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

Men’s Leather Jackets & How To Wear Them – Bomber + Motorcycle

In this article/video, I wanted to do an update to my (4 year old!) men’s essential leather jacket story. A lot of the information in my previous article is still valid, so think of this as more of a supplement for why you should own a leather jacket instead of completely replacing it. As for the types of leather jackets I’m featuring in this video/article, you’ll likely notice that some are missing and that’s for a specific reason – I just don’t like them and they tend to not look great on most men. See the video below for an explanation of what styles I don’t prefer and why.

For the best ways to wear your leather jacket(s), check out the new video and my previous article and video here.

Biker Jacket

In my previous story, I mentioned that I didn’t like the biker style very much because they have a lot going on and should only be worn if you have a very specific rock and roll style. I still think this is true if you go with the traditional or classic-style biker jacket with the belt, chrome hardware and shiny leather. But, over the years, I discovered a slightly updated version that does away with the belt and replaces the shiny hardware and leather with matte options. Basically, this style of biker jacket removes all the things I disliked about the traditional versions, and now I’ve got to say, I’m much more of a fan.

As for how to wear them, I’d style with a t-shirt or sweater in white, black, or grey, dark wash or black jeans/chinos, and a pair of black boots. If you want to “dress it up” a bit, then pair with a casual collared shirt (leave untucked) in black, green, or burgundy, and some chinos or wool trousers.

$2395 – Burberry leather biker jacket – Burberry consistently makes some of my favorite leather jackets. You’ll pay for it, but if you can swing it, they’re totally worth the price and the fit is incredible. Remember, leather jackets are a BIFL piece.
$420 – AllSaints cargo leather jacket – all the hardware on this jacket is completely blacked out which I always prefer, but is tough to find. AllSaints’ leather jackets are worth the price and for the quality and construction, they’re a steal!
$420 – AllSaints leather biker jacket
$133 – AllSaints dark green shirt – this is the shirt Dorian wore throughout the video. The dark green color and cut of the shirt is super flattering for all shapes and sizes, especially if you’re thin or huskier.

Leather Bomber Jacket

I’ve said it a gazillion times and I’ll continue to say it, over and over again (all these articles feature bomber jackets) – regardless of your age and body type, from super thin to more rotund gentleman, every single man should have at least one bomber jacket in his closet because it’s a super versatile year-round item that can be worn a myriad of ways. Now whether you go with leather, suede or fabric options, that’s up to you. Frankly, I’d have each option, if your budget allows.

As for how to wear a leather bomber jacket, I always like to keep it simple. Pair with a crewneck sweater or t-shirt, dark wash jeans, and sneakers or boots. To make it more formal, I would pair with a white collared shirt, black tie, and wool trousers. The beauty of a bomber is that you can pretty much wear it with any kind of shirt – just pair with chinos, jeans or trousers on the darker side and you’ll never go wrong.

$500 – AllSaints leather bomber jacket – classic, classic, classic.
$500 – AllSaints leather bomber jacket in greyish blue – if you already own black, mix it up with this neutral-like color. Wear how you normally would with a black or brown jacket.
$465 – AllSaints leather and wool bomber – Dorian wore this in my Fall Shoes video and it’s such a sleek take on an all leather jacket. Super timeless and stylish.

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.

Men’s Fall & Winter Accessories 2017

In this article and video, I wanted to show and discuss some of my favorite accessories for the Fall & Winter Seasons. Also, please be sure to not miss out on my whole series dedicated to the best men’s Fall & Winter Essentials.


Watch Straps

Fall and winter is a great time of year to change out the straps of your watches for more appropriate colors for the season. As for materials, I don’t have a preference, but leather, perlon and suede are some of my favorites. The best colors for this time are always going to be:

  • Browns
  • Oranges
  • Burgundy
  • Taupe/Gray/Green

The pictured straps, as well as many others types and styles are available at my favorite site for reasonably-priced straps:

I talked to the owner, Sofie, and she was kind enough to offer you an additional 10% off your purchase if you use offer code: AshleyWeston

Suede Belts

Since you’ll be wearing heavier fabrics during this time of year, it’s time to bring out the suede belts to add a more visual texture to your outfits to compliment them. I prefer a dark brown or gray color this time of year and the below options have these choices available.

