Date night is always a great opportunity to get dressed up and spend some quality time with your significant other. Depending on what your date entails, you may be stuck on what to wear. Whether you’re going out for drinks and want to dress to impress, or you’re looking for a laid back look, it can sometimes be a struggle to pull together the right outfit. No matter if it’s your first date of you’re fiftieth, we’ve hand picked for you our favourite date ideas and what to wear for them.

Dinner & A Movie

Restaurant SIZED

Dinner and a movie is always a safe bet for a date. You can save any awkward first date conversations at the restaurant with discussions on the film, and you will probably get to eat some pretty great food too. If you’re not so sure about what to wear for this kind of date, we believe it’s best to opt for a smart casual look. Striking a balance can be tricky, as you’ll want to wear something comfortable enough for the cinema, that transfers to the more formal setting of a restaurant.


For men, a pair of smart trousers serve you well as they are perfect for dressing up or down. If you’re opting for a smarter outfit, they look great with a pair of loafers and a jumper or shirt.

Dinner Outfit Men

SHOP: Vivienne Westwood Green Jumper/Polo Ralph Lauren Black Chinos/G.H. Bass & Co. Black Loafers


For women, a dress is always best as they’re a no fuss wardrobe must have. A pair of smart boots and a bag will finish off the look.

Dinner Outfit Women

SHOP: Michael Kors Patterned Dress/Michael Kors Black Crossbody Bag/Michael Kors Black Ankle Boot



Picnic SIZED

While the sun is still shining, make the most of the great outdoors and take a picnic to the park. A picnic can be what you make of it, and whether you want a more laid back affair with homemade sandwiches, or a romantic occasion with cheese and wine, you’re bound to have a great time. As you’ll be sitting on the floor, you’ll want to feel comfortable, so we recommend a more casual look for this kind of date.


For men, if it’s warm out, a pair of shorts are perfect, and paired with some canvas shoes you’ll have your daytime casual look on point.

Picnic Outfit Men

SHOP: Polo Ralph Lauren Blue Polo Shirt/J Lindeberg Beige Shorts/Converse Low Ox Trainer


For women, a floral playsuit is ideal, and will give you more freedom of movement than a dress on this kind of date. Wear with sandals for a stylish, yet laid back look.

Picnic Outfit Women

SHOP: Rebecca Taylor Floral Playsuit/Moncler Henriette Espadrille/Michael Kors Sand Saddle Bag


Museum SIZED

Casual wear and culture go hand in hand, especially on a date. If you’re planning to adventure around museums you’ll want to be comfortable. That doesn’t mean your outfit needs to lack in style, of course. If your date will involve a lot of walking from place to place, footwear is the most important thing to focus on. A fuss free daytime look is ideal.


For the men, a casual shirt and a pair of trainers are a great combination. Jeans will pull together the look.

Museum Outfit Men

SHOP: Barbour Grey Shirt/True Religion Tony Skinny Jeans/Adidas Black Stan Smith Trainer


For women, a pair of leggings teamed with a long shirt and boots will keep you going throughout the day.

Museum Outfit Women

SHOP: Polo Ralph Lauren Denim Shirt/Polo Ralph Lauren Black Leggings/Ugg Mini Chestnut Boots



Cocktails SIZED

If you’re planning to skip the dinner and head straight for the drinks, what’s better than sipping on cocktails? A bustling cocktail bar is a great place to unwind on your date. With a large choice of drinks on offer, you’ll certainly have a lot to talk about. Normally heading for drinks would require you to get out your glad rags, so it’s a great opportunity to get dressed up.


For men, a white shirt and smart trousers will work a treat. Add a contrasting suit jacket for warmth and to give a bit of an edge to your evening attire.

Cocktails Outfit Men

SHOP: Vivienne Westwood White Shirt/Vivienne Westwood Green Trousers/G.H. Bass & Co Brown Loafers



For women, an LBD and a pair of heels are an easy yet stylish outfit choice.

Cocktails Outfit Women

SHOP: Rebecca Taylor Black Dress/Michael Kors Black Leather Clutch Bag/Sam Edelman Studded Heel