From Top to Bottom, Here’s What You Should Wear to a First Date

First Date Men What to Wear
Courtesy of Unsplash
When you buy something through our retail links, we may earn commission and the retailer may receive certain auditable data for accounting purposes.

It can be a bit of a scramble deciding what to wear for a date, especially if pressed for time. The short of it is: smart-casual. This is the ultimate sweet spot. You’re not wearing white tie and arriving on a flying carpet made of diamonds, but nor are you rocking up in soup-stained boxers and tattered slippers.

Smart-casual is showing off, but not showing all. What’s useful about this is that you can lean into to either more casual or more formal depending on the specificities of the date. Despite smart-casual being a good general guide, there are a few things that need emphasising when going on a first date: great shoes, an amazing jacket/coat and an attractive cologne.

The main thing when dressing for a first date is to feel relaxed and comfortable. You don’t want to look desperately attention grabbing, or looking uncomfortable because you read online somewhere you must wear a leather jacket or a rainbow bowler hat as a conversation starter. Remember, this is a relatively fictionalised meeting and everyone is putting on a bit of a front, so, just go with it, don’t overthink your clothes and live within the comfort of your own style. It is about dressing with confidence.

So sit back and hopefully you’ll enjoy your date as much as you will enjoy reading our comprehensive first date dressing guide.


1. Put Your Best Foot Forward

Forgo all other tips before this one. Good shoes have the ability to turn around the most drab of outfits, so make sure you’re hitting the top end of your smart-casual wardrobe when it comes to shoe choice. Chelsea boots are a good choice or some less formal brogues (see below). This will pitch your shoes within the realms of smart, but not intense. You want your dress to reflect that your are at least somewhat relaxed too. Also in this smart-casual range is a pair of quality white leather trainers. They have the ability to smooth outfits out and add a bit of je ne sais quoi magic that is needed on a date.

Samuel Hubbard ‘Tipping Point’ Wingtip Oxford

Samuel Hubbard Brogue First Date Courtesy of Nordstrom


Veja Leather Sneakers

Veja Leather Sneakers First Date Courtesy of Mr Porter



2. Perfect First/Last Impressions

Obviously don’t turn up in a shearling bomber jacket in the middle of a summer heatwave just because it’s your best jacket. However, if it is possible to sling on your finest jacket (Very GoodJ acket) or coat, you should. It is the first and last piece of clothing they’ll see you in. Think of it as the parenthesis (the brackets) around which their impression of you will sit neatly between.

Mr P Virgin Wool and Camel Hair-Blend Overcoat

Mr P Overcoat First Date Courtesy of Mr Porter


Everlane The Chore Jacket

Everlane Chore Jacket Date Courtesy of Everlane


3. Seriously Attractive Cologne

A cologne drapes from your outfit like an invisible accessory, sometimes with more power than anything visible. We all know the experience: you’ve smelt someone’s incredible cologne as they walk past and your mind scrambles in heady enjoyment. That’s the sort of influence you want to be putting out into the cosmos; just don’t treat the application process as a second shower. Check out the Spy Guide for more cologne inspiration.

For our first date selections, you want something unique, luxurious and seriously attractive. That’s why we’ve chosen Terre D’Hermès, which has top notes of grapefruit and orange, a middle note of flint and bas notes of oakmoss and benzoin. It is earthy, natural and zesty aroma, which suggests an untainted, pure and exciting version of yourself. Our second choice from Malin and Goetz has notes of leather, bell pepper, ginger, musk, wood notes, which sits at the spicier end of the spectrum, but still gives off a natural and inviting scent.

Terre D’Hermès

Hermes Fragrance First Date Courtesy of Nordstrom


Malin and Goetz Leather Eau de Parfum

Malin and Goetz Cologne Date Courtesy of Bloomingdales


4. Quality Foundations

No. Those zany socks with the robots and multicolored grapefruit don’t make you look interesting. It’s a physical manifestation of insecurity. You don’t need them and they are doing far more harm than good. When looking for basics make them of high quality and ideally, make sure they’re new. Some good quality socks will make you feel more comfortable, confident and self-assured. See our Spy Guide for socks to make sure you’re picking the right ones.

If things do heat up on the first date (not that it’s always a good idea) you’ll be glad to have purchased some new and good quality boxers. This pack of three from Italian fashion house Armani will be more than suitable.

3 Pack of Emporio Armani Boxers

Armani Boxers First Date Courtesy of Bloomingdales


4 Pack of Calvin Klein Boxers

Calvin Klein Boxers First Date. Courtesy of Nordstrom


5. Shirt Simplicity

For the top half, we recommend going for a shirt on the big evening/day. No double cuffs, no shirt studs, no cufflinks; nothing that excessive. Just a good old fashioned oxford shirt should do you right. This Polo Ralph Lauren shirt below is of excellent quality, it comes in a nice shade of blue and the colorful logo gives just a hint of style and playfulness.

That being said, a good quality white t-shirt isn’t out of the question, if worn with something smarter. For example, with suit pants, or a relaxed fitting suit, good quality white trainers and a chic overcoat. A white t-shirt can add the casual element that a full suit is missing. Try our Spy Guide when looking for the perfect white t-shirt.

Polo Ralph Lauren Long Sleeve Oxford Shirt

Polo Ralph Lauren Shirt Date Courtesy of Revolve


Incotex Slim-Fit Cotton-Corduroy Shirt

Incotex Corduroy Shirt First Date Courtesy of Mr Porter


6. A Statement Timepiece

You want to aim for a three-quarter range of luxury. You don’t want to peak early and put your most expensive boulder of a watch on. Equally, don’t wear a tattered or scratched watch. Men’s Health recommend to ‘always, ALWAYS wear a watch’, which we whole-heartedly agree with.

For the rest of your accessories, it is a tricky area as it gets quite personal, but generally go light. Maybe a ring or a bracelet and a belt. But our best advice? Spare the theatrics.

Movado Stainless Steel & Leather-Strap Watch

Movado Watch First Date Courtesy of SAKS


Nixon Rollo Leather Strap Watch

Nixon Watch First Date Courtesy of SAKS


7. Subtle, Dark Bottom Half

Dark jeans always look smarter, more fresh and more purposeful than a lighter wash. Avoid rips and varying washes. A dark selvage denim is a go and should be a staple of any man’s wardrobe. If you don’t fancy jeans, alternatively try, some impeccable suit pants in navy or black. On your bottom half you aren’t really trying to express anything, you can do this with the other things, so keep it dark, keep it simple and just try to match it to your amazing jacket and shoes.

RRL Mid-Rise Selvage Denim Slim-Leg

RRL Jeans First Date Courtesy of Moda Operandi


Saks Fifth Avenue Windowpane Check Suit Trousers

Saks Trousers First Date Courtesy of Saks


8. Consider These Gems…

A Roll Neck

Swap out your shirt for this thespian/poet/intellectual vibe. If worn with a relaxed suit and white sneakers it can really help modernize the suit and bring it into the smart-casual domain. Check out our guide for choosing the best on the market here.

A Leather Jacket

Research done by The Essential Man shows that women ‘when asked what single piece of clothing would a woman love seeing her date wear, the clear winner was a perfectly fitted leather jacket… beat[ing] a tailored suit (24.3%) by a little more than double, and completely crushed hoodies (2.8% of the votes, sorry readers in Silicon Valley).’

If you can pull off a leather jacket, then more power to you buddy. The statistics look on your side, but it is a difficult one to get right. Perhaps all you need is just a great Spy Guide to help you find the right one.

That’s it from us. Best of luck!


Here's some advice for the date itself