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!

Wool Blazers & Sport Coats

I’m sure you’ve already seen my article/video about a Navy Wool Blazer in my Wardrobe Essentials Series, riiiiiggghhht? If not, then please read and watch it first before we talk about Fall and Winter wool blazers/sport coats, because I’m going to assume we’re on the same page in regard to the differences between a blazer, sport coat and suit jacket as well as how your blazer should fit your body type as well as the finer details of what to look for in a quality blazer. Otherwise, you will probably be lost or think this article is a little anemic. There will be a few critical differences between your year-round blazers and your specific Fall and Winter wool blazers. So let’s get into them.

1. Fabric Weight

The most important difference during this time of year is the fabric weight of your blazer.

You want a much heavier wool fabric, like Harris Tweed, for three reasons:

  1. It will keep you much warmer during this time of year.
  2. The heavier weight pairs better with similar weighted fabrics during this time of year – Like your wool ties and pocket squares, wool trousers, sweaters, cardigans, etc.
  3. If it has a tighter weave, like Harris Tweed, it’ll be more durable, robust and repel water and snow better.

To get technical for a moment, a typical weight you should look for is around 12 ounces, but you can go all the way up to 16 to 20 ounces. For year-round wool blazers, I prefer a fabric weight of between 8 to 10 ounces, depending on your climate. In comparison, for hotter climates/seasons, I usually go with somewhere around 6 ounces for the fabric weight.

You’ll instantly notice the difference of fabric weights when you feel the blazer in-person. It’s a little harder to see it in in pictures, so I would suggest going to a store that carries suits to see it for yourself.

Long story short, you want a thicker wool for this time of year.

2. Color

The second difference is the colors for the time of year. Unlike the year-round wool blazers, this is the time of year where you can wear richer, more jewel-toned colors, all based on your skin tone, of course.

The best way I can describe colors is to think of the leaves changing to their fall colors and those are the colors you want for the season. So that typically means these colors:

  • Browns
  • Burgandys
  • Greens
  • Blues
  • Oranges

I went over all these colors and how to wear them based on your skin tone in my introduction article & video to this series.

3. Patterns

The last and final thing to consider for your Fall & Winter wool blazers are the patterns. Since you’ll be wearing heavier items, bold and heavier patterns work great this time of year.

My favorites are:

All of these patterns are included in my selects from various brands below.

Best Ways To Wear A Wool Blazer During Fall & Winter

MensFallWinterEssentialsWoolBlazerAshleyWeston

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H&M Dark Khaki (Green) Blazer
J.Crew Cotton-Cashmere Crewneck Sweater in Jacquard
The Tie Bar Kingsley Attune
H&M Wool Suit Pants
Aldo Acerrassi boot
Rolex Submariner Date
Tom Ford Snowdon Sunglasses

MensFallWinterEssentialsWoolBlazerAshleyWeston-10

 

MensFallWinterEssentialsWoolBlazerAshleyWeston-11 MensFallWinterEssentialsWoolBlazerAshleyWeston-4

Topman Light Brown Wool Rich Formal Coat
The Tie Bar Chambray Shirt 
The Tie Bar Wentworth Plaid 
The Tie Bar Kingsley Attune Pocket Square 
The Tie Bar Metallic Navy Tie Bar
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Johnston & Murphy Cormac Double Buckle Monk Strap
John Varvatos Prince Sunglasses

MensFallWinterEssentialsWoolBlazerAshleyWeston-12

MensFallWinterEssentialsWoolBlazerAshleyWeston-5

MensFallWinterEssentialsWoolBlazerAshleyWeston-6

H&M Wool-Blend Blazer Slim Fit
Brooks Brothers Milano Spread Collar Dress Shirt
The Tie Bar Score Check Tie 
The Tie Bar Olive Green Tie Bar
The Tie Bar Southeast Plaid Pocket Square
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Allen Edmonds Strand Cap-Toe Oxfords with Dainite Rubber Sole
IWC Portugieser Automatic Dress Watch
Tom Ford Snowdon Sunglasses 

All of these blazers are from companies that I love. Zegna, Canali, and Brooks Brothers’ blazers have superior construction and the fit, color, and pattern are exactly what I look for in a standout blazer for my clients. For more budget-friendly options, I really like J.Crew’s english tweed sportcoats. The weight of these blazers are perfect and the solid textured colors (brown, grey, and navy) will never go out of style. For a nice camel or dark green blazer, Topman and H&M, respectively, make these nice blazers. The fabric isn’t as thick as I’d prefer, but the price point is hard to beat so I’m willing to overlook that.

$2,895 – Ermenegildo Zegna Windowpane Two-Button Sport Coat
$1,595 – Canali Tic Two-Button Sport Coat
$538 – Brooks Brothers Milano Fit Multi-Windowpane Sport Coat
$418 – Brooks Brothers Fitzgerald Fit Blue Harris Tweed Tic with Windowpane Sport Coat
$350 – J. Crew Ludlow Legacy Blazer in American Wool
$220 –Topman Light Brown Wool Rich Formal Coat
$200 – TopMan Selected Homme Navy Blazer
$70 – H&M Dark Khaki Blazer

Wool Ties & Pocket Squares

I’ve already talked pretty extensively about ties and pocket squares in my Men’s Essential Accessories series, so if you haven’t sen those articles/videos and don’t know the size of ties you should be wearing or the best ways to fold your pocket squares, check them out. The wool ties & pocket squares I’ll be discussing below are essential for the Fall and Winter seasons because they will compliment the items in your Fall/Winter Wardrobe nicely.

