Updated:
Readtime: 10 min
Every product is carefully selected by our editors and experts. If you buy from a link, we may earn a commission. Learn more. For more information on how we test products, click here.
First dates can be nerve-racking enough without having to worry about what you’re wearing. You’ve got the usual questions running through your head: Will we get along? Will there be awkward silences? Will they look anything like their dating profile?
And then most importantly, what the hell am I going to wear?
While there’s no magic outfit that’ll guarantee a second date, putting some thought into what you wear can certainly help you make a good first impression. And no, that doesn’t mean you need to rush out and buy an entirely new wardrobe or dress like someone you’re not.
The trick is to find a fit that:
a) suits the occasion
b) fits you well
c) makes you feel comfortable and confident.
So, whether you’re heading out for a bougie dinner, grabbing a drink at the pub or keeping it casual with a coffee, here’s what to wear on a first date.
Related Read: A Stylist’s Guide to Dressing Better
What to Wear on a First Date At a Glance
Not sure where to start? The best first-date outfit really depends on where you’re going and what you’ve got planned. Here’s a quick guide to getting the dress code right.
| Date | What to Wear |
| Dinner at a nice restaurant | Tailored trousers, a button-down linen shirt, leather loafers, optional unstructured blazer |
| Drinks at the pub/bar | Dark jeans, chinos or pleated pants, a tailored T-shirt, and clean sneakers |
| Coffee date | Relaxed chinos or jeans, a plain T-shirt, and an overshirt and/or sandals |
| Movie date | Jeans or trousers, graphic T-shirt, lightweight jacket, and sneakers |
| Outdoor or activity date | Chinos or bermuda shorts, T-shirt, sneakers or sandals |
| Beach or picnic date | Linen short-sleeve shirt, beach shorts, and sandals |
These are, of course, just suggestions. You can wear whatever you want on a first date, but if you’re someone who constantly struggles to find the right fit for the occasion, the above is a good starting point.
What to Wear on a First Date: The Golden Rules
Before we get into specific outfits, there are a few first-date general rules worth remembering:
- Dress for the occasion: A nice restaurant calls for a different outfit than a walk along the beach. If you’re unsure about the venue dress code, check before you go.
- Make sure your clothes fit: Even the most expensive outfit can look ordinary if it’s too tight, too baggy or poorly fitted.
- Wear something you feel comfortable in: A first date probably isn’t the best time to experiment with a completely new look. Stick to clothes that make you feel like yourself.
- Pay attention to the little details: Clean shoes, ironed clothes, tidy nails and a little grooming can make a bigger difference than you might think.
- Don’t overdo the fragrance: A little cologne can be very attractive. Enough that the other side of the restaurant can smell you? Not so much.
- When in doubt, lean smart casual: A well-fitting pair of trousers or dark jeans, a quality T-shirt or shirt, and clean sneakers or loafers will work for most first-date situations.
6 Outfit Ideas for Different Date Occasions
1. Dinner at a Nice Restaurant or Bar
If you’ve booked a nice restaurant or bar for your first date, it’s worth putting a little extra effort into your outfit. You don’t necessarily need to wear a suit (unless the restaurant is really fancy), but you should definitely look like you’ve made an extra effort.
You can’t go wrong with a well-fitting pair of tailored trousers or chinos paired with a button-down shirt. On your feet, leather or suede loafers. If the restaurant or bar is particularly nice, you can also throw on an unstructured blazer.
What to wear:
- Tailored trousers or chinos in black, navy, charcoal or beige
- Button-down shirt, knitted polo or lightweight jumper
- Leather loafers or Chelsea boots
- Optional unstructured blazer
- Minimal accessories, such as a watch and bracelet
What to avoid: Ripped jeans, dirty sneakers, anything too casual.
2. Drinks at the Pub
Heading to the pub for a first date? Always a good choice. It’s relaxed, there’s usually enough background noise to cover the occasional awkward silence, and you can always order another drink if things are going well.
Your outfit should follow the same chilled approach (although please remember that doesn’t mean turning up in your oldest footy shirt and thongs).
A nice pair of straight-leg jeans or chinos with a plain T-shirt, camp collar shirt or polo will never lead you astray. You can add an overshirt, denim jacket or bomber if the weather calls for it. On your feet, opt for clean sneakers (although if you’re heading to more of a gastro pub, boots or loafers can help dress up the outfit).
What to wear:
- Straight-leg or slim-straight jeans, or chinos
- Plain, quality T-shirt, polo or casual button-up
- Overshirt, denim jacket or bomber jacket
- Clean leather or suede sneakers, or Chelsea boots
- A watch or a few understated accessories like a ring or two
What to avoid: Anything overly formal (like a full suit, unless you’re coming straight from work), or anything overly casual (no singlets or gym clothes).
3. Coffee Date
Coffee dates are one of the best first-date ideas. They’re super low-pressure, affordable, and a good opportunity to see whether there’s a connection before committing your entire Saturday to someone you’ve never met. While the dress code might be relaxed, that doesn’t mean you should show up in a stained T-shirt or in sweatpants.
