Men’s Winter Style Do’s and Don’ts | Men’s Winter Style Tips

Winter can be a tough time for your personal style. Cold weather and the elements can lull you into just giving up, but don’t do it! These few simple tips can keep you looking sharp and feeling great, no matter how cold it gets! For more tips, make sure to check out our Fall/Winter Essentials Series!

Here are our Winter Style Do’s and Don’ts!

Winter Style Do’s

Do Add Some Colorful Jewel-toned Accessories

The right hats, scarves, and gloves are crucial for warmth and style. They’re also a great opportunity to add some color and pattern to brighten up your look. Colors like emerald green, a mustardy yellow, dark purples, reds, and blues are all easy to incorporate into your winter wardrobe and pack a stylish punch of color.

Picks:

Scarf 1

Scarf 2

Scarf 3

Hat 1

Hat 2

Hat 3

Gloves 1

Gloves 2

Gloves 3

 

Do Invest In Quality Outerwear

We talk a lot about where and when to invest, and outside of dress shoes & boots, outerwear is the other major area we really recommend investing in. You get what you pay for and with the right investment, a high-quality coat, peacoat, or jacket will last for years to come, keep you warm, and have you looking stylish.

Picks:

Overcoat

Overcoat 2

Parka

Puffer Parka

Parka 2

Peacoat

Peacoat 2

 

Do Get The Right thermals

There are many great brands offering very thin/lightweight thermals that’ll layer comfortably underneath your clothes and keep you warm. The key is to get a trim fit, that way they’ll lay flat and layer easily under everything from jeans to suits. Our pick below is light, warm and you can wear these as a base layer underneath your clothes or on their own as a long sleeve shirt.

Thermals Pick

 

Winter Style Don’ts

Don’t Neglect Your Skin

You may not think so, but cold-weather skincare is just as important as warm weather skincare. The cold, dry weather can be incredibly harsh on your skin and strip away it’s protection, so it’s super important to cleanse and moisturize properly and stay hydrated. There’s nothing more distracting and unattractive than dry, dull skin.

Luckily, our friends at Geologie have you covered. Geologie puts together a simple routine formulated for daily use. The products are personalized to your skin’s needs and work great for every skin type. We tested out their set that comes with 4 different products:  Everyday Face Wash, Vital Morning Face Cream w/ SPF, Repairing Night Cream & Nourishing Eye Cream. It even includes 2 bottles of face wash, one for your sink and one for your shower or to take with you to the gym. Plus, just for our readers and viewers, you can get 30% off your purchase with code Ashley30! Shop here and enter the code at checkout.

 

Don’t Forget To Layer

We talked about it for Fall, and it’s just as applicable in Winter.  Proper layering can help you regulate your temperature and look stylish no matter how cold it is, making sure you’re comfortable going from the cold outside to warm inside (subway, office, etc.).

 

Don’t Forget To Winterize your boots

Boots are essential footwear for Winter (our go-to picks for this year are right here) and the right pair can look amazing and last a long time. But, you’ve got to prepare them with the right leather treatments to keep them from getting ruined in the inclement weather.

Boot Treatment Kit

Top 5 Men’s Shoes & Boots For Fall 2019

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

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

 

 

Lace-Up Boots

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

Picks:

Allen Edmonds 1 (from the video)

Allen Edmonds 2

Kenneth Cole

Johnston & Murphy

 

Leather High Tops

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

Picks:

Wolverine (from the video)

Common Projects

 

Captoe Brogue Dress Shoes

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

Picks:

Allen Edmonds (from the video)

Kenneth Cole

J. Crew

Brooks Brothers

 

Chukka Boots

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

Johnston & Murphy Leather (from the video)

Wolf & Sheppard Suede

Allen Edmonds Suede

Allen Edmonds Leather

 

Chelsea Boots

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

Picks:

Kenneth Cole (from the video)

To Boot (similar to video pick)

Cole Haan

Johnston & Murphy

Men’s Fall Style Essentials For 2019

Fall and cooler weather will be here before you know it and it’s time to start thinking about transitioning your wardrobe.
A key thing to think about with your fall wardrobe is changing temperatures, you want items that layer easily or can be versatile enough for varying temps. Like with the rest of the items in your Essential Wardrobe you want pieces that will have you looking sharp no matter your height, body shape, or age.