 

Material

For your ties and pocket squares during this season, you need to go all in with wool. There’s also technically cashmere, but there’s not a lot of them being made and I find them to be obscenely expensive when a wool tie looks just as good.

The reason you go all in on wool is because you want your accessories to compliment the fabric weights of the items you’ll be wearing during the various seasons, so if you were wearing silk or linen ties, which are for Spring and Summer, with your heavier wool suits or sport coats, it would look really off.

Colors

As I mentioned in the Series intro, this is the time of year to wear some nice, rich colors, like:

  • greens
  • shades of blues
  • burnt oranges
  • grays
  • burgundy
  • browns

Patterns

As far as patterns, it’s also the best time of year to wear plaids, paisleys and polka dots because they’re visually heavy and pair so well with your Fall and Winter wardrobe.

The one area that I see men really have an issue, though, is with matching these patterns and colors together with their outfits or other accessories.

A good rule of thumb is:

If your tie is a bolder pattern, like a paisley or plaid, then you want your pocket square to be more subtle or as close to a solid color as possible. It doesn’t have to be a solid, but when in doubt, go for a solid one. This ensures you don’t have too many patterns clashing. (See the video above and outfit images below for examples)

And the inverse is true for a patterned pocket square – go for a solid or very subtle patterned tie.

This helps balance these items out so you don’t look like a goofball.

Best ways to wear Wool Ties and Pocket Squares

fallwinteressentialstiespocketsquareashleyweston fallwinteressentialstiespocketsquareashleyweston2TopMan Selected Homme Brown Wool Rich Suit Jacket
The Tie Bar Chambray Shirt 
The Tie Bar Wentworth Plaid 
The Tie Bar Kingsley Attune Pocket Square 
The Tie Bar Metallic Navy Tie Bar
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Johnston & Murphy Nolen Double Monkstrap Shoes
John Varvatos Prince Sunglasses
fallwinteressentialstiespocketsquareashleyweston3 fallwinteressentialstiespocketsquareashleyweston4H&M Wool-Blend Blazer Slim Fit
Burberry Slim Fit Cotton Poplin Shirt
The Tie Bar Score Check Tie 
The Tie Bar Olive Green Tie Bar
The Tie Bar Southeast Plaid Pocket Square
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Allen Edmonds Strand Cap-Toe Oxfords with Dainite Rubber Sole
IWC Portugieser Automatic Dress Watch
Tom Ford Snowdon Sunglasses 

The Best Wool Ties

Notes About My Recommendations

The ties from Tom Ford, Alexander Olch, and Thom Sweeney are pricey, but you’re paying for a high quality, luxurious accessory that’s timeless. If you’re going to shell out this amount of money for a tie, then you want to make sure it’s easy to wear and it’ll never go out of style.

For fun patterned ties that are also easy on the wallet, I’m a huge fan of The Tie Bar (and no, they’re not paying me to say this). For great textured wool ties in solid colors, I love J.Crew. They also made a charcoal chalk stripe tie that is really easy to wear with your existing wardrobe.

$250 – Tom Ford Dot Wool Tie
$180 – Drake’s 8cm Houndstooth Wool and Silk-Blend Tie
$160 – Alexander Olch ‘The Spot’ Knit Necktie
$60 – J. Crew American Wool Tie in Charcoal
$20 – The Tie Bar Webster Medallions Tie
$20 – The Tie Bar Score Check Tie
$20 – The Tie Bar Woolf Houndstooth Tie
$20 – The Tie Bar Wentworth Plaid Tie 

The Best Pocket Squares

Notes About My Recommendations

Brunello Cucinelli makes probably the best – in terms of color, pattern, and quality – pocket squares out there, in my opinion. The Hugo Boss and Alexander Olch pocket square and rounds are all the perfect shade of grey so they’ll pop really nicely from your darker suits or sportcoats.

The striped J.Crew pocket square will go with pretty much every Fall suit/sportcoat you have. For some great patterened options at an incredible price point, I love the double sided ones by The Tie Bar.

$95 – Armani Collezioni Chevron Patter Pocket Square
$95 – Marwood Slub Pocket Square
$60 – Boss Wool Patterned Pocket Square
$60 – Alexander Olch ‘The Birdseye’ Wool Pocket Round
$60 – Alexander Olch ‘The Windowpane’ Wool Pocket Round
$30 – J. Crew English Wool-Silk Pocket Square in Stripe
$10 – The Tie Bar Kingsley Attune Pocket Square
$10 – The Tie Bar Quest Tooth Pocket Square
$10 – The Tie Bar Wentworth Houndstooth Pocket Square
$10 – The Tie Bar Southeast Plaid Pocket Square

Men’s Dress Shoes – Monk Straps, Brogues, Wingtips

Let’s talk about my favorite and what I consider the best men’s dress shoes for Fall and Winter – Monk straps, Brogues, and Wingtips.

