Fall & Winter Style Tips

Whether you are fresh out of college or segueing into a new career, keeping a fashionable and up-to-date wardrobe is essential for any man of distinction. Knowing what to wear in the colder seasons can not only keep you more comfortable, it lends a certain air of distinction and class to a man. Here are some tips for acquiring the right pieces and putting together some classic outfits for the colder months.

Think in Layers

When a t-shirt is not enough and your down ski jacket is too much, you need to learn how to effectively layer your clothing. Not only will this keep you more comfortable, it will allow you to vary your wardrobe depending on your activities. You probably threw a flannel on over a basic tee in high school, but you can get more creative with your adult wardrobe.

You can pick up some warm vests that go perfectly over button-ups or layered over a thick sweater once the temperature drops. Hoodies are a great, casual, versatile layering option as well. If you live in an area where winters are brutal, you will also want to purchase some quality long underwear that fits well and doesn’t create any unsightly bulk beneath wool slacks or your favorite pair of heavy denim jeans. The ridiculous snow pants of your youth should now only be worn on the slopes.

Footwear Considerations


If you are employed in a laborious, physical job, your waterproofed, felt-lined work boots may be all you need for the week. However, they are not acceptable for social occasions, church or other venues. When you’re not on the job, try a thick-soled but lighter boot, preferably in a soft gray or other stain-forgiving color.

For those that work in office environments, penny loafers, polished ankle boots and heavy moccasins are all great options. Should you be a big fan of thick socks, make sure to wear them when you go shoe shopping to avoid a costly and painful size miscalculation. For those who live in wet climates, a pair of insulated Timberland boots like the ones in this list of the top 10 best men’s winter boots are essential for any outdoor work you do, from shoveling snow to digging out the car.

Winter-Appropriate Pants

Put those thin, almost-white khakis in storage! Fall and winter demand a darker color scheme and different fabrics to help keep you warm. Some of the best options are wool, thick tweed or twill. Corduroy is also another excellent option that stands the test of time. Keep in mind that fall and winter pants will be more expensive than summer clothing, and for good reason.

The fabric is thicker and harder to work with, but they will also last much longer than your summer pants do. Keep this in mind when you buy and consider that you may be wearing these pants for several years to come. Avoid trendy styles and focus on time-honored classics in both cut and color. If you work in a sector that demands professional attire, you may want to have your pants altered to fit you perfectly so that you can be proud of your appearance no matter what the weather is dishing up.

Considering a Topcoat

If you wear suits and other dress clothes frequently, you really should consider purchasing a topcoat. Usually made of a heavy wool or synthetic blend, a topcoat keeps you looking professional without sacrificing warmth.

Nothing looks sillier than a down jacket pulled on over a suit, so really think about your situation and how cold it gets where you live before you make a decision. If the expense of a good topcoat makes you nervous, head to a local tailor and get measured for one. This will reassure you that your investment will fit properly and keep you toasty for years to come.

Warm Accessories 

When planning your fall and winter wardrobe, accessories are easy to overlook. However, having the perfect compliments to your fall and winter outfits an be the icing on the cake in both function and aesthetics. You will need a warm, quality scarf to keep your neck and jaw protected. Hats are quite varied and will give you the opportunity to show off your style. Everything from a Stetson to a crazy knitted skullcap can work, depending on your clothing choices.

The same can be said of gloves. You will want to keep a pair of thin leather gloves for driving and to go with your dress clothes, while having thicker cloth or rawhide gloves are good for working outside. If you reside in an area with frigid winters, you may also want to consider a face mask. While a ski mask can be frightening or make you look like a robber, a face mask that is designed for normal wear can save you from windburn, frostbite and a lot of uncomfortable shaving.

While fashions can come and go, there are plenty of classic looks you can experiment with for fall and winter. By carefully considering the expected wardrobe for your work and home life, you can stay warm and presentable in every season.