what to wear on a date

Pre-date Nerves

Going on a date can be equal parts exciting and nerve wracking.

What you’re going to wear is always top of mind – and this is definitely a stressful quandary for some. As they say, first impressions are everything. This can be inspiring while you’re getting dressed, but if you have no idea what to wear it can also make you go mad.

I’m sure we’ve all been through the routine of trying on five different ensembles on the verge of having a mental breakdown – and then settling on wearing the first outfit you tried on anyway. In order to take the panic out of dressing yourself for a date, we’ve put together a simple guide to nailing your outfit so your sole focus can be enjoying yourself.

Here is the biggest ” what to wear on a date ” problem…

The #1 Solution to What to Wear on a Date Problem

When dressing for a first date, or any date for that matter, the priority should be that you feel comfortable and confident in what you’re wearing. Knowing that you look good is the perfect antidote to any pre-date nerves.

As a general rule of thumb, stick to simple yet smart-looking pieces. These will be easy to put together and the finished look is sure to look good. You may be tempted to dress up, which is perfectly fine, just make sure you don’t cross into the territory of overdressed.

This will ensure that your clothes aren’t distracting to you or your date so the both of you can focus on having a good time. Of course you want to look your best, but being dressed to the nines isn’t always necessary in order to achieve that.

If you understand that, you will never have to worry about what to wear on a date.

Other Pre-Date Considerations

Also, when dressing for a date you should take into consideration what sort of activities your date will consist of. If your date is during the day and you’re planning on doing more walking about, say going to a market or strolling around a park or museum, you will definitely want to dress for ultimate comfort.

You should dress in layers so you can remove one if you get too warm – no one wants pit stains. Also, make sure you’re wearing comfortable footwear so sore feet don’t put a damper on the date. You still want to make sure you’re looking your best, so go for pieces that look high-quality.

Time of The Day

For a date that’s happening in the evening where you’ll be more stationary, say a show or dinner, you have a bit more freedom to dress up. Reach for more formal pieces, like a blazer and formal shoes just to bring your impression to the next level.


The weather is also something that must be taken into account when dressing for a date. Dressing depending on the weather can change your look drastically, but there are ways that you can look stylish no matter the weather. It’s important not to disregard the weather in favor of your favorite outfit, because although you might feel comfortable in it, the weather could have other ideas and you could end up overheated or overexposed to the elements.

If the weather is hot, dress in lighter materials to stay cool. If the weather is expected to be cooler, layer up in warmer pieces. If the weather is somewhere in between or a bit unpredictable, definitely dress in layers so you can be prepared for anything.


Universal, Go-to Looks

For a date, there are a few key looks that we recommend going for if you’re in a quandary as to what to wear. A simple yet smart ensemble that would be perfect for a date would be dark wash jeans with a neutral colored oxford shirt. This outfit strikes the perfect balance between smart and casual so that you’ll look polished but feel comfortable.

You could also swap out the jeans for neutral colored chinos for a different look. You could also add a blazer on top for a slightly more formal look, just be careful the material it’s in. Wool or tweed is too stuffy, both literally and figuratively, so opt for something a bit more lightweight.

If your date is more casual and earlier in the day, go for jeans and a T-shirt and layer up with an over-shirt. It’s a simple outfit, but simplicity is the best route for a date outfit. If it’s chillier, add a bomber jacket, denim jacket, or a leather jacket.

What if The Weather is Too Hot?

These are classic and stylish jackets that will the perfect finishing touch on your outfit. If it’s expected to be hot, this can present a challenge as clothing for hot weather isn’t always considered the most stylish. In this event, go for chino shorts or nice-looking denim shorts. On top, wear a short sleeved oxford or T-shirt to stay cool.

The shoes are definitely something your date will notice right away, so your best options will be ones that have a smart look to them. Think styles like desert boots, boat shoes, loafers, or even formal shoes. These are all classic and versatile styles that will get you style kudos from your date.


How About Walking Date?

If you’re going to be doing a lot of walking on your date, we recommend wearing trainers or plimsolls so that you’ll be comfortable. Although they are casual shoes, you can opt for a polished-looking pair so you’ll still get kudos on your outfit. Pairing smart shoes with a more casual outfit will make you look put-together without making you look overdressed.


Any Accessories?

In terms of accessories, there are a few that you can add to your outfit to bring everything together. If it’s a day date, sunglasses are a must. Sunglasses just have a way of upping your sex appeal, but since it’s a day date they can be passed off as purely functional. A watch is also an accessory you could incorporate, as it will add a bit more interest to your outfit and show that you’re detail-oriented.

It may be tempting to put on all of your flashiest accessories, but it will only come off as if you’re trying to compensate for something. As a general rule, don’t over accessorize – just go for a couple of simple accessories that will tie your ensemble together.

To Summarize

While there are several guidelines that are good to follow when dressing for a date, the most important thing is that you’re comfortable. Comfortable in the literal sense, but also in the sense that you feel confident and will be able to simply focus on enjoying yourself. Just make sure you’re dressing correctly or the sort of date you’re going on and for the weather, and finally just try your best not to overthink it.

If you’re in doubt go for a simple, comfortable, but put-together that you know you’ll feel confident in. Dressing for a date can be nerve-wracking, but if you stick to the easy but stylish pieces we’ve laid out it can take a lot of the pressure out of it.

The Idle Man is a purely menswear based retailer catering to the style conscious man. Hosting brands such as Barbour, YMC, Fred Perry and Lacoste, The Idle Man is a go-to destination for men. Alongside the online shop The Idle Man Manual is a blog dedicated to offering men style advice as well as stories and guides about music, grooming and lifestyle.


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