Quick note: Wingtips are technically Brogues, so I’ll be lumping them together throughout this article. Just know when I refer to Brogues that I also mean Wingtips.

I prefer these during the cooler parts of the year because they go much better with the heavier wool and cotton items you wear in your Fall and Winter outfits. Don’t get me wrong, they also work year-round, but I think there’s better options out there for the other parts of the year. Check out my Summer Essentials Ebook and Wardrobe Essentials Series for details about those options.

Below are the things I look for in a good pair of Monk Straps or Brogues.

MATERIAL

As I said in my Fall/Winter boots story, I love a good calf skin. Don’t get me wrong, I love a suede monk strap or brogue, as well, but if you live in an area with snow or rain, you’ll regret the day you wear them outside. So let’s wait to get into those until Spring or Summer.

SHAPE

I will say this about dress shoes until the day I die, but you want a nice, slim profile with a rounded toe box. Ain’t nobody got time for square or large, bulky toe boxes! – See the video near the top of the article if you’re unsure about what they look like.

COLOR

As for colors, I love a nice dark chocolaty brown, or even a medium brown, like a walnut. Black is also good, but the first color I’d get is brown because it goes better with all the Fall colors in your wardrobe. All these colors are represented in my suggestions at the bottom of this article.

SOLES

If you live somewhere with a bit of rain, ice or snow, then you can and should definitely have these with Dainite or rubber inset soles for added traction. If you don’t live in that kind of climate, then a regular leather bottom that you’ll find on 99% of dress shoes is perfectly acceptable, but I’d probably look for a Dainite or rubber insert sole as my default. There’s also lugged soles, which are pretty popular right now (and I included some in my selects below), but I have a feeling they won’t be around for the long haul. They’ve already come and gone with fashion a few times in my lifetime. When it comes to Fall/Winter boots, though, I love me a lugged sole.

MONK STRAP SPECIFICS

I prefer a double buckle because a single buckle looks less refined. (Example in the video at the top).

If you get black Monk Straps, make sure the buckle is silver, because gold or brass tends to look gaudy, but is perfectly fine on brown monks (examples in the video).

Also, please make sure the buckles are on the smaller side as opposed to some big ass buckles you’ll find on a colonial gentleman.

As for medallion toes and other flourishes, I like all of them, so check out my recommendations below.

 

Best Ways To Wear Dress Shoes

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H&M Blazer Slim Fit
Burberry White Slim-Fit Poplin Dress Shirt
The Tie Bar Navy “Score Check” Tie
The Tie Bar Olive Green 1″ Tie Bar
The Tie Bar Grey Southeast Plaid Wool Pocket Square
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt
Allen Edmonds Black Strand Dress Shoes
Tom Ford Snowdon Sunglasses
IWC Portugieser Automatic Watch

fallwinteressentialsdressshoesmonkstrapsashleyweston

fallwinteressentialsdressshoesmonkstrapsashleyweston2

Topman Light Brown Wool Rich Formal Coat
Burberry Slim Fit Cotton Poplin Dress Shirt
The Tie Bar Webster Medallions Tie
J.Crew Slim Merino Wool Cardigan
John Varvatos Grand Sunglasses
J.Crew Ludlow Suit Pant in English Donegal Tweed
Johnston & Murphy Nolen Double Monkstrap Shoes

Brogues & Wingtips

Budget Friendly

$130 – Aldo Bartolello
$165 – Johnston & Murphy Jennings Wingtip
$195 – Vince Camuto Tallden – Wingtip Oxford (2 colors)
$225 – Vince Camuto Benli Oxford

Designer

Allen Edmonds Strand Brown Cap Toe

$395 – Allen Edmonds Strand Cap-Toe Brown Oxfords with Dainite Rubber Sole

These, to me, are the quintessential Brogue. If you’ve seen my other dress shoe article then you know my love of Allen Edmonds. They make amazing products with great value – and they don’t pay me to say that. I’m just a huge fan.

I love this color and the Dainite soles. They’re just perfection.

$395 – Allen Edmonds McAllister Wingtip with Dainite Rubber Sole
$395 – Allen Edmonds Strand Cap-Toe Black Oxfords with Dainite Rubber Sole
$650 – Church’s Toronto Cap-Toe Oxford Brogues
$780 – Prada Runway Hybrid Wing-Tip Oxford 
$1,990 – Tom Ford Austin Cap Toe Oxford Shoe 

Monk Straps

Budget Friendly

Johnston Murphy Nolen Double Monk Strap Brown

$185 – Johnston & Murphy Nolen Double Monk Cap Toe

These hit all the points I look for in a double monk – the beautiful chocolaty brown with the matching soles, the silver hardware and the rubber tread inset for added traction. On top of that, they’re a GREAT price and my clients always comment about how comfortable they are. My other favorites are the Allen Edmonds Monks below, if you’re looking for something higher quality.

