Style Rules For Modern Living

Style Rules For Modern Living


Sir Plus started out at Spitalfields market, selling boxer shorts made from shirt makers’ off-cuts (surplus, geddit?). Today, it specialises in grandad shirts and Nehru collars, and has three bricks-and-mortar places in Portobello, Islington and Piccadilly. Founder Henry Hales spoke to SLMan about his style rules, from the cool chinos alternative to his new favourite suitcase.

My last purchase was a pair of Paraboots. They’re awesome, almost like a French Doc Martens boot – outrageously expensive, but really well made and a very cool brand. I’m currently wearing them with a pair of chinos and some thick wool and cashmere socks from Falke. The boots have a thick sole, so they’re good to wear when you’re out and about on the market, which I am most days. Thick cords are another great trouser alternative and look just as cool as chinos. I normally wear Sir Plus, of course – especially if I am working – but I love Patagonia for outerwear. It does great fleeces. When I’m outdoors on the market stall, I’ll layer up and wear a beanie hat from William Locke. On my wish list at the moment is a duffle coat from Gloverall.

I wear navy and charcoal colours the most because they go with everything. My failsafe formula for dressing is a pair of navy chinos, a white grandad-collar shirt and grey Nehru cardigan. I’d wear that with a pair of North 99 black waterproof sneakers, which are stylish but also handy if you are caught out in bad weather. A white shirt is always a good option if you’re struggling to get dressed in the morning. It works with everything and always looks like you’ve made an effort. I love grandad-collar shirts. Essentially collarless, I think they look cooler than a standard oxford or button-down and work better under knitwear. Having a collar can be awkward; do you tuck it into the neck of a jumper? Or wear it outside? It’s a headache. My go-to footwear is anything in black leather because that goes with every colour. For me, brown footwear verges on being agricultural.

The best advice I’ve ever received is to buy good-quality statement pieces that will last. A great bomber jacket, a great denim jacket, a durable overcoat – these are things you will wear forever and which won’t date. Margaret Howell on Redchurch Street is my go-to brand for jackets that are worth the money. I don’t have to wear a suit to work, but a great suit is another worthy investment. If you pay for a good one, you can wear it forever. Charlie Casely-Hayford has incredible style and creates amazing tailoring, so I’d go see him for a suit. I have a charcoal, mottled-wool, single-breasted suit from him which I love. I wear it with an Hermès tie and some classic black Derby shoes from Crockett & Jones.

Don’t get caught up in fashion trends. Big logos have been a thing for a while now in menswear and I just don’t like them. I don’t think branded garms are cool and they’ll look dated soon. Prints are fine as long as they are subtle, not too floral and kept to shirting.

My Rimowa suitcase is my favourite luxury item. I got it for my birthday and it has changed my life. It’s black, has a laptop case in the side of it, and it’s a serious step-up from my Antler carry-on. I saw someone with one once and thought it looked cool, but it is life changing. I travel a lot, so it is already well used.
End Clothing in Soho is an incredibly cool store. I went the other day and was blown away by how everything was presented. Hornets on Kensington Church Street is another top store of mine. It’s an institution; a man called Bill Hornets runs the store and everyone in the area knows him. If you’ve not been, it’s worth a visit just to meet Bill as he’s such a character. I bought my first suit from him, so I feel really nostalgic whenever I go back there.
For shoes, I always rely on Doc Martens as they’re really durable and warm when I am working outdoors. I love Nike trainers, but I am currently wearing Veja. I’ve got a white and black pair, which seems to be the most popular trainer style out there at the moment. Everyone is wearing them. For denim, I wear Hiut, which is a brand created by a guy called David, who bought a factory in Cardigan in Wales, where he makes all his jeans. It’s a really well curated brand with the ethos of doing one thing and doing it well.

My weekend style is very formulaic. Always a pair of navy chinos and boots, and I am normally found in a workman’s jacket from my collection. Uniqlo is great for basics and I’ll go there to buy essentials like good white tees and maybe some linen shirts. In the summer, I’ll switch out my boots for a pair of desert boots from Clarks – or maybe Birkenstocks if it is really hot – but the chinos and workwear jacket still apply. I would never wear bright colours, even in the summer, as I think charcoal looks great all year round. When it’s warmer, you can wear it with camel or another lighter shade of grey; in winter, I team it with darker colours like navy or black.

Aesop is a great brand for gifting. You can never go wrong with an Aesop soap or lotion. Thomas Clipper would be my top choice of grooming brand. It does good colognes and is still a unique place for scents. Generally I will go gift shopping in Liberty as there are so many options there for whoever you’re buying for.

I enjoy holiday packing and don’t really waver from my basics of: Riz swim shorts, a linen shirt from Sir Plus, Finlay & Co sunglasses and Borsalino Panama hat. I love a vintage Hawaiian shirt and you can pick up some really cool ones from east London. Or Polo Ralph Lauren does new versions which have that same vintage feel. In the evening, you can’t go wrong with a pair of Orlebar Brown tailored shorts.
My rules on tailoring are don’t make it too fussy and ensure there is a bit of give if you are buying off the rail. This gives you room to get it taken in to fit properly. Don’t be tempted by an elaborate lining – you will regret it. Because I don’t wear suiting very often, I like to be adventurous with the cut and like wearing three-piece suits or double-breasted jackets to events like weddings. The important thing is that you are comfortable. You can always spot a guy at a party who is uncomfortable in his suit.
I am not a big fan of jewellery. I don’t love lots of busy accessories, so tend to choose the simpler, minimalist brands. I love Comme des Garçons for wallets and Want Les Essentiels for weekend bags. Ralph Lauren does great classic belts which last forever and for watches you can’t go wrong with Casio. I am currently wearing a Casio Illuminator F-19W but I have my eyes on a silver Apple Watch. I know that’s a bit of a style faux-pas but I’ve been thinking about it for a while and I am near taking the plunge to buy one.
Three words to describe my style would be minimal, workwear, wearable. Quality and durability are really important things I look for when I’m buying and designing clothes. I can’t stand things that are poorly made.
Bill Cunningham is my style hero. He was the original street-style photographer – and all-time workwear legend. He was into the workman jacket before anyone else and it’s a trend that’s stuck. Right now, Matt Smith would be my dream customer. He always looks very cool in an effortless way, which is really what Sir Plus is about, so it’d be great to see him wearing the collection.

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