Men’s Fall Style Essentials For 2019

Fall and cooler weather will be here before you know it and it’s time to start thinking about transitioning your wardrobe.
A 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.

One quick note, while I love them, you’re not going to see henleys on this list because there are only a select few men that actually look good in them. We did an in-depth article on henleys previously and you can check out why I feel so strongly that only certain men can wear them.

Now, onto our picks for the Men’s Fall Style Essentials you need right now!

 

Denim Jacket

Classic, stylish and easy to layer, a denim jacket is a great pick for fall. Make sure the fit isn’t boxy – you want a slim fit. Also, we recommend a medium to light wash as they pair easily w your dark wash denim and with other go-to fall pants like chinos and corduroys.

Picks:

Uniqlo

AllSaints

Levis

Everlane

 

Crewneck sweater or sweatshirt

I love these because of their casual vibe and versatility, they can function as an outerwear piece over a tee or be layered underneath something else (like that denim jacket we just mentioned) when it gets colder. Stick with solid colors like light grey, charcoal, black, dark green, and burgundy.  You can go with cotton options or look for lightweight merino wool versions.

Picks:

H&M

J.Crew

Brooks Brothers

Todd Snyder

 

Suede or wool bomber jacket

Yes, our love of bomber jackets is well documented, and for good reason, they look great on everyone. The softer, more textured material or wool or suede complements the Fall season.

Picks:

Officine Generale

APC

H&M

Brooks Brothers

 

Casual Collared Shirt

We love a solid flannel or a check pattern and you definitely should have one or two of these in your closet to mix in with your wardrobe. These are great on their own or layered underneath a sweater or jacket or both if it’s chilly. Don’t forget: the length of the shirt should hit around mid-crotch/mid zipper. This allows you to wear untucked for a casual look or tucked in for a more polished look.

Some of our absolute favorite collared shirts come from The Tie Bar and they just launched a new line of fall casual shirts and, just like all their other shirts – they’re fantastic! They fit true to size, come in various sizes for all body types and are very high-quality relative to the price. Dorian has, over the last year or so, completely replaced his collared shirts with ones by the Tie Bar.

Picks:

The Tie Bar Casual Shirts

 

Chinos or corduroy pants

Both are classic go-tos for the Fall season. The darker autumn colors: dark green, darker brown, burgundy are perfect for this time of year and the thicker material makes them extra warm.

Picks:

Uniqlo

J.Crew

Rag & Bone

Our Favorite Budget-Friendly Chinos

 

Suede or leather Boots

Fall is the perfect time for suede footwear and to break out your boots. Chukka, desert, or work boots in light or dark brown suede are super versatile with denim or chinos.

Picks:

AllSaints

Allen Edmonds #1

Allen Edmonds #2

Johnston Murphy

Men’s Fall Style Do’s and Don’ts

Fall is here and it’s time to give your wardrobe some consideration as the weather cools down and the season and style challenges change. Temperatures can be unpredictable and you’ve got some new occasions you’re prepping for. Don’t worry, we’ve got you! Dialing in a great Essential Fall Wardrobe doesn’t have to involve a lot of major changes, just some smart choices and a few tweaks.

So, to help you prep your closet and your wardrobe, we’re running down some of our key fall style tips with our Fall Style Do’s and Don’ts.

 

Fall Style Do’s

Continue To Wear Color

Just because it’s fall and its getting colder doesn’t mean you should stop wearing color. Instead of bright or pastel colors that you would typically wear in spring and summer, opt for darker jewel tones and earth tones to mix in with your neutral greys, black, and navy.

 

Layer Your Clothing

The temperatures in Fall can vary a lot, it’s warmer in the day and gets cold at night and it can be tough to deal with sometimes!  So, proper layering is just the skill you need to master as it can help you regulate your temperature and look stylish. Start with a t-shirt or casual button-down as your base layer, then add a sweatshirt or sweater on top, and next, a bomber jacket, wool jacket, or sportcoat layered on top.

