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

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.

21 Things Men Should Never Wear

In this video, I talk about the 21 things men should never wear! These are the things that’ll curl your toenails, and offend even your grandmother. Just don.do.it.

 

1. Gaudy Rings & Pinky Rings

2. Too Much Cologne
Too Much Cologne Ashley Weston

3. Socks with Sandals

4. Sandals In General

5. Shorts That Go Past Your Knees

6. Old dirty shoes
Dirty Shoes Ashley Weston

7. Cartoon printed boxers

8. T-Shirts with Brand Logos

9. Baggy, Ill-Fitting Clothing

10. Tank Tops
Tank Tops

11. Skinny Jeans

12. Pointy & Square-Toed Shoes

13. Deep V-Neck T-Shirts
Vneck

14. Big, Square, or Monogrammed Belt Buckles

15. Leather Bracelets

16. Elongated Shirts

17. Soul Patch
Soul Patch Ashley Weston

18. Crocs

19. Earrings and Facial Rings

20. Short-Sleeve Sweaters

21. Dress Shoes with Tennis Shoe Soles

THE #ASKAW SHOW: EPISODE 09 W/ Andrew Snavely FROM PrimerMagazine.com

In this episode, my special guest – Andrew Snavely from PrimerMagazine.com answer some of the most scintillating questions for the readers/viewers.

Have a question you’d like me to answer? Ask in the comments of the above youtube video or send me an email.

In this episode, we answer:

Q: I’ve lost a significant amount of weight and now all of my clothes are clownishly large on me. Can a tailor make my clothes fit again or should I just buy all new ones?

A: See the video above for the answer and my men’s clothing fit guide for how your clothes should fit.

Q: I watched your T-Shirt video and if I have a nice looking tee with a pretty minimalist design, does that hinder a look the same way a straight up graphic tee would?

A: Short answer – sort of. See the video for the longer answer.

Q: As a shorter man (5’6″), I find it difficult to find stuff that fits me and looks good. I was hoping you can provide some general style tips for shorter men.

A: See TheModestMan.com for a great site for shorter men style. But in our experience, as long as your clothing fits properly, there’s not much else to worry about.

Q: I recently picked up a Briefcase in a navy/ tan leather color way, would I match my wallet/watch/belt/etc. To the bag? What would you do in my situation?

A: Don’t think about it too much. Andrew is less of a stickler here, but I am more of a stickler. See video for details.

Men’s Summer Essentials Ebook

In this ebook, I’ll detail the items you need for summer, why you need them, and where to get them – in designer and budget-friendly options.

These items will work very well with the rest of your year-round essentials, so if you haven’t seen that series, check it out first.

My goal is to ensure you’re comfortable, wearing appropriate colors and items for the season, while looking amazing and not like a douchebag.

So download the book, pour a glass of… something (I prefer rosé) and let me show you the good stuff!






The Polo Shirt

A Polo Shirt is a great, versatile item that I put all my clients in at some point of us working together. They’re timeless and a cornerstone of any good spring or summer outfit. I often recommend wearing them in place of t-shirts, as they give a casual outfit a bit of polish – which is never a bad thing. No matter your age or body type, every guy needs a few polo shirts in his wardrobe.

A good polo shirt will:

  1. Fit like a glove.
  2. Enhance the good parts of your physique and hide the imperfections.
  3. Make you look more polished and put together.
  4. Layer incredibly well.
  5. Only have short sleeves – long sleeved polos have no place in your wardrobe.

Fabric

Fabric choice is the biggest thing to consider when choosing a polo shirt and heavily dependent on your body type. The fabric you choose will determine how good (or bad) you look in a polo shirt.

Piqué Cotton

Piqué cotton polo shirts are made with cotton yarn and have thin ribbing visible in the garment. The texture is soft, and if you look closely you can see the tightly raised cords that give a waffle-like appearance.

Piqué polos are best for heavier-set men with wider physiques because the textured fabric hugs the body without conforming to the less flattering areas of the chest and stomach. When I’m working with a client who’s worried about his belly being accentuated, I always go with pique cotton. Think of the fabric as airbrushing your torso and hiding the problem areas.