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

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

 

Denim Jacket

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

Picks:

Uniqlo

AllSaints

Levis

Everlane

 

Crewneck sweater or sweatshirt

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

Picks:

H&M

J.Crew

Brooks Brothers

Todd Snyder

 

Suede or wool bomber jacket

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

Picks:

Officine Generale

APC

H&M

Brooks Brothers

 

Casual Collared Shirt

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

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

Picks:

The Tie Bar Casual Shirts

 

Chinos or corduroy pants

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

Picks:

Uniqlo

J.Crew

Rag & Bone

Our Favorite Budget-Friendly Chinos

 

Suede or leather Boots

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

Picks:

AllSaints

Allen Edmonds #1

Allen Edmonds #2

Johnston Murphy

Men’s Fall Style Do’s and Don’ts

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

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

 

Fall Style Do’s

Continue To Wear Color

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

 

Layer Your Clothing

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

 

Invest In A Pair Of Boots

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

Boot Picks

Allen Edmonds #1

Allen Edmonds #2

Allen Edmonds #3

Clark’s

Johnston Murphy

Red Wing

Wolverine

 

Fall Style Don’ts

Just Wear Jeans Exclusively

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

 

Flash Lots Of Bare Ankle

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

 

Wear Lightweight Fabrics

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

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

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

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

Desert/Chukka Boots

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

Picks

Zegna

Allen Edmonds

Clark’s

Budget-Friendly Clarks

Johnston Murphy #1

Johnston Murphy #2

Work Boots

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

Picks

O’Keefe

Red Wing Beckman

Allen Edmonds #1

Allen Edmonds #2

Wolverine 1000 Mile

Danner Jack

Dress Boots

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

Picks

Edward Green

Brooks Brothers Peal & Co.

Grenson

Mezlan

Allen Edmonds #1

Allen Edmonds #1

Aldo 

Calvin Klein

The 5 Shoes Every Man Should Own

In my Men’s Wardrobe Essentials Series, as well as my Summer Essentials Ebook, I touched on shoes a little bit, but the most-requested video/article for a while has been the number and type of shoes every man should own.

So here it is: These are the quintessential shoes that every man should have in his closet for year-round wear. Anything outside of these are specialty items, like snow boots, so they’re not included in this article.

Have questions? Curious what others think?

Join us in the comments section of the video above.

1. Athletic/Running Shoes

Nike Roshe FlyKnit - Grey

Buy the Nike Roshe FlyKnit in gray

There’s nothing better than a sleek pair of athletic shoes. Not only can they function as your gym shoes, but they can  be worn with your casual outfits, as well.

I recommend sticking with a black/white, black/grey/white (like above), or navy/white color to ensure that your sneakers compliment all your outfits. Other crazy colors like neon green or a bright red will only draw attention away from your outfit which is why I’m not recommending those colors. You probably wouldn’t know it, but these shoes are one of my clients and almost a year old.

Since all of the shoes I’m recommending have white soles, I highly recommend Jason Markk’s Essential Shoe Cleaner Kit. Just give the soles a quick scrub with the included brush and soap every few weeks and they’ll look good-as-new for a long time.

Other Options

Nike SB Stefan Janoski Max
Adidas Pureboost LTD Shoe
Nike Roshe Two FlyKnit

 

2. White Sneakers

 

Buy the Adidas Stan Smith Sneakers

The second pair of shoes you should own, is what I’d consider an absolute essential to any well-dressed man’s wardrobe, which is why they were also included in my Men’s Wardrobe Essentials series.

They’re clean, classy and look great with a lot of your casual, even up to a little more dressy, outfits. Throw on a nice fitted blazer and some dark wash jeans with them and they’ll look amazing. See here for outfit inspiration images.

Under no circumstance should you wear these with a suit, though. That’s a trend that’s been floating around for a few years and I just think you’re not doing a suit justice by dumbing it down with sneakers.

A quick note, because it’s been brought up in the comments of my White Sneaker Video – Jordan’s and Air Force Ones are not the same as these – even if they’re white – because the shape and profile of those shoes are completely different. Notice how sleek and simple the profile of the above shoe is – THAT’S what makes all the difference. Jordan’s and Air Force Ones are chunky looking and have a very specific look that a lot of men can’t pull off.

Designer Options

 

Saint Laurent leather sneakers
Acne Studios leather sneakers
WANT Les Essentiels de la Vie leather sneaker
Common Projects BBall leather sneakers

Budget-Friendly Options

Converse Chuck Taylor All Star II Ox’ Canvas
Converse Jack Purcell Sneaker
Nike Tennis Classic Ultra Leather
Vans Authentic Sneakers

 

3. Suede Driving Moccasins

 

Tod's Gommino Driving Shoes in Suede

Tod’s Braided Tie Drivers

The third pair of shoes you should own are suede driving moccasins. I’ve already covered these in my Summer Essentials Ebook, but they’re also great shoes during the other parts of the year, depending on your climate.

