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

You can be an absolute beast or warrior at work and play, but when it comes to what to wear on a first date…yeah, that can be a hellish experience. The one good thing about the pandemic is that it’s changed the way everyone dresses. Everyone is opting for casual, comfortable clothing. And navigating where to go on a first date’s easier due to Covid; you know from the get-go that you’re going to be outside. So, if you’ve got a leather jacket, now’s the time to show it off.  This article has a few helpful pointers on what to wear on the first date. They are:

  • How to sartorially-speaking prep yourself for the date.
  • What not to wear to a first date.
  • What to wear on the first date.

First date wardrobe mindset

When choosing what to wear on a first date; pretend that you’re attending a Zoom meeting. That means you’ll have a casually cool top on, but unlike the Zoom, you’ll be wearing pants not pajama bottoms. When rummaging through your closet or shopping to find something to wear, remember this cardinal rule: You want to feel comfortable on a first date. Never wear anything on a first date that itches! Second cardinal rule: Just be yourself, well maybe a tad better than yourself on the first date, and it’ll work out. 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.

What not to wear

  • Anything that has a distinct odor. It might be your favorite baseball jacket or fill in the blank, if it hasn’t seen the inside of a washer in the last six months or so, that’s a no.
  • Nothing wrinkled. The only exception is a linen shirt or pants. If it looks like it was mashed between your mattress and box spring, or has more fold lines than an origami swan, nope.
  • Unless you’re dashing off to a date after painting a house or a canvas, don’t wear anything stained.
  • Don’t wear anything that’s either too big or too small on you. It’s distracting, and there’s a good chance that your date will be more fixated on the ill-fitting clothing than your sparkling personality.

What to wear on the first date

We’ve created what we’d like to call a blueprint on what to wear on the first date. Unless you’re planning on hiking a mountain trail, eating at a Michelin starred resto, or playing any type of sport, our roundup of clothing options is the perfect answer to what to wear on a first date.  And if you do decide that you’re going to an elevated resto for brunch or cocktails, adding a blazer to jeans or chinos sets the right look.

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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

And yes, the pandemic has even changed the way we think about footwear. These days, since most first dates are at open air venues — outdoor cafes or pubs, farmer’s markets, and such, opting for a smart looking shoe that fits the venue makes sense. Chelsea boots are always good choice to wear as they go with anything. If you know ahead of time that your first date is going to involve lots of walking, you can never go wrong with a pair of stylish dad shoes or white sneakers. Hitting a weekend brunch, try a pair of espadrilles. These cottons topped shoes are the right mix of smart and casual. You can elevate any outfit with a pair of lace up suede shoes. it’s a winning combination.

Common Projects Original Achilles Leather Sneakers

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Courtesy of Mr Porter


Banana Republic Hinto Suede Oxford

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Courtesy of Banana Republic


Tom’s Alpargatas Rope Espadrille

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Courtesy of Tom's


2. Perfect First/Last Impressions

Jackets are often called “toppers” because they literally top off an outfit. And with temps veering wildly these days, it makes sense to toss on something over your shirt. 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.

Levi’s Trucker Jacket- Stone Wash

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Courtesy of Levi's



H&M Linen Bomber Jacket

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Courtesy of H&M


Bonobos Stretch Cotton Chore Jacket

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Courtesy of Bonobos


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.

Third choice is Maison Margiela Replica By the Fireplaces. Maison Margiela has a slew of unisex scents that aromatically recall favorite places and atmospheres. Their By the Fire is a warm, sensuous and slightly spicy juice that’s not overpowering. Its key notes are clove oil, chestnut and vanilla accords. Somewhere deep in the fragrance are touches of leather and tobacco.

Terre D’Hermès

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Courtesy of Nordstrom


Malin and Goetz Leather Eau de Parfum

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Courtesy of Bloomingdales


Maison Margiela ‘Replica’ By the Fireplace

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Courtesy of Sephora



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

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Courtesy of Bloomingdales


Polo Ralph Lauren Men’s 5-Pack Classic Fit Moisture Wicking Cotton Boxer Briefs

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Courtesy of Macy's

5. Shirt Simplicity

As mentioned earlier, the top half or the shirt should be something you’d wear for a casual office meeting or Zoom. No double cuffs, no shirt studs, no cufflinks; nothing that excessive. Just a good old fashioned button down shirt should do you right. This Portuguese Flannel Linen shirt below is of excellent quality, it comes in a nice shade of blue and gives just a hint of style and playfulness.

Here’s another style tip. Hitting an outdoor pub, resto or wandering around a street fair, and you’d like to add some flair to your outfit, layer the button down over a graphic print, vintage, or contrasting color T-shirt. Obviously said button down should be worn open. If you’re not into a long sleeve button down, a short sleeve button down has that same tailored vibe. Coalatree’s Switchback shirt is made from recycled coffee grounds, is odor and wrinkle-resistant, comes in four color options, and yes, can be worn open over a tee. Another option is a Breton striped T or long sleeve shirt. Striped shirts are a classic summer style and look equally well paired with chinos or dark jeans. We like the one created specifically for Mr Porter. Made from soft cotton jersey, it can be worn alone, under a jacket, or used as a layering piece.

Portugese Flannel Linen Shirt

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Courtesy of East Dane


Coalatree Switchback Shirt

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Courtesy of Coalatree

Mr P Striped Long Sleeve Cotton Jersey T-Shirt

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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

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Courtesy of SAKS


Nixon Rollo Leather Strap Watch

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Courtesy of SAKS


Bulova Miyota Watch

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Courtesy of Bloomingdale's



7. Subtle Bottom Half

Dark jeans always look smarter, more fresh and more purposeful than a lighter wash. Avoid rips and varying washes. Tik Tok has killed the skinny jean, so dark colored relaxed fit or baggy jeans are not only fashion forward, but they’re also comfortable. If you don’t fancy jeans, or want to rev it up a notch, some chinos or carpenter pants. Keep it simple and just try to match it to your amazing jacket and shoes.

Levi’s 501 Original Fit Jeans

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Courtedy of Levi's


 Bonobos Stretch Washed Chinos

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Courtesy of Bonobos


 Wrangler Authentics Classic Carpenter Jeans

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Courtesy of Amazon

8. Consider These Gems…

A  Camp Collared Shirt

Camp collars and Hawaiian print shirts are always a summer staple. These classic styles have a boxy cut and come in an array of colors and prints. Because of the cut, if they’re worn untucked, they look just as sharp as tucked in. We like Mavrans Army Game Weekend Shirt. This shirt is the blend of the above mentioned styles and has nifty detailing on the sleeves. Made from recycled plastic bottles and coconut husks with a touch of stretch, this shirt is cool and sustainable. If you tend to sweat a little when you’re nervous, this shirt has anti-stink tech woven into every fiber, has a UPF 50 and dries fast…great if you get caught in the rain. You can even wear it under a blazer, and it’ll look sharp.

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Courtesy of Mavrans

A Leather Jacket

Yes, we mentioned leather jackets earlier, but here’s some more helpful trivia for you. 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