The Men's 5-Step Guide to Classic Style


Digging through old, scratched-up pictures from the 1800's to early 1900's has taught me one thing - we've lost a sense of class. It seemed that no matter what the men of that era were doing, be it working in the fields, selling stock on Wall Street or taking their lady out on the town, they had a touch of class that has since been buried under layers of converse, sagging pants, deep v's and flat-bills. To a certain degree, this has to do with cultural trends, yet despite this shift in fads, you'll notice very little shift in taste -- women are still attracted to the rugged - yet fashionable - man. The men of today who pay attention to the way in which they present themselves from attitude to language to fashion command a high level of attention and respect as much as they did 100 years ago.

The way we dress affects the way we think, the way we feel, the way we act, and the way others react to us.
— Julie Rasband

I want to provide you dudes who wear ladies pants a few tips on class from the experts. Here are five ways you can spice up your look with less money than your Air Jordans cost.

The Humble Tie Clip

This small piece of metal - perhaps an inch or two wide - is like adding a jewel to a crown. Small - to be sure - but powerful. The difference is subtle and sometimes hard to pinpoint, but it rounds out your suit in a way very few accessories will. Of course, to pull off the tie clip, you need to be wearing a tie...

Anyway, here's a few things to keep in mind:

1. Shorter than tie width

Your tie clip should not be hanging off into outer space past the edge of your tie. It'll look clumsy, not suave.

2. Match your metals

Wearing a watch with a silver band? Great! Wear a silver tie clip as well. Same goes for your buckles and cuff links.

3. Let it Show

If you're wearing a coat or vest, adjust your clip up or down so that it's showing just a couple of inches above the buttons.

Pocket Square

Pocket Squares are another small but impactful addition to your wardrobe. One simple, white pocket square can be folded in numerous ways from casual to formal, dropped in the pocket of nearly any suit and you're well on your way to dapper. If you're feeling bold, branch out and experiment with patterns and colors - one successful pairing could label you "the fashionable one" amongst your friends. Here are a few pointers:

1. Service

Pocket Squares are historically a tool for hygiene and service. If a dinner guest spills their wine, quietly extend to them your linen pocket square. You're the hero and the gentleman.

2. Aesthetics

Pocket Squares have adapted to a more stylistic piece and are often silk. Though not quite as versatile or handy, they can add a bit of flair to your attire.

3. Patterns

Patterns are a dangerous territory - they can easily be done wrong. If you're new to the pocket square, my suggestion would be to stick to the classic solids and match them with your shirt or tie.



A watch might be one of your most versatile, classic, fashion statements as it tells a lot about a man. Wearing one is as much about fashion as it is about telling time. Here are a few things to remember:

1. Match your Leather

Your watch band should match another piece of your outfit whether this be your shoes or belt. Don't make the mistake of wearing a black-banded watch with brown shoes.

2. Let your taste shine through

Watches are one of the few pieces of your wardrobe where you can generally get away with whatever you want. Find one that you really like and go for it! In more formal situations, however, remember that less is more.

Watches have the tendency to run on the pricey side - if you want to invest in quality, expect to spend a couple of hundred dollars if not more. Remember, in the end, you're investing in something that will last for years.



A bad belt can ruin your style in a heart beat. None of these piano belts, please. Find a well-made, leather belt with a clean, refined buckle. They key principles to remember with belts are to:

1. Match your Leather (again)

If you are wearing brown leather shoes, or a brown leather watch band, choose a brown leather belt, not a black one!

2. Classic Buckles

If you care at all about making a refined statement in the way you dress (which is the entire point of this post), the gaudy, bejeweled, batman, rodeo, and seat belt buckles have to go. It's time you grew up a bit opted for a classic style.

3. Length (fit)

When choosing a belt, pay special attention to the distance of overlap. Once your belt crosses around in front and buckles, you should not have a length of belt flopping around out to the side. Make sure it's just a few inches overlapping which you can thread back through your first belt-loop.

If you're thinking about investing in one good belt, I would encourage you to opt for a slim, simple black or brown (remember to match your leather) belt with a silver buckle. Silver will be your most versatile and subtle choice of buckle where as gold, though also a classic look, doesn't prove as versatile across the board.


If you're up for pushing modern fashion a bit, kick it old school with a pair of suspenders. The key to suspenders - as with any out-of-the-norm fashion accessory - is to wear them with confidence. Suspenders, like other clothing pieces, come in a vast variety of quality and the difference is obvious. The sets that I prefer (but don't yet have... whoops!) will button on to the inside of your waistband for a more complimentary, put-together look. Remember:

1. Don't pair suspenders with a belt

While wearing suspenders with a pair of pants that have beltloops is okay, threading those beltloops with a belt as well, is widely considered faux pas. Keep them separate.

2. Match your leathers (catching on yet?)

If you are wearing suspenders that have leather button-holsters, you'll want the leather to match your belt, shoes and/or watchband.

3. Patterns

Suspenders come in a variety of colors and patterns. Try to keep the colors neutral for a classic look (Black, Grey, Navy, Dark Red) and match them to some other part of your wardrobe, be it your pants, jacket, or tie.


Spruce up your style with a few small pieces and take one more step toward joining the ranks of Sean Connery, Clark Gable, Dean Martin and Frank Sinatra.

Haha just kidding, we'll never join their ranks. But best of luck!

Jacob Jolibois is the founder of The Archer's Guild. He has a habit of starting a large number of projects and is oddly enthusiastic about Disney. Ultimately, he's hoping to rid the world of mediocrity, lots of people at a time (one is too slow). Recently, he backpacked across 11 countries with Micah Webber.