If you’ve never worn a pair, then you really should try them because they’re the most comfortable middle ground between a dress shoe and a sneaker and after they’ve been broken in a little bit, they’ll feel like you’re wearing a pair of socks.

I have these ones here by Tod’s that I really love. Stick with dark brown first, then you can add a tan color and then navy which will cover you for any outfit you can wear outside of a suit – which you should never wear driving mocs with. The construction is fantastic and they hug your feet nicely –
which is important because a lot of cheaply made driving mocs tend to look loose around your feet which is to be avoided.

There’s three things to remember about driving moccasins:

Only wear no-show socks with them. I did a whole video about socks so check out the link in the video description.
Before you wear them for the first time, make sure you Scotchguard them in order to protect the suede from dirt & liquids as much as possible.
They’re going to get dirty, it’s inevitable with suede. So buy them knowing they’re going to have a shorter shelf life than the rest of your shoes, but trust me, you won’t care because they’re so damn comfortable.

Designer Options

Tod’s Textured Suede Tie Drivers
Tod’s Braided Tie Drivers
Prada Suede Slip-On Moccasin, Oltremare
Brook’s Brothers Suede Driving Mocs

Budget-Friendly Options

Jack Erwin Parker Driving Loafer 
FRYE Russel Venetian
Johnston & Murphy Perforated Driving Loafer 

4. Oxford Or Derby Dress Shoes

ferragamo-marte-plain-toe-derby-ashley-weston1

Prada Plain Toe Blutchers

The fourth pair of shoes you should own are Oxford or Derby dress shoe with a sleek profile and round toe. I’ve covered these extensively before, but every man needs at least a black and possibly brown pair of dress shoes in his wardrobe. They go well with all outfits outside of a super casual outfit (think: t-shirt and jeans). And since you should at least own one suit, these are necessary because you can’t get away with wearing any other shoes with your suit. Remember: the goal is to have you looking amazing, no matter the scenario or outfit.

I prefer plain toe, but you can also get cap toes, but I will grab a pair of plain toed Oxfords or Derbys over any other kind of dress shoe 99% of the time.

As for brogueing, burnished toes, oxblood or other unique colors, don’t get me wrong, I love them, but that’s like two levels down the road if you’re new to dressing better. They’re very specific and won’t go with a lot of your outfits, so grab them after you’ve invested in a classic black and dark brown oxford.

Designer Options

Giorgio Armani Plain-Toe Patent Leather Bluchers
Allen Edmonds Park Avenue Cap-Toe Oxfords
Allen Edmonds Carlyle
Prada Plain Toe Blutchers

Budget-Friendly Options

Aldo Craosa 
Jack Erwin Joe Cap-Toe Oxford
Johnston & Murphy Hyde Park ll Cap-toe

5. Brown Leather Boots

Purdey Brown Men's Grain Leather Boot With Dainite Sole

Crockett & Jones Islay Wingtip Boot

The final pair of shoes – in this case – boots you should own are a pair of brown leather boots.
They’re utilitarian in that you can wear them in a lot of adverse weather situations as well as in more elevated casual outfits. I prefer brown because boots are usually more geared toward the cooler months, and brown is a great fall/winter color and it goes AMAZINGLY well with the dark wash jeans and wool trousers you should already own. But don’t be mistaken, you can also wear these year-round.

It’s been asked this a few times by viewers, so unless you’re going for the lumberjack or American/Japanese worker-style look, don’t wear these boots with a suit because these ARE NOT DRESS BOOTS.

I love the pebbled brown leather and goodyear welting of the Purdey boots above, which is why they’re my top choice. Trust me, I spent a lot of time finding the best boots out there and these are hands down my favorite.

If you want to know how to tie your boots properly like this so don’t have a bunch of excess laces flopping around, check out my video about how to properly tie men’s shoelaces.

Designer Options


O’Keefe Algy Split-Toe Weatherproof Pebble-Grain Leather Boots
Crockett & Jones Islay Wingtip Boot

Frye Jones Lace Up Boots

Budget-Friendly Options

Aldo Acerrassi
Johnston & Murphy Karnes Cap Toe Boot
Aldo Etausen Boots
Wolverine 1000 Mile Boot