$99 – Kenneth Cole Regal Bearing Leather Monk Strap Dress Shoe (2 colors)
$160 – Aldo Caresien 
$225 – Vince Camuto Briant Double Monk Strap Shoe (2 colors) 

Designer

Allen Edmonds St Johns Black Double Monk Strap

$395 – Allen Edmonds St. Johns Black Double Monk Strap 


$395 – Allen Edmonds St. Johns Brown Double Monk Strap  
$395 – Allen Edmonds Mora 2.0 (3 colors)
$435 – Crockett & Jones Lowndes (2 colors) 
$700 – Brooks Brothers Peal & Co. Double Monk Strap

Men’s Crewneck Sweaters and Cardigans

My favorite sweaters for this time of year are crewnecks and cardigans – either regular or shawl collar styles. They’re great because not only do they keep you warm, but they allow you to create a bunch of new looks depending on how you layer them with the other items you own.

Before I go any further, I want to make sure you’ve already seen my v-neck sweater article and video, because:

  • You should already own some v-neck sweaters since they look amazing on every body type and can be worn year-round.
  • You know the do’s and dont’s with sweaters and how they should fit your body type because I’m going to discuss  crewnecks and cardigans as if you already know these guidelines.

Crewneck Sweaters

Brook's Brothers Golden Fleece Merino Wool Charcoal Crewneck

$300 – Brook’s Brothers Golden Fleece 3-D Knit Fine-Gauge Merino Wool Charcoal Crewneck Sweater

I like crewnecks because they can be worn over t-shirts, unlike v-neck sweaters which look weird with t-shirts under them, and they look great in casual outfits or can take a more dressy outfit, like a suited look, and dress it down, while still adding a nice, warm layer to your outfit.

The two things you have to do, though, and I’ll say this forever, is:

  1. Really nail the fit
  2. Know how to wear them, based on your body type.

If you are a broader guy, then crewnecks 100% of the time have to be worn as a layering piece only. So underneath a jacket, blazer or suit – never on their own because, otherwise, it’ll create a huge swath of fabric on your torso and accentuate your size. Trust me, you don’t want this. (Watch my video at the top for examples).

Fit

For any body type, you always want to make sure your crewneck sweater fits like a glove. Make sure you can’t pinch more than an inch of fabric on the back of your tricep and no more than 2 inches of fabric on one side of your belly.

As for length, ensure the sleeves generally stop around the bend of your wrist, and make sure it is no longer than just past your belt buckle area.

The thing that drives me nuts is when I see guys wearing crewnecks with big bunchy sleeves and rolled or rippled mid-sections. Bleh!

Budget Friendly

$26 – Zara Basic Fine Knit Sweater
$40 – TopMan Grey Ripple Textured Raglan Slim Fit Sweater 
$50 – H&M Merino Wool Sweater
$55 – TopMan SELECTED HOMME Black And White Woven Long Sleeve T-Shirt
$70 – H&M Textured Knit Cashmere Sweater 
$158 – J.Crew Lightweight Italian Cashmere Crewneck Sweater 

Designer

$190 – A.P.C. Bros Sweatshirt 
$230 – John Smedley Marcus Crew Neck Merino Wool Sweater (3 colors)
$300 – Brook’s Brothers Golden Fleece 3-D Knit Fine-Gauge Merino Wool Brown Crewneck Sweater
$375 – Vince Heathered Cashmere Sweater
$675 – Brunello Cucinelli Cotton Crewneck Spa Sweatshirt
$950 – Prada Cashmere and Silk Blend Sweater 

Cardigans: Regular and Shawl-Collar

J. Crew Slim Merino Wool Navy Cardigan

$90 – J. Crew Slim Merino Wool Cardigan Navy Sweater

Now let’s move on to cardigans – specifically, regular and shawl collar styles.

Just like crewnecks, they’re great worn over most shirts (even with ties) except v-neck t-shirts (unless it’s a really shallow “V”, otherwise it just looks weird with the double “v”) or polo shirts because the collars never lay or look right with cardigans.

Regular cardigans can pretty much be worn underneath everything up to a suit, while shawl collar cardigans, since they’re usually made of thicker wool or cotton, are typically worn on their own. Think of shawl collar cardigans as knit jackets, basically and wear them in their place.

If you’re a larger guy, regular cardigans are to be worn buttoned up AND only underneath another item as a layering piece. If you were to wear it on it’s own, it’ll make you look super big and wide. (examples shown in the video at the top).

If you have a regular or slim body type, then you can wear regular cardigans on their own, but almost always buttoned up – leave the bottom button undone so it lays nicely and doesn’t look bunched up while you’re sitting. I think when they’re worn unbuttoned, they lose their structure and get really floppy and messy looking.

For shawl collar cardigans, if you’re a broader guy, you should absolutely wear them on their own, but never buttoned up. Leaving it unbuttoned breaks up your width nicely and looks great and hides those problem areas around the midsection and upper body. I really love them for this body type.

If you’re any other body type, you can wear your shawl collar cardigan buttoned or unbuttoned, but remember to leave the bottom button undone, of course.

FIT

As to how your cardigans should fit, the same crewneck rules apply:

Pinch no more than 2 inches on one side of your stomach and no more than an inch on the back of your tricep.

It should hit pretty close to past your belt buckle and the sleeves should end somewhere around the bend of your wrist.

