A classic coat. The bike, not so much.

Fall is upon us in earnest, and winter’s approaching. With it comes the dilemma: what outerwear is both stylish and functional? Bomber jacket, leather coat or parka? Multiple layers or one thick pad of wool or down? Here’s a basic guide to keeping warm while you still look cool.

Know Your Style

By now you should be choosing clothes that suit your body type and personality. The goal is to fit them with outerwear that not only provides protection from the elements, but also finishes your look.

If you’re thin, you can pull off a tight leather jacket or bomber. For the larger man, a more structured jacket or overcoat that squares your shoulders can give you a strong silhouette. Try on a variety of jackets, and ask for opinions on what looks good on you.

Another bit of advice: always try on coats and jackets while you’re wearing the clothes you’ll most often wear with them. That $500 leather coat that fits perfectly over just a t-shirt might not fit right when you’re wearing your favorite sweater. If you’ll be wearing button-down shirts or suits with your coat, make sure the necklines work together.

The Fashionable Choice: Layers

Here in Seattle the weather changes so much from day to day that on a typical December day I might need a light jacket, a thick wool overcoat and rain gear, all in the same day. My answer to this problem is to have a variety of options in the hall closet.

What I rely on most days is a system of layering that keeps me from looking too “thick” while enabling me to discard or add layers to meet the changing temperature. I almost always start with an undershirt. For temperate weather, a simple, cheap Hanes or Fruit-of-the-Loom t-shirt works fine. Mix and match the colors to work with your wardrobe (especially if the T will be visible), and you might find a V-neck or A-shirt (the style colloquially known as the “wife-beater”) works best with lower shirt necklines.

Then comes your shirt, then perhaps a sweater or (if you’re really going casual) a hoodie, topped with your choice of jacket:

Denim jackets are a perennial favorite, protect moderately against wind, and as long as you’re not wearing jeans at the same time, can make for a great layered casual look. (Of course, you can wear it with jeans for that ’70s metalhead look.) Try both light and dark denim, and maybe a similar style or military jacket in cotton twill.

Men's Air Force A-2 Flight Leather Bomber Jacket

Leather jackets offer superior protection from wind, and hold in heat well if they’re thick enough or have a good lining. For a casual look, find a bomber in brown. For dates and going out on the town, find something in a dressier 3/4-length (to the hip) coat. A well-made and looked-after leather coat should last for years, if not decades. Skip the leather trenchcoat, though.

Langham or Pullman jackets are a modern outerwear choice based on a classic look. They’re like an outerwear version of the Pendleton shirt, often in the same traditional plaid. I’ve seen them in both wool and oilcloth, which is cotton that has been treated with linseed oil to make it water-resistant. This is definitely a casual look, great for going out to the stadium. Langham jackets tend to be more of a 3/4-length option.

The Comfortable Choice: Coats

When it’s freezing, it’s freezing, and I know I just want to be warm. Add some rain and you’re not going to be very comfortable in a denim jacket. So at some point you’ll need to turn to outerwear that’s built to keep you as protected as possible. Also, if you wear a suit to work you’ll look a little funny with a leather bomber over top.

Let’s look at the classic coat styles:

Overcoats (also known as topcoats) are longer, usually down to the knees. They offer the best protection for a suit and look best over collared shirts. A nice wool overcoat will do a great job of keeping you warm while offering moderate water-resistance. You’ll definitely need a place to hang your overcoat when you reach your destination, though. One common type of overcoat is the Chesterfield coat, which has no defined waist.

BGSD Men's Wool Blend Peacoat

Trenchcoats like the iconic Burberry or London Fog are a great choice for a day that’s warm enough for rain instead of snow. Typically made of thinner material than an overcoat, a trench‘s first job is repelling moisture. They’re also a classic look over a collared shirt or suit. While the classic trench is a full-length coat, newer trenchcoat styles are 3/4-length. As I mentioned above, skip the leather trenchcoat unless your name is Neo.

Peacoats seem to never go out of style. Usually cut at a 3/4-length and made of wool, the peacoat is an great all-purpose option that can look good on a night out but also get you to work in comfort.  You can use a hoodie as an intermediate layer between your street clothes and peacoat for a funky casual look.

Parkas are sportswear, best suited to winter football games and climates where wearing any other type of coat would result in hypothermia. When you look for a parka, make sure it’s close fitting around the neckline, wrists and hips. A down filling will provide maximum warmth and a dual snap/zipper will prevent wind from whistling through. For more options, consider ski jackets, which also offer superior water resistance and the room to layer underneath without looking like the Michelin Man.

While these are the major options, there are many other styles and sub-styles you’ll find out there. Take your time shopping, try everything on and ask for opinions. If you have a favorite coat, let me know.

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For advanced users only. Really advanced. (Photo by Jim Epler)

Please welcome Schmidty, Tao of Bachelorhood’s very first guest poster. Schmidty is a Image Management consultant and runs a blog called Man Vs. Style. He helps men increase all aspects of their own personal sense of style, helping them to increase confidence, impress women, get a promotion or become a VIP. To check out Schmidty’s work, find him at

One of the problems associated with being a single man is not having a girl’s opinion.

Now, most of the time this is probably a good thing. However, when it comes to dressing ourselves in a stylish manner, it does disadvantage us somewhat.

Why? Because let’s face it, men in general probably don’t have the best eye when it comes to what looks good and what doesn’t.

I will be the first to admit that I did not have a good eye for style. To this day, it probably still isn’t that good, but I can forgo this need by following a few simple rules and paying attention to a few specific things.

