What to wear on a 1st date for men

First dates are always very exciting but also quite stressful for both sides, but you can make them a little bit better by wearing things that will make you feel confident. No matter if you prefer looking effortless or making sure that the date notices your hard work, there is always the factor of dressing appropriately for the occasion. So whether it is a picnic date, fancy dinner, movie screening or something more adventurous you will need the perfect outfit to be ready a day before since choices made in a hurry are not the best ones.

We are coming to your rescue with a list of looks for 10 different types of activities that you might do on your first date.

  1. Dinner at a Fancy Restaurant

Not to put pressure on you but if the date is in a fancy restaurant you might as well wear your fanciest clothes. All you need is classic pieces that either you already own or should invest in at some point in your life.

First is the Nice Button Up; wearing short sleeved breathable shirts in fun colors is great in summer but if the date is set in colder months you can always wear darker and warmer shirts, even a denim one could look good.

Chinos; As for the pants, chinos are the best kind since they are not so formal and at the same time, not so casual. You look smart but not office smart isn’t it all we need on a nice dinner date? You can even brave colored chinos.

Smart shoes; This is where you can experiment with different styles and colors. Often a dark brown pair of oxfords is the piece that will bring your outfit together.

Finish the look up with a slick nice watch as the only accessory (but if you love your jewels you can always incorporate them in a formal outfit), a trendy hairstyle and you are good to go.

Luxury examples:

TOPMAN White Rigid Long Sleeve Oxford Shirt + TOPMAN Black Straight Leg Chinos + GO COSTUME Cole Haan Williams Taupe Oxford Shoes + MVMT MODERN SPORT MONOCHROME Watch

2. Picnic in the park

If your first date is a picnic lunch, then you and your partner are probably quite outgoing and fairly romantic. The first thing that comes to mind is comfort since you are going to sit on the ground for over two hours. Then after that is trying to not dress overwhelmingly extra if that’s not your usual thing, of course.

Here is the perfect outfit for a nice sunny picnic day.

A Graphic T-shirt; this is a fail-safe piece for when you are outside all day. You have the freedom to choose any color and any print that you like except, tacky quotes that might throw people off.

Loose trousers or shorts; At your preference, this two can be great companions for a graphic tee and also very comfortable for the stretching that you might do.

Sneakers; classic dark sneakers are perfect for picnics since light colored ones will get green.

Sunglasses; This one’s reason is not only the blinding sun but also the stylish look that it will give you.

Luxury examples:

Oversize T-shirt with Gucci logo + JIL SANDERS loose fit trousers + GUCCI Leather high-top with tiger + Prada Square Heritage 52mm Half Frame Sunglasses

Affordable examples:

TOPMAN White ‘California’ T-Shirt + ZARA men’s STRIPED SHORTS + Chuck Taylor All Stars + OAKLEY STRINGER Sunglasses

3. Exploring downtown
Chatting in outdoor cafes, visiting historical monuments and parks of your city, there are all kinds of fun things to do outside that will keep you busy. The weather is naturally important while dressing for this date.

White T-shirt; a simple white T-shirt will never fail to be stylish and sharp. It is also very easy to style with many things.

Dark wash Jeans; it doesn’t matter if you like straight leg or skinny jeans, you will look great in either of them.

Leather Jacket; this one is in case if it’s a bit cold outside and you want to wear a cool classic outerwear that adds a bit of character to your simple look.

Boots; a nicely worn in pair of Dr. Martens will accompany your dark jeans and white T-shirt perfectly.

Rings; two or three silver rings that match your jackets hardware would be the only accessories that your outfit needs.

Luxury examples:

YEEZY plain white T-shirt + Maison Margiela blue dark wash 5-pocket Jeans + Golden Goose Deluxe Brand Chiodo Golden Biker Jacket

Affordable examples:

Adidas logo white T-shirt + Topman Washed Black Rigid Tapered Jean + Diesel Leather Jacket + Dr. Martens Men’s Leather Boots

4. Drinks in a Pub
Pubs can be dark and crowdie sometimes, but you should still make an effort to look good for your date. And you might as well rock your street style and be a bit more original.