Regular Cardigans

Budget Friendly

$30 – Zara Viscose Cardigan 
$90 – J. Crew Slim Merino Wool Cardigan Sweater (3 colors)
$120 – Club Monaco Soft Wool Cardigan

Designer

$230 – Club Monaco Cashmere Cardigan
$300 – Vince Mixed Rib Cardigan 
$415 – Boglioli Cotton Cardigan

Shawl Collar Cardigan

Budget Friendly


$30 – Only & Sons Shawl Neck Cardigan with Mix Yarn Detail
$118 – J. Crew Shawl Collar Cardigan Sweater
$150 – J. Crew Cotton Shawl Collar Cardigan Sweater 

Designer

 

$275 – Rag & Bone Avery Navy Shawl Cardigan
$275 – Rag & Bone Avery Shawl Army Green Cardigan
$598 – Brooks Brothers Cashmere Shawl Collar Cardigan
$1,590 – Tom Ford Iconic Shawl-Collar Cardigan

Colors

As for colors, I mentioned them in the series intro video, so check that video and article out for details about the colors that will go well with your skin color.

MATERIALS

And lastly, before I show you how I’d style these sweaters, let’s go over the best materials for your sweaters.

If you run warmer, you want your sweaters to be cotton blends, otherwise wool and cashmere are my two favorites.

Best ways to wear your sweater

fallwinteressentialsovercoatcamelsweaterashleyweston

H&M Double Breasted Coat
H&M Merino Wool Sweater
A/X Pima Tee
Burberry Slim Fit Wool Trousers
Johnston & Murphy Jennings Wingtip
Tom Ford Snowdon Sunglasses

MensFallWinterEssentialsSweatersCardiganAshleyWeston

Topman Light Brown Wool Coat
Burberry Slim Fit Cotton Poplin Dress Shirt
The Tie Bar Webster Medallions Tie
J.Crew Slim Merino Wool Cardigan
John Varvatos Grand Sunglasses
J.Crew Ludlow Suit Pant in English Donegal Tweed
Johnston & Murphy Nolen Double Monkstrap Shoes

1Chiwetel Ejiofor Martian Style Ashley Weston2

Rag & Bone Avery Shawl Collar Cardigan
Brooks Brothers Milano Button-Down Collar Dress Shirt
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Casual Belt
Johnston & Murphy Conard Cap Toe Chukka 

Fall Winter Coats – Parkas

When I first released my Overcoats and Peacoats video and article, all the New Englanders, Canadians and Northern Europeans complained that they couldn’t wear my favorite pieces because they just weren’t warm enough. I admit – being in Southern California definitely skews my perspective in this regard.

So let’s rectify this!

To me, there’s really only one winter jacket that I like and that looks great on everyone and keeps you nice and warm and that’s a Parka. But not all of them are created equally.

First and foremost, I keep getting asked for a “stylish” winter jacket. Honestly, when you get into crazy cold weather, I think utility should supercede style. That’s not to say parkas aren’t stylish, but no one is going to look at you in your parka and think how amazing an outfit looks.

They’re designed to go over an outfit and be taken off the second you go indoors. So if you really want to look stylish in cold weather, either throw on a fall jacket, overcoat, peacoat and layer, like your life depends on it.

 

What To look for in a good parka

Length

Depending on your climate and how cold it gets determines how long your parka should be. The longer it is, the colder your climate.

So you would wear a waist or hip-length parka if you were in an area that gets cold, but not crazy snowy.

Or if you were in the tundra, you’d wear a parka that hits your knees, or even past that.

But if you live in a climate that is somewhere in the middle, then go with a parka that hits mid-thigh.

Just don’t be that guy in San Diego wearing a knee length parka – it’s too much and looks weird.

Colors

I love Navy, Black or Olive. Do make sure the material isn’t shiny.

If I had to chose a color, I prefer Navy because it’s a very dark color, like Black, but is easily wearable. Olive is also a great color. Black can sometimes look a bit jarring in such a big jacket. But you can’t really go wrong with any of those colors.

Fit

Make sure your parka fits relatively well. That means the shoulders should fit snugly and the body should lightly hug your torso. When trying on parkas, make sure you’re wearing at least a sweater and shirt underneath so you can ensure it won’t be too tight when actually wearing it. Also make sure to zip up that bad boy in case it feels too tight in the body!

Lining

I prefer a down lining, but synthetic is also acceptable. I always find down to be a little warmer, but as always, your mileage may vary.

Detachable Fur Collar

It’s a convenience thing. So I wouldn’t disqualify a jacket for this reason, but it’s a nice thing to have because it creates a slightly different look, so I like the option whenever possible.

How To Style Your Parka

Even though they’re mostly a utility item and style takes a backseat, I couldn’t help styling a parka outfit for you. One of my favorite parkas is by Parajumpers. They do such a great job with the fit of their jackets. Anyways, I styled it over a grey crewneck sweater, wool trousers, and wingtips. And of course, I threw on a scarf and some gloves.

