First dates are all about making a good impression. Maybe you’ve finally found the courage to ask out that cute co-worker, or perhaps you’ve successfully navigated the world of online dating and scored your first date. Regardless, you’ll want to bring your A-game, and it all starts with your choice of outfit. Not that we’re trying to put any pressure on you, but knowing how to dress on a first date will significantly affect the outcome. Make the wrong choice, and the date is over before it even started. Find that perfect outfit, and you’ll be set for success because when you look good, you feel good.

Luckily, we’ve prepared a foolproof men’s style guide that covers everything from a casual outfit for a date at the bar to a little bit more dressy option for a quiet candlelight dinner. As you may have noticed, the venue will impact your choice. So, first things first, figure out where you’re taking your date and dress accordingly.

First Date at a Coffee Shop or a Bar

Whether you’re going to grab a cup of coffee or share a couple of drinks at the local bar, you’re generally going to want to wear something a little more on the casual side. Now, don’t mistake casual for scruffy. Throwing on your old favorite band t-shirt and a pair of baggy jeans is not an option. Instead, you can either go with a smart casual or old school bad boy style.

Outfit Number One:

If you’re going for a casual coffee date during the day, opt for a laidback outfit that you feel comfortable in. For the top, we recommend a lightweight V-neck sweater. It’s comfortable, simple, and a classic piece of clothes that everyone has in their wardrobe. V-necks are also a bit more outgoing when compared to their crewneck counterparts. Pair the sweater with matching cotton chinos that are not too dressy, but not too casual like a pair of everyday jeans. 

Finish off this outfit with some stylish footwear like a pair of sleek yet comfortable loafers. They are an ideal choice for this versatile outfit as they offer the comfort of sneakers and the elegant and sleek look of dress shoes. Basically, you’re getting the best of both worlds. Now, we said this was a date during the day, but the best part about this outfit is that it will serve you just fine even if you opt to wear it during the night. Just make sure to color coordinate accordingly and choose darker colors such as navy blue or black.

Outfit Number Two:

The first outfit we recommended is excellent if you want to go with a safe option. Now, there’s absolutely nothing wrong with wearing a casual first date outfit that’s more on the safe side. Still, for those who are eager to showcase their adventurous spirit right from the get-go, we recommend a more bold approach. Old school bad boy is one of those first date outfits guys love, and girls can’t resist. 

Nothing spells confidence more than a laid back, yet elegant bad boy style. However, there’s a thin line between stylish and cheesy when dressing like this. Most men find it difficult not to make it look forced or unnatural. That being said, if you have a rebellious side that you want to show, this is the outfit for you.

Starting from the top, you’ve probably already guessed, you want to toss on a great leather jacket. The iconic bad boy look is nothing without a sleek racer-style jacket. Underneath the jacket, you’ll want to keep it as simple as possible. Think of a plain white t-shirt or a darker henley shirt. For your bottom half, go with a pair of raw denim jeans that fit you well. Finish the outfit with a pair of chukka boots. You can also add some accessories just don’t go over the top with bracelets and rings.

First Date at a Coffee Shop or a Bar

Coffee shop date outfit

First Date at a Restaurant

If you’re off on a dinner or restaurant date, you’ll want to wear something a little smarter, as you’ll want to be appropriate for the restaurant, so go all out and dress to the nines. Of course, this depends on the restaurant you’re going to, as certain places will have dress codes that you’ll have to adhere to.

The most common question we hear is, “what should I wear on a first date at a restaurant?”. Contrary to our casual date recommendations, dinner dates are a whole other story and call for a more formal approach. Here’s what we got for you:

Outfit Number One: 

Feeling formal and sophisticated? Show it off with a classic navy or a dark grey suit. Now, you don’t have to go all-out on the formal side. Instead, we suggest playing it down a bit and experimenting with the color of your shirt and tie. You can always go with white, but a light blue shirt might be more interesting in this case. Now, for your shoes, you’ll want to go with a formal pair of dress shoes that match the color of your suit. Something that spells out sophistication, yet is playful, is a pair of monk strap shoes.

First Date at a Restaurant

Restaurant date outfit

Outfit Number Two:

Not a suit kind of guy? Don’t worry, we have you covered. Take your trusty V-neck sweater and throw it on top of a dress shirt. V-necks are perfect for layering as their neckline shows off the collar of the shirt and the optional tie. For the bottom half, we suggest going with a pair of smooth, wool knit slacks and a pair of dressy slip-on loafers. This outfit is not too flashy, not too flamboyant, yet will leave the impression that you are confident and energetic.

So there you have it, a few outfits that will set you up for a successful first date. We mostly left out the choice of color, because that comes down to personal preference. Still, a good rule of thumb is that light colors work better for daytime dates, while darker colors are more suitable for dates during the evening.

We hope you enjoyed our what to wear on a first date men edition guide for more articles on relationships, dating, and love in general, make sure to keep up with our blog.