A lot has changed in the world of dating, but one thing remains reliably constant: date night style. From formal dinners to casual bowling dates, the perfect men's date night outfit should combine sophistication and comfort for any setting.
So how do you strike this balance to make the impression you want? Learn what to wear on a first date, how to choose men’s casual date outfits without looking underdressed and what you should probably not include in your date night ensemble. (Hint: No wrinkles.)
Date Night Outfit Essentials
Men should have a few date night staples in their wardrobe at all times. These essential articles can dress up or dress down to match your plans for the evening — and with vibrant patterns, classic cuts and performance fabrics, there’s something for every closet.
Best Shirts for Date Night
Every outfit starts with a great shirt. Made with performance fabrics and available in multiple styles, button-down shirts are a go-to date night option. Long-sleeve button-downs dress up an outfit when you need a touch of style, while short-sleeve button-downs bring a casual date night outfit up a notch.
You also can’t go wrong with a standard polo shirt. Choose a polo in a solid color or interesting pattern, and wear it tucked or untucked depending on how formal you’re feeling.
The Right Pants
What pants should you wear on date night? The answer is almost always khakis. They complement every body type and skin tone, they add traditional style to a modern outfit and they look great with whatever shirt you choose.
If you’d like another date night pant option, consider high-quality jeans (no rips!) and other types of casual pants, such as linen pants or performance pants. Slacks are also a great option if you’re heading to the theater or a restaurant with a dress code.
Remember the Outerwear
There are two benefits to bringing lightweight outerwear on a date: you stay warm if the weather turns, and you have something to drape over your date’s shoulders if they feel cold. We love how sweaters and pullovers look with polos and button-downs, but vests are another comfortable option for date night.
Add Accessories
When it comes to making a memorable impression, it’s all about the details. A classic leather belt instantly elevates every men's date night outfit, especially when it coordinates with dress shoes. Speaking of shoes, find the best combination of formal and comfortable shoes available in your closet so you’re not concerned about pinched toes or slipping heels. And don’t forget another accessory: a splash of dapper men’s cologne!
What To Wear on a First Date
Once you’ve got the basics in your wardrobe, it’s time to plan out your ensemble. Here are our best first-date outfits for both casual and sophisticated occasions, designed to keep you from looking (and feeling) stuffy.
Casual First Date Outfits
First dates can be romantic without being formal. If you’re planning on an evening of axe throwing, walking down the boardwalk, attending a football game, or another sweet and understated first date idea, figuring out combine performance wear with a traditional style.
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Combine a short-sleeve button-down shirt with khaki shorts and sneakers, and wear a quarter-zip pullover if the weather turns cool.
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Wear a polo untucked with performance pants, boat shoes and a nice hoodie.
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Add a long-sleeve tee to a nice pair of jeans and canvas shoes, and add a knit shacket (shirt jacket) on top.
Sophisticated First Date Outfits
For occasions that call for candlelight, long-stem roses and sparkling Champagne, it’s time to step up your date night attire. What to wear on a dinner date can be similar to a casual first date outfit — with a few important changes.
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Wear a blazer on top of a long-sleeve button-down, and add a pair of nice slacks and dress shoes.
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Layer your outfit with a crewneck sweater on top of a polo or dress shirt, and wear it with khaki pants and leather sneakers.
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Go all out with a suit and tie, and accessorize with your best watch and dress shoes.
Date Night Styling Tips
Even the best first-date outfits need a little styling help. After all, they’re just clothes — the real impression comes from you! Follow these last tips to feel confident in your men's date night outfit.
What Not To Wear
There are so many choices when it comes to what to wear on a date — but there are a few items that should not end up on your list.
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Graphic tees, especially if they say something inappropriate
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Wrinkled or unwashed clothes
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Anything too casual, such as sweatpants or ripped jeans
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Sandals (unless your date is on the beach or on a boat)
Avoid wearing anything that suggests you didn’t pick it out, especially for your date, or that you didn’t take care in picking it out. If you wouldn’t wear it to work, don’t wear it on a date.
How To Feel Confident
On the other hand, adding a few moments to your prep can add a huge boost to your confidence during your date. Before the big night, make sure to follow these steps to feel your best across the table (or axe-throwing booth).
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Get a haircut beforehand (a few days before is ideal)
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Shave or trim your facial hair right before your date
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Give yourself lots of time to get ready
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Don’t try on your date night outfit for the first time right before the date
The best way to feel confident on a date is to choose comfortable clothes and shoes. When you feel great in what you’re wearing, your body language shows — and you can relax and have fun.
Make a Connection With the Right Date Night Outfit
Dressing well for a date tells your partner that you value your time with them — and that includes preparation time! For more first-date outfit tips, dig deeper into how to dress each of these wardrobe staples, including how to wear a short-sleeve button-down shirt. Whether it’s your first date or your fiftieth, choosing a high-quality date night outfit keeps the focus on the conversation, not your clothes.
