What Men Should Wear on a First Date – the Ultimate Guide

Take on your first date with confidence and style, wearing one of our specially curated first date outfits for men. Be prepared to never have a first-date again…
First dates can be nerve-wracking, even for guys who have been on their fair share of them.. There’s a lot to think about before your first date. Where are you going? What will you talk about? And more importantly, what will you wear? If you’re unsure what to wear, you will most likely end up making a rushed, last minute decision which will inevitably make you even more nervous.

Going on a first date can be scary for everyone, whether it’s a first date with a friend you’ve known forever or a blind first date with someone you’ve never met before, you’re going to be a little bit nervous. One of the best ways to combat those pre-date nerves is knowing what to wear. Your first date outfit is vital in making a good first impression, it should reflect your personality and also be appropriate for whatever first date activity you choose to do.

Knowing what your first date outfit will be eliminates half of the nerves you may be feeling. Whether you need a more casual date outfit to do a fun activity such as bowling or maybe you need a more formal dinner date outfit to wear to a fancy restaurant, it’s always good to be prepared in advance and know what to wear. If you’re more of an outdoorsy kind of guy or maybe a more extravagant person, there’s an endless choice of first date outfit options for men here at

Assembling a good outfit to make a lasting impression on your first date will take some planning and style expertise, which is where comes in to help. Our curated first date outfits for men are guaranteed to help you get your first-date look right every time, but hopefully not too many times…

The Casual Guy
Let’s start with a classic casual date outfit for men. Whether you’re going for day drinks or going to play bowling or crazy golf, whatever fun, casual activity you’re doing we have the perfect first date outfit for you.

The classic t-shirt and jeans combo will never let you down when it comes to picking an outfit. It’s important that you are comfortable in the outfit you’re wearing so that you’re in turn, comfortable on the date. Try our KnowledgeCotton Apparel Locust Striped Long Sleeve TShirt paired with the G-Star 3301 Slim Jeans for the ultimate laidback look. Add a trendy jacket such as the Carhartt WIP Michigan Coat for an extra layer, with handy pockets to keep your wallet for easy access.

Finally, to complete the effortlessly casual but put-together look, a pair of classic trainers is foolproof. have a wide variety of men’s trainers that are ideal for a casual first date. Comfort is key, especially if you’re going to be taking part in an active first date. For this outfit we would suggest the Vans Fillmore Decon Suede Canvas Trainers, to compliment the casual look effortlessly.

The Extravagant Man

If you’re more of an outgoing guy, you’re going to want to choose an outfit that shows off your personality. Whether that’s with a statement shirt, jacket or perhaps a statement shoe, choosing a more “out there” item to add to your outfit, ensures that your date will get a taste for your personality at first glance. We recommend choosing a simple shirt such as the Tommy Jeans Original Stretch Slim Shirt, paired with some classic slim fit jeans like the Jack & Jones Original 029 Slim Jeans to build upon with some more colourful accessories.

One way to show off your more extravagant style is through a statement shoe. By choosing an eye-catching shoe it allows for the rest of your outfit to be simple and easy to throw together. The Jeffery West Leather Chelsea Boot in an embossed, muted multi-colour floral print is sure to catch your date’s attention. If you like the look of these boots but want something a bit more wild, browse the full Jeffrey West shoe collection at to find your perfect shoe.

Finish off the outfit with the classic Schott Perfecto Leather Jacket, to add a little edge to the outfit and to compliment the more extravagant shoe choice. If you want to add a little more personality to this outgoing outfit, opt for a statement belt such as Vivienne Westwood Orb Square Buckle Belt to bring the whole look together. This outfit is guaranteed to catch your date’s attention in the best way.

The Outdoorsy Guy

If the outdoors is more your thing, maybe you’re going on a date to the park or perhaps a stroll along the coast – whatever you’re doing we’ve got the perfect outfit for you. The key to a stylish yet functional outdoorsy outfit is a warm jacket and practical shoes. The Superdry Highwayman Wool Sherpa Trucker Jacket is the optimal jacket for as date outdoors as it’s not only going to keep you warm with its sherpa material but the blue checkered style adds a little more personality to the outfit.

The Palladium Pampa Waterproof Hi Essential Leather Boots are ideal for an outdoors date, as they not only look stylish but are waterproof and durable too. This means you can be comfy and not have to worry about your feet hurting whilst you’re enjoying your date.

If the outdoors date makes its way inside, having a stylish long sleeve or t-shirt underneath is essential. The Tommy Jeans Essential Crew Knit in black pairs well with the blue checked Superdry sherpa jacket if you wish to wear it open and is also trendy enough to wear by itself. Couple the crew knit sweater with the Schott Ranger 70 Cargo Trousers and you’ve got the perfect base layer for your outdoor date outfit.

If the date is going to take place when it’s a bit colder outside, why not choose a hat to go with your outfit? A good option for this particular look would be The North Face Chunky Knit Watchman Beanie in grey. Browse for more hats and men’s accessories options to spruce up your look.

The Sophisticated Man

Going on a fancy first date and unsure what to wear? Whether you’re going to an upscale restaurant or the new fancy cocktail bar in town, we have the perfect outfit for you here at

The key to an effortless formal look that is still put-together is a smart shirt and a pair of shiny leather shoes. Every man should have a classic button down oxford shirt in his wardrobe, they’re versatile, ideal for any occasion and would be a fail-safe option for any man’s first date outfit. Try the GANT Button Down Oxford Shirt in capri blue paired with the Lois Jeans Sierra Tailored Jeans for a simple yet smart outfit sure to catch your date’s attention.

It’s important to always put your best foot forward going into a first date. It helps if the best foot is wearing a pair of smart leather shoes such as the Jeffery West Leather Chelsea Boot. If the black chelsea boot is still a little too reserved for your taste, why not try a statement smart shoe such as Jeffrey West’s Derby Leather Shoes in burgundy, to add a little colour to your outfit.

Finally, no formal date look is complete without a smart belt, ideal for tucking in that smart oxford shirt to give a more streamlined look. Why not try the GANT Retro Shield Leather Belt to add an understated accessory to your outfit, or if that’s not the right belt for you we have more options in our men’s accessories collection at

For the quintessential fancy dinner date outfit, discover a range of sharp shirts and smart shoes here at

Are you ready?

Hopefully you’re now prepared to take on your first date with confidence and style in one of our curated outfits. Remember, as long as you’ve prepared the perfect first date outfit that’s true to your personality and style, there’s nothing to worry about. Who knows, maybe your outfit will get you a second date?

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