Best Men’s Fall Jackets For 2019 | Best Men’s Outerwear

The right versatile jackets can take your style a long way during Fall and you’re definitely going to need a few options for your Essential Fall Wardrobe. It’s important to have picks that are both dressy and casual but also versatile enough for a variety of situations and light enough to allow for layering.

Before we jump in, there’s one thing you won’t notice on this list, and for good reason, that’s puffer vests. We’re not fans of puffer vests because their usage is pretty limited and they’re just not that stylish. These are the cliche items for the tech bros the past few years – wearing these over their gingham shirts and baggy chinos is…meh. You can do better!

Here are all of our tips and picks for the Best Men’s Fall Jackets for 2019!

 

The Denim Jacket

Timeless and great on a variety of body types, this go-to is perfect with casual looks. Important note: nail the fit. A lot of denim jackets are boxy which you want to avoid. A trim fit will look sharp and compliment your frame, you want them to be fitted throughout the torso (like the pic above), especially if you’re a bigger guy. Specifically, you want to barely be able to button it across your chest. For more, we’ve got a full fit breakdown right here. Wear them with everything from a t-shirt, sweatshirt, to an oxford/flannel and pair it with either denim or chinosIn terms of washes: medium blue, black or light grey as they can easily be worn your existing pants. Avoid matching the wash of your jacket with your jeans, the Canadian Tuxedo isn’t a good look. Protip for the older gentlemen out there: upgrade to a version in suede for a great look. 

Picks:

AllSaints

Everlane

Levis

Todd Snyder

Suede 1: Todd Snyder

Suede 2: John Varvatos

Outfit Details:

Jacket (similar)

Sunglasses

Sweater

T-Shirt

Pants

Boots

Watch Strap

 

The Wool Sport Coat

The perfect way to dress up everything from denim to wool trousers, a great sport coat is super versatile. Look for versions in tweed, herringbone or other weaves and patterns, and we recommend wool or wool blends with some texture and thickness, they’re great for the Fall season. Look for dark fall colors like charcoal, navy, dark green and brown. Solids or patterns like herringbone, houndstooth, or windowpane are perfect!

Picks:

J.Crew

Brooks Brothers 1 

Brooks Brothers 2 

H&M

Outfit Details:

Jacket (similar)

Sunglasses

Sweater

T-Shirt

Pants

Boots

 

Wool or Suede Bomber Jacket

Another way to add some weight and texture to your casual jacket rotation that’s perfect for this year is with a bomber in suede or wool.  By now you know how much I love bombers (perfect for every body type and age range) and a wool/suede version is the perfect casual fall jacket. The fabric can easily take you from day to night and be dressed up or down. Navy, black, brown and grey will pair easily with your existing wardrobe.

Picks:

ASOS

APC

All Saints

Calibrate

Hugo Boss

Outfit Details:

Jacket

Sunglasses

Sweater

T-Shirt

Pants

Belt (similar)

Sneakers

Watch Strap

How To Dress Well When You’re Over 40

Just because you’re over 40 doesn’t mean you shouldn’t be giving some consideration to how you dress. While the majority of our style tips are applicable no matter what your age is, for you older guys out there there are a few extra things to keep in mind. Above all else, it’s about both embracing your age and confidence, and crafting a style and wardrobe that enhances everything you’ve got going for you.

Here’s how to dress well when you’re over 40!

 

 

Dress Your Age

The older you get, the more important it is to dress your age. There’s nothing sadder than an older guy trying too hard to look young. Embrace your age and all the great things that come along with it. We’ll discuss further in a minute but this doesn’t just go for the items you choose, it has to do with the fit and how you wear your clothes as well. It’s important to always strive for a tailored fit. In terms of specific items we recommend,  suede bomber or collared jackets, wool or cashmere blend sportcoats paired with chinos, dark wash jeans, or wool trousers are all excellent places to start. You can easily dress these items up with a collared shirt and dress shoes or dress them down with a sweater or t-shirt and sneakers.