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Parajumpers Navy Harraseeket
Topman Premium Dark Grey Ribbed Slim Fit Sweater
Brooks Brothers Leather Gloves with Black Watch Cuffs
H&M Wool Pants
Brooks Brothers Cashmere Scarf
Allen Edmonds Strand Dress Shoes
Tom Ford Snowdon Sunglasses

The Best Parkas For Men

Parajumpers Harraseeket

$1,125 –Parajumpers Navy Harraseeket

A quick note about the parkas below – You really get what you pay for. Even though there’s some budget-friendly options, I wouldn’t consider them even close to the same quality as the other parkas near the middle and top of the list. These really should be investment pieces and the overall cost of ownership will go significantly down per year if you get a high-quality jacket since it’ll last many, many years.

$2,195 – Moncler Rethel Parka (2 colors)
$1,295 – Nobis ‘The Maverick’ (2 colors)
$1,150 – Mackage Edward Hip Length Down Winter Parka with Fur (2 colors)
$1,125 – Parajumpers Harraseeket (Black or Olive)
$1,100 – Canada Goose Balmoral Parka Black Label
$1,095 – Andrew Marc Everest Fur-Trim Hooded Parka, Jet Black
$900 – Canada Goose Chateau Parka w/ Fur Trimmed Hood, Navy
$900 – Theory Jayse Padded Coal Parka
$700 – Arc’teryz Therme Parka (2 colors)
$300 – The North Face Thermoball Triclimate Black Parka
$100 – TopMan Black Short Parka 
$100 – TopMan Premium Forest Green Parka
$60 – H&M Padded Parka

Fall and Winter Casual Jackets

The best jackets for the Fall (and Winter if you live in a climate like Southern California) are bombers, trucker & flight jackets, as well as utility (aka M65 aka Safari aka Field) jackets. Now, which one you should wear depends on your body type and how you’ll be wearing it. But I’ll get into that shortly.

The goal with your jacket, just like everything else in your wardrobe, should be to create a sharp, polished look and not draw attention away from the rest of your outfit. With that being said, your jacket is a great place to insert those Fall colors ( I specifically like dark green, camel, navy or black for these jackets) I was talking about in the series intro.

If you want something a little more formal or heavier, check out my Men’s Overcoat, Topcoat and Peacoat article and video.

Trucker/Flight Jackets

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$735 – Todd Snyder x Private White V.C. Shearling Melton Wool Bomber Jacket

I love a good wool or suede trucker or flight jacket for the Fall. I’m lumping these together because they look very similar. A trucker is basically a denim jacket but in a different material. I’m not going to discuss denim jackets because those are really a spring/summer item because they’re not very warm.

A trucker usually has buttons on the front and a flight jacket has a zipper front. You want to make sure your jacket stops at hip level, like a bomber would, and is fitted through your shoulders and torso. There are a ton of trucker jackets out there that have shearling or fur collars, which I really love, but I’d recommend choosing a jacket where you have the option of removing the collar, that way, you can get two different looks out of one jacket.

If you’re a broader guy, I wouldn’t recommend this jacket because the combination of the collar and shorter length of the jacket will make you look really top heavy. With your body type, whenever you have a jacket that stops at hip level, you want to make sure it’s as streamlined as possible, like a bomber.

Budget Friendly

$160 – TopMan Charcoal Wool Rich Formal Jacket
$160 – TopMan Khaki Wool Mix Flight Jacket
$150 – TopMan Black Faux Fur Collar Flight Jacket
$90 – Zara Oversized Denim Jacket 
$77 – TopMan Kahki Faux Fur Lined Flight Jacket 

Designer

$900 – Vince Suede Trucker Jacket
$950 – Vince Suede Flight Jacket
$540 – All Saints Sol Jacket 
$285 – All Saints Stram Denim Jacket 

Bomber Jackets

A.P.C. Louis W Suede Bomber Jacket

$1,455 – A.P.C. Louis W Suede Bomber Jacket

Speaking of bomber jackets, I consider them the utility infielder of the jacket world. I use them all the time with clients because they look great on every man, regardless of his body type. They break up your body at the waist nicely, keeping everything proportional.

If you’re a guy with a larger midsection, the one thing to watch out for with bomber jackets is zipping it up. If you do that, you just created a large swath of fabric that’ll actually accentuate your mid-section. So if you’ve got a bit of a belly or are just a bigger guy, do not zip up your bomber jacket, ever. And I’m not joking about that, either.

Budget Friendly

$138 – J. Crew Wallace & Barnes Boiled Wool Bomber Jacket
$100 – TopMan Navy Bomber Jacket Containing Wool
$100 – TopMan Stone Bomber Jacket Containing Wool 
$80 – Zara Faux Suede Bomber Jacket (Stone and Navy Blue)
$80 – Zara Faux Suede Bomber Jacket with Stripe

Designer

$1,495 – Rag & Bone Gallagher Leather Bomber Jacket
$795 – Hugo Boss Embossed Suede Navy Bomber Jacket 
$700 – John Varvatos Burnished Leather Bomber Jacket
$650 – PS by Paul Smith Bouclé-Panelled Wool-Blend Twill Bomber Jacket

Utility Jackets

Parajumpers Genesee Urban Anthracite

$800 – Parajumpers Genesee Urban Anthracite

The last type of jacket I love for Fall and Winter is a utility jacket, aka Safari, Field, or an M65 jacket.