$128 – Brooks Brother Suede Belt – the best color for the time of year.
$80 – Torino Suede Belts (Various colors – I like espresso & navy)
$25 – H&M Suede Belt

Wool Ties & Pocket Squares

Wool ties and wool knit ties and pocket squares compliment the textures you’ll be wearing this season. For how to wear them, watch the video at the top. Just know that you’ll never go wrong with the rule: Whatever item has a pattern (tie or pocket square), make sure the other item isn’t patterned. So if you’re wearing a patterned tie, wear a plain pocket square with a similar colored tipping.

The colors I love this time of year are:

  • Browns
  • Oranges
  • Burgundy
  • Grays
  • Greens


I’ve talked at length about my favorite pocket squares and how to wear them, so see my wool ties & pocket squares video/article for details.

Wool Knit Caps

They’re great this time of year to keep your head warm and they can look good  but remain functional when paired with some of your  casual jackets or even heavier Winter jackets.

Gray, Blue and Black caps are my favorite colors because they go with everything, but you can certainly mix it up with other colors, if you prefer. There’s one caveat when wearing them, though.

$90 – A.P.C. Wool Knit Cap – Multiple Colors
$10 – H&M Rib-Knit Cap

Leather Gloves

Leather looks great this time of year and help elevate your appearance by adding a sophisticated touch, while keeping your hands warm. Black or brown are easiest to wear, so I say just get one or both of those colors.

$30 to $40 – H&M Leather Gloves
$100 to $600 – Various Quality Brands @ Mr. Porter


Keeping your neck warm should be a priority, but why not have your scarf also look good? As far as colors and patterns are concerned, I honestly view them like men’s socks, where you can definitely go crazy with them, so if you think a plain color is boring, go with some patterns. Generally, you want to go with the same general color palette of the season – so blue, gray, black, brown, orange, burgundy and green all look great this time of year.

As for materials, I don’t think it matters much, it just depends on what you prefer. I love a good wool or cashmere scarf, but a cotton one is also good, depending on how thick and warm you want yours to be. But, there may be a reason to avoid certain materials or colors.

I’ve discussed how to tie men’s scarves at length so check that out, too.

$10 to $100 – H&M Scarves – they make some of my favorite budget friendly scarves.
$15 to $50 – Uniqlo Scarves – also great budget-friendly options.
$50 to $500 – Mr. Porter has a great selection of many high quality scarves.

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!

Henley Shirts

Henley shirts are one of the few items that, to me, don’t really have a specific season they’re best worn in because there’s so many different versions for men. Other shirts, like T-Shirts, Polo Shirts and Dress Shirts don’t really have this problem since they’re pretty standard across the board no matter the season.

I love henleys, because they look sexy and masculine, especially when the top 1 or 2 buttons are undone to draw the eyes to your chest and shoulders to show off your physique in a flattering way. Hence, the image below.

BUT, and this is a big mistake I see a lot of men making – they’re not for every everyone. More on that shortly.

Let’s get into what to look for in your henleys based on the time of year.

Intro - Short Sleeve Sexy henley


Generally, henleys will be made out of cotton, so there’s really not much choice outside of that, but you still need to consider fabric weights depending on the time of year. The main thing to know is that lighter weights should be worn in warmer months or in warmer climates and thicker, heavier fabrics in cooler months or climates. You can get them in everything from a lightweight summer weave, where it feels like a t-shirt, to thicker, quilted versions which will keep you warm during the cooler months.

You don’t have to worry too much when buying them because, based on the time of year, the brands will carry the appropriate weights. But I still want you to be aware of it just in case.