 

Stick To The Classics

Just like dressing your age, as you get older it becomes even more important to stick to classic, timeless items. Leave the trends to the younger guys and embrace the distinguished style that you can pull off. For example, some classic items that should be the foundation of your wardrobe are: suits/blazers, oxfords, dress boots, chinos, Harrington, bomber or standing collared jackets, and polo shirts.

 

Class It Up

Many men mistake getting older and trying too hard with dressing too casually. Yes, there’s always a place in your wardrobe for well-fitting basics, but take your casual wear up a notch. A polo shirt instead of a t-shirt works well, leather loafers or driving mocs instead of sneakers instantly adds class to a casual outfit. And if you want to add personality to your outfits more, that’s always done through accessories – not the main items in your wardrobe. Understated, distinguished and in-control is what we love to see older men doing. Screaming “Look at me!” with crazy outfits or “funny” t-shirts is just immature.

 

Nail the fit

We talk about it all the time and have an entire series dedicated to its importance, because, above all else, this is key. Many older men tend to wear clothing that’s one or two sizes too big to hide problem spots on their bodies or for pure comfort. Big mistake – it actually starts bringing attention to you hiding something and being insecure about it. Wearing-tailored clothing will always allow you to present your best self as opposed to wearing too tight or too baggy of clothing, which is just unflattering.

Dressing Well On A Budget | Affordable Men’s Fashion Tips

Despite what you may think, dressing stylishly and well doesn’t have to involve a lot of money. We’ve talked time and again about how achieving style has everything to do with choosing the right items for a timeless essential wardrobe and nothing to do with how much you pay for something. Whether it’s the right budget-friendly denim and chinos, or affordable accessories that add a bit of personality, you can dress well on a budget, no matter what it is. Another bonus: women care more about how you dress, not what you spend on clothing, trust us.

So, with that, here are a few simple ways that you can dress well on a budget.

 

The Right Fit

It doesn’t matter how much you spend on clothes if they don’t fit they’ll look like crap! A well-fitting $75 bomber will look way better than an ill-fitting $2000 suit. If you handle this part properly, you’ve done 80% of the hard work. Don’t worry, we’ve got you covered with Fit Guides for nearly every wardrobe item in your closet.

 

Nail The Details

Small tweaks like well-chosen accessories (watch, pocket square, a tie bar, or watch band) will elevate an average look to a new level. These items can all be super affordable and when put together with a well-chosen, well-fitting outfit they’re really going to take your style to the next level with a bare minimum of investment.

 

The Right Shoes

There’s no quicker way to ruin a solid, stylish outfit than with a bad pair of shoes. Plus, it’s a fact women will notice your shoes and regardless of how much you spend, they should be clean, in good shape, and timeless in style. Don’t forget to consider the right shoe choice for the situation you’re dressing for. A shoe that’s too casual or overly-dressy with the wrong outfit is just as bad as shoes that are in terrible shape.

 

Dress for the situation

Dressing out of touch for the situation just makes you look like you’re trying too hard or you’ve got no taste, and neither one is something you want to impart to an observer. Whether you spent a lot or a little, if you’re overdressing for a barbeque or underdressing for a work event or wedding, nobody is going to care about your budget, they’re only going to notice how out of place you look.

Do Women Care How Much You Spend On Clothes?

One of the most common comments we see and hear time and again is “Women only care about men who spend a lot on clothing.” Now we believe that style is made up of a lot more things than just the clothes you wear and we talk a lot about how to build a stylish essential wardrobe on any budget. But, it is a fair question to ask.

So do women care how much you spend on clothes? Tune in and find out what we think!

Style and money are unrelated

Fit, and to a lesser extent, materials, denotes how “rich” you can look. You can be wearing a $5k suit but if it fits poorly and isn’t properly tailored, you’re still going to look like crap. But if you’re wearing a $500 suit that’s tailored perfectly and fits your body type well, you’re going to look like a million bucks. Dressing well in clothes that fit you isn’t expensive. Dressing poorly in designer clothing is very expensive and a complete waste of time and money, not to mention, no women will care if your suit is expensive if you look like a mess in it. Since we’re talking about fit, we’ve got Fit Guides for everything, so don’t forget to check ’em out!

