What to wear on a first date for men

Deciding what to wear on a first date can be an endless struggle for men. Because, let’s be frank, you will be instantly judged based on what you wear. We live in a world where a cheap loafer or ill-fitting shirt is a marker of style suicide rather than endearing quirks. But with this guide, you’ll be deleting those dating apps in no time. Discover how to make the best first impression by looking and feeling your best on a first date. Whether you’re going for casual drinks or a fancy dinner - find out how to accessorise your first date look the right way. Embrace your inner James Dean… not your inner James Corden.

Date: Tinder date at your go-to bar
Tip: Everyday classics

Edwin Small Bracelet De Beauvoir One Necklace Faris Square Midi Silver Bangle

When you’re a dating aficionado, the date at your local bar/pub becomes a comfortable classic in your dating repertoire. You’re in a familiar environment, you’ve approved the mood, and you know the drinks bill won’t leave you solely eating ramen until payday. Dress cool and casual to make a solid first impression. First dates can be daunting, especially if you think you’ve found the needle in the Tinder haystack. So dress in your everyday classics and feel at ease. If the small-talk is even more terrible face-to-face than it was over text, you don’t want to have spent valuable time putting together your best look. Or if love is on the cards, you don’t want to have blown your best look on your first date. Wear your best fitting jeans and a casual shirt for an effortless-looking ensemble. Accessorise with your everyday ring, pendant or bracelet for just the right amount of attention to detail. This look will show you’re not overly keen, but you have a solid style and flair for dressing.

Date: Sit-down dinner at an overpriced restaurant
Tip: Ditch the jazzy shirt and go for a bold accessory

Silver Cube Necklace In Resin Plana Ora Ring Yellow Gold Plated Monkey Skull Pendant Necklace

Rebekah Ann Jewellery | Yellow Gold Plated Monkey Skull Pendant Necklace | £111.00 


This type of date is inherently full of pressure. You’re splashing out, so you must like this girl (or guy). You want to go the extra mile, and taking her to a romantic restaurant is the millennials version of ‘wearing your heart on your sleeve’. The location and fine food already gives them the subtle hint that you’re upping your game, and whilst you need an outfit to match the ambiance, you don’t want to overdo it. Keep your outfit slick and chic. Wear casual trousers with a nice blazer and shirt, keeping patterns and prints minimal. The key twist lies in a bold accessory that conveys just the right amount of confidence. Whether this takes the form of a bold brooch or striking pendant is down to personal preference. But choose something that shows you are considerate and tasteful when it comes to what you wear. Imagine how chic the two pendants above would look with an all black outfit and unbuttoned shirt. L. Skelly’s plana ora ring will add an edge to any outfit, but would look especially impressive on your high-end dinner date.

Date: Coffee date on your lunch break
Tip: Cool cufflinks and a signet ring

Rhino Cuff Links Redchurch Gold Ring Gold Plated Vintage Caravelle Skeleton Cufflinks

When you have a high-pressured job, dating often takes the form of lunch slots and late late night drinks (with the latter running the risk of seeming like a seedy offer!) A lunchtime coffee date is your best bet - short and sweet with the option of escaping back to the office if needs be! You’re already in your work clothes, and so you may not have the opportunity to dazzle your date with your killer style. But not all is lost. With a considered approach to your accessories, you can still pull out all the stops. If you have to suit up for work, why not invest in a pair of sleek cufflinks to show your date that your refined sense of style extends to your workwear. Love nature? With every purchase of the rhino cufflinks by Alexander Jewell, a small donation is placed towards WildAid, a charity combating the hunting of rhinos for their horns. A signet ring is a conservative yet stylish way to uplift your work attire. PHIRA LONDON’s jewellery is endlessly chic. With these picks, your coffee date will ensure a dinner date will soon be on the cards.

Date: The gimmicky ‘I’m fun and spontaneous’ date
Tip: Play it extra-cool with a pendant

Gold Vermeil Sky Necklace With Wisteria Resin Chain With Ebony Inlay Leo Charm

We’ve all been on a date like this. In an attempt to seem fun and light-hearted, you’ve suggested a retro bowling date or a crazy golf extravaganza. Before you let the regret sink in, remember this is a great opportunity to shine through your style. You may be among cheesy surroundings, but don’t let your style drop to tragic levels. A quirky shirt will show your date you don’t take yourself too seriously. When I say quirky, I mean those patterned silk shirts that seem slightly garish from afar, but are in fact made of silk and radiate charm. (The kind Alex Turner wears - so you know it’s a winner!) Choose a stylish and fashion-forward pendant to imbue your outfit with an edge. Not only will your fun-filled date show the lucky guy or girl that you’re spontaneous and confident. But it’ll also show her that you know good style.