Man wearing black knit tie and red dress pants

Men’s Winter Style Guide According to the Experts Hint: It's all about texture

With the cold turn of weather, it’s a rude awakening that it’s time to start considering your winter wardrobe.

Though gearing up for winter can be as easy as throwing on layers of coats, there’s definitely a way to do winter with more panache.

We believe that practicality doesn’t have to eliminate style. After all, finding your personal style within the perimeters of function is what makes getting dressed such an art.

Table of Contents

 Accessories According to Ian Michael Crumm

Photography by Kris Mae of KM Photography Studio

Levi’s Men’s Faux Leather Sherpa Aviator Bomber Jacket

  •  The rib knit cuffs and hem make this comfortable
  • comfort and fit

The GentleManual: Are accessories generally the same year-round? How do you use accessories to stand out?

Ian Michael Crumm: Accessories change every season. In the summer I’m all about straw fedora hats, baseball caps and leather bracelets.

As temperatures drop, start to swap hats out for wool options. This year I’m wearing a lot of wide brimmed styles.

As temperatures drop even more I go with easy to wrap scarves, fingerless gloves (easiest for texting) and thicker, printed socks.

Spring is a time when I break out more rings and silver bracelets as I tend to limit how much I wear in the winter.

There’s enough layers/items with the scarves, hats and gloves. Throughout the year I wear sunglasses.

All kinds. They’re one of my favorite items in my collection. I think I bought my first “designer” pair of sunglasses when I was eight and I’ve been collecting them ever since.

Of course, I love watches too.

GM: How much is too much?

Ian Michael Crumm: Never say never. Some days I like wearing one ring, or a bracelet. Maybe it’s a new pair of sunglasses.

Other days it’s a ring and a bracelet and new sunglasses, a hat, bag and don’t forget statement cufflinks.

You’re wearing “too much” if you look in the mirror and feel less than fantastic.

It’s not too much if you look in the mirror and love the ring, bracelet, new sunglasses, hat, bag and cufflinks. Wear what makes you happen. Style is built, not bought.

GM: Is there a particular one that you favor?

Ian Michael Crumm: Oh yes. Sunglasses as I mentioned above. I love a clean pair of aviators or bright colored wayfarers.

Right now I’m wearing a John Lennon inspired pair from Gotti Switzerland. They’re lightweight and have a 360 swivel storage feature.


Color According to Fraquoh and Franchomme of Attire Club


Mens Corduroy Shirt Button Down Long Sleeve Ribbed Fall Tops Slim Fit Casual Warm Shirts

  • Warm fabric
  • comfortable and breathable
  • Long Sleeve

Contrary to popular belief, wintertime can be a great time to wear colors and to discover new ways of coordinating colors.

During winter, many people chose to only wear neutrals, as these colors don’t show potential slush or rain stains.

The fact that men tend to wear a lot of neutrals during winter is not only the result of a sensible need being fulfilled, but is also a reflection of a psychological need.

Neutral colors like brown or beige make us feel safe and cozy, which is why so many appeal to them so often in the first place.

However, the cold season is full of black and grays, so why not go on a winter color adventure?

Winter is a great time to explore new color palettes and to play with shades and tints.

Most winter clothes feature muted colors and subdued patterns, but this does not mean that you should only stick with neutral colors.

Neutral colors can be matched to deep hues, which can be further matched to brighter and lighter colors.

To create elegant and sophisticated outfits, try to avoid wearing too many neutrals at a time.

Men gravitate towards wearing a lot of browns, grays, black, white, tan and khaki during the winter time.

Neutral colors can be the main colors of your outfits, but they should not be the only ones.

These colors mixed with the rough materials of winter clothes, can make your outfits look depressed, which is why it is recommended that you place at least one pop of color in each outfit you create.

The pop of color can be one of your main pieces or one of your accessories: a red tie on a dark blue shirt can make a big difference, a teal scarf on a khaki jacket can make an outfit dance and an orange scarf on a brown sweater can make you look polished and refined.

If you want to have dynamic and stylish outfits, you can opt for several pieces in darker colors mixed with one piece in a bright accent color.

A pop of color on an outfit that features mostly dark colors is like a ray of light on a cloudy winter day. You can go even further, and add a second splash of color.

Wearing color is a great way to express your personality and to let people know who you are without explicitly declaring it.

Your clothes are an indicator of who you are, so why shouldn’t you be in control of the image you project?

In the end, it’s your choice whether you present yourself as borderline boring or as a man who pays attention to details and is in charge of himself.

Fabric According to Matthew and Steve of The Sharp Suit


Amazon Essentials Men’s V-Neck Sweater

  • Comfortable and versatile
  • Comfort and fit
  •  The collar, hem, and cuffs to keep you warm

Despite his cold disposition, Jack Frost’s yearly winter arrival comes with a pleasant invitation to all stylish men:

Shed ye tired, well-worn spring and summer fabrics and instead opt for more varied drapery during these cold, dark months!

(We imagine Jack Frost would talk with a hint of an Old English accent).

And to Mr. Frost’s invitation we at The Sharp Suit say, “Hallelujah”, because winter is a great opportunity to incorporate a diverse range of fabrics into your personal style.

There’s an endless array of fabrics to choose from: wool, linen, flannel, denim, silk, and leather, just to name a few.

Some of our favorite winter staples are variations of these fabrics, and we wanted to feature 2 of our favorites that we love, incorporating into our Jack Frost-approved outfits.

Corduroy, a type of velvet, adds a texture to pants that can be challenging to wear during the warmer months.

Plus they’re one of the few pants fabrics that men can wear in nearly any color they want (so they’re great for layering with other clothes during winter).

Cashmere clothes have neat, dense fibers that look polished and are both stylish and functional during the holidays.

The dense fibers provide extra warmth in colder temperatures, and the clean look of the fibers is perfect over a collared shirt and tie during holiday celebrations.

Finally, wool is the most versatile of these winter fabrics and comes in nearly any color and thread size you can imagine.

Thicker fibers are great for outer wear layers like chunky sweaters, while smaller fibers are great on more surprising items, like ties and pocket squares.

Experiment with which fabrics suit your style best (like these wool ties we love for holiday get-togethers), and then be sure to thank Jack Frost for bringing us this colder, stylish weather!

Rather than looking like you pulled the first items out of your closet and layered them on in a jumbled mess, pay attention to the details of your outfit and style will never be compromised for function.

More so, you’ll have an outfit that acknowledges the season and can serve as a nod to your personality.

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