A pair of well-fitting jeans or relaxed pleated pants with a T-shirt or casual shirt is a good option. If it’s chilly, add a lightweight knit, cardigan or overshirt.
What to wear:
- Relaxed jeans, pleated trousers, bermuda shorts or chinos
- Plain T-shirt, casual shirt or knitted polo
- Lightweight knit, cardigan or overshirt
- Clean sneakers, casual loafers or nice sandals
- Simple accessories (watch, bracelet, sunnies)
What to avoid: Gym clothes, tracksuit pants or anything with a stain/holes.
4. Movie Date
A movie date might not give you much opportunity to talk for the first couple of hours, but at least you can take comfort in knowing your outfit doesn’t need to be complicated.
Because you’ll be sitting for a while, the main consideration is comfort. A pair of relaxed trousers or jeans with a good-quality T-shirt and an overshirt or lightweight jacket is an easy win. Cinemas also have a habit of being freezing, so bringing an extra layer is never a bad idea.
What to wear:
- Comfortable straight-leg jeans or relaxed trousers
- Graphic T-shirt
- Overshirt, cardigan or lightweight jacket
- Clean sneakers or casual boots
- A simple watch
What to avoid: Anything uncomfortable to sit in for two hours, or a jacket so bulky it takes up half the cinema seat.
5. Outdoor or Activity Date
Whether you’re heading out for a coastal walk, playing mini golf, visiting a farmer’s market or showing off your bowling skills, an activity date calls for something that’s stylish and practical.
The most important thing is to dress appropriately for what you’re doing (like, if you’re planning to walk a few kilometres, comfortable shoes are much more important than looking fashionable).
That said, practical doesn’t have to mean a boring outfit. A nice pair of tailored shorts or denim bermudas with a quality T-shirt or polo will make you look effortlessly cool while also keeping you comfy.
What to wear:
- Comfortable chinos, relaxed trousers or bermuda shorts
- T-shirt or polo
- Lightweight jacket or overshirt
- Comfortable sneakers for walking/the activity you’re doing
- Sunglasses and a hat
What to avoid: Brand-new shoes you haven’t worn in or restrictive clothing.
6. Beach or Picnic Date
If your first date involves sunshine, a picnic rug or a walk along the beach, you can rest easy knowing you’re allowed to keep things pretty casual.
A linen shirt paired with bermuda shorts is a classic warm-weather combo. Alternatively, a plain T-shirt with lightweight cotton trousers or shorts works just as well. On your feet, take your pick: thongs, sandals, sneakers… anything goes on a beach or picnic date.
What to wear:
- Linen or cotton shirt, worn open over a T-shirt or buttoned up
- Tailored shorts or lightweight linen trousers
- Canvas sneakers, leather sandals or loafers
- Sunglasses, hat, watch
- A lightweight layer if you’re staying out into the evening
What to avoid: Heavy fabrics or anything that’ll leave you sweating through your shirt before the date’s even started.
The Bottom Line: Dress Like Yourself (Just a Little Better)
Ultimately, knowing what to wear on a first date comes down to dressing for the occasion, putting in a little effort and choosing something that makes you feel good. You don’t need an expensive outfit or an entirely new wardrobe to make a great first impression. A well-fitting shirt, a decent pair of trousers and clean shoes can go a long way. And remember, while a good outfit might help you feel more confident walking into a date, whether there’s a second one comes down to chemistry, not your choice of shoes.
First Date Outfit FAQs
In most cases, a full suit isn’t necessary unless you’re heading somewhere particularly formal. For most dinner dates (even fine dining dinner dates), tailored trousers, a button-down shirt and an optional blazer would be more than enough.
Focus on wearing clothes that fit well, suit the occasion and make you feel comfortable. Good grooming, clean shoes, neat clothing and a little attention to detail can make a strong first impression without requiring an expensive outfit.
Beyond choosing an outfit, a little preparation goes a long way. Have a shower, tidy up your facial hair, check your nails, clean your shoes and make sure your clothes are fresh and wrinkle-free. It’s also worth confirming the time and location beforehand. And, perhaps most importantly, turn up on time.
There’s no universal list of forbidden first-date outfits, but dirty shoes, stained clothing, overly strong cologne and anything that makes you uncomfortable are worth avoiding. It’s also a good idea to steer clear of clothes that don’t suit the venue. Above all, don’t dress like someone you’re not just to impress your date.
More Man of Many Style Guides
- Your Summer Office Dressing Guide
- Best Spring Perfumes
- Best Men’s Bags
- The Complete Guide to Men’s Accessories
- How to Wear Graphic T-Shirts
- A Beginner’s Guide to Wearing Colour
- Smart Casual Men’s Dress Code Guide
- Types of Loafers for Men and How to Wear Them
- A Fashion Expert’s Guide to Dressing Better
- How To Style The Relaxed Fit Trend Without Looking Messy
Comments
We love hearing from you. or to leave a comment.