Check out how much more flattering the piqué cotton polo is on the same guy compared to a cotton/silk blend polo. I bet his hands are covering his belly button divot in the cotton polo shirt picture, too. It’s an old photographer’s trick. Notice his chest area looks a little more smoothed out? Please don’t think I’m recommending this polo, it’s pretty bad (that’s a horrible sleeve length) but it highlights the “airbrushing” effect that piqué cotton has very nicely.

Pique Cotton Vs Cotton or Silk Blended Polos Ashley Weston

Cotton & Cotton Blended Polos

If you’re in decent shape, skip the piqué polos and grab a few cotton/cotton-silk blended polo shirts. The material looks better on your body type and is softer and more comfortable than pique cotton. These polos have a sleek, modern look that are great on their own or underneath a jacket. Beware, it’ll shine a spotlight on your body’s imperfections if you’re not in good shape!

SilkBLendPolo - Ashley Weston

Colors, Patterns, Piping, Etc.

Avoid any patterns or collar/sleeve piping and stick with the basic (and best) colors to begin. Grab a few white, black, navy, and charcoal/gray colored polos. They’ll give you the most versatility with the rest of your Essential Wardrobe and will work with any skin tone and body type.

If you’ve got the basic colors already, definitely get some brighter colors that compliment your skin tone and/or throw some stripes in there, too. I would universally avoid plaids or any other wackier patterns, it’s just too much and looks tacky.

To Tuck or Not To Tuck

If you’re wearing a polo shirt without a jacket, then don’t tuck your shirt into your pants. I know golfers do this, but you’re not on a golf course and it looks horrible tucked in.

If you’re wearing a jacket, then loosely tuck in the front part of the shirt by your belt buckle like in my 3 ways to wear images below. The shirt should still cover the top half of your belt buckle – you don’t want to completely see the buckle. I love doing this on my clients because it breaks up the outfit when you see a little of the belt buckle and gives it a little polish without overdoing it.

Leggo my Logo

Please don’t get a shirt with a huge logo all over it. Just. Don’t. Logos that are small and the same color of the rest of the shirt are passable, but if you have the option, go logo-less.

How Should A Polo Shirt Fit?

Check out my Men’s Polo Shirt Fit Guide for details.

The Best Polo Shirts for Men

Designer Options

For a pique polo, I recommend the Sunspel Riviera Polo Shirt. This shirt was made for Daniel Craig as James Bond in Casino Royale. A black or navy polo pairs well with either dark wash jeans or grey wool trousers. For a silk/cotton blend polo shirt, I love John Varvatos and Burberry. The shirt’s impressive construction and fit is well worth the price.

John Varvatos Hampton Polo 

Sunspel Charcoal Jersey Polo Shirt

Ermenegildo Zegna Mercerized Cotton Polo Shirt 

Burberry Navy Silk Cotton Polo

Theory Black Boyd Polo

Budget-Friendly Options

I’m a big fan of H&M’s cotton polo shirts. Actually, I would probably get those over the designer options a majority of the time. They won’t last forever, but they’re cheap enough to replace every season or two. They have a clean design with a great fit and a price that you can’t beat. The model in the first picture below is wearing the H&M Polo.

H&M Polo Shirt 

Uniqlo Navy Dry Pique Short Sleeve Polo Shirt

J.Crew Black Pique Cotton Polo

3 Ways to Wear a Polo Shirt

(Sunglass lenses sold separately)

H&M Polo Shirt

J.Crew Broken-In Chino in 484 Fit

Vans Authentic Sneakers

True Vintage Revival Glasses 

Polo-Shirt-Outfit-2-Ashley-Weston-Mens-Wardrobe-Essentials

The jacket and chinos are actually from Dsquared2, but they’re for an upcoming season and not available in stores at the time of writing. So I added the best substitutes below.

