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.

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: CheapestNatoStraps.com

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

Scarves

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!

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

fallwinteressentialsdressshoesbroguesashleyweston3 fallwinteressentialsdressshoesbroguesashleyweston4

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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

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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