Just by making simple fashion decisions, you can boost your self-esteem, make you more productive and improve your career opportunities. Every week, I help 1,000+ men make the most of their wardrobe with fashion tips to upgrade your life.
An Italian guy on vacation wearing them with a linen suit?
Or is it just the shoe you throw on when you don’t feel like lacing anything up?
Truth is, most men are wearing loafers wrong.
Not because loafers are hard to style, or they’re outdated, or too “European.”
Men are wearing them wrong because they treat them like an afterthought.
And a loafer is not an afterthought shoe.
Somehow this became a shoe men reach for when they don’t feel like trying. It’s easy. It’s there.
It doesn’t require laces or thought.
And that’s exactly why so many guys get it wrong.
When you remove laces, you remove structure.
When you remove structure, everything else has to be sharp.
The trouser length matters more. The taper matters more. The fabric matters more.
A loafer will only make all those flaws more visible.
It’s actually one of the most intentional shoes you can put on.
A loafer can expose your style choices immediately.
That’s why on some men it looks effortless and expensive, and on others it looks fashion confused.
There are a few main types, and this is where most people mix it up.
A penny loafer is the clean one with the small leather strap across the top.
It’s the most versatile and the least flashy.
This loafer you can find a bunch of different options to fit your budget.
This can be paired with tailored trousers and a knit polo, or even dark denim and a blazer if the fit is sharp.
A tassel loafer carries a bit more tradition.
This is the loafer that you would think your grandpa wears but it all comes from heritage; it is the loafer that can also read old money vibes.
That's why on a younger guy it can actually feel like a subtle flex.
The tassels add a small detail that gives it personality.
If you’re going for a more mature, established look, it shines with fuller-cut trousers, softer tailoring, maybe even pleats.
A horsebit loafer features a metal detail across the front, and it can be mostly seen with the younger gentleman especially for proms and formal events, and it’s often paired with very tight, cropped trousers.
That look had a moment. If you love it, wear it.
But if you’re trying to evolve your style, consider giving the shoe a little more room to breathe.
The horsebit actually pairs better with tailored trousers that fall clean and aren’t too slim.
The hardware already draws attention, so you don’t need the pants to draw more attention.
So when you think about loafers now, you can see they’re not going anywhere.
They’ve been around for decades, they’ve moved through different eras of menswear, and they’ve survived all of them.
Loafers are simple on the surface, which is exactly why they require more awareness than people expect.
They sit lower on the foot, they show more ankle, and they don’t have laces to visually tighten everything up.
That means your trousers, your break, and the overall silhouette matter more than they would with a bulky sneaker or a nice oxford shoe.
The moment you understand how loafers shape the overall look, they become less about the shoe itself and more about building a wardrobe that reflects your taste and personal style to dress with real confidence.
I just returned from a much needed vacation from snowy New England to somewhere much warmer.
I haven’t done much extended travel recently, so this was an opportunity to reacquaint myself with the process of packing for a major trip, and the guidelines that I’ve discovered in my previous travels for packing and traveling efficiently.
It’s not a big bag but some careful packing meant I could carry enough clothes with room for souvenirs
Since childhood it was drilled into me that I should be able to handle all my bags on my own across airports, train stations, buses, and cobbled streets.
Too many suitcases or one suitcase that is too large can be difficult to handle or to fit into baggage compartments, and can make you late for your connections.
As a result, I am a two-bag person at most, both carry-on size.
An experience in my teens when I arrived in Bermuda on a family trip with no clothes while my bag took a sojourn to Boston, means that I have been reluctant to check bags since, although I will counter check or gate-check on a direct flight.
For flying, a hard-sided rolling suitcase is most useful, as it stands up well to being tossed and dropped by baggage handlers when checked, but also slots neatly into overhead compartments.
A rolling suitcase can be paired with a backpack or large tote as the personal item or as the primary carryon.
I'm also a fan of duffel bags, more for the look than the practical function as a heavy duffel can be difficult to carry long distances, although they're super handy for just chucking in the car on road trips.
I’m not a big fan of backpacks aesthetically, and I find them unwieldy to handle when boarding or exiting vehicles, but they’re most useful when your trip is going to have you walking long distances between modes of transportation.
