Dressing to Impress – A Man’s Guide to First Date Outfits

Edward Pritchard is the Owner and Manager at Pritchards, a designer menswear specialist. He’s the great-great grandson of the original founder, who first opened up shop over 180 years ago, so it’s safe to say that impeccable style runs in the family. In this blog post, he shares his insider tips for nailing the dress code on a first date.

After weeks of messaging back and forth with a charming stranger online, you’ve finally arranged a time and place for your first face-to-face meeting. Now there’s just one thing left to do: plan a dashing date night outfit that will help you sweep them off their feet. After all, you only get one chance to make a first impression, so you want to make sure it’s a good one.

Dressing for the first date can be tricky business, and there’s a fine line between looking over- and underdressed. Here, I’ve shared what to wear to make a great impression on every kind of date, including casual meet-ups at the pub, high-end wining and dining, and even outdoorsy adventures.

A casual drink at the pub

If you’re headed out for a casual drink at your local, you don’t want to look too dressy or formal, but you want it to be clear that you’ve made an effort for your special someone, too. The key to getting this look right is striking a balance between laid back and put-together: a sloppy T-shirt, old jeans and shabby trainers just isn’t going to cut it, even if it is the sort of thing you’d usually wear to the pub.

Instead, go for an Oxford button-down shirt in a cool blue shade, a pair of dark or black jeans, and a pair of smart boots. This will project a sense of cool, natural confidence, without coming off as too stuffy or try-hard. If you want to make the look a little bit more casual, layer the shirt over a grey T-shirt, roll up the sleeves, and wear it with a pair of dark chinos.  

Photo by Mohammad Faruque on Unsplash

A classy dinner date

If you’ll be meeting your date at a high-end restaurant, or heading out to a classy late-night bar, then a slightly more formal look should be adopted. When it comes to swanky wining and dining, you can’t go wrong with a sharp tailored jacket, a crisp shirt with a subtle pattern or print, and some dark-wash denim. Compete the look with a smart pair of boots, or, if you really want to impress, a well-polished pair of brogues.

Outdoor adventures and active dates

If your date prefers long hikes or bike rides to candlelit dinners, then you’ll need to put together an outfit that’s ready for anything. A plaid shirt or cosy crew neck jumper, a pair of dark jeans, and walking boots or trainers should tick all the right boxes, and you won’t need to worry too much about things getting a little muddy.

Don’t forget about accessories

The small details can make a real difference, so don’t neglect your accessories. I’d always recommend keeping it simple: you don’t want to turn up wearing more jewellery than your date, so all you need is a classic wallet, a watch, and a pair of elegant cufflinks if you’re wearing a shirt. Pay attention to the state of your wallet, too: pulling out a shabby old style that’s falling apart at the seams isn’t going to impress anyone, so if it’s in need of an update, now is the time to invest in a new one.

If the day of your first date with that special someone is drawing near, then don’t panic: just follow my advice, and you’ll soon be dressed to impress.

Photo by Vadim Sherbakov on Unsplash

Edward Pritchard

Posted by Edward Pritchard

Edward Pritchard is the Owner and Manager at Pritchards, a designer menswear specialist. He’s the great-great grandson of the original founder, who first opened up shop over 180 years ago, so it’s safe to say that impeccable style runs in the family.

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