 

Invest In A Pair Of Boots

Boots are essential footwear for Fall/Winter and the right pair can look amazing and last a long time. Think of chukkas and casual and dress boots as your go-to base shoe for non-sneaker situations.  We’ve discussed some of our favorite boots before and here are a few of our favorite picks:

Boot Picks

Allen Edmonds #1

Allen Edmonds #2

Allen Edmonds #3

Clark’s

Johnston Murphy

Red Wing

Wolverine

 

Fall Style Don’ts

Just Wear Jeans Exclusively

It can be tempting to only wear jeans during the Fall but we encourage you to branch out to thicker chinos and wool trousers to mix up your rotation.

 

Flash Lots Of Bare Ankle

Obviously, if you’re in a climate where it’s still warm then this doesn’t apply to you. But if your Fall is on the cooler side, then it’s just not seasonally appropriate (or comfortable). If you want to go with a cuff on your pants try doing it with boots or heavier footwear.

 

Wear Lightweight Fabrics

No man should be wearing linen, lightweight chino cloth, or seersucker anything during Fall and Winter months. Put ’em away and store those until Spring. Heavier cotton, denim, wool and wool blends, and leather should be your fabrics of choice.

5 Men’s Spring Style Essentials For 2019

Spring is here and it’s time to take a look at your wardrobe. Depending on where you live in the country it could still be cool or already getting warm. That means versatile items that layer well to keep you warm or make it simple to dress sharply when it’s warm out.  Don’t forget to check out all of our picks below!

5. Chambray Shirt

One of my favorite essential pieces, its rugged look is perfect for the transitional wardrobe. Wear on its own with chinos or layer it under a sweater or a bomber jacket.

Picks:

Zegna

Saturdays NYC

Amazon Goodthreads

J.Crew

4. Leather Chukka Boot

The perfect versatile boot for your casual and dressy wardrobe.  I recommend dark brown leather (as opposed to suede) for versatility and protection against any spring rain.

Picks:

Clarks

Budget-Friendly Clarks

Johnston Murphy

Allen Edmonds

3. Lightweight Jacket – Denim or Nylon/Cotton Bomber

Temperatures can be unpredictable in Spring so a versatile, lightweight outer layer is just what you need.  These jackets work just as well with a button up as they do with a t-shirt.

Picks:

Levis

J. Crew 1

Topman

APC

Gap

J.Crew 2

Bonobos

Paul Smith

2. Sweatshirt

A baggy hoodie is not what we’re talking about, we mean a well-fitting crewneck sweatshirt. It looks great casually with chinos and denim and is a great alternative to a sweater.

Picks:

J.Crew

Everlane

Todd Snyder

Rag & Bone

1. Chinos

Your go-to pants for Spring, they’re super comfortable and durable. There are versions at every budget and come in stretch and non-stretch varieties these days.  Go with basic colors like khaki, navy, grey, and olive for maximum versatility.  For more tips, check out our full chino rundown.

Picks:

Rag & Bone Fit 2

Bonobos

Uniqlo

J.Crew

Gap 

3 Boot Styles Every Man Should Own For Fall/Winter 2018

Boots are a fall/winter staple and the right pair (or two) should be versatile enough for a variety of outfits and occasions. I think Chelsea boots are more of a spring/summer style so we’re focusing on shoes that will get you through the colder, wetter months of the year and work better with heavier clothing.

One thing to remember, look at boots as an investment, good ones aren’t cheap, but properly taken care of they can last you many years. There are a ton of options out there and we’ll include our picks, but we’ve narrowed it down to three basic styles that you should have in your closet.

Desert/Chukka Boots

The most versatile and least seasonal, you can wear these nearly year round. They’re light and comfortable and work well with both casual looks (jeans, chinos) and more dressy looks (with sweaters and blazers).