Designer Doesn’t Always Mean Good

Covering yourself in designer labels to show how much you spend on clothes actually just shows a lack of class and tact. Wearing a $500 Gucci T-shirt is silly for two reasons: one, they’re knocked off so easily that often people assume it’s fake anyway, and two, did you really just pay $500 for a $2 shirt with a Gucci logo screen printed on it? To women, it makes you look like more of a sucker and its incredibly off-putting. Looking good is about the details and subtlety – women pick up on these more than most men know. 

Dress Within Your Means

We mention it a lot around here but it bears repeating, style is achievable at literally any budget. If you’re spending more than what your means allow on your clothing, that’s an instant alarm to a woman. It shows you’re either insecure or irresponsible financially. Either way, very unattractive. Be honest about your budget and stick with what works for it, it’s a much, much better look. Don’t believe us? We’ve got recommendations for budget-friendly denim, chinos, and more.

Dress For The Situation

If you’re wearing expensive clothing, but it’s inappropriate for the situation, women will be repelled. Wearing your brash, iced-out Hublot watch to a black-tie affair is just gauche. Flashy shows of money like this are inappropriate and they send up red flags like “insecure”, “ignorant”, “tacky”. Subtlety and class are infinitely more important to women, even when they don’t know it. EVERY woman, regardless of who they are, would jump James Bond’s bones because he’s subtle, confident, and elegant in his style. Remember that. 

The Verdict: Absolutely Not

Take it from a woman (and an incredibly accomplished one at that), the right women care about so many things that aren’t money and how much of it you spend (or pretend to spend) on your clothing. Style is about so much more than just what you wear and women know this. Style can be achieved no matter what your budget is, even if it’s zero, so don’t forget that!

 

Why A Man’s Watch Matters To Women

We often talk about how important accessories are to your overall look and wardrobe. When done well, they add that extra 10% that pulls everything together and really lets your personality shine. We don’t recommend a ton of accessories but watches are one of the most important ones. It’s true that the watch you wear says a lot about you, whether you like it or not. That’s especially true when it comes to the opposite sex. Since you’re probably going to ask, no, it doesn’t matter AT ALL how expensive your watch is, let’s just get that straight. But that doesn’t mean watches aren’t something women care about.

Here are the reason why a man’s watch matters to women!

 

SHOWS SOMETHING ABOUT YOUR LIFESTYLE

Whether you’re wearing a Timex, Apple Watch, or a Rolex, the watch you wear will give a woman a few clues as to what your lifestyle is like, and that’s important when we are getting to know you. Maybe you’re a sporty guy and you’re into a G-Shock. Or, you’re more of a tech guy and an Apple watch is your vibe. Either way, it lets women know a bit about who you are.

 

SHOWS YOU PAY ATTENTION TO THE DETAILS

Like with all of your wardrobe, the details matter and women notice the details.  From the fit of your clothes to your haircut, each small component combines to form an important part of the whole.  Watches are no different. The right watch and style choices on your wrist show you care about the right details.

 

SHOWS HOW CULTURED YOU ARE OR AREN’T

Maybe you think watches are redundant since you have a phone, sure, we get that. But, going that extra step is going to add another layer to your style and show that you’re about more than just the absolute bare minimum, and that’s definitely really sexy. But, it’s important to consider what you’re wearing and when just like your shoe choice. You wouldn’t wear Jordans to a wedding so you should consider what watch choices you’re making too.

 

INDICATES WHERE YOU MIGHT BE IN LIFE

No matter where you are on your journey, personal or style-wise, your watch choice is a big indicator of where you are and where you are going. Like we said before, women (well, the right women anyway) aren’t concerned with how fancy or expensive your watch is, but knowing where you’re at and where you’re going is important.

Top 5 Men’s Shoes & Boots For Fall 2019

Now that Fall is officially here it’s an important time to consider your shoe rotation. Since we’ll probably get asked, no, this doesn’t mean these are the ONLY shoes you should wear during the Fall. Year-round essentials like sneakers and lace-up oxfords will always look stylish no matter what time of year. But, these are some specific style upgrades we’ve chosen to complement your wardrobe for this time of year. Make sure you check out our other shoe suggestions and our Fall Essentials to make sure you’ve got your Fall wardrobe dialed in for maximum style and versatility.

