A Fashion Stylist’s Guide to Date Night Outfits for Men

Whether you’re going on a first date or a fourth date, you want to make a great impression. In the early days of a relationship, this means focusing on all of the little details of every single date, including your own outfit. Even if you don’t put a lot of thought into what you’re wearing on a daily basis, you should when you’re going out with someone special.

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Putting effort into a nice outfit for your date, even if it’s just a casual outing, shows that you care and that the date actually means something to you. What you wear says a lot about who you are as a person. In fact, research has found that even small changes to your appearance can affect how others see you.

The only problem? You might feel like you don’t have the style know-how to actually put together a decent look. If you’re used to wearing your old favorite jeans and sneakers everywhere you go, trying to come up with a suitable date night look for a nice restaurant might feel like a big struggle. To help you come up with an appropriate outfit for any date, we consulted expert stylist Michelle Barrett. She shares her tips, along with a few outfit ideas, below.

Meet the Expert

Michelle Barrett is a personal stylist who has previously worked with celebrities like Katy Perry and Ewan McGregor. She helps clients build capsule wardrobes at Capsule Closet Stylist.

What to Consider When Picking an Outfit

Deciding what to wear on a date shouldn’t be completely random. Sure, there are some go-to looks that will come in handy in a wide variety of situations (more on that in a minute), but you also need to make sure you’re dressing appropriately for the type of date you’re going on. These are some factors to keep in mind while you’re searching through your closet or hitting the mall.

Time of Day

Is your date in the morning or the evening? Morning dates, like grabbing coffee or brunch, tend to be more on the casual side. You’re not going to wear dress pants and a button-down for lunch. Evening dates usually tend to err more on the dressed-up side, although of course, it depends on where you’re going.

Venue

Where you’re headed for the date is super important when figuring out what to wear. If you’re going to a fancy restaurant, you’ll want to get more dressed up. A walk in the park? Nice jeans and a shirt will suffice. If you’re going to an event or a country club, you can always look up if there’s a dress code so there are no surprises.

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Who Your Date Is

You never want to wear something that feels completely inauthentic to who you are. That said, you should also pay attention to the type of person your date is when selecting an outfit. “Try to compliment who your date is,” suggests Barrett. “If your date is very smart in all his or her profile images then you should be too. If not, then you can afford to go more casual.” Again, don’t change who you are, but keep their style in mind.

How Neat Your Clothes Look

You could be wearing a gorgeous button-down shirt in the perfect color, but if it’s wrinkled and/or stained, the effect is pretty much gone. “Make sure the clothes are clean and pressed,” Barrett says. “There is looking casual and then there is looking unkempt.”

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Style Tips and Advice

Finding a good date outfit can easily leave you feeling overwhelmed, especially if you are a fashion rookie. Keep these general tips in mind to help make things more manageable.

Get Advice From a Friend

Barrett recommends getting advice from a friend you can trust, if possible (or maybe a sibling or cousin). “A good friend will look at you from the perspective of your date,” she says. They can tell you honestly what they think of your outfit or they can help you put one together.

Keep Colors Simple

There’s nothing wrong with bright colors, but if you’re trying to make a certain impression, you may want to stick with some basics. Barrett recommends going for a navy, white, charcoal grey, red, dark green, or stone suit, saying they’re a good starting point for nearly any type of outfit and accessory. Avoid splashy logos or graphic designs that can easily look a little too casual. “Make sure your outfit does not speak louder than you do. Keep it classic and simple,” she reminds.

Be Yourself

Finding the right outfit doesn’t mean pretending to be someone you’re not. If you’re the guy who is always in jeans and sneakers, just find a way to elevate that look instead of wearing a suit you feel awkward in. “If you dress in something that is too far removed from who you are and end up going on another date, you will have to keep that up,” Barrett points out. Plus, wearing something you genuinely like will leave you feeling more confident.

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While your date will more than likely pay attention to your outfit in some way, it’s also about you both getting to know each other. “Do not worry about trying to impress your date with expensive clothes or fitted clothes to show off your body,” Barrett adds. “The first date is about you both deciding if you want to see each other again.” Make sure your personality comes through your clothes in some way while also dressing appropriately.

Stay Comfortable

Make sure your outfit feels as good as it looks. That means avoiding anything that fits too tight or requires a lot of adjustments. If you’re literally uncomfortable in your clothes, it will affect your confidence and can leave you distracted, which is the last thing you want.

Build a Capsule Wardrobe

A capsule wardrobe is essentially a set of basic clothing that can be mixed and matched into a bunch of different outfits. Capsule wardrobes generally focus on classic, timeless items of clothing rather than anything too trendy. It might take some time to build a good one, but a capsule wardrobe can make getting dressed a lot easier in the long run.

What Not to Wear

Self-expression is important, and wearing something more unique can be fun, but there are still some things you probably want to avoid wearing, especially if it’s one of your first few dates with this person.

“Avoid anything too bright, patterned, or controversial,” Barrett warns. She also advises against anything too trendy or inappropriate for your age. “If you are back in the dating game after a divorce, do not try to dress like a teenager before you got married. That does not mean you have to dress like your dad, you can still be fashionable and stylish.”

Go-To Date Outfit Ideas

Having a slew of go-to date outfits is where a great capsule wardrobe comes in. Barrett suggests stocking your closet with the below items:

  • A plain white button-down shirt
  • A mid to dark wash pair of straight leg jeans
  • A knitted or jersey hoodie in a solid shade with no huge logo
  • A dark slim suit
  • A few solid-colored or striped t-shirts in navy, white, black, or grey
  • A pair of black brogue shoes or similar
  • A pair of sneakers in a neutral color (think navy, grey, black, white, or charcoal)
  • A casual checkered or plaid shirt in navy, bottle green, grey, or black
  • A casual pair of chino style pants
  • A polo shirt in a solid neutral
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    “Depending on your date and where you are going, you could create a range of outfits from this small collection,” she says. For example, “If you are out for dinner with a smart date, you could go for the dark suit, brogues, and plain white shirt. Alternatively, if you want to appear smart, but not like you have just come from the office, you could still wear the suit, but team it with a t-shirt or the polo shirt.”

    Courtesy of Getty Images

    Casual Daytime Date Outfit Ideas

    Daytime dates are typically more casual than dressed up (unless you have an event or daytime wedding, of course). “I would keep it less dressy and more casual or smart casual,” Barrett says. “To define smart casual: you have made an effort and do not look like you have just gotten out of bed.”

    Some easy outfit ideas using Barrett’s capsule wardrobe selection include:

  • Dark, straight jeans with a striped t-shirt and sneakers
  • Dark, straight jeans with a casual shirt and sneakers
  • Dark, straight jeans with a hoodie and sneakers
  • Chino style pants and a hoodie or t-shirt
  • Make sure the clothes are neat and clean and stick with solid colors instead of graphic designs to keep the look casual in a good way.

    Fancy Nighttime Date Outfit Ideas

    An evening date usually means you want to put more effort into your look. “You are more likely to be going somewhere which might require a dress code,” Barrett notes. “Check before you go, particularly if your date has suggested the location.”

    She suggests opting for a more dressed-up look or smart casual depending on where you’re going. Some suggestions from her capsule wardrobe include:

  • Jeans, a suit jacket, and a white shirt
  • Jeans, a striped t-shirt, and a suit jacket
  • Chino style pants with a casual shirt
  • Chino style pants and a polo shirt
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