Reliance on Girls’ Opinions

We often rely heavily on girls’ opinions, especially if we have been together for a while. Maybe to keep them happy, or maybe just because it is so much easier than having to think for ourselves. This approach to style and dressing ourselves is flawed, because if you end up breaking up:

  1. Your “sense of style” will be lost when you need it most (i.e., to meet other girls).
  2. Girls’ opinions actually differ widely anyway, almost as much as each man’s does towards which football team to follow.

Why Girls’ Opinions can be Good

In order to not need a woman’s opinion, we must first establish why they are usually helpful, and why a woman’s sense of male style might be better than our own.

Below are four main things that set a women’s opinion apart from a typical mans thoughts:

  1. They have a high attention to detail.
  2. They have a very good idea about what to wear for each occasion.
  3. They look at the outfit with a holistic approach.
  4. They are inquisitive.

I will now go into a bit more detail for each one, looking at what we need to do to master each of these.

High Attention to Detail

Anal-retentive, some might call it. And it is annoying when someone picks up the most smallest of flaws in anything, let alone what you are wearing.

But, ultimately,  who are we generally trying to impress?


That’s right, so if women pay attention to detail when you ask them for their opinion, then don’t you think that the other women you encounter in your everyday life are also paying this much attention to detail, and even judging you by it?

The truth is that they are. How many times have you heard people (and especially women) say that your shoes are the most important part of your outfit, even though theoretically they only make up less than 10% of what you are wearing? Because it is the detail.

Some details that we should, but don’t always, pay attention to are:

  1. Watches. First of all make sure you are wearing one. A good looking watch will always get noticed.
  2. Shoes. If nothing else make sure they are clean and not trashed—a mistake that too many men make.
  3. Grooming. Make sure you are well-groomed, from trimming unwanted eyebrow hair to your personal scent to clipping your nails.
  4. Accessories. Women love their accessories, but men don’t use them enough. A good watch, cool sunnies, a single chain, a pocket square in your suit all go a long way.

What to Wear for Each Occasion

I have rocked up to so many events and places where my friends have worn track pants or something equally as casual and looked so far out of place it is not funny, and the only reason is that they had no idea that they should have dressed up a bit more. A bit funny at times, but a bit sad at others.

On the other hand, it is also stupid to wear a tuxedo to a Sunday barbeque.

In order to overcome this embarrassment (although some guys are not even embarrassed, which is actually even more embarrassing), there are a couple things you can do that might seem obvious, but nevertheless should be reinforced for the next time you come across this situation.

  1. Ask the host or organizer what to wear. When I say this, I don’t mean, “Is it black tie?” or “Is it smart casual?” because these definitions in themselves hold lots of ambiguity. So ask specifically, “Is it jeans and a shirt?” or “Is it shirt and slacks?”
  2. Chat to other mates about what they are wearing. Seems a bit gay I know, but as long as you are dressed with the same formality as the guys you are going with, then it doesn’t matter that everyone else at the event is in a different level of dress, because you have mini-social-proof within your own social circle.

Look at Your Outfit with a Holistic Approach

Very, very simple, but often overlooked.

Theoretically, the general principle behind style is that when an individual looks at you, your style should tell a story, first starting with your face and head, and then working its way down to your feet. This sounds a bit Zen, but if you notice when a woman looks at you, even for a split second, they follow this exact path.

Hence, we need to have an “unbroken” approach to our entire outfit.

Some men will think only about the top half and then wear some dress pants in a really bad color that just doesn’t go, but they don’t realize it.

The best way to overcome this is when you finish getting dressed, be sure to take a quick look in the mirror to see the entire outfit together. It takes 20 seconds, but is well worth it.

If you want to avoid this altogether, a technique that I use and teach my clients is “if in doubt, always wear dark blue straight-leg jeans”— an article of clothing that goes with almost anything.

Be Inquisitive

Being inquisitive is not that hard really, it’s just that most of the time men neglect to do it. Since I started being inquisitive about different brands and types of clothes and outfits that other people were wearing or that I saw in stores, choosing and putting together my own outfits has become so very much easier.

Practical things that you can do to be inquisitive:

  1. If you see a friend wearing something you think looks good, ask where they got it from.
  2. Keep pictures of stylish outfits you see on the web and in magazines, and take photos of good outfits you see on mannequins in a store (I do this really quickly with my iPhone, so people think I am writing a text).

Always be on the search for the next “new” thing to wear to your next event.

Keeping it top of mind when you are aimlessly walking past the shops on your way to lunch, or walking down the street and passing by lots of people will help you to always have something stylish to buy (and wear) the next time you need it.

Get a Expert’s Opinion—Free

If you still cannot seem to master style based on the suggestions above, and you still need an opinion, then the best thing to do is get it from someone with an eye for style. How to do this for free? Just ask in the clothing store that you are going to buy from.

If you need a new jacket, then wear the jeans, shoes and shirt that you plan on potentially wearing with it when you go shopping. Ask the person who works in that store, “Does this go?”  or “What would you recommend with this?” Very simple, and it is supposed to be part of the service. Chances are that the sales assistant will have a fair idea, as that is what they do every day.

Final Words

So next time you are putting together your next stylish outfit before you go out, lacking an external opinion, try to do the following:

  1. Pay attention to detail (and include detail where possible).
  2. Wear the right clothes for the occasion.
  3. Take a holistic look at your outfit.

And continually, be inquisitive.

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