Choosing the Best First Date Outfit For Men 

It’s important to make a good impression on a first date, and that includes which outfit you choose to wear and how you style it. Men can have just as much fun with fashion as anyone else, mixing and matching apparel to create the perfect date-ready look. However, jitters can get the best of anyone, so gaining insight on the trendiest going-out looks can make a world of difference. Wondering what to wear on a date for men? Take a look at the guide below to see the best men’s date outfits.

Date Outfits for Guys

Put your best foot forward by showcasing your unique style. You should feel comfortable and at ease while flattering your assets, but how you dress also depends on the date activity and weather. Are you hiking together? Is this a candlelit dinner? Are you going to a concert or sports event? Take this into consideration when choosing an outfit, but know that you can always dress outfits up or down to suit the occasion. Pro tip: Make sure you tell your date what you’re doing in advance so they can plan too!

Casual First Date Outfit: Guys

Let’s say you're going on a classic dinner date. You’ve picked a local, charming cafe and you want to dress to impress without feeling too formal. A classic, casual first date outfit for men is a button-down shirt or shirt jacket over a plain white tee shirt. Pair with dark denim or slim-fit pants, a vest if it’s cold, and closed-toe, polished shoes with navy or black socks. Accessories can include a nice watch and/or necklace. Think UNIONBAY’s Switchback Flannel Shirt in Battleship over a plain white-tee shirt matched with the Luca Slim Utility Pants in Ruins. If you’re feeling cold, layer with the Cameron Quilted Vest in True Navy.

What to Wear on a First Date for Drinks

When going out for drinks, you want to look sharp and sleek. While the date isn’t about clothes, the right outfit can help you feel more confident, plus your date will know you put thought and effort into your appearance. A great first date outfit for men includes a nice button-down men's shirt with short or long sleeves like the Fisher Short Sleeve Shirt in Chambray. This is best paired with fitting, flattering mens pants such as the Rainier Travel UBF + 50 Tech Pants in Charcoal.

Fashionable men’s shorts can also work if it’s summer weather. Depending on the season, you can accessorize with a nice watch, a stylish scarf, or a cozy but fitting jacket.

How to Incorporate Pieces You Already Own for a Fresh Look

Wondering what to wear on a casual first date with apparel you already own? We’ve got you covered. Take stock of your wardrobe and ask yourself what makes you feel and look your best. Your date wants to get to know your authentic self, so prepare a look that displays your personal style in the best way. Reimagine how you can mix and match items in your closet to pick the perfect casual date outfit for men.

Searching for inspiration? Date-ready clothing can include a fun, colorful print shirt such as the Pier Chambray Woven Shirt in Dusty Orange with dark denim or slim-fitting pants.

Layer with a sophisticated, solid block jacket or sweater like the Zion Sherpa Mock Neck Fleece in Powder.

Tips on Dressing for the Right Activity

Considering what to wear on a first date for guys? You can be fashionable no matter the occasion. For instance, a more athletic date like hiking, rock climbing, or going for a bike ride may change your outerwear decisions, but you don’t have to throw out style for comfort. Remain comfortable and ready to move with a pair of neutral, slim-fitting joggers like the Neo Ripstop Jogger Pants in Droid. Best paired with a tee-shirt and lightweight sweater or hoodie like the Ryder French Terry Hoodie in Pewter. These trending choices will make you feel like you didn’t even try, but your date will notice your cool, casual appearance.

What Not Wear on a First Date

The key is to dress appropriately for the occasion, and to wear clean, wrinkle-free clothes. Check for stains, creases, holes, and dirty shoes, as these do not positively characterize you and your personality. Also, keep in mind, if you agreed upon a certain outing like a dinner date, then make sure you don some flattering and activity-appropriate apparel like a button-down shirt and form-fitting pants.

Shop UNIONBAY to Find the Best First Date Outfit for Men

When you’re needing inspiration or the right dinner date outfit, turn to UNIONBAY’s online catalog. Revitalize your wardrobe with the trendiest pieces so you know what to wear on a first date for men. Shop the latest UNIONBAY items today to look dashing on your date. From mens shirts to hoodies for men, we have you covered for your first day needs!