Philipp Plein Coat So Cool

Ermenegildo Zegna Mercerized Cotton Polo Shirt

Brooks Brothers Slim Fit Dark Khaki Garment-Dyed Chinos

Nike Tennis Classic Sneakers

Allen Edmonds Black Poplar Belt

IWC Portugieser Automatic Watch

John Varvatos Lafayette Sunglasses

 

Polo-Shirt-Outfit-3-Ashley-Weston-Mens-Wardrobe-Essentials

Burberry Modern Fit Wool Part Canvas Jacket 

Burberry Silk Cotton Polo Shirt 

Levis Chino 511 Slim Fit Jeans 

Salvatore Ferragamo Penny Loafer Shoe

Allen Edmonds Brown Poplar Dress Belt

Piaget Altiplano Watch

John Varvatos Lafayette Sunglasses

Outfit Inspiration

 

Wool Pants And Trousers

Wool pants and trousers are an essential item because they’re the middle ground between jeans/chinos and a full suit. In situations when jeans or chinos might be a bit too informal and a suit is overkill, the wool pant/trouser fits this spot perfectly. They’re also amazing because they look damn good on every body type.

I want to clear the air about something first, because it’s important for you to know this:

The category of wool trousers is quite broad and basically includes any pants that are made of wool. This means trousers made of a more lightweight fabric, like suit pants, and the traditional, heavier-weight wool trouser are all considered “wool trousers.” If you want to get technical, I’m specifically meaning a wool fabric weight of anywhere from about 10-12oz and up.

When I say wool trousers from this point forward, I only mean the thick/heavier-weight wool trousers because the lightweight fabrics, like suit pants, look flimsy and unpolished when worn with items outside of a suit jacket. The thicker weight of the wool trousers I recommend below will not wrinkle as easily, lay cleaner on the legs and look great with everything from a sweater or overcoat/peacoat and semi-spread collared shirt (oxford button down dress shirt, too) to a leather jacket and t-shirt. Basically anything in your essential wardrobe will look great with the recommended wool trousers.

Some of my older readers often ask about “slacks” or “suit trousers” and my answer is always the same: don’t bother. You should never be wearing slacks or suit pants or similar without a full suit. Its flimsy looking, tacky and the mark of a guy who doesn’t know what he’s doing.

To Pleat or Not To Pleat

I don’t care how old or young you are or what your body type is – whether you’re thin or a larger guy, you should NEVER, EVER have pleated wool pants. Honestly, I f*#@%ing hate them because they’re so unnecessary and are unflattering on every guy. I’ll be the first to dance on their grave if they ever completely go away. I’ve never seen a guy look good while wearing them – ever.

What Colors Should You Get?

I’d recommend having at least two pairs of wool pants in your wardrobe. My first choice would be gray, then dark blue, and then brown, if blue or gray wasn’t available. Black is OK, but I’d consider that my last option, if I were you. It’s just too heavy of a fabric to wear black in, as it’ll look more imposing.

How Should Men’s Wool Trousers Fit?

See my How Should Dress Pants and Wool Trousers fit article.

The Best Wool Pants And Trousers For Men

Designer Options

Brooks Brothers Regent Fit Stretch Wool Trousers

Burberry Slim Fit Travel Tailoring Wool Trousers 

Ermenegildo Zegna Flat-Front Black Wool Trousers 

Budget-Friendly Options

Topman Navy Skinny Fit Wool Suit Pants

H&M Wool Suit Pants Skinny Fit

Uniqlo Men Stretch Wool Slim Fit Flat Front Pants 

2 Ways To Wear Wool Pants And Trousers

Wool-Trousers-Pants-Outfit-2-Ashley-Weston-Mens-Wardrobe-Essentials

Topman Premium Dark Grey Ribbed Slim Fit Sweater 

Brooks Brothers Red Fleece White Solid Oxford Sport Shirt

Brooks Brothers Regent Fit Stretch Wool Trousers

Allen Edmonds Poplar Belt 

Baume & Mercier CLIFTON – 10112

Allen Edmonds Carlyle Plain Toe Oxfords

Wool-Trousers-Pants-Outfit-1-Ashley-Weston-Mens-Wardrobe-Essentials

Brooks Brothers Saxxon Wool Herringbone Chesterfield

Brooks Brothers Cashmere Turtleneck 

Brooks Brothers Regent Fit Stretch Wool Trousers

Allen Edmonds Carlyle Plain Toe Oxfords

B&M – clifton automatic

Wool Pants and Trousers Outfit Inspiration

Credits

Photography: Justiin Charles
Model: Joseph Boyd at Wilhelmina Models
Hair/Makeup: Brendan Robertson for Exclusive Artists Management using Clarins Skincare and Kevin Murphy Hair Care

The V-Neck Sweater

The V-Neck Sweater is an essential because you’re going to need warm layering pieces for the cooler parts of the year and it allows you to mix and match your Essential Wardrobe a little better by layering it with a blazer or suit, over an oxford or semi-spread collar dress shirt and paired with simple dark wash jeans or wool trousers and a white sneaker, boots or oxford dress shoes. So how could I leave it off this list?