Henley Fabric Ashley Weston 2


Like all your clothing, including henleys, they should have a trim fit throughout the body and arms – no matter your body type. You never want it too loose anywhere because that’s when you’ll look sloppy and not put together. You shouldn’t be able to pinch more than 1-2 inches of fabric on one side of your stomach and no more than an inch around the bicep.

The image below highlights the proper fit around the torso and sleeves.

Fit - Perfect fitting henley shirt

I mentioned earlier that henleys aren’t for everyone, so let’s get into that right now since we’re talking about fit.

For Thin Gentleman

If you’re a thin guy, no matter your height, if you want to wear a henley, you absolutely need to nail the fit, especially if you’re going to wear a long sleeve version. If the fit is too loose, it’ll make you look thinner and more frail than you are – not good!

I only like long sleeve henleys on thinner men if they’re layered underneath a jacket, like the below right image. When worn on their own, it really spotlights and elongates your thinner torso, like image on the left. So if you’re a thinner guy and want to wear a henley on its own, then wear a short sleeve version since it’ll look similar to your t-shirts.

Henley Fit Ashley Weston

Bigger Gentleman

If you’re a rotund gentleman (aka you’re not in the greatest shape and have a belly), you cannot wear a henley shirt, period. Allow me to show you why and explain. See exhibit A:

Fit - Big Guy - Bad Example of henley

Because of the button placket on the front, coupled with the lack of a collar, a henley will shine a massive spotlight on your bigger neck and torso. This is when a polo shirt is perfect and should be used instead, because a polo shirt’s collar will visually keep your torso balanced and in proportion, so your top half doesn’t look so big compared to your bottom half. The image below of James Corden shows a guy with the exact same body type as the image above, but in a polo shirt. Talk about a night and day difference…

Fit - Big Guy - Good Example - Polo Shirt1

Best Ways To Wear A Henley Shirt

Think of your short sleeve henley as a t-shirt, they’re interchangeable in the same outfits, so that means they can be worn on their own or underneath a jacket.

How To Wear Henley - Short Sleeve

J. Crew Slim Broken-In Short Sleeve Henley
J. Brand Tyler Taper Fit in Rasalas
Allen Edmonds Hampton Ave Tan Leather Belt 
I would pair this look with white sneakers – Nike Tennis Classic Sneakers

For a long sleeve, you would normally wear these during the cooler months as a layering piece, so I styled Dorian in a long sleeve henley shirt underneath a bomber jacket, dark wash jeans, and sneakers.



Burberry Lightweight Lambskin Bomber Jacket 
J. Crew Wallace & Barnes Wool Henley Sweater
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Black Dress Belt  
Johnston & Murphy Conard Cap Toe Black Chukka

IWC Portugieser Automatic Watch
Ray Ban RB4258 Sunglasses 

During the warmer months you can wear them with the sleeves pushed up. As I mentioned in one of my other videos, women LOVE to see sleeves rolled/pushed up around your forearms.

How To Wear Henleys - Henley Sleeves Pushed Up On Forearms

My Favorite Henley Shirts

Here are some great short sleeve and long sleeve (lightweight and heavyweight) henley options that I love.

Short Sleeve Henleys

Short Sleeve Henley 1 Ashley Weston

$125 – Rag & Bone Classic Short-Sleeve Henley
$35 – J. Crew Slim Broken-In Short Sleeve Henley (White, Navy, Heather Grey, Black)

Long Sleeve Henleys

Rag & Bone Long Sleeve Henley Ashley Weston

$250 – Rag & Bone Giles Merino Wool-Blend Heavyweight Long Sleeve Henley Shirt
$40 – J. Crew Slim Broken-in Lightweight Long Sleeve Henley
$15 – H&M Jersey Lightweight Long Sleeve Henley 

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-2 MensFallWinterEssentialsWoolBlazerAshleyWeston-3

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-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




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.



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.


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


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