What to wear on a date: 10 items of clothing to guarantee a second date

Mens clothes to make you look great and feel confident

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If you’re single, the bleak mid-winter is perhaps the time of year when you’re thinking most about changing your relationship status. In 2019 that probably means hitting the dating apps and swiping right, but when the time comes to meet IRL, deciding what to wear to make sure you measure up to your profile pic can be hard. 

While beauty is in the eye of the beholder, there are some loose rules and dressing for a date is all about treading some very fine lines. Dress too formally and you might risk looking unapproachable, but if you look too casual you might leave your date unimpressed. 

Exhibit too much individual style and you might come across as a bit full of yourself, but too little and you risk blending into the masses. You get the picture.

But fear not. We’ve selected 10 items to guide you through the night, from making a good first impression to the walk home. 

Sadly we can’t play cupid or help you dodge an awkward date, but if you feel confident and comfortable with how you look, you’re guaranteed to find the experience more fun.

1. Tom Ford Shelton Velvet Tuxedo Jacket

The burgundy jacket fit for the red carpet

Reasons to buy
+Shawl lapels add a modern twist to a traditional garment+Velvet finish memory

Maybe you’ve pulled out all the stops and booked a highly exclusive restaurant, or maybe your date is just very hard to impress. Either way, if you need to make a big entrance, this is the jacket to turn up in. Tom Ford’s Shelton tuxedo jacket comes in burgundy, which is a traditionally romantic hue, as well as being one of the colours of this season. 

The velvet finish is irresistibly tactile – boyfriend material? – and it might be hard for your date to keep their hands off (you hope). At the very least it should provide a talking point – not least how you’ve managed to avoid looking like Ron Burgundy. But this is a special garment with a special price tag, so at £2,590 you’ll have to be pretty serious about your date to invest.

2. Paul Smith Wool and Cashmere Bomber Jacket

The smart casual jacket

Reasons to buy
+Dark navy colour is slimming+Luxe finish is impressive

You might think a bomber jacket is too casual for a date, but Paul Smith has created one that perfectly fits that tricky ‘smart casual’ dress code that’s required for lots of dates. By using a rich wool and cashmere blend on the outside, and adding sleek Cupro lining on the inside, Paul Smith has elevated the bomber jacket to the status of luxury item. 

As you might expect, the the signature stripes in the inside cuffs to make it feel extra special. The jacket is perfect for a date as it allows you to tick that trendy streetwear box, while still making it look like you’ve made an effort. 

3. Folk Assembly Cotton-Poplin Shirt

Relaxed version of a classic

Reasons to buy
+Poplin fabric makes for a relaxed look+Classic style and colour goes with anything
Reasons to avoid
-White shirt will show spills

You’d be surprised how many people are looking for ‘normal’ when it comes to a partner. And it doesn’t get any more normal when it comes to dressing for a date than the crisp white shirt. But this Folk shirt takes a relaxed approach to the classic look, using cotton poplin to give a more textured feel. 

This is a good thing because most standard shiny white polyester shirts run the risk of making it look like you’ve come straight from work – no way to flatter your date – whereas the Folk shirt shows you took the trouble to go home and dress down a couple of notches. 

Starting with a classic wardrobe staple like the white shirt still gives you the chance to express yourself with details and accessories like shoes or belt. And with a very normal price tag, you’ll still have some change left for those important additions.

4. Gucci Leather and Suede Sneakers

Show stopping kicks for a bright future

Reasons to buy
+Quirky features are a talking point+Comfortable while still smart 

Whether it is acceptable to wear trainers on a date is a point of contention. Many old-school romantics would say it’s a big no-no. But now that we have a trend for pairing trainers with (the right kind of) wool trousers, it is possible to team a pair of high end sneakers such as these from Gucci with a sleek and smart outfit. There are a number of features that make these particular retro sneakers date ready. 

First of all is just how covetable (not to mention expensive) they are. Dropping a significant amount of money on a pair of sneakers makes a statement that you care about fashion and footwear in particular. 

Then there are all the quirky details, like the use of webbing for the signature Gucci stripes and the scalloped edges of the leather panels. The distinctive shoes might make for a talking point during those awkward first few minutes of a date, but you won’t want to wear them in the rain!

5. Acne Studios Ryder Wool Trousers

The trousers that define smart casual

Reasons to buy
+Bang on trend while still smart+An incredibly versatile investment piece
Reasons to avoid
-Dry clean only

With the addition of an elasticated waistband to a pair of sleek, wool trousers, Acne Studios have captured the current trend for combining formal and sportswear cues. The fairly high hem around the ankles and straight leg also nail current trends in terms of cut.