Picks

Zegna

Allen Edmonds

Clark’s

Budget-Friendly Clarks

Johnston Murphy #1

Johnston Murphy #2

Work Boots

What you probably think of when you think of boots, these are more rugged and have thicker/chunkier soles. The look great with jeans and chinos and will get you through the colder months and weather with ease. They can come in a variety of styles, some very casual, others a bit more dressy.

Picks

O’Keefe

Red Wing Beckman

Allen Edmonds #1

Allen Edmonds #2

Wolverine 1000 Mile

Danner Jack

Dress Boots

Yes, you can and should dress up your boots. Just make sure you’ve got the right styles. Think of these like the hightop versions of your dress shoes. They should have a thinner, dressier sole and nice leather. Look for them in cap toe or wingtip versions. Formality note: some dressier styles come with a bit more tread (called a lug sole) which can still look good with dressier clothes, but it will make them slightly less formal.

Picks

Edward Green

Brooks Brothers Peal & Co.

Grenson

Mezlan

Allen Edmonds #1

Allen Edmonds #1

Aldo 

Calvin Klein

The Essential Business Casual Details & Outfits

To me, business casual for men’s outfits is a loose definition, but it definitely has an upper and lower range of what’s appropriate. The only true way to determine what it means is by looking at it in relation to the current dress code of the company or function you’re dealing with.

Things to avoid in business casual

Ties

There are rare exceptions, but when in doubt, go without.

Shorts

These are too casual no matter how they’re worn and I’d argue that a man shouldn’t wear shorts in 95% of situations, anyways.

T-Shirts

While I love them, they have no place in a business casual outfit.

Not Tucking In Your Shirt

The sin of all sins for a business casual outfit, no matter your body type, is not tucking in your collared shirts. Polo shirts should only be worn untucked, but the exact opposite is true for collared shirts. It just looks sloppy.

 

Now let’s go over the typical outfits and when they’re appropriate to wear.

Standard Business Casual

For most companies, whether they require a suit (maybe no tie) or a blazer or collared shirt everyday, there are two types of business casual outfits. How close the dress code is to a full suit will determine whether you should wear a jacket or not. Also, depending on the time of year, you may go for lighter or heavier weighted fabrics for your jackets and pants. Hotter = lighter.

With A Jacket

If you are required to wear a suit and tie everyday, definitely go with this one.

Sport Coat/Blazer

Here’s another article I wrote about heavier sport coats/blazers for the Fall & Winter months. Please, whatever you do, don’t wear a suit jacket in place of this. The fabric is too thin and it won’t match the fabric weight of the pants you’ll be wearing.

Oxford Button Down Shirt or Semi-Spread Collared Shirt

Make sure either of these are tucked in to your pants. Definitely wear a belt that matches your shoe color, as well.

Wool trousers, Chino Pants or Dark Wash Jeans

The more formal the dress code, the more likely you should wear wool trousers. Chinos are a little less formal or more used during spring and summer, while jeans a little less so than chinos and typically used year-round. Never, ever – unless the suit pants are a very thick wool (similar to wool trouser weight) – should you wear suit pants without the accompanying jacket.

Oxford Dress Shoes, Monk straps, Brogues, WingtipsBoots (Dress or Chukka) or Loafers

The second you’re not wearing a full suit and tie, you can basically wear anything but sneakers with your business casual outfit. I’d default to Oxfords, Monk Straps or Loafers – either in suede or leather, but any of the options above are acceptable.

Without a jacket

If the dress code or occasion is slightly more casual, you can forgo the jacket and wear this business casual outfit, instead. There’s a few small points to consider.

V-neck sweater

If the weather is too warm, then definitely swap out the sweater for a blazer from the previous section, or, if it can be more casual, go to the next outfit, instead.

Shirt

Same as the previous outfit. You can wear a tie, like in the above picture, but it’s not necessary at all.

