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

Best Budget-Friendly Men’s Fall Essentials For 2019

Key pieces for a sharp Fall wardrobe don’t have to be expensive, and a few wallet-friendly updates can add a ton of style to your overall look. As we mentioned in our previous Fall Essentials piece, the 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.

Here are our picks for the Best Budget-Friendly Fall Essentials for 2019!

 

H&M Wool crewneck sweater – $20

A simple versatile item that can be worn a ton of different ways, from casual to dressy.  We love the one from H&M, it’s budget-friendly and super stylish.

H&M Wool Crewneck

H&M Merino Crewneck

 

The Tie Bar Wool Knit Tie – $25

An easy way to add some texture and personality to dressier looks, these simple additions are great with suits or chinos.  We love the options from the Tie Bar specifically, the bang-for-the-buck is outstanding.

Tie Bar Wool Knit Ties

Tie Bar Wool Ties

 

H&M Quilted Jacket – $79.99

Budget-friendly quilted jackets are very tough to come by but this one from H&M hits all the marks. A solid price, great casual style, and a nice light weight make for a very versatile jacket for your Fall layering.

 

Suede / Perlon / Wool watch straps – $5-$20

A super simple (and cheap!) way to mix up your accessory game. Try something in suede or perlon for some added texture and style to your watch.

Suede Straps

Leather and Suede Nato Straps

Perlon Straps

Wool Straps

 

Uniqlo Corduroy Jeans & Chinos – $39.90

We discussed these in our previous Fall Essentials video, and for good reason, a few solid pairs of pants can really set your rotation up nicely. We really love the corduroys and chinos from Uniqlo because they’re super affordable and great quality for the money.  The range of colors is great too, so make sure you invest in a few pairs to mix up your rotation from denim.

Uniqlo Corduroy Jeans

Uniqlo Chino Pants

 

Leather Lace-Up or Chukka Boots – $130 – $250

A solid and versatile lace-up boot or chukka boot is an indispensable style foundation for fall.  Keep in mind that affordability is relative and you get what you pay for. Ultimately, It’s tough to find anything of quality below $150 or so. The picks below are a great mix of quality and affordable prices.

Picks:

Johnston & Murphy 1

Johnston & Murphy 2

Kenneth Cole 1

Kenneth Cole 2

Clarks

 

Wool Scarf – $13-$60

Easy warmth when you need it and it can be a great accessory.  Go for solid black, grey or navy for an understated look or opt for a pattern like plaid or a bolder color for more of a statement.  Wool blends and cashmere are the most comfortable.

Picks:

Uniqlo 1

Uniqlo 2

Gap

H&M 1

H&M 2

 

Uniqlo Suede Belt – $30

You’ve hopefully got a few casual and dress belts in leather already, but adding a suede version is an easy way to change up your accessory game and add some nice texture to your outfit. As another option, a nice braided leather belt is a cool update as well.

Uniqlo Suede Belt

Uniqlo Braided Belt

 

Flannel Shirts – $30 – $50

We discussed the importance of great casual button-ups for fall and there are a number of good flannel options that are perfect for the cooler months.  You can go for a solid color or a bolder plaid and these are great as a layer under a denim or bomber jacket or just worn on their own. We love the ones from Uniqlo the most but there are other great picks we love below as well.

Picks:

Uniqlo

Gap

J.Crew Factory

 

H&M Blazer – $70

Another super versatile jacket, we love that this blazer can add a bit of polish to any casual outfit, like with denim or chinos, or it can be dressed up with some trousers and a tie. The checked pattern is a nice way to add a bit of personality but in a subtle way and you can even layer a sweater underneath for added warmth.

Picks:

H&M 1

H&M 2

Uniqlo 1

Uniqlo 2

J. Crew Factory

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.

Should Men Match Clothing To Their Hair and Eye Color?

We get asked a ton of questions about how to match clothing and what colors to wear, and more specifically, how to match with one’s hair and eye color. So, in this week’s 2 Minute Tuesday, we’re giving you the real truth about how men should match clothing to hair and eye color, and the answer might surprise you.

Don’t forget, if you’ve got questions for us, make sure to drop them in the comments section of the video, we’d love to hear from you and we’ll try to answer them in a future episode!

 

The Truth

To sum it up, the answer is, no you don’t need to worry about matching your clothing to your hair and eye color.

Why Not?

This is a common case of overthinking things a bit too much. In the past, we’ve given you a few tips on how your skin color should relate to specific wardrobe color choices, but after that, you really don’t need to worry about it. Honestly, we believe this is just a falsehood that’s out there, whether it’s coming from other content creators or sites, who knows, but it’s taking it too far. Obviously thinking about how you’re dressing and putting colors together is really important. But, there’s a line between worrying about doing things the right way and wasting time focusing on things that don’t really matter.  So, give yourself a break, focus on building the right essential wardrobe, and don’t overthink matching your clothes too much!

