Style Advice / October 29th, 2013

How to Dress Better | The Ultimate Style Guide For Men Starting Out

So you finally gathered enough courage to explore the realm of men’s style.

Welcome my friend.

While the road can be a bumpy one for a rookie, the journey is worth it.

You may be intimidated and more than a little lost deciding where to start.

Take courage in the fact that many men have been down this road before.

In fact, I just received a question from one of my Facebook followers asking for some advice on improving his style since he is just starting out.

His name is Elias from Vancouver, British Columbia and this is his dilemma:

 “I really love your blog and after several failed attempts, I am willing to become a better dresser. The problem I have is I always purchase the wrong items. It’s so confusing shopping and being bombarded by sales reps in stores. Can you please give me a list of what to purchase as a starting point?”

This is a great question from Elias given how many men share this same issue. It’s tough  not knowing what items to purchase when on the journey to improve your style.

What better way to answer Elias’ question than by creating a blog post about it?

Before I break down my suggestions, I feel it’s important to mention you should do some research prior to buying anything and come up with a checklist of what you really need. I like to approach this with the following steps in mind:

  • Take a look at your closet and throw away anything you never wear.I you haven’t worn it in 6 months it’s safe to assume it will be a permanent dust collector.
  • Based on the items remaining, sort them in a pile that is relevant to you. Some men sort their items by season while others by work and personal use. This is the clothing that you actually wear and value.

There’s no right or wrong way to organize your wardrobe. The key aspect is you must be willing to stick with it. Trust me, it will make things much easier when planning your future clothing purchases.

Given the large, diverse world we live in, the list I’m about to share with you is not going to be perfectly suitable for everyone. For example, if you live in a country that has a much colder climate, adjust the options I present accordingly.

On to the list.

One (1) Navy Blue Blazer

One of the first clothing purchases you make as a man should be something that is extremely versatile, looks great and can be used as a layering option.

That’s exactly what a navy blazer will provide you.

Fit is critical here. I suggest at least purchasing a made-to-measure suit but if that’s not an option, try on a bunch of blazers and purchase the one that most closely matches your body type.

You will then have to bring your blazer to your tailor for adjustments to ensure a better fit. Do not have a tailor? Here is how to find a great one.

One (1) Charcoal & One (1) Navy Suit

The suit of choice for men not familiar with style is a black one.

While a black suit is a good option, there are two more that are preferable to the formal classic.

These are the charcoal and navy suits

The charcoal and navy suit can be worn in any environment and you will never feel out of place. However, you may find yourself the center of attention, especially if the suit fits you really well.

Like the navy blue blazer mentioned above, made-to-measure is your best bet. If your budget is tight, it’s acceptable to get an off-the-rack suit and have your tailor make adjustments.

At the very least try to purchase a canvassed suit versus one that is fused. Fused suits tend to breakdown over time given the way they’re constructed.

Two (2) Dress Shirts of Each: White, Blue & Pink

Dress shirts come in an overwhelming set of cuts, colors and fit, which usually means confusion for the everyday male.

I recommend you build your core selection with whites, blues and pinks first as they all look great on men and can be paired with other colors easily. It’s all about reducing the amount of thinking time when deciding what to wear.

In addition to color, I prefer more modern, slim fitted shirts over classic cuts. Be careful, most shirts made by designers are built for the average male based on recent statistics. If you don’t fit this mold, you have a lot of shopping to do.

Here is the good news – Once you find a brand that works, it makes sense to stick with it as the fit should be very similar.

One (1) Pair Each of Denim: Blue & Black

A good pair of jeans provides comfort, versatility and durability unlike any other pair of pants you can have in your wardrobe.

It’s the reason why jeans are so iconic.

As with most aspects of men’s style, fit plays a crucial role in ensuring the right pair for you. Learn the various cut of jeans available, as the options are many.

Personally, I would go with slim or straight (classic) cut jeans as they go with pretty much anything. Keep in mind that cuts with the same name can vary in length and size based on the brand so research is necessary.

A Few V-Neck White T-Shirts

Most men would automatically assume I’m adding the white t-shirt to use as an undershirt for your dress shirts but that’s not the case. In fact, I would strongly advise against this as I feel it looks sloppy and unattractive on a man.

Instead use the white t-shirt as a base layer under a cashmere sweater, cardigan or on its own with a nice pair of jeans. A white t-shirt that fits well will go with anything.

A Few Cashmere Sweaters

Cashmere sweaters are a great way to add color to your look, as a layering option or even on its own.

Purchasing sweaters made of cashmere provide superior quality garments that don’t skimp on comfort.

Plus, the look of a cashmere sweater over a slim fitted dress shirt is the definition of business casual and looks great on men.

One (1) Pair of Classic Chinos

Chinos are one of those items that look very similar brand-to-brand but in reality, are extremely different from one another.

Finding a pair that can be dressed up or down is tricky but well worth the effort in finding.  There’s something extremely elegant when pairing chinos with brown wingtips, a brown belt and a navy blue blazer.

Test it out for yourself.

One (1) Light Grey Cardigan

If you’re one of those guys that think cardigans are a women’s garment I suggest you read my earlier blog post here.

Cardigans historically were made for men and have a long history in British Navy.

A grey cardigan is the ultimate layering option and looks just as great under a blazer as it does dressed down with a pair of blue jeans.

Various Shoes in Black & Brown

Shoe’s are possibly the most important part of your style. I said this many times and it’s worth repeating again.

If you have $1,000 to spend on your style, at least half of that should be spent on a good pair of shoes. it’s that damn important.

At a minimum, purchase a pair of black and brown oxfords for formal occasions and work your way down to more casual varieties such as brogues and double monk straps.

Click here if you want to learn more about dress shoes.

One (1) Charcoal or Camel Colored Pea Coat

Nothing will be used more in the colder months then a well constructed pea coat.

Since you will be wearing this so often, I would recommend you not skimp on price. A high quality pea coat should provide years of enjoyment and warmth during its lifespan, which will more then make up for the cost.

100% wool or wool/cashmere blends are the way to go when it comes to the pea coat.

One (1) Classic Watch

Consider a high quality watch the icing on the cake when it comes to building your wardrobe.

It makes the most sense to get a white-faced watch with either silver or gold dials as this provides you with many options when pairing with your new clothing.

If possible, purchase a watch that has an interchangeable strap to provide even more versatility. (Have you noticed how much of  believe I am in regards to versatile pieces? It’s important!)

There you have it. By no means is this a complete list and should be used as a guide for the man looking to dive into timeless style.

It’s also worth mentioning that this list should make up the core of your wardrobe with the ability to branch out from here to show off your unique personality.

I hope this post has been helpful to you Elias and to all of you who took the time to read this lengthy post. Feel free to add to this list of timeless items in the comments below as, like always, I’m very interested in your responses.