Pants

Wool trousers or dark wash jeans. Chino pants have a fabric weight that is too light to go well with v-neck sweaters.

Shoes

Same as previous outfit.

 

Casual Business Casual

This type of business casual outfit is appropriate if there’s a pretty casual dress code normally, or the event is very informal. If you see “business casual” as a requirement anywhere, this is the least formal outfit you can wear that is still appropriate for the dress code. Anything less than this is not business casual.

Harrington Jacket 

This is one of my favorite jackets of all time and fits this outfit perfectly. Obviously, only wear this if the weather is requiring a jacket.

Polo Shirt or Oxford Button Down

I’d probably default to a polo shirt unless you knew for a fact you were going to wear the Harrington Jacket or the weather is cooler. Unless you’re a slimmer guy, an Oxford Button Down worn without a jacket on top of it doesn’t look too good. No matter what, though, make sure the polo shirt fits like a glove or you’re going to look like a goofball and if you wear the oxford, please tuck it in.

Chino Pants or Dark Wash Jeans

Chino pants are the default in an outfit like this, but dark wash jeans are just as appropriate. I’d let the time of year or weather dictate whether I went with chinos or dark wash jeans. The colder it is, the more I’d lean toward wearing the jeans over the chinos.

Sneakers, Loafers, Dress Shoes or Chukka Boots

The more classy you want to make this casual outfit, the more I’d learn toward dressy shoes.

 

That’s it! Hope this is helpful!

Men’s Denim/Jean Jackets & How To Wear Them

After I released my Top 5 Fall Essentials article/video, I received a lot of questions about how to style different washes of denim jackets. I heard you loud and clear, so here’s some of my favorite ways to style them.

Light Wash

To avoid looking like you’re wearing a Canadian tuxedo, wear light wash denim jackets with chinos. You can pretty much get away with any color, but my favorites are navy, green, brown, and burgundy. My classic go-to formula is a t-shirt, chinos, and chukka boots. Crewneck sweaters or oxford button-downs are also good options as well.

$230 – Allsaints denim jacket – One of my favorite denim jackets currently available. I love the lighter wash and distressed touches and the slim fit is incredibly flattering, which is really hard to find in denim jackets. It fits true to size.
$20 – Topman striped t-shirt
$68 – J.Crew slim-fit stretch chino pant in green and brown (click here for their straight leg chinos)
$128 – Brooks Brothers suede belt in brown
$295 – Allen Edmonds plain-toe chukka boots
$318 – John Varvatos sunglasses
$5 – Perlon Watch Strap

Alternate Denim Jacket 

$90 – Levi’s denim jacket (in Queen) – You can never go wrong with this iconic denim jacket. Go with the next size down for this one because it’s not as fitted as the AllSaints one above and you always want a snug fit in the arms and body for all your denim jackets.

Dark Wash

If you only have the budget for one denim jacket, a dark washed one is what I’d choose. I love how dark the wash is because it’s easier to dress it up or down and it also has a slimming effect. I would avoid wearing jeans with a dark wash jacket unless they’re black because I don’t think it looks great and typically most men don’t know how to pair different washes of denim well. You can never go wrong with a pair of chinos and a crewneck t-shirt or sweater. If you want to dress the jacket up more, than pair it with some wool trousers and a collared shirt like I did in my fall accessory essentials article/video.

$118 – J.Crew denim jacket – Definitely go a size down than normal because you want a snug fit. Otherwise, the fit will be boxy which looks unflattering on every man regardless of your body type.
$24 – J.Crew t-shirt
$225 – J.Crew striped sweater
$40 – Uniqlo chinos in navy
$179 – Johnston & Murphy chukka boots
$415 – Tom Ford sunglasses 52mm

Alternate Denim Jacket 

$90 – Levi’s denim jacket (in Rinse) – Go with the next size down because you want a snug fit.

