The following is a guest post from Mark at Northern Threads.

DATE NIGHT – two words that can easily strike fear into the heart of any man. If someone tells you that there’s no point in making any real effort, don’t listen to them.

I recently went on a date in what I thought was a passable casual outfit only to arrive and see she was dressed up to the nines. So then you’re casting nervous glances at your scuffed trainers while she feels over-dressed. Not the ideal start to a date.

The general rule of thumb is: give yourself some time and put the effort in as it’ll definitely be worth it.

I’m assuming you’ve already booked the table, bought the tickets or whatever it is you’re doing… can’t help you with that one. But below you’ll find some sure-fire tips that can’t see you wrong in preparation for your date. And preparation is everything; if you look good, then you feel good too.

We’re gonna focus mostly on dressing correctly, but first, a few quickies on grooming:

  • Is your date checking her reflection in your forehead? That’s because you should’ve exfoliated.
  • Nose/ear hair isn’t a good look on anyone. Trim it off.
  • Feeling nervous and sweaty? Make sure you’re using a decent deodorant to combat it – roll-ons can sometimes work better than sprays.
  • Don’t hide under a hat – wash and style your hair, then show it off.

The Dinner Date

It’s the most classic of dates out there so you need to put together an outfit to match. Firstly a jacket is a must. I don’t mean a tuxedo or suit jacket; this isn’t a dinner at The White House. A blazer is a good multi-purpose option. If you’re out during the day before the dinner, then go with a smart sport jacket.

Best to go for a short jacket without a hood or fussy toggles and details… something simple and clean that can also be easily draped over your date’s shoulders if she’s feeling cold. Team this up with a well-fitting shirt in a fresh colour—pale blue or white are always good options.

On the bottom half, comfortable yet smart looking chinos work excellently alongside classic, heritage shoes such as hand-crafted brogues from Grenson.

The Pub/Bar Date

If you’re heading to a pub or bar then straight away you’re spending time in a much more informal setting where a few drinks are flowing. So the easiest mistake to make is to go too dressed up—take it easy and use it as an opportunity to dress comfortably but still with an edge of understated style.

Work wear is a no-no; looking like you’ve headed there straight from work and made no effort isn’t gonna come off well. Stay away from plain blue jeans, sweats and athletic pants—you want to be relaxed but not in-front-of-the-tv level of relaxed.

Polo by Fred Perry, denim by Fifth&Brannan, desert boots by Clarks

Top half we’re talking about knitted sweaters in pastel colours, a suede bomber jacket is a fantastic option, or go for a polo shirt from one of the reputable brands like Fred Perry. On the bottom you can go for linen trousers or dark-wash jeans in black or deep indigo with desert boots or espadrilles.

The Cinema Date

Let’s face it: if you’re going to be spending a large chunk of your date sitting in a dark room, then you can maybe leave the monocle and walking cane in the house. Levi’s jeans are an easy option that always looks great along with a box fresh pair of sneakers – no scuffs or soles hanging off!

This is one place where it is okay for a t-shirt to make an appearance, as long as there aren’t any in-your-face prints – go for simple stripes or a slick contrast pocket tee. A vintage leather jacket is a great way to finish the outfit off,  and with plenty of pockets, you’ll always have a place to keep all your stuff.

Oh, and by the way…

Pay attention to your shoes. It’s probably the last part of the outfit we think of and the one we put the least effort into. But we shouldn’t. It takes a heroic display of charm to win back your date after they’ve clamped eyes on your shoddy shoes.

Thanks Mark! What to wear on a date depends largely on the type of date. If you have a well-rounded casual wardrobe (you know, the clothes you live in when not wearing a suit or walking around in your underwear), you should be just fine in 90% of situations.

Any follow-up questions for me or Mark? Do you have a special date coming up and you’re completely baffled about what to wear? Let us know in the comments below.

 

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8 Responses

  1. BK on

    If you’re in a city that’s got the service, definitely check out Uber for picking your date up and getting to dinner. It’s a bit pricy, but it’s about as classy as it gets and you can find discount codes easy. Check it out!

    uber.com/invite/ubersave

  2. Christopher on

    Really cool article and I agree with all of this. Thanks for it. 

    Also, Primer just did an article on the same topic. Not that I’m saying there is any connection. In fact what I really like is both articles are by guest posters and both of them cover completely different areas and date options. Between these two articles we’re totally covered. 

    Well done. Thanks again. 

  3. mic on

    Sorry, this isn’t right. Women usually aren’t impressed by tee shirts or polo shirts. Also, “plain blue jeans” are good for many pubs and bars, as long as they’re not faded or light-colored. Probably not as impressive as dark-wash jeans, but better in most women’s eyes than “trousers.”

    • Barron on

      If it’s a casual movie date (and assuming it’s warm), I don’t see anything wrong with a polo or T-shirt, as long as they fit well.

  4. mic on

    To elaborate, the trick with “plain blue jeans” is fit. Baggy looks awful, but the right fit can make the plain kind fine for a date. Dark-wash can better hide mediocre fit. Speaking of fit, the type of man who can successfully wear a tee shirt or polo shirt on a date probably is rather muscular.

    • Barron on

      Dark wash can definitely hide mediocre fit, but it’s still important to get the best fit possible. I wouldn’t want guys to take shortcuts just because they think a darker wash denim will hide ill fit.