There’s a lot to consider when you’re choosing what to wear for a date.
You want to look like the best version of yourself without seeming like you’ve made too much of an effort, all the while dressing appropriately for the occasion and location. It’s a tricky balancing act, which is why we’re here with this cheat sheet to help.
Let’s start with the most important factor: confidence. There’s nothing more attractive than a guy who’s sure of himself, so whatever you’re wearing needs to make you feel good. A word of advice – while it’s important to go for something which makes you feel natural, it’s generally best to take it up a notch formality-wise and avoid anything super casual.
The key is finding pieces which strike the fine balance between elevated and relaxed. A knitted polo. A relaxed Oxford shirt. A Harrington jacket. A V-neck jumper or rugby jersey. As long as it doesn’t feel like something you’d wear to chill at home and doesn’t err into corporate workwear or formalwear, you’re on the right track.
On the bottom half, a good pair of classic straight leg jeans or trousers will do the job – if the idea of a straight leg fills you with anxiety, then a slim leg would work, too. For shoes, smart trainers, loafers or a derby are usually the best options – just make sure whichever you choose looks clean and fresh (if you’re after help in the shoe cleaning department, check out Crep Protect’s comprehensive range of products).
When it comes to colour palette, we’d recommend sticking to the tried and tested shades you can’t go wrong with as a base (white, navy, black, neutrals), which you can inject with certain colours which suit your complexion – blues, burgundy and jewel tones for those with cool undertones while those who are warmer should tend towards greens, browns and yellows.
If you’re still at a loss for what to wear, there are some menswear pros who do smart-casj well on the red carpet - Jacob Elordi, Callum Turner, Brad Pitt, Jeremy Allen White and Michael B. Jordan. They often forgo the traditional suit and shirt for a look that’s a little more relaxed, and in doing so end up with some of the best looks going. Follow their lead and you’re bound to make a good first impression.
Keep scrolling for our top tips. You and your date can thank us later.
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Tops
Gant Shield Piqué Rugger
A rugby shirt always nails the smart-casual brief. As a general rule, we’d suggest sticking to block neutral colours like black, navy, grey or white rather than the traditional colourful stripes. Luckily, Gant’s rugger comes in all four.
Buy now £90.00, Gant
Arket Oxford Shirt
A plain Oxford shirt makes for a great date night ‘fit. The defining characteristics – namely a chest patch pocket, relaxed fit, substantial textile and button-down collar – make the silhouette feel more relaxed than a dress shirt but still much smarter than a T-shirt. As with all menswear staples, Arket has a strong selection.
Buy now £57.00, Arket
Mango Man 100% merino wool V-neck sweater
It’s surprising how much difference a neckline can make. Though a crew neck would also work for a date, the V-neck feels much more considered in comparison. Wear it with a T-shirt underneath to make it a touch more casual or solo if you’re feeling like you want to show a bit of skin.
Buy now £49.99, Mango
Mithridate Jagger Polo
If there’s one designer you can trust to do smart casual well, it’s Daniel W. Fletcher. He’s recently taken the helm at Mithridate, and his first collection for the brand – which debuted at London Fashion Week – did not disappoint.
It’s full of his signatures, from sharp tailoring to shirting, rugby tops and polos, so pretty much anything you pick would look great when you’re dressing up.
Buy now £250.00, Mithridate
Bottoms
Dickies Original 874 Work Pant (Unisex)
Every guy needs a quality pair of black trousers at the ready. Enter: Dickies’ Original 874 Work Pant. The stiff fabric gives them an expensive-looking finish, while the fit is the perfect straight leg. Tens all round.
Buy now £70.00, Dickies
Uniqlo Pleated Wide Trousers
Uniqlo’s trouser selection is unrivalled on the high street. Though they’ve got everything from chinos to jeans and track pants, it’s the Pleated Wide range which takes the top spot for us. They’re crafted using a super soft two-way stretch fabric, which looks great and feels even better.
Buy now £39.90, Uniqlo
Levi’s 501 Original Jeans
If you’re going for jeans, we’d recommend going for a rigid denim in a classic fit like straight or slim. A pair which ticks all of the boxes? Levi’s iconic 501s. Since it’s a silhouette which has been around since 1873, it’s an investment that’s sure to last.
Buy now £90.00, Levi’s
Shoes
Duke & Dexter Wilde leather penny loafers
Loafers are a useful menswear tool. They’re one of the few shoe rack investments which can smarten up pretty much any outfit without feeling forced. Duke + Dexter is well-versed in loafers, with classic styles, like this all-black pair, as well as summery two-tone designs and illustrated options.
Buy now £240.00, Selfridges
Axel Arigato Dice Lo Sneaker
You’re probably familiar with Scandi label Axel Arigato. Ever since the brand’s iconic Clean 90 experienced viral success, the brand has been a menswear staple for celebs and influencers alike. Now, there are 15 silhouettes to choose from, but our current go-to for a smart-casual vibe is the Dice Lo.
Buy now £230.00, Axel Arigato
Grenson Dermot Derbies
Derbies, which are characterised by the pieces of leather which are sewn on top for the lacing structure, are perhaps the most casual of smart shoes. They’re a substantial alternative to loafers, which look great with jeans and work pants. Heritage brand Grenson always has a good selection, but at the moment it’s the Dermot taking first place.
Buy now £540.00, Grenson
Accessories
Missoma Mens Filia Curb Chain Necklace
With necklaces, it’s generally best to keep them subtle. Avoid anything that’s hyper-masculine (gunmetal, chunky chains, dog tags, etc.) and instead go for designs which are simple and understated: think along the lines of Connell’s Chain and you’ll be on the right track.
Try to stick to precious metals wherever possible, or else risk ending up with a green-stained neck after a couple of wears – you can actually find quite a few well-priced options in genuine sterling silver, so you don’t need to spend a fortune for quality. Missoma’s Filia Curb Chain Necklace fits the brief perfectly.
Buy now £135.00, Missoma
Hamilton American Classic Boulton Mechanical Watch
From the Cartier Tank to Jaeger-LeCoultre’s Reverso, it’s all about the rectangular watch in 2025. But if you don’t have a small fortune to spend on your chosen timepiece, you could get Hamilton’s Boulton, instead.
Though it’s still a hefty investment, it’s definitely worth it. It has many of the same features as the big time watches – namely a handwinding mechanical movement, leather strap and stainless steel case – just for a few grand less. Or if you’re after an affordable option, you could try Fossil’s Carraway.
Buy now £840.00, Hamilton
Miansai Solar Signet Ring Gold Vermeil
When you spot a guy with rings on, it’s a sign he’s considered his fashion choices – so it’s a definite green flag in the dating world. Miansai has a great selection of sterling silver and gold vermeil designs, which are unusual yet wearable.
Take this Solar Signet, for example. It follows the same silhouette as a classic signet but is given the brand’s signature twist with textured detailing.
Buy now £160.00, Miansai