Grey Or Black Wash

Tall, dark, and handsome is how I describe the outfit you’ll be wearing with a grey (or black) denim jacket. Keep it all black – t-shirt, jeans, and boots. You can also go with a white t-shirt but I love how sharp an all black outfit looks with a gray denim jacket adding that perfect pop of monochrome color – it’s especially perfect for a night out.

$285 – AllSaints denim jacket
$75 – AllSaints black t-shirt
$168 – Diesel jeans
$750 – Prada chelsea boots
$415 – Tom Ford sunglasses in black

Alternate Denim Jacket 

$98 – Levis denim jacket

Fall and Winter Boots & Shoes 2017

In this article and video, I wanted to show you some of my favorite boots and shoes for this Fall & Winter. If you missed my big men’s Fall & Winter Essentials series, you should definitely check that out first, since this is more of a supplement to that instead of the other way around.

Suede Boots

Although you can certainly go with leather boots, I am a huge fan of these suede ones by Allen Edmonds. Everything from the superior construction, to the neutral taupe grey color, which I’ll often use in place of black or brown, easily makes this boot a winner in my eyes.

$350 – Allen Edmonds taupe suede boots
$620 – AllSaints bomber jacket
$24 – J.Crew t-shirt
$118 – Banana Republic slim-fit jeans

Alternate Suede Boots

$285 – AllSaints suede boot

Suede Chukka/Desert Boots

Another favorite of mine are these suede chukkas (aka desert boots) which lend a very Autumn feel to any outfit. Again, just like with the boots I mentioned before, you can certainly go with regular leather Chukka boots, as well. But I love these, specifically because they have a slim profile and a comfortable crepe sole which will feel like you’re wearing sneakers. Pair them with jeans or chinos for a put-together casual look.

$295 – Allen Edmonds chukka boots
$230 – Allsaints denim jacket – One of my favorite denim jackets currently available. I love the lighter wash and distressed touches and the slim fit is incredibly flattering, which is really hard to find in denim jackets.
$20 – Topman striped t-shirt
$68 – J.Crew slim-fit stretch chino pant in green and brown (click here for their straight leg chinos) – I’m shocked at how spot on the fits and materials are.
$128 – Brooks Brothers suede belt in brown
$318 – John Varvatos sunglasses
$10 – Perlon Watch Strap

Alternate Chukka Boots

$168 – Banana Republic suede chukkas

Double Monk Strap Dress Shoes

Dress them up with a suit of down with jeans and a blazer. Double monk straps are timeless and will forever be a Fall (and Spring!) favorite of mine.

$120 – Johnston & Murphy double monk straps
$62 – J.Crew merino wool cardigan (currently on sale for 30% off)
$49 – Brooks Brothers navy plaid shirt
$358 – Brooks Brothers green sportcoat
$168 – Diesel slim fit jeans

Alternate Double Monk Straps

$150 – Aldo double monk straps

Grey Sneakers

Outside of white sneakers, grey is a Fall favorite of mine because it’s another neutral color that compliments the darker, more jewel-toned colors you’ll be wearing this season. You can go with suede, leather, or a fabric material, but just make sure to keep the design simple like these ones.

$215 – AllSaints Low Top Sneakers
$80 – J.Crew cardigan bomber (currently on sale for 30% off)
$24 – J.Crew white t-shirt
$118 – Banana Republic slim fit jeans

Alternate Sneakers

$80 – Converse Jack Purcell suede sneakers (or fabric option here) – I also like these suede sneakers as well.

Top 5 Men’s Fall Essentials 2017

Since Fall is upon us, I wanted to do an update and supplement to my Men’s Fall & Winter Essentials series. So don’t think of this as a replacement for the series, think of it as a next-tier type of video and article. Enjoy!
 

1 & 2. Denim Jacket + Chino Pants

My first pick for the season is a denim jacket. It’s perfect for this time of year and works equally well during Springtime, too. Not only does it look good on every body type, but you can layer the heck out of them depending on how cool or warm the weather is. I recommend my go-to styling formula for denim jackets: wear with a t-shirt or crewneck sweater and a pair of chinos and boots.

