Contrary to the belief that getting a date solves out the hardest part, leaving nothing but fun and indulging activities onward, planning the actual date – while putting together the perfect outfit to go with it – could prove to be in fact the most challenging part of it all, to say at least. Regardless if it’s a first, a second or a fifth date, the main purpose is still to impress her, to prove you have it all under control.

Like with every date, it all starts by choosing an activity – which leads to a suitable location, which in the end gets you either set up for the day, or for the night. Planning what to wear on a date has much to do with all of the above factors, but while keen on stepping up the game, you must not overlook to highlight your personal style. Whether you’re dressing in the sharpest of men’s suits or a casual ensemble, remain true to yourself so that in the end you can feel comfortable.

Keep in mind that all of the following looks can easily be adjusted to suit your own fashion taste. Sometimes replacing a color, a fabric, an accessory or a pair of shoes can help things fall perfectly into place. Read on after the break to borrow inspiration on how to look your best on a date.

Men what to wear on a date

Day Time Date and The Casual Look

Again, casual does not mean sloppy and does not mean dressing just like you would normally do for grabbing up the newspaper, or to walk your dog for a few blocks. Going casual means embracing a relaxed attitude, while still scoring points where it matters: style, posture, polish, good taste.

With day time offering up so many interesting/consuming activities to indulge in, the most important aspect you should take into consideration if you’re choosing a date during the early hours is to keep your outfit uncomplicated and practical. Day time dates usually involve lots of walking, exploring the city, maybe visiting art galleries or museum, at times followed by lunch, a cup of coffee and more of the wandering plans.

The Mediterranean Style

It’s easy for a guy to look handsome during summer by sporting a laid-back, all-white look, based on simplicity and borrowing nautical inspiration. A subdued silhouette, clean lines and a neutral color palette represent an easy, yet reliable recipe for success. Combine slim chinos with Breton stripe t-shirts and add a lightweight cardigan into the mix, just to be ready in case the date prolongs until late into the evening.


Shop the style: A.P.C. Striped Cotton-Jersey T-Shirt at Mr Porter; Off White Slim Chinos at Topman; Maison Martin Margiela Cardigan at Yoox; Swims – Rubber and Mesh Boat Shoes at Mr Porter; Ray-Ban Flat Brow Wayfarer Sunglasses at ASOS

The Cool Preppy Style

When aiming for a cool preppy look it is important to make use of modern elements and an edged casualness in order for the look to translate as relevant, rather than geeky. A printed bomber jacket, a pair of slim-fit bleached jeans and a cool backpack will serve you just right on an active date.

Shop the style: Taxonomy Bomber Jacket at Topman; Sebago ‘Docksides’ at Sebago; Timex Originals Unisex Indiglo Weekender Watch at Watchshop.com; Steve Slim-Fit Bleached Jeans at Mango; River Island Backpack at ASOS; Saint Laurent Slim-Fit Cotton Shirt at Mr Porter; Black Suede Belt at Mango

The Casual-Smart Style

Of course, there are guys who want to look sharp even on a casual date and for them a casual-smart look mixing the sartorial flare with a touch of coziness represents the best way to go. Tailored shorts are still cause for endless debates on whether, as a garment, they can stand as a polished/smart option. We think it all lies in getting the style, cut, length and accessorizing right.


Shop the style: J.Crew Button-Down Collar Cotton Oxford Shirt at Mr Porter; Lacoste 80th Anniversary Silicone Strap Watch at Nordstrom; Milton Textured Shawl Cardi at Reiss; Pinots Formal Shorts With Turn Ups at Reiss; Brick Slip On Loafers at Topman

Evening Date and The Formal Look

When stepping out for an evening date it is mandatory to put your best outfit on and make use of all your confidence to go along with it. If the setting is a fancy restaurant, needless to point out that you have to step it up with a more formal outfit. If you’re going out for drinks, you can forget about the tie, but you should still hold onto that perfectly tailored blazer. You can mix textures to add a little extra something to your already dashing outfit, or you can sport a bold colored suit if the setting allows for it.

The Bold Formal Style

Not every guy can pull off an electric blue suit, but those who can should definitely take advantage of it, especially during an evening date. Nothing betrays greater confidence both in yourself, and in your personal style, quite like the use of a daring color to accent your sartorial sensibility. A printed tie, a dress watch and a pair of cool specs can effortlessly bring your outfit to an even higher level of sophistication.


Shop the style: Selected Homme ‘Walton’ Blazer at Topman; Ray-Ban 3016 Clubmaster at Sunglasses Shop; Langham G Dye Dobby Shirt White at Reiss; Selected Homme ‘Walton’ Trousers at Topman; Lanvin Burnished-Leather Oxford Shoes at Mr Porter; IWC Schaffhausen Portofino Automatic Watch at IWC.com; Spring Paisley Powder Blue Tie at TheTieBar

The Mix&Match Formal Style

If a composed and perfectly coordinated formal look does not suit your style, or does not match the level of formality required by your date’s location, you can take a few steps back, loose the tie, replace the oxfords with something just below the formal dress code, and proceed with mixing and matching textures and colors. The dusted hues make for a wonderful palette in combination with midnight blue tones.


Shop the style: Pluto Super Slim Shirt in Pale Blue at Reiss; Black Buckle Leather Belt at ASOS; Navy textured skinny fit blazer at Topman; Linen Blend Suit Trousers at Mango; Suede Derby Shoes at Mango; Lanvin Silk Pocket Square at Mr. Porter

The Short Suit Style

Representing the practical take on summer for the ever sophisticated gentleman, the short suit is already perceived as that cool, untamed alternative for a perfectly put-together outfit. It can be styled with ease in order to transition from day to night, it can be made out of both separates and coordinated pieces, and most importantly it will make you look good and stand out, even in the busiest crowd.


Shop the style: Sunny blazer T at Selected Homme; Paul Smith London Byard Heart-Print Cotton Shirt at Mr Porter; Sunny shorts T at Selected Homme; Tan suede slip on loafers at Topman; Jaeger-LeCoultre Master Control at jaeger-lecoultre.com; Lanvin New Alber Silk-Grenadine Bow Tie at Mr Porter

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