Series Intro & How to Match Clothing Colors To Your Skin Tone

In this series, I’m going to show you the must-have Fall and Winter items that every well-dressed gentleman should own. That means I’ll be talking about:

  • Boots and Shoes
  • Coats & Jackets
  • Shirts & Sweaters
  • Suits
  • And various Accessories

Like always, I only recommend products that I’ve personally touched and worked with – in all budget ranges. I’m fortunate in that I get to touch hundreds of menswear items a week, so when I say something is great, it’s not because I got paid to sell you a bunch of cheap [email protected]*t like everyone else – it’s because I have actual experience with these items.

This series is a supplement to my Men’s Wardrobe Essentials Series. In that series, I covered the year-round essentials that you should have in your closet already. If you haven’t read/watched those articles and videos, do that first so we’re on the same page.

The Best Colors & Patterns For The Season

fall-winter-colors-patterns-men-ashley-westonSince I don’t want to go over colors and matching them in every single video in this series, let’s talk about Fall and Winter colors and patterns and how to match them to your outfit and skin tone.

The appropriate colors for this time of year are:

  • Mid to darker greens
  • Shades of browns (camel to dark brown)
  • Shades of blues (light chambray to navy)
  • Shades of gray (light, medium and dark)
  • Burgundy and wine colors
  • Darker or “burnt” Orange

As for patterns, this is what I like to call “plaid season”. It’s the best time of year to wear plaid because its more visually heavy and pairs nicely with the heavier clothing you’ll be wearing, like sweaters, wool coats and wool trousers. For outerwear and Fall/Winter suiting, I love a good windowpane, as well.

HOW TO Match & wear COLORS BASED ON YOUR SKIN TONE

If you’re darker skinned, this is less of an issue because those colors look great on you. But if you’re pale or yellow-toned, this can be a disaster if you don’t know what you’re doing.

PALE or Yellow Skin

If you’re pale or yellow skin toned, make sure that your camel, burgundy, or burnt orange pieces are an outer layer and not a base layer. Let me show you what I mean.

You’ll notice in the below photo that I have my pale model wearing a camel sweater. But you’ll also hopefully notice that there is a white ring of a t-shirt sticking out from under the collar.

This is VERY important because that little sliver of white provides separation between the skin and sweater. The camel color would completely wash out his skin tone and make him look sickly if it wasn’t there. It’s much more apparent in person than images, too.

fallwinteressentialsovercoatcamelsweaterashleyweston

Below is the same model wearing a burnt orange sweater, but you’ll notice that I have a gray plaid shirt under the sweater to provide that necessary separation of the sweater from his skin. If that wasn’t there, the orange would bring out the pink tones in his skin – which would make him look red and flushed.

orangesweaterplaidshirt-ashley-weston

And lastly, going back to my white sneaker article/video, I styled my model in a burgundy bomber jacket with a black t-shirt. The shirt provides the necessary visual separation to not bring out the pink tones in his skin.

If I had him in a black jacket and burgundy t-shirt, instead, he would look oddly red-faced. This combination, though, would look awesome on someone with darker skin.

burgundyjacket-2

So to recap: If you have a pale or yellow skin tone and want to mix Fall/Winter colors into your wardrobe, just make sure it’s an outerwear piece with visible neutrals (white, grey, black, navy) underneath.

DARKER SKIN

Now, if you’re darker skinned, you can still follow the pale/yellow skin rules above because it’s the classic way to wear color and looks good on everyone. So when in doubt, wear your statement color as outer layers. But with darker skin tones, you have the added advantage of being able to wear all these colors in your shirts and sweaters and then have neutral outer colors because the contrast looks great with your skin tone.

Here’s some examples of outfits that look great on darker/warmer skin tones that would look horrible on a guy with yellow or pale skin:

darkerskintoneoutfits-ashley-weston2

Just do me a favor, though. Don’t go overboard with color. Have one standout color in your outfit and then pair it with neutrals everywhere else. When you start throwing burgundys, greens, blues and browns all in one outfit, it’s just too much going on.

How To Wear PLAIDS AND PATTERNS

It’s a great time of year to incorporate them into your wardrobe. I prefer to keep the plaids to collared shirts because it looks good on everybody and is really hard to mess up. You can wear them on their own, with the sleeves rolled up, or throw on a nice solid colored sport coat, bomber or trucker jacket over it and the shirt will look great.

As I mentioned earlier, I also love a good windowpane. This looks great on pants, suits, sport coats/blazers and overcoats.

The key to wearing patterns is to make sure the rest of the items in your outfit – pants or jacket/sweater/coat are solid neutral colors. It’s when you start mixing patterns that’ll get you in trouble real quick.

So pick an item in your outfit (normally a shirt, sweater, jacket or coat) for a pattern and then have everything else be a solid color. And also make sure that just like with your ties and pocket squares, you want a color in your plaid to be a similar shade of one of the colors in your pants or jacket/sweater. Then you’ll have a nice, classy and cohesive look.

My Favorite COLOR COMBINATIONS For The Season

Here’s some color combinations I love and use with my clients during this time of year:

  • Green and blue
  • Gray and brown
  • Blue and brown
  • Burgundy and blue
  • Burnt orange and blue

These are my go-to colors and if you stick to these combinations, you’ll look sharp and timeless during this season.

So without further adieu, let’s get into the Men’s Fall and Winter Essentials.