As well as being bang on trend, these trousers manage to be extremely versatile. Dress them down with trainers and a T-shirt or up with smart shoes and Folk’s poplin shirt. The black colour also lends itself to being worn with virtually anything. There is just one thing ruled out by that waistline, and that is going completely formal with a tucked in shirt. 

The price tag will quickly seem like a wise investment considering how many different outfits could be based on these trousers. A worthy purchase if you’ve been busy on the apps and have a lot of dates lined up!

6. APC Petit New Standard Skinny-Fit Dry Selvedge Jeans

The perfect pair?

Reasons to buy
+High quality selvedge denim+Competitively priced in the busy jeans market
Reasons to avoid
-Skinny fit won’t flatter all shapes

The jeans market is crowded to say the least and finding the right pair that’s the perfect wash and fit is perhaps as hard as finding ‘the one’ on the dating scene itself. But this pair from APC, with their high quality Japanese denim, rich indigo colour and skinny silhouette are as good a place to start. 

They are as handsome as any from the big names in denim, and slightly cleaner visually, with no design stitched into the rear pocket and no external label. They’re reasonably priced as far as designer denim goes, too. Just as with dating, when it comes to buying jeans, try plenty on, and don’t commit until the right one comes along - you’ll know when you’ve found them.

7. Oliver Spencer Talbot Melange Rollneck Sweater

The sweater that’s snug and smart

Reasons to buy
+Flattering fit to athletic builds+100% wool
Reasons to avoid
-Not everyone loves a rollneck

Rollnecks aren’t everyone’s cup of tea, but they are pretty handy on a cold weather date. The sleek fit and high neck adds a notch of formality over a regular sweater, and means you can stay in your knitwear for the duration of the evening while keeping smart. The disguised collar means you can even get away with a thermal layer underneath. 

This would be our pick for those romantic outdoor ice skating moments.  The multi-coloured staircase stitch on Oliver Spencer’s Talbot sweater needs to be seen from nearby to appreciate the melange of colours, which will hopefully be all the encouragement your date needs to get up close and personal. The price is also tempting for a 100% wool garment.

8. Mulberry Grain Veg Tanned Leather Wallet

Classic quality from the famous leather brand

Reasons to buy
+Luxurious leather construction+Better than flashing the cash

As the night draws to a close it’s time to tackle the thorny issue of settling the bill. Whatever your approach, paying from a proper grown up wallet says that you are mature and financially solvent. If you’re still using one of those Velcro numbers, it’s time to upgrade. 

If you can stretch to this pocket book from the classiest purveyors of leather goods, Mulberry, it won’t just speak of solvency but of outright prosperity. That is an attractive quality to many, but generosity is even more attractive, so don’t forget to leave a decent tip for the waiting staff. Apple Pay might be trying to supersede the wallet but this one is sure to impress.

9. Reiss Wool Blend Overcoat

The overcoat perfect for sharing

Reasons to buy
+Classic design matches with most outfits+Will stay relevant for many seasons to come
Reasons to avoid
-Minimal design might compromise on warmth

If you want to partake in that end of night tradition, gallantly but slightly cornily wrapping you date up in your coat as you walk to the tube station or taxi rank, you need a big, warm overcoat, preferably without dog hairs and so on. This version from Reiss is a clean, minimal take on the classic, with just two buttons, a single breasted design and neat lapels. 

While it’s light on twiddly bits, it’s heavily constructed with a wool-rich blend, partial lining and bound seams. It is the sort of price you would expect to pay from the mid-range London brand, and the simple, elegant design is probably a safe bet when it comes to investing in a garment you’ll wear for a few years. The only problem is that this elegant coat might just be too good to share.

10. Clarks Wallabee Black Suede Shoes

The shoes to soften the smartest outfits

Reasons to buy
+Instantly recognisable design+Extremely comfy crepe soles
Reasons to avoid
-Suede doesn’t mix well with rain

If you do plump for a more traditional shoes over trainers, you might not want them to be super-shiny, at the risk of appearing to have come straight from work. The great thing about these black Wallabees is that while they work with most levels of formality, right up to a suit and tie. The suede finish and familiar design softens the look. 

A wedge-shaped sole buys you an extra inch of height and confidence, but is much more comfortable than a traditional leather soled shoe. So for those dates when the conversation flows well, way past the time of the last train, that long walk home needn’t be painful. Even the dreaded walk of shame, if you’re lucky enough to get that far, can be conducted with a creped soled spring in your step.