Why a V-Neck and Not a Crew Neck?

Crewnecks are okay, but they’re a more casual item. So for this reason, a V-Neck sweater is essential because it’s the classy mofo of the sweater world. V-necks add a touch of dressy formality that you just won’t get with a crewneck.

I love crewnecks, don’t get me wrong, but most guys don’t know how to wear them so then it starts looking really sloppy. I know some guys like the crew neck and tie or suit look, but I would choose a v-neck or cardigan sweater over a crewneck in this case almost every time.

V-Neck Sweater Do’s and Dont’s

Do

Don’t

  • Wear them with a dress shirt and have the collar resting on top of the “v”
  • Wear them with shorts
  • Wear them over Polo Shirts (ever)
  • Wear them over T-Shirts (ever)
  • Wear them without any shirt underneath – gross!
  • Wear them if they have any holes, pilling or they’re worn thin around the elbows

Fabrics

I prefer the V-Neck Sweaters I work with to be made of wool, – either regular or merino wool. Cashmere is also a great fabric, but it’s definitely on the pricier side. If you run a little warmer, then go for a wool/silk or cotton-blended sweater – Pima cotton is also great, but it stretches out very easily.

Colors

You need at least 1 black V-Neck Sweater in your closet. If you’ve got a black one already, grab a navy and/or charcoal gray version. These colors will go with everything else in your Essential Wardrobe. If you want a 3rd option, then a darker brown will also go pretty well with your wardrobe, too.

How Should a V-Neck Sweater Fit on a guy?

Check out my V-Neck Sweater fit guide for how (all) your sweater(s) should fit.

The Best Men’s V-Neck Sweaters

Designer Options

I love these because the fit, fabric weight, and overall construction is impeccable and I’ve worked with these brands many, many times.

Ermenegildo Zegna Black V-Neck Sweater

J.Lindeberg Black V-Neck Sweater

Burberry Navy V-Neck Sweater

Brooks Brothers Navy Saxxon V-Neck Sweater

Vince Navy V-Neck Sweater

Budget-Friendly Options

I love each one of these v-neck sweaters, especially the H&M and Life After Denim sweaters. Even though they’re budget-friendly, the quality, fabric weight, and overall fit is really good.

J.Crew Black Wool V-Neck Sweater

Life After Denim Charcoal Tournament V-Neck Sweater

H&M Dark Blue Wool V-Neck Sweater

H&M Gray Wool V-Neck Sweater

2 Ways to Wear A V-Neck Sweater

V-neck-sweater-Ashley-Weston-Mens-Wardrobe-Essentials

J Crew Rugged Cotton V-Neck Sweater 

Brooks Brothers Milano Fit Heathered Gingham French Cuff Dress Shirt

Brooks Brothers Milano Fit Plain-Front Flannel Trousers

The Tie Bar Black Grenafaux tie

Allen Edmonds Wide Basic Dress Belt

Johnston & Murphy Fielden Cap-Toe 

V-neck-sweater-Ashley-Weston-Mens-Wardrobe-Essentials-3

Brooks Brothers Navy Saxxon V-Neck Sweater

Brooks Brothers Red Fleece Gingham Sport Shirt

J Brand Tyler Fit Jeans Tumble

Allen Edmonds Carlyle Plain-toe Oxfords

Baume & Mercier -clifton-automatic

Men’s V-Neck Sweater Outfit Inspiration

Credits

Photography: Justiin Charles
Model: Joseph Boyd at Wilhelmina Models
Hair/Makeup: Brendan Robertson for Exclusive Artists Management using Clarins Skincare and Kevin Murphy Hair Care