Herring Shoes

Men’s shoes for dating

23 November 2021

This blog isn’t just for those who are single and on the dating scene, hopefully it helps encourage those of us who already have partners, and perhaps don’t have enough date nights, to make a bit more effort.

A lovely shot of Hugo and Lily. Hugo is wearing the Herring Canterbury

Let’s face it, we are well and truly in the digital age of dating and whether you like it or not, it’s here to stay, but I think it should be embraced, especially after the last couple of years where going out and meeting someone in a bar has become virtually impossible. Dating sites and apps offer a safe place to get to know someone and help you make a decision on whether you want to take things to the next step; it can be a huge confidence booster too.

So, you’ve found your perfect match online and the time has come for that first ‘in-person’ date. There’s no doubt you need to look your best to impress and this starts with what you’re wearing. You don’t want to just throw on the first pair of shoes you come across in your porch or wear the same clothes you wear down the pub with your mates. It’s time to bring your A-game.

The most important rule: Dress for the occasion.

You don’t want to be in a tuxedo and black patent shoes if you’re just meeting up for a coffee! Most physical dates will involve meeting for either lunch or dinner. I would suggest if you are meeting for lunch or a coffee even, that you take the more ‘smart/casual’ approach. I would go with dark coloured jeans (preferably not baggy, but they don’t have to be budgie smugglers either) paired with a chequered or patterned shirt with the sleeves rolled up. This will give a fantastic first impression when paired with our Grays, Orkney, or Canterbury chukka boots. Chukkas aren’t over the top and just enough on the smart side to show you have put some thought into what you’re wearing. If you aren’t much of a shirt man then I would wear a plain tee and team this with a pair of smart trainers/sneakers, such as the Sebastian or Goodwood and if you can match the colour of your tee with them, even better! Also consider a pair of suede Chelseas, such as the Bronson. These are the epitome of ‘smart/casual’ and work with both of the above dress options.

Carl has matched his shoes and tee to get the smart/casual look. He is wearing the Herring Sebastian

Dinner date? Now we start to think more on the smarter side. You don’t have to go down the ‘black tie’ route unless you’re going to a ball or a themed evening (how cool would a murder mystery night be for a first date?), but I would certainly wear something along the lines of a textured blazer, your best quality dark coloured chinos and a linen shirt. The latter doesn’t have to be plain, but I would avoid too much of a pattern. Details, such as a nice belt, will make a difference too especially as you should be tucking your shirt in. The obvious choice of footwear is a pair of brogues, and this is where the Carnaby come into its own. They are a modern-day classic made on a sophisticated but not pointy last. The chestnut calf will go with anything. I defy you to make these shoes look bad! I would also consider the Munster, which are a bit more understated, but extremely refined. The Byron are a solid option too for those of you like a monk style and love to mix it up a little.

Herring Munster

It’s good to be creative and maybe you have planned a country walk for your date, ending up in a nice cosy pub with a roaring fire and hot chocolate. For this I would go country chic, such as a big woolly jumper and waxed jacket would set the tone nicely and we’ve got you covered. Check out our offerings for country clothing here from Peregrine. Footwear wise, you need something with good grip and you can afford to go a bit more chunky with your shoe choice. My first option would be the Leconfield long wing brogue in burgundy or tan: they’re timeless country styled brogues. Or go for the Hardwick, which would be ideal for those who like the chunky look but don’t want the weight. For the real shoe aficionado, the Kirkoswold ticks a lot of boxes, especially in the waxy finish. If your walk is a bit more hardcore and there’s some climbing involved, then the Trekker is the one you need. OK, it may not be the most stylish pair, but they suit the occasion down to a tee.

Herring Leconfield in Tan Grain

I could go on all day, but I think we have covered enough bases and I hope it has helped to give you some ideas.

Don’t forget, the above is not set in stone, first and foremost you have to make sure you are comfortable, confident and happy in whatever you’re wearing (as covered by Caz here). The better you feel, the happier you will be, and the date is more likely to be a success. You’ll be planning your second date before you know it 😉

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