This jacket differs from my other favorites because if it fits well, it’ll hit somewhere between mid to lower crotch – so it’s a great option if you want a longer jacket. But please, nothing longer or shorter than that, otherwise it’ll throw off the proportions of your body.
I really like this style for heavier men, almost more than a bomber or trucker style because the slightly longer jacket length and pockets on the front break up your broader torso and will make you look smaller.

And if you’re a thinner guy – just beware of this style of jacket that has a hood in the collar because it will look too bulky/heavy around your thinner frame, especially the neck area, and will actually make you look skinnier. Instead, you need your jacket to have a standing collar or at least a collar that’s free from any puffiness.

Regardless of your body type, this type of jacket needs to be very fitted throughout so it doesn’t look like you’re swimming in a bunch of pockets and fabric. This is important because it can make a thin guy look skinnier and a broader gentlemen look even heavier than he is.

Budget Friendly

$200 – J. Crew Field Mechanic Olive Jacket
$200 – J. Crew Field Mechanic Navy Jacket
$180 – TopMan Grey Bonded Wool Blend Parka
$130 – Calvin Klein Four-Pocket Utility Jacket (2 colors)

Designer

$7,400 – Tom Ford Suede Military Jacket
$1,600 – Todd Snyder Suede Quad Jacket in Tobacco
$1,500 – Moncler Ampere
$750 – Club Monaco Golden Bear Field Coat 

Materials

I like suede or leather for Fall/Winter because it’s visually heavier, but just be careful about wearing suede in wet or snowy weather. But if you don’t want leather or suede, you can use a cotton or wool bomber or trucker, as well.

For utility jackets, anything but leather goes. They look a little too 70’s pornstar-ish to me.

Best Ways To Wear Your Fall Jackets

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fallwinteressentials-bomber-jacket-ashleyweston

J. Crew Wallace & Barnes Boiled Wool Bomber Jacket
Brook’s Brothers Golden Fleece 3-D Knit Fine-Gauge Merino Wool Brown Crewneck Sweater
Allen Edmonds Black Poplar Dress Belt
Burberry Slim Fit Wool Trousers
Allen Edmonds First Avenue Dress Boots
Rolex Submariner Date Watch
Tom Ford Snowdon Sunglasses

fallwinteressentials-bomber-jacket-ashleyweston3 fallwinteressentials-bomber-jacket-ashleyweston4Topman Khaki (Green) Wool Flight Jacket
H&M Premium Cotton Shirt
Allen Edmonds Black Poplar Dress Belt
Burberry Slim Fit Wool Trousers
Allen Edmonds First Avenue Dress Boots
Rolex Submariner Date Watch
Tom Ford Snowdon Sunglasses

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fallwinteressentialsutility-jacketashleywestonoutfit2

Parajumpers Genesee Urban Jacket
H&M Premium Cotton Shirt
Diesel Buster 0607A Jeans
Allen Edmonds Black Poplar Dress Belt
Allen Edmonds Long Branch Wingtip Boots
Tom Ford Black Snowdon Sunglasses

Fall and Winter Boots For Men

There’s 3 types of Fall and Winter Boots for men that I love for this time of year – Dress, casual and chukka boots.

The reason I love boots for Fall/Winter is that they go so well with jeans, wool trousers and fall/winter suits. They also do a great job of keeping your feet warm and protected from the elements – while looking classy and more refined than a pair of hiking boots or something that’s just a straight utility item.

Now, if you live in an area with a good amount of snow or rain, then you should probably have specialty boots for the crazy days, too, but those are outside the scope of this article. 

The difference between dress and casual boots

Dress boots are more formal and can be worn with a suit or wool trousers. They have a sleeker profile, usually leather or dainite soles, and are made out of shinier calf skin, as opposed to cow hide. Dress boots are like dress shoes with a shaft, basically.

Casual boots usually have more room in the toe box, the leather is usually a thicker cowhide that is more matte, and the soles usually have lugs on them. They look a little less dressy and sophisticated, which is why they look so great with jeans, but you can also still wear them with wool trousers.

My Requirements for a good Fall/Winter Boot

These items apply to all the types of boots – dress, casual and chukka boots:

1. A slim profile and not chunky

Timberlands (right) are the exact opposite of what I’m looking for in a good boot. You want a nice, rounded toe box with a slim profile as well as sole like the image below.

dressvsworkbootashleywestoncropped

2. Plain, Cap Toe or Broguing

I like all 3 of them, but just like with my dress shoes, I’ll always prefer a plain or cap-toe, but broguing is also acceptable. Broguing is not really my preference because I think a lot of guys overdo it with the broguing, burnished toes, etc. Too much can easily look gaudy if you’ve got too much going on in your outfit.

plaincaptoebroguingashleyweston

3. Lugged, Dainite or Rubber soles

These will give great grip in any type of weather. A normal dress boot has smooth leather on the bottom and you will slip and slide like crazy in wet weather. If you’re not in a climate with rain/snow, then you can go with straight leather bottoms typically found on most dress boots, but I see no reason to do that when any rubber bottom aside from lugged will look very similar with the extra benefit of additional traction.

mensleatherbootsolesashleyweston

4. Be brown or black leather

Go with nice dark chocolate or walnut brown first, then get black if you don’t have them already. Brown is a great fall/winter color and is easier to wear with casual AND more formal outfits. But be careful about getting a really specific brown color, like oxblood. As I’ve said in my other shoe videos, it’s a great color but doesn’t compliment a lot of outfits, so get that color once you’ve got these basics down.

