slim and regular fits will be best for most guys.
When it comes to ultra-casual pants, a pair that tapers at the ankle with half to no break (i.e., folds very little or not at all over the tops of your shoes) works better than a full break.
It assures a clean-cut look, and it’s perfect for showing off a great pair of trainers.
If jeans in the workplace or business dress are a requirement then of course take this advice with caution even on a casual Friday.
Avoid cotton sweatpants that turn ratty and shapeless easily. Save those for watching the game at home, preferably with the windows closed! What you want instead is a fabric with a bit of stretch that will still look new after several washings.
That means high-quality elastane fabrics (the brand names Lycra and Spandex are types of elastane fibers) or poly blends.
Obviously, track pants should be mobile and moisture wicking. They’re for exercise (and comfort) first. But the ideal pair is also sleek and tasteful—one you can work out in and then wear to lunch with your friends.
#3. Casual Men’s Tops – Henleys And T-shirts
Henleys and t-shirts should hug the body like a second skin. If they’re too big, they’ll look sloppy.
Just as with jackets, it's also important to make sure the shoulder points sit on your actual shoulders.
You want t-shirt sleeves to stop around mid-bicep and not flare out at the base. Henley sleeves should fit similar to a dress shirt.
Both should fit like a dress shirt does around the midsection—close to the body, but not tight enough to cause puckering or stretching.
When you try on a t-shirt or henley, raise your arms in the air to check the length. If your midsection shows, it’s too short. When your arms are relaxed at your sides, the shirt shouldn’t hang below your butt—if it does, it’s too long.
High-end natural fibers, like cotton or Merino wool, are great for these pieces. But spandex and PRIMA cotton blends can be even better, giving you a nice fit with a bit of stretch.
What to avoid? Cheap cotton weaves from fast fashion stores. You’ll be throwing them in the trash after a handful of washes.
Good ultra-casual tops will wick away sweat, last hundreds of washes, and be shrink resistant. Elastane blends will give you all of that, so check the tag.
#4. Casual Men’s Knitwear – Hoodies
Hoodies get a bad rap in the style game, but if done right, they can look just as good as any other casual sweater.
Fit a hoodie just a little bit looser than the henley or t-shirt you’re wearing under it.
You can gauge fit by feel—you should be able to move unimpeded, but it shouldn’t look baggy around the midriff.
Pay attention to length—if it hangs down past your butt, it's way too long.
You can follow the same rules as for t-shirts and henleys. Merino wool or elastane blends will regulate temperature while also absorbing perspiration.
Hoodies have been around for as long as people have needed practical protection from the cold.
The modern hoodie was introduced in the US in the 1930s and marketed to laborers working in freezing conditions. Now the hoodie has ascended beyond utilitarianism thanks to its appearance in movies like Rocky and its popularity in hip-hop culture.
It’s still practical comfort wear for cold weather, but it can be part of a stylish ensemble too.
#5. Casual Men’s Shoes – Trainers
In order to know how your tennis shoes should fit, you need to know the unique shape of your feet. Do a “wet test” to find out: wet your foot and step on a piece of brown paper, then trace your footprint.
If your footprint shows the entire sole, you may lack supportive arches and could suffer from overpronation (feet rolling inward). You'll need shoes with strong arch support.
If it only shows your heel and ball, then you have strong arches but risk under-pronation (feet rolling outward). Your shoes will need cushioning with a soft midsole.
Either way, you want them to fit like any supportive tennis shoe, but contribute to a slightly elevated casual look.
If you want to binge on casual shoes, check out Richie Le. This guy knows sneakers!
Breathable fabric or leather trainers are the most stylish from an aesthetic point of view.
Prime knits, like Nike Flyknit Racers and Adidas NMD’s, are breathable and versatile. Leather sneakers (Adidas Stan Smiths, Adidas Superstars) are a classic, especially in plain white.
Canvas (think old-school Converse Chuck Taylors) is durable, working as hard as you do to hold off the elements. The only downside is it can be difficult to keep clean.
For trainers, this ties closely with the fit. If they don’t offer the support of a workout and running shoe, they’re not doing their job. That’s really all there is to it.
Bonus: Optional Extras
- Sunglasses are a timeless accessory, especially with casual wear. Wayfarers or a similar classic style are perfect for this.
- Duffel bags can be chosen with coordinating in mind—it doesn’t have to match exactly, but pay attention to quality and versatility the same way you would with athletic shoes.
- Good grooming makes it clear that even when you’re dressed down, you’re dressed down on purpose. Make sure your hair is neat and beard is trimmed and even.
- Consider wearing an understated or sporty fragrance. The right cologne can complement casual apparel while adding a hint of mystique and sex appeal.
- Keep jewelry simple and practical. A casual watch, rings, or a bracelet make a comfortable outfit distinctive. Just don’t go overboard—you don’t want a sleazy Jersey Shore vibe.
The key to look put together in ultra-casual clothing is to consider fit.
Fabric and function are worth looking at, but by comparison, they’re cherries on top.
A carefully considered ultra-casual outfit (even if that sounds like an oxymoron) is true weekend warrior attire. It can take you from the gym to running errands to taking the kids to the park, looking relaxed yet polished.