So, with that, here are our picks for the top 5 shoes and boots you need this Fall!

 

 

Lace-Up Boots

Fall is boot season and a sharp pair is an absolute necessity. There are a myriad of styles these days and a wide range of price points but if you’re just getting into the game, stick with the basics:  a sharp, slightly dressy pair of captoe or round toe boots. The right pair is sleek and sexy, pairs easily with your jeans and chinos as well as your heavier suits.

Picks:

Allen Edmonds 1 (from the video)

Allen Edmonds 2

Kenneth Cole

Johnston & Murphy

 

Leather High Tops

Dressy and casual shoes are pretty interchangeable these days, and a nice leather high top can work with a variety of different looks. This isn’t a basketball sneaker, it’s more of a cool hybrid between a boot and a standard leather sneaker so don’t be afraid to dress this one up.

Picks:

Wolverine (from the video)

Common Projects

 

Captoe Brogue Dress Shoes

Assuming you have a solid pair of oxford lace-ups in your rotation, a brogued pair is the next logical step. You can find conservative pairs to wear with suits or more informal pairs to wear with chinos and denim. Don’t forget, it’s important to invest in quality where you can and shoes are one of the best places to invest. We recommend these in either brown or black but black is the most versatile.

Picks:

Allen Edmonds (from the video)

Kenneth Cole

J. Crew

Brooks Brothers

 

Chukka Boots

The dress boot’s slightly more low-key cousin, the chukka silhouette is extremely versatile and looks just as good with a suit as it does with denim and chinos. This style looks great in brown or black leather and also is an excellent style to look for in suede.  We love suede for the fall season because it adds just a bit of texture to your overall look.

Johnston & Murphy Leather (from the video)

Wolf & Sheppard Suede

Allen Edmonds Suede

Allen Edmonds Leather

 

Chelsea Boots

If you don’t already have a Chelsea boot in your rotation, now’s the time.  It’s a great alternative to a dress boot for your heavier suits, wool trousers, and black or dark wash denim.  For Fall we are recommending a black leather or dark brown suede as the choices here.  These picks are great because they will work for you year-round, no matter what you’re wearing. One warning though, if you’re on the bigger/broader side Chelsea boots aren’t a great choice for your body type, so just stick to lace-up boots.

Picks:

Kenneth Cole (from the video)

To Boot (similar to video pick)

Cole Haan

Johnston & Murphy

Best Budget-Friendly Men’s Fall Essentials For 2019

Key pieces for a sharp Fall wardrobe don’t have to be expensive, and a few wallet-friendly updates can add a ton of style to your overall look. As we mentioned in our previous Fall Essentials piece, the key thing to think about with your fall wardrobe is changing temperatures, you want items that layer easily or can be versatile enough for varying temps. Like with the rest of the items in your Essential Wardrobe you want pieces that will have you looking sharp no matter your height, body shape, or age.

Here are our picks for the Best Budget-Friendly Fall Essentials for 2019!

 

H&M Wool crewneck sweater – $20

A simple versatile item that can be worn a ton of different ways, from casual to dressy.  We love the one from H&M, it’s budget-friendly and super stylish.

H&M Wool Crewneck

H&M Merino Crewneck

 

The Tie Bar Wool Knit Tie – $25

An easy way to add some texture and personality to dressier looks, these simple additions are great with suits or chinos.  We love the options from the Tie Bar specifically, the bang-for-the-buck is outstanding.

Tie Bar Wool Knit Ties

Tie Bar Wool Ties

 

H&M Quilted Jacket – $79.99

Budget-friendly quilted jackets are very tough to come by but this one from H&M hits all the marks. A solid price, great casual style, and a nice light weight make for a very versatile jacket for your Fall layering.

 

Suede / Perlon / Wool watch straps – $5-$20

A super simple (and cheap!) way to mix up your accessory game. Try something in suede or perlon for some added texture and style to your watch.