And please, whatever you do, don’t get those terrible boots that are already worn in. It’s much better for you to wear them in yourself and really personalize their look to your actual lifestyle.

5. NOT be Suede

For Fall and Winter boots, suede is the last material you should consider, unless you live in a dry climate like Southern California where it rains maybe 3 or 4 times a year. Otherwise, they’ll get screwed up very quickly with any amount of rain or snow. I don’t care how much scotch guard you use, nothing can stand up to that much abuse. So save the suede shoes for spring, please.

Can I wear boots with a suit?

Yes, but only when these 2 conditions are met:

  1. You’re wearing a heavier wool or tweed suit.
    For a visually heavy item like boots, you should understand fabric weights and pairing them with similar items. Even straight up dress boots can look odd with lighter weight wool suits. Make sure the wool is atlas 12oz thick. The easiest way to tell what a heavy wool suit feels like in person, is it should be as thick as a wool sweater (not as soft, though!)
  2. Your pants are hemmed to have no break.
    The hem of your pants will look sloppy and bunched at the ankle, otherwise. You can technically cuff the hem of your suit pants to do this, but if they’re super long, it’ll never look quite right. So I usually just get the pants hemmed to no break for this. But that means you can’t wear this suit with anything but boots now…unless you have your tailor let out the hem when the seasons change.

How To Tie Your Boots

Check out my shoe and boot tying video for how to tie your shoelaces properly.

Best Ways To Wear Boots For Men

fallwinteressentialsbootsashleywestonoutfit1

Topman Black Cotton Bomber Jacket 
TopMan Ribbed Turtle Neck Slim Fit
Rolex Oyster Perpetual Submariner Date
Tom Ford Black Snowdon Sunglasses
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt

fallwinteressentialsbootsashleywestonoutfit2

Parajumpers Anthracite Urban Genesee Jacket
Brooks Brothers Milano Fit Button-Down Collar Dress Shirt
Rolex Oyster Perpetual Submariner Date
Tom Ford Black Snowdon Sunglasses
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt

fallwinteressentialsbootsashleywestonoutfit3

Topman Faux Suede Flight Jacket (It’s technically a Peuterey jacket, but it’s only available in Europe)
Brooks Brothers Milano Fit Spread Collar Dress Shirt
IWC Portuguese Automatic Watch
Tom Ford Black Snowdon Sunglasses
H&M Black Melange Wool Suit Pants
Allen Edmonds Decatur Ave Dress Belt

The Best Fall Winter Boots For Men

Casual Boots

Budget Friendly

Aldo Acerrassi

$200 – Aldo Acerrassi

$175 – Aldo Etausen Boot (2 colors)
$175 – Johnston & Murphy Conard Wingtip Boot (3 colors)
$220 – Jack Erwin Carter Wingtip Boot (2 colors)

Designer

$350 – Allen Edmonds Long Branch Wingtip Boots


$318 – FRYE Tyler Lace Up (2 colors)
$395 – Wolverine 1000 Mile Boot 
$725 – Crockett & Jones Coniston Tan Boot
$775 – Crockett & Jones Islay Wingtip Boot

Dress Boots

Budget Friendly

Calvin Klein Darsey Brown Boot

$140 – Calvin Klein Darsey Dark Brown Leather Boots

$60 – Stafford Deacon Wingtip Leather Boots (2 Colors)
$135 – Stacy Adams Madison Boot (2 colors)
$140 – Calvin Klein Darsey Black Leather Boot

Designer

Allen Edmonds First Avenue Black Boot

$995 – Saint Laurent Polished Leather 

$645 – O’Keefe Algy Split-Toe Weatherproof Pebble-Grain Leather Boots
$748 – Brooks Brothers Peal & Co. Leather Wingtip Boots
$1,098 – Brooks Brothers Peal & Co. Cordovan Boots

Chukka Boots

Budget Friendly

Johnston & Murphy Fulton Chukka Black

$140 – Johnston & Murphy Fulton Black Chukka

$130 – Clark’s Desert Boot in Brown Suede
$75 – Aldo Granges Chukka Boot
$175 –Johnston & Murphy Conard Cap Toe Chukka (2 colors)
$198 – Johnston & Murphy Fulton Brown Chukka
$225 – Vince Camuto Branx Two-Eye Chukka (2 colors)

Designer

Allen Edmonds Dundee 2.0 Chocolate

 

$250 – Allen Edmonds Dundee 2.0 Suede Boots (2 colors)
$378 – FRYE Weston Chukka (3 colors)
$1,500 – John Lobb Elmer Chukka

 

That’s it! I hope you liked the article. Please share it via one of the buttons below if you did. 🙂