Are you planning a romantic night with your significant other or a new date and stressing about what to wear? With our article, you’ll never have to worry about what clothing to rock up in; for every weather and season, we have compiled the most stylish men’s date night outfit ideas for you to dress to impress!

Piece Together The Perfect Men’s Date Night Outfit

Remaining comfy but confident can be a difficult hurdle to tackle when trying to impress your date. Our collection of on-trend ‘fits will help you boost your look to a new level, keeping yourself cool in summer and cosy in winter, all while tailoring your clothing to the style you love. So, to give you that much-needed inspo, here is the best menswear choices for your next date night:


Date Night Men’s Dinner Outfits

Dinner date nights usually call for more formal attire. So, why not pair a piece from our men’s shirts collection with dark jeans or chinos for that classy yet comfy look? To scale up your outfit a notch, simply add a blazer – also perfect if you’re planning to head on your date straight from the office.

Why darker colours, we hear you ask? Dark shades instantly make your look appear more stylish and, most importantly, smarter. They are super flattering when paired with light, neutral shades. They are a versatile option you simply cannot go wrong with, whether it be a five-star dinner or a more casual brunch.

Adding finer details to your men’s clothing, such as a few staple pieces of jewellery or a tasteful watch, will help to elevate your look and make you feel as chic as can be.

Finally, add some dress shoes to make your outfit undeniably sauve; make sure you’re not overdoing this, though, in case you stray too far from your true style!

date night dinner outfit

Date Night Outfits Casual

Simplicity and relaxation are essential for a casual yet cosy look; blend your personal style and comfort with elegance and style to create the ultimate outfit.

Layering multiple simple pieces can help build character and depth to your outfit. Try knitwear such as cable knit jumpers, roll neck jumpers or anything made out of cashmere, paired with loosely tailored trousers and casual trainers or boots.

During the warmer months, thinner tees, polos and hoodies with a pair of jeans are a relaxed, everyday and uncomplicated ‘fit that is still impressive and foolproof- ideal for those mini golf or cinema dates. For something a little bolder, try patterned or splattered tops, and as usual, remember to accessorise to complete your look.


Date Night Outfits Summer

Summer can be the best time of year for romance to flourish; banish sweating with a light and airy look that keeps you looking and feeling fresh on your date.

Thinner and more casual tees or linen men’s shirts are a great way to keep your clothes feeling breathable. They’ll air out your body whilst maintaining an eye-catching, super trendy outfit paired with shorts or jeans.

Opting for lighter shades instead of dressy dark colours is also a must-have for those warmer dates. Patterned and floral shirts can be a good choice as long as you don’t go over the top and stay authentic to yourself. Even plain white dress shirts are good options in summer; unbutton a few buttons, and you are ready to go.

Accessories such as sunglasses and hats will enhance your look, adding edge and tying your outfit together. Remember, a little bit goes a long way, so don’t overdo it by adding too many accessories that hide your actual clothing. For footwear, stick to comfy, light trainers that’ll keep you cool.

Stick to light trainers and shoes that won’t make your feet feel heavy and sweaty to maintain happiness and a groomed look.

Looking for more summery and holiday feel outfits? Have a look at our article on men’s holiday outfit ideas.

summer pt2

Accessories that can help add more to your look are:

  • Sunglasses
  • Watches
  • Belts
  • Rings
  • Bracelets
  • Necklaces


If you’re wanting to find out more on different accessories, have a look at this article by Classy Men Collection

Autumn Date Night Outfit

Autumn can be a tricky season to dress for. Colder mornings yet warmer afternoons mean that you can quickly find yourself lugging around your layers. But don’t fret; we’ve got you covered with our top autumn menswear picks!

As we head into winter, autumn is the time for bulkier ‘fits. Layering will be your best friend, helping you to add depth while keeping your style minimalist. Pair one of our simple men’s t-shirts with a flannel shirt for an easy yet super versatile look perfect for all date occasions.

On cooler days, thin, knitted turtle necks with a piece from our men’s trousers collection are the way to go. Scale up your look with a blazer or long wool trench coat. We recommend sticking to subtle, neutral shades, both light and dark, avoiding bold colours that give more of a spring/summer vibe.

If you’re wanting to find out more on different autumn clothing items, have a look at this article by Fashion Beans.


Date Night Outfit Winter

Keeping warm and toasty whilst staying looking fresh and stylish can be difficult. Sturdy, hard-wearing jeans are great paired with thicker jumpers such as turtle necks or crew necks and sophisticated coats; add some texture and feel with wool, knitwear cardigans or men’s trousers such as corduroys.

Layer on a beanie or scarf for some extra oomph and pair with thicker boots such as Chelsea boots, Dr Martens or trainers to keep your feet warm when you get out for your date.

Hooded parker coats are fur-lined and thick alternatives to smarter woollen trench coats, which allow you to keep your style relaxed and every day whilst also looking fashionable and stylish.

Take a look at our previous article to show you the best winter jackets for men.

MC Online Brown Aviator Jacket Lifestyle Shot

Now you can head out on your date!

We hope we have helped you feel prepared for any date or weather; keep your style and intertwine it with our new stylish ideas and outfits to enhance and impress your date to the max!

If you enjoyed looking at our men’s date night outfit ideas, then feel free to take a look at our Instagram to find out about our latest products, new offers and discount codes and even more of all the best outfits and clothing items you can use to achieve your desired look.

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