Suede Straps

Leather and Suede Nato Straps

Perlon Straps

Wool Straps

 

Uniqlo Corduroy Jeans & Chinos – $39.90

We discussed these in our previous Fall Essentials video, and for good reason, a few solid pairs of pants can really set your rotation up nicely. We really love the corduroys and chinos from Uniqlo because they’re super affordable and great quality for the money.  The range of colors is great too, so make sure you invest in a few pairs to mix up your rotation from denim.

Uniqlo Corduroy Jeans

Uniqlo Chino Pants

 

Leather Lace-Up or Chukka Boots – $130 – $250

A solid and versatile lace-up boot or chukka boot is an indispensable style foundation for fall.  Keep in mind that affordability is relative and you get what you pay for. Ultimately, It’s tough to find anything of quality below $150 or so. The picks below are a great mix of quality and affordable prices.

Picks:

Johnston & Murphy 1

Johnston & Murphy 2

Kenneth Cole 1

Kenneth Cole 2

Clarks

 

Wool Scarf – $13-$60

Easy warmth when you need it and it can be a great accessory.  Go for solid black, grey or navy for an understated look or opt for a pattern like plaid or a bolder color for more of a statement.  Wool blends and cashmere are the most comfortable.

Picks:

Uniqlo 1

Uniqlo 2

Gap

H&M 1

H&M 2

 

Uniqlo Suede Belt – $30

You’ve hopefully got a few casual and dress belts in leather already, but adding a suede version is an easy way to change up your accessory game and add some nice texture to your outfit. As another option, a nice braided leather belt is a cool update as well.

Uniqlo Suede Belt

Uniqlo Braided Belt

 

Flannel Shirts – $30 – $50

We discussed the importance of great casual button-ups for fall and there are a number of good flannel options that are perfect for the cooler months.  You can go for a solid color or a bolder plaid and these are great as a layer under a denim or bomber jacket or just worn on their own. We love the ones from Uniqlo the most but there are other great picks we love below as well.

Picks:

Uniqlo

Gap

J.Crew Factory

 

H&M Blazer – $70

Another super versatile jacket, we love that this blazer can add a bit of polish to any casual outfit, like with denim or chinos, or it can be dressed up with some trousers and a tie. The checked pattern is a nice way to add a bit of personality but in a subtle way and you can even layer a sweater underneath for added warmth.

Picks:

H&M 1

H&M 2

Uniqlo 1

Uniqlo 2

J. Crew Factory

5 Style Hacks Women LOVE (and will notice!)

Sometimes a few simple hacks can make a huge difference in your overall look, and trust us, women are definitely going to notice. The great thing is, these are super simple, in some cases, cost zero money, and are tricks that anyone can pull off.

Here are 5 style hacks women LOVE, and will notice!

 

Tuck in your shirt in the front just a bit

A small move that adds a little bit of polish but never looks too formal, this quick trick is a super-easy way to show you’ve got some serious style skills.

 

Add a watch or slim metal cuff

A little arm candy is really sexy and adds a noticeable, stylish touch to your outfit. Make sure you use good judgment and don’t over-accessorize though, it can look amateurish. We’ve run down a few more accessorizing tips, our favorite metal cuffs, and watch tips in the past as well.

 

A black or navy bomber jacket

There’s something really sexy about this item, it’s just a style that compliments every man no matter his body shape, height or age. Obviously there are other jacket styles out there but this one is always so irresistible because it looks so fresh and understated.  It’s great casually or dressed up and goes with every type of pants.

Picks:

Officine Generale

APC

H&M

Brooks Brothers

 

Stick with a simple outfit formula

Sometimes (ok, most often times) less is more. At the end of the day, it’s when you look like you’re trying too hard that turns women off. Our favorite formula women will definitely love? A great-fitting tee, tucked slightly in, some slim dark wash jeans, a bomber jacket on top and a pair of fresh kicks on the bottom. Understated, stylish and very sexy.

 

A fresh haircut

Yup, it’s that simple, and there’s nothing sexier. It might not seem like a big deal or even noticeable, but trust me, women notice. We’ve run down all of the best haircuts women love before, (and a few women don’t like) so check those out!