What To Wear On A Cold-Weather Date: 11 Outfit Options For Men

What To Wear On A Cold-Weather Date: 11 Outfit Options For Men

Winter is approaching, and deciding what to wear on dates can be difficult for men. Undoubtedly, you desire to own the latest stylish menswear that provides warmth and comfort. But how should you dress on a cold-weather date? You’ll need an outfit that includes outerwear, footwear, and accessories. Here are 11 casual, formal, and semi-formal outfit options you may try.

Source: javi_indy/Shutterstock.com

1. Casual Men’s Jeans

On a day when the weather is dry, athletic or slim-fit men’s jeans are a must-have. Create a sporty and warm look in a pair of jeans with a dress shirt or knit sweater and a sports coat or leather jacket. Jeans in medium blue, dark blue, light blue, black, and coal are stylish options. If it is cold, accessorize and wear a scarf and hat to complement your outfit.

2. Casual Pants for Men

Dressing casually yet comfortably on a date can help keep you calm, especially on the first date. For busy working guys, iron-free straight-fit khaki pants are the perfect solution. Choose khakis in heather gray, black, navy, sand, or tan. You can dress khakis up or down by choosing a casual coat, slim-fit suit separate, or dinner jacket. Shirts with a slim-fit stretch collar will maximize comfort. Finish the look with a pair of dress shoes or casual boots.

3. Modern Fit Wool Sport Coat

Be at ease on your date in a softly constructed sport coat made of wool. Under your sport coat, wear an interlock polo shirt. Complement a blue modern-fit wool sport coat by wearing a guy’s charcoal chinos in a soft cotton blend. Set off the outfit with a pair of black sparkle-fabric formal loafers.

4. Shawl Collar Cardigan

For a casual date with your girl, you can add a classic cardigan to finish your look. Combinations such as a navy and rust shawl collar cardigan, medium-wash jeans, and a deep-hued button-down sport shirt are perfect for cooler weather. Add a cashmere scarf as an accessory for style. A pair of black cap-toe boots will perfectly accessorize this outfit.

5. Slim-Fit Stretch Collar Dress Shirt

Enhance your look regardless of what you wear on a date arrayed in slim-fit mens dress shirts. Winter color options include burgundy, gray, navy blue, viola, petal, white, and black. Create a casual but sophisticated expression by wearing a white shirt with a wool or polyester caramel vest. Include a pair of charcoal or gold windowpane suit separates pants and tan wingtip Oxfords footwear. Accessorize with a gray and camel plaid bucket hat to complete the casual outfit.

6. Men’s Leather Jacket

During your cold-weather date, keep warm with a leather jacket. Pair the outerwear with a black long-sleeve shirt and black Chukka boots to impress your lady. Wear the leather jacket with medium-wash, cotton jeans. A trendy jeans style today is the slightly tapered legs that complement men’s boots.


Source: Alex from the Rock/Shutterstock.com

7. Dress Boots for Men

Dress boots are footwear for men that looks like dress shoes with an upper ankle covering. Men usually wear dress boots as formal wear when the temperature is cold. You can wear these types of boots on special occasions or events.

Incorporating dress boots for men with suit separates makes a fashionable statement on a date. Dress to impress on a semi-formal date arrayed in smooth genuine leather. Wear black dress boots with paisley, gray, or red check suit separates.

8. Wool Blazer

Stay comfy and warm fashioned in a softly polished blazer made of super 120s wool. Combine a classic style wool navy blazer with a white dress shirt and navy and red paisley tie. Burgundy double monk strap dress shoes add some polish. You can take your loved one to a fine restaurant, or a formal event decked in this winter outfit.

9. Semi-Formal Wool Vested Suit

Are you and your lady heading to a wedding this winter? Make the occasion special by dressing in a vested wool suit, two-button jacket, and flat front slacks. Wear the vested suit in light gray with burgundy, a charcoal tie, and a white Oxford dress shirt. Black cap-toe lace-up shoes and a light gray vested suit with burgundy, charcoal, and white outfit items are magnificent for photographs. These colors are trendy for fall and winter menswear.

10. Turtleneck Sweater

Turtleneck sweaters continue to be trendy and are included in most men’s wardrobes. The latest trend in turtlenecks is the modern fit knit in navy and gray. A blazer or a leather jacket complements a turtleneck sweater. You can pair this combo with dress slacks and dress boots or shoes for semi-formal fashion. Alternatively, dress down the combo by adding jeans or khakis with a pair of sneakers, loafers, or cap-toe boots.


Source: AS photostudio/Shutterstock.com

11. Tuxedo

Tuxedos gained popularity in the 1880s in the United States. Men wore formal outfits, including a dress shirt, vest, and high-waisted jacket. It was formal wear then and still is today.

Young men rent or purchase tuxedos for the prom, and men of all ages wear formal attire at weddings or other special occasions. Accessorize the garment with cufflinks, cummerbund, and bow tie, and put on Oxford shoes.

Creating a Cold-Weather Dating Wardrobe

If you are self-conscious about what to wear on a date, dress comfortably. Wear warm textiles, including wool, cotton, and denim. Complement your casual and formal outfits for dating with quality dress shoes or boots, ties, belts, cufflinks, and socks. Use the outfit options above for casual, semi-formal, and formal special occasions, such as dates, proms, and weddings.

Back To Top