What To Wear to a Winter Happy Hour: A Casual Guy’s How-to

What To Wear to a Winter Happy Hour: A Casual Guy’s How-to

What does it mean when you see an invitation say “business casual attire” for a happy hour? If you’re invited to a get-together after work, what should you wear? When going to a winter happy hour, you usually want to strike a delicate balance between expressing your personal style, casual comfort and formal dress. There are exceptions for a few happy hours, but most are casual enough to be worthy of a classy, comfortable outfit. What to wear to a winter happy hour depends on functional considerations like the weather and how to put an outfit together.

Things To Keep in Mind

What you wear can help you blend into a crowd or get others to notice you. When you consider your choices for happy hour, a few things should guide you in one direction or another.

Where You’re Going

Before you choose your outfit, consider your destination. Often, you will enjoy cocktails or appetizers at a casual bar or restaurant. However, some bars are upscale and require a dressier look. Nightclubs might have a dress code requiring a specific type of shirts, pants, or shoes. Parties may have different expectations than a happy hour with a dinner reservation to follow. Finally, consider whether you’re going to a happy hour indoors or on an outdoor patio. You may not have to worry about cold evenings if you are in the south. However, in most places, you will probably have to wear heavier clothing outside. Mens hoodies offer the option to be warm, comfortable and stylish all at the same time.

Who You’re Going With

Your dress for a social occasion such as a happy hour is undoubtedly affected by who you’re going with. If you aim to impress a date, you will likely choose a more formal outfit, like a button-down shirt. Work pants may be more in tune with a business crowd if you’re going with coworkers.



Weather is a major factor that often dictates both the look you want to achieve and the clothing that you wear. Traditional winter colors will have you grabbing ivory, black and gray pants and tops. Sweaters and turtlenecks replace simple v-necks and short-sleeved shirts. Accessories, such as scarves and jackets, help to complete your look. In colder areas, the weather will have a large role in the materials of your clothing. You will likely gravitate toward wool, flannel and other warmer fabrics.


The best way to instill confidence in your appearance is to dress as comfortably as possible. Besides dressing for warmth, you want to choose materials that feel nice against your skin and allow you to move freely. At the same time, you want to adhere to your sense of style. Knits and cashmere are warm, soft and look great on everyone. Footwear is essential for polishing your winter look. While sneakers are appropriate for many occasions and outfits, boots create effortless style in the winter.

Winter Happy Hour Outfit Ideas

Here are some of our favorite outfit ideas to give you inspiration on what to wear to a winter happy hour.

Outfit #1: Henley, Pants, Dress Boots

Henley shirts are great because of how versatile they are. You can easily dress up a long sleeve henley with chinos and laced ankle boots. A maroon, charcoal or muted blue shirt with cream pants and dark leather shoes is sure to fit a night out with friends or colleagues. You can make your look even more formal with a blazer and suede Chelsea boots.

Outfit #2: Hoodie, Dark Jeans, Sneakers

A pullover hoodie is perfect if you want a more casual look for happy hour. It’s warm and comfortable, yet stylish. A festive green or red hoodie with dark jeans is a move that can be both trendy and sharp. Sneakers finish the look by making you look casual yet put together. You can achieve a fancier look with a white hoodie and black jeans. Black, red or white sneakers would complement the final ensemble.


Outfit #3: Flannel, Jeans, Boots

Flannels give you the perfect opportunity to wear white jeans to happy hour. You can also wear several types of boots and still look dressy. A flannel button-down allows you to pull off a wintry festive look with more colors than you could find in a traditional dress shirt. On the other hand, muted flannels manage to look formal when paired with black, blue or white jeans. As far as boots go, you cannot go wrong with any style, really, ranging from black combat footwear to tan Chelsea boots.

Outfit #4: Sweater, Pants, Dress Shoes

An outfit that is a nice fit for casual or business happy hour is a light sweater, quality pants and dress shoes or boots. You can mix up the colors and even wear a blazer over your sweater to create a more classy appearance. For a winter ensemble, you can match a black sports jacket with a gray sweater, white or blue slimfit tee, cream-colored pants and leather Oxfords. You can also dress your look up by replacing the tee with a polo or a collared long-sleeved shirt.

Happy Hour Ready

A winter happy hour is a great chance to be social with dates, friends and colleagues. What you wear is crucial to creating a lasting impression. Whether it’s a casual happy hour with your friends or a work happy hour with your boss, always make sure your outfit fits the occasion. Have fun upgrading your happy hour wardrobe with outfit choices like those above.