by George Mickum

In many respects, winter is the easiest time of year to dress for. There are fewer conventions and fewer unspoken approaches, and there is less stress on dress codes. The weather is predominantly cold, and people like to stay fully covered. However, dressing for the winter is not as simple as it may seem. Dressing with a politically correct flair is always something to be thought out rather than assumed.

All winter attire should have sleeves. The sleeveless look is best left for the summer months. Even if a garment is cashmere or quilted, a sleeveless style does not suit the winter aesthetic. Short sleeves are questionable past November. While it can be hot indoors, one must preempt discomfort by wearing a lighter base layer.

Winter boots are ugly, cumbersome, and unflattering. However, at times, they are a necessary evil. They are not, though, acceptable to wear in every place of business—or for every evening event. There are many options instead, but none are easy. At times, it can be a struggle to be politically correct. I recommend you carry shoes that fit the occasion and a bag (perhaps, a Goyard tote bag) that can get wet (so you can put your snow boots inside). Often, the coat check will be able to keep these items for you. You can also try to purchase boots that are less practical for the snow but look as presentable as regular shoes. This is much simpler for women as more boots are designed with this in mind. But I personally suggest that you stay away from this idea. Shoes that look appropriate but are still waterproof and warm are rare. Plus, you can end up losing all around with shoes that are not as attractive or flattering as they could be and still have cold, wet feet.

Presentation of oneself includes one’s outerwear. A winter coat that is not a ski coat is a key piece of any wardrobe. Keep in mind that sportswear such as ski attire is not acceptable to wear in a work environment. Gentlemen should have a darker palette overcoat, and women should have something similar. Fur is acceptable for both genders and is extremely effective for keeping you warm. There are informal and formal furs, so you should be mindful of the context when you wear them. For instance, you would not wear a shearling coat over a cocktail dress to a cocktail party. Business or formal accessories like simple and warm cashmere scarves and leather gloves finish off winter outfits nicely.

1. Alexander McQueen Double-Breasted Virgin Wool Coat. Great for gentlemen to wear to work or to evening events. The gold zipper embellishments add a fun flair to this minimalist style that keeps you warm and dressed appropriately for almost every event. ($1,668; saksfifthavenue.com)

2. Jimmy Choo Leather & Rabbit Fur Mid-Calf Boots.
Fur-lined for added warmth, these exquisite boots are acceptable as both business attire to wear to the office and as passable snow boots for everyday outings. Treat with water-proofing spray to enhance snow durability. ($1,150; saksfifthavenue.com)

3. Bottega Veneta Wool Banjo Scarf. Masculine and stern yet whimsical and sophisticated, this textured cashmere scarf pairs perfectly with virtually any outerwear piece. ($790; saksfifthavenue.com)

4. Max Mara Fur-Collar Cashmere Coat. This scrumptious winter coat by Max Mara is a lovely all-purpose coat, both formal and suitable for everyday wear. Its great staple color will match almost anything. ($5,990; saksfifthavenue.com)