Oversized black band tee; make sure to be a fan of the group or at least be aware of their music since band tees always start conversations.

White long sleeved tee; this might be not everyone’s cup of tea but if you at least try you might like how it looks. Now, this combination is all over the street fashion scene.

Cargo pants; if you want to go full on street style then loose cropped cargo pants are the ones to choose.

Dad sneakers; you definitely know about the shoe of the year, so don’t hesitate to wear them to a pub. It is perfect for almost every occasion.

Luxury examples:

Official Metallica DEATH REAPER T-SHIRT + Dolce & Gabbana

Affordable examples:

Impact Men’s Joy Division Unknown Pleasures T-Shirt + Topman JOG ON White Premium T-Shirt + Urban Outfitters pantalon cargo pants + Fila Disruptors

5. Movie screening

This date is all about the cozy feelings and your outfit should also be very comfortable and settle. Now there is always the classic button up and trousers look with flowers in your hands, but why shouldn’t we break the boundaries.

Hoodie; it often gets really cold in theaters and hoodies can keep you warm while still looking very stylish. An oversized black hoodie with a print or a logo on it is perfect for this occasion.

Straight leg black jeans; straight leg jeans are all you need to instantly look interesting and trendy.

Classic Vans; this look needed a pair of settle sneakers to bring it all together. What better option than the classic black and white Vans or if you are feeling a little adventures high top ones would be great as well.

Luxury examples:

Yeezy season 5 Calabasas Hoodie + Raf Simons straight-leg jeans + ALYX Mesh-Trimmed Canvas Sneakers

Affordable examples:

ASOS DESIGN oversized hoodie in charcoal + ASOS DESIGN skater jeans in black + Original Vans

6. A gig

We all know how charming musicians can be so when going to a gig be prepared to look not less of a groovy guy yourself. A laid back artist who is enjoying his off day by listening to his colleagues is the look that you should go for.

Straight leg light wash jeans; form fitting blue Levi’s will keep your date’s eyes only on you.

Grey linen shirt; leave first two buttons undone, roll the sleeves up a couple of times, tuck it in synching the waist with a belt or leave it hanging loose, either way, it will look great.

Military boots; any black boot will be perfect for this outfit. And definitely, no other shoe will do it a justice.

Layered necklaces; your exposed chest will need stylish coverage and layered necklaces will do the job effortlessly.

Luxury examples:

CREW Slim-Fit Button-Down Collar Puppytooth Linen Shirt + Valentino 50 Straight leg jeans + Moschino Military Lace-Up Boots

Affordable examples:

Topman SELECTED HOMME Grey Long Sleeve Shirt + TOMMY JEANS Blue Cropped ‘Randy’ Jeans + Dr. Martens Tract Fold boots

7. Sight seeing

You will have to be prepared for a lot of walking, sweating and talking for this one. But it’s your choice and you probably know how to handle the situation. But if the dressing is a problem for you we have your outfit sorted.

A Blue shirt; a long sleeve light shirt will keep you protected from the sun and will give you a very sophisticated look.

Short shorts; if you didn’t know already short shorts are back in trend in men’s fashion. So try it out till it lusts. The color can be as loud and as settle you want it to be.

Converse; high top super stars are all you need to achieve that Armie Hammer look.

A backpack; you will need it to carry your water, sweater and other things in. A brown canvas backpack will fit the laid back summery look.

Luxury examples:

Burberry equestrian embroidered shirt + Thom Browne Cotton Twill Rugby Shorts Gucci high top sneakers + Gucci men’s Backpack

Affordable examples:

Zara TWILL SHIRT + Topman Black Stretch Skinny Fit Chino Shorts + Converse men’s high top sneakers + Asos Canvas Backpack

8. Going to a museum

If you both love admiring art, then you can easily dress a lot more creative on your first date. You will talk a lot about art and not so much about yourselves
that’s why you should dress to impress.