My second choice are olive, tan and burgandy chino pants. Some of my favorite colors for the season are olive green, brown, and burgundy, which you can easily wear with your other casual jackets and sportcoats.

Outfit Details & Notes

$230 – Allsaints denim jacket – One of my favorite denim jackets currently available. I love the lighter wash and distressed touches and the slim fit is incredibly flattering, which is really hard to find in denim jackets.
$20 – Topman striped t-shirt
$68 – J.Crew slim-fit stretch chino pant in green and brown (click here for their straight leg chinos) – I’m shocked at how spot on the fits and material are. The color choices and friendly price have me stocking up on a handful of these for Dorian this Fall (Seriously, I’ve already added the green and brown ones to his closet!).
$128 – Brooks Brothers suede belt in brown
$295 – Allen Edmonds plain-toe chukka boots
$318 – John Varvatos sunglasses
$5 – Perlon Watch Strap

Alternate Denim Jacket & Chinos

$70 – Levi’s trucker jacket – You can never go wrong with the brand’s iconic denim jacket.
$225 – Rag & Bone slim fit chinos – I’m a huge fan of their chinos because they use a stiffer fabric that’s lays really nicely along the ankles and is super flattering on all shapes and sizes, especially if you’re a hefty fella.

3 & 4. Patterned Sweater & Boots

My third Fall Essential is a patterned sweater. Hopefully, you’ve already got the basic, plain sweaters, so now it’s time to add one that has a subtle pattern because it’s an easy way to add a visually interesting element to your outfits. Also, a pattern helps draw attention away from the torso which is especially beneficial if you’re a slim or husky guy.

My fourth Fall Essential is a pair of boots. You can go with leather or suede, dress or casual boots, but for me, I’m all about the taupe suede boots featured below. These are my hands-down favorite for the season because the color is the perfect dark brownish-grey so they can be used in place of brown or black boots.

Outfit Details & Notes

$100 – Topman acid wash bomber jacket
$148 – Brooks Brothers cotton cashmere birds-eye sweater – The softness, color and subtle pattern instantly caught my eye. No matter your shape or size, this sweater is flattering on everyone. They run slightly larger, so you should size down for the best fit possible.
$10 – Topman slim fit t-shirt in white
$118 – Banana Republic slim fit jeans
$350 – Allen Edmonds suede boots in dark taupe
$98 – Brooks Brothers silver buckle leather belt in brown 
$125 – Ray-Ban black sunglasses
$25 – Brown Leather Watch Strap

Alternate Patterned Sweater & Boots

$89 – Banana Republic wool birdseye sweater – I’m so impressed with not only the fit, but by the superior wool you can get for under $100. The brand sourced the wool from Zegna’s factory, which is always high quality and can easily set you back $600+.
$178 – Banana Republic suede work boot

5. Chambray Shirt

My final pick for the season is a chambray shirt. It looks great on its own or layered underneath a cardigan or jacket. I recommend wearing yours with chinos or wool trousers.

Outfit Details & Notes

$55 – Topman chambray shirt – I’m a huge fan of the lighter wash, but it’s worth mentioning that this shirt runs pretty slim, so if you’re a bigger guy, see my alternate choice below.
$68 – J.Crew slim-fit stretch chino pants in green and brown (click here for straight leg chino)
$98 – Brooks Brothers silver buckle leather belt in brown
$179 – Johnston & Murphy chukka boots in mahogany 
$625 – This Is Ground briefcase
$318 – John Varvatos sunglasses
$25 – Brown Leather Watch Strap

Alternate Chambray Shirt

$55 – The Tie Bar chambray shirt – If you don’t want a super slim fit and/or you’re a larger man, then get this shirt instead.

 

Thanks for reading!