On this trip, I was going to be going from train to plane to car with little walking in between, so I tried using a deep tote bag as my personal carryon item.
The open top made my items accessible even when stowed under the seat, and on arrival I had a stylish tote for a daily use bag. I’d travel with the tote again.
This carried my camera, books, notebook, a change of clothes, and toiletries
The main consideration when it comes to packing clothes for travel, even beyond the kind of activities and setting you’re heading to, is climate.
In the case of my recent trip, I was headed somewhere warm, but it was still below freezing for the first leg of the journey.
I layered a sweatshirt under a nylon bomber jacket, giving me options for the train and the flight.
A mid-weight nylon jacket provides a decent layer of insulation and wind protection, but can also roll up fairly compact in a carryon or overhead compartment.
A hooded sweatshirt is a reliable choice for a long flight, keeping you warm on an air conditioned plane.
On arrival at the destination airport, both outer layers went into my carry-on tote bag until I reached the hotel,
although the sweatshirt came back out again when the trade winds blew through in the evenings.
Wearing these layers gave me functionality across several climates without taking up too much
space.
Ultimately, how much you pack will be a function of how long you'll be on the road, but there are still ways to cheat this inevitability by knowing your destination and packing for interoperability among everything you bring.
Reusability is key in maximising your packing space, and pants are the most reusable items besides outerwear.
I feel like two pairs of pants are about all you need
for a trip under two weeks.
That way you have the opportunity to swap them out, to pack two different pairs that cover different kinds of activities, or to provide backup for each other if one pair gets stained or dirty.
Having shirts that can be worn a couple different ways, like an OCBD worn open as an overshirt or buttoned and tucked for dinner at a nice restaurant can also stretch your wardrobe.
Chambray workshirts work equally well as a casual top, although they’re slightly less appropriate for a nice restaurant.
An understated camp collar shirt can be a beach coverup, a casual daily piece, or be worn to dinner.
Layering a colored tee under an open shirt can change up a look without requiring much packing space.
Also, you're on vacation, so no one is going to
care if you repeat outfits.
When it comes to stretching your travel wardrobe, having access to laundry facilities simplifies packing, allowing you to clean your clothes halfway through and thus pack half as many days worth of clothing.
Even if you don't have a washing machine where you're staying, hand-washing can stretch your wardrobe significantly.
On a trip to central Turkey, I mainly relied on a single cotton-linen shirt that I hand washed every other day, hanging it to dry overnight.
The arid climate made sure that each morning it was ready to be worn again.
You can do the same with socks and underwear, to stretch the less-glamorous parts of your wardrobe and save luggage space for stylish looks.
Your hotel room may not have a drying rack but clothes hangers will do the trick
My suitcase came with a small nylon zipper bag that folds away, presumably for dirty clothes or shoes. I augmented this with a sturdy canvas drawstring bag.
Having somewhere to put your dirty clothes is ideal, particularly if you're traveling between places without doing laundry.
You don't really want your smelly socks and dusty shirts mingling with the clean outfits you’ll wear later in the trip.
You can also just take the whole bag and toss it into the main compartment of your suitcase, simplifying repacking on the return.
Even if you don't use it for dirty clothes, it’s good to pack a laundry bag as it could serve double duty as a beach bag or on a grocery run.
When it comes to shoes, I’m a firm believer in packing two pairs at most.
Like pants, this gives you the opportunity to cover different stylistic and performance requirements, usually one more practical and one more style-focused.
For this trip, my practical choice was one pair of canvas sneakers, classic and simple enough to wear most places while being hardy enough for a hike on volcanic beaches or jungle trails.
They were my sturdy walking-around shoes in town and in more rugged spots, while being comfortable enough for long-distance travel and changes between modes of transport.
Do You Need My Help?
Have you ever found yourself staring at the closet not knowing what to wear?
Do you need help with coordinating pieces?
Do you constantly struggle putting an outfit together and want to turn that confusion into confidence?
Then let's talk about how we can improve your look.
Just by making simple fashion decisions, you can boost your self-esteem, make you more productive and improve your career opportunities. Every week, I help 1,000+ men make the most of their wardrobe with fashion tips to upgrade your life.
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