Straight leg trousers; wear black silky loose trousers that reach your ankles with a nice hard belt synching it on the waist.

Long sleeve simple T-shirt; wear a light breezy T-shirt in any other color that you like. But be careful with prints since your socks are going to be the center of attention.

Black leather sandals with bold socks; as we know sandals with socks combination was a Fashion Faux Pas for a very long time, but recently designers like Rick Owens heavily featured it in menswear collections and the street style world embraced it really well. So don’t be afraid to show off your fun socks especially when going to an art gallery.

Tote bag; A nice off white tote bag with a print on it will compliment your outfit very well.

Rings and layered necklaces; silver accessories will always add charm to your outfit.

Luxury examples:

Maiso Margiela RELAXED FIT CREPE TROUSERS + CRAIG GREEN fin detail long sleeve top + RICK OWENS X BIRKENSTOCK + Raf Simons x Robert Mapplethorpe tote

Affordable examples:

Zara LOOSE FIT TROUSERS WITH BELT + Topman FARAH Navy ‘Trafford’ Striped Ringer T-Shirt + Mens Birkenstock + Safari Animals Canvas Tote Bag by James Barker

9. An Evening stroll on bikes

This date might be the most fun one yet and the clothes shouldn’t be the center of attention. They should be more in a comfortable and easy going style. Now it doesn’t mean that you have to wear literal biking shorts as well. Don’t you worry…

Joggers; wearing joggers casually in public is the best thing ever invented in fashion especially when you are riding bikes. But they certainly don’t have to look too lazy. Thin joggers with stripes on the sides of the legs look very much put together.

A striped long sleeve shirt; shirts elevate joggers from loungewear to a whole new level so don’t be afraid to pair them together.

White sneakers; a pair of Adidas Stan Smiths are the perfect shoe choice for your casual biking look.

Fanny pack; throw a little black fanny pack on your shoulder and your evening outfit will be complete.

Luxury examples:

Rick Owens Rick Owens Cargo Joggers SS17 Walrus + NEIL BARRETT striped jersey + Saint Laurent White Court Classic Sneakers + OFF-WHITE black Cordura logo print belt bag

Affordable examples:

Zara SIDE STRIPE JOGGING PANTS + Topman SELECTED HOMME Navy Stripe Long Sleeve Jumper + Vans Authentic White + UO Champion Neoprene Prime Sling Bag

10. A day in an Amusement Park

Now this date is the most fun and interactive one out of all that were mentioned above. As you probably already guessed it, your outfit should be simple and fun as well.

Color blocking polo shirt; bold colors and blocking them is very fun and trendy right now. And also, a colorful polo shirt will suit the happy place very well.

Loose Cream shorts; they will bring the bold colors together and compliment your tan.

Sneakers; pick a color on your shirt and wear sneakers that match it perfectly. That’s a great solution for colorful outfits and hard decisions of paring shoes with them.

Sunglasses; classic Ray Bans fit a lot of face shapes and you probably already have them in your collection.

Sporty watch; A big black watch will add some roughness to balance the happy colors.

Luxury examples:

Tommy Hilfiger Aiden Color Block Short Sleeve Rugby Polo in Navy/Red + Woolrich chino shorts + Saint Laurent Signature Court Hi-top sneakers + Ray-Ban ORIGINAL WAYFARER

Affordable examples:

Lazy Oaf All Teams Rugby Jersey + TOMMY JEANS Stone Shorts + Vans Unisex SK8 Black Hi Top Trainers + Topman sunglasses

It is always hard to dress for the first date since you want to impress but not jump on your date’s face with a crazy outfit. But whatever you end up wearing just make sure that you yourself like the outfit and feel good in it. The partner will feel your confidence right away and admire that, even if they don’t like what you are wearing.

No matter where you went, what you did or did you end up starting a relationship with that person, you will definitely always remember the first date and what you wore to it. So it better be a good outfit for you to not cringe every time you think about it, instead, “at least I dressed well” will be the thought in your head.