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I Used An Online Stylist For A Week And Here's What Happened

Two subscription boxes. One week. Loads of mild discomfort.

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My current styling principle relies on using small, cheap pieces on the top half of my 6-foot-3-inch frame to distract from the shambles below the waist.

Most of my good shirts are Christmas presents from family. That snazzy yellow watch? Something to take your eyes away from the knackered jeans and even more battered trainers I often wear. Someone once described my fashion sense as "preppy without pomp", but I'd call it more "preppy without pennies". Uniqlo is a constant saviour.


Wanting to improve, I tracked down two UK menswear companies, The Chapar and Enclothed, to see what they could do to kick my fashion sense into shape.

Both companies work by taking a small deposit from your debit card when signing up. The goal is to try everything in each box, send back the stuff you don't like, and then pay for the things you keep.


Once you've set up a profile, you also get a phone call from an online stylist to figure out what things you like to wear and where you normally shop.

For Enclothed, my personal stylist Anika was very excited about my lack of smart-casual clothes and was very keen to update my look from "hungover third-year university student" to "modern young professional" (my words, not hers).

My Chapar stylist Chelsea asked me what sizing problems I've encountered when shopping on the high street, as well as my thoughts on red trousers. (They are an abomination only useful in identifying bad eggs.)

On the left, I'm wearing my normal clothes; on the right I'm wearing an outfit from Enclothed.

My first style transformation felt a bit "teenager told to dress smart-casual for a church barbecue".

A solid brown suede shoe went well with functional straight-cut Levi's jeans. The T-shirt, while a solid colour and good fit (always raise your arms when wearing a tee, and if it shows your belly, then it's too small — make sure the shoulder stitching lines up with your shoulder too), doesn't scream out £50 worth of garment.

I'd say I was neither overwhelmed nor underwhelmed by my first experience – just pretty whelmed. It's an outfit that I'd have no problem wearing to the pub, but it's also an outfit I doubt anyone would class me as a sharp dresser for wearing.


Day two brought with it a problem many a tall person has; buying trousers as a tall man is next to impossible.

I have long legs and a high bum (a sports physio once said it resembles a duck), which means finding well-fitting jeans of the right length is impossible.

Either I go for a straight fit that can end up looking swampy on my matchstick pins, like the Enclothed on the left...or I opt for a skinner fit and end up with a pressure cooker of crotch section like in The Chapar's selection.

In both outfits my trouser trouble was remedied by a good navy shirt. Again, Anika showed her eye for T-shirts with a smart Ben Sherman tee that l'd get a lot of mileage out of, both at work and down the pub, and I adored Chelsea's choice of denim shirt – well-fitting, simple lines. Perfect.

I felt confident in both outfits – both an improvement on the clothes I normally wear, and both not giving away that I'd been to see a stylist.

Both companies encourage spending money on quality, high-value brands such as Levi's, Gant, and Scotch & Soda. The starting price of most of the items in each box was around £50, with some pieces hitting the £300-400 mark.

As someone who struggles to justify spending more than £40 on anything other than a night out, I did baulk at how much a pair of high-quality jeans go for. However, I really did appreciate the difference in fit and movement when wearing the more up-market pieces.

Pocket space seemed to be an increasing premium as my fashion improved. The Chapar outfit on the left gave me very little space for a bus pass, let alone a wallet.

Then again, considering most well-dressed people carry card holders over wallets, that's probably intentional.


There's a bit in the film Crazy Stupid Love where Steve Carrell describes what it's like to dress well. It's the greatest, most honest monologue on high-quality menswear and goes thusly:

"I have 18 layers of clothes on. I'm wearing a shirt and a tie and a sweater and a suede jacket that just seals in all the heat. Seals in all the juices. I'm just ... It's all sweat under here. This is just sweat from here down. I'm ... This sweater, this is called slim-cut, but it feels like a scuba suit."

Blazer game on point.

Your blazer game could not touch mine during this week.

Can you wear a light-pink blazer to a work meeting?

Your blazer game could not touch my blazer game during this week.


I'm a 32 waist, but currently can't shop at Topman because I struggle to get its slim chinos and jeans past my knees.

I often have to buy a 36 waist when buying trousers from ASOS because six years of rugby, bad gym sessions, and big weekend drinking has left my body broad in odd places.

For those who like to try on everything before they buy it, subscription boxes can be a bit more hit-and-miss than you're typically used to.

At the end of the week, I really began to appreciate Anika's flair for choosing a good shirt. Every selection she made was bang on the money with a well-fitting choices in a number of nice colours. The Gant shirt (left) she selected for me is perhaps one of the best-fitting shirts I've ever worn, with good length on the sleeve and a strong collar. Enclothed's box left me feeling a little bit like my dad at times with its selection, but there's a lot to admire about what I describe as "golf-course chic".

Over to The Chapar, and my final selection was a combination of outfits from days two and four. I adored that denim shirt for its simple unfussy design and the light-grey trousers – while a sauna for my boys down south and a blank cheque for disaster given my messy eating style, it made for a smart addition to my wardrobe. Loved the neon shoelaces too.

A good T-shirt there, a solid jean choice here, Enclothed's box really seemed to drive home the importance of men having high-quality staple pieces in their wardrobe.

It's often said women are better at buying clothes than men because women understand how versatile a good white T-shirt can be. Enclothed's box was about plugging those important gaps in my style board.

Not only did The Chapar box come with close to £1,500 worth of clothing, but Chelsea sent over a number of suggestions as to how I could wear the clothes from top to toe.

So should you try out subscription boxes? Here's my advice:

Do approach things with an open mind. Both stylists sent clothing that I wouldn't normally go for, but I was pleasantly surprised.

Don't stress about sending stuff back. While you shouldn't eat a mustard-filled hot dog when wearing clothes you plan to send back, don't feel guilty if it's not for you.

Do give your bank balance a look. Being a dope dresser costs money.

Don't be afraid to make a great leap with your clothing, though. For a pair of jeans, £90 may seem steep at first, but when you work out cost per wear, it can make for a better purchasing decision than typical high-street jeans that burst at the crotch after two months.

Do give it time. While both companies were pretty on the money about how I wanted to dress, both Anika and Chelsea told me that there was a bedding-in process when it came to achieving your fashion goals.

And lastly, don't hold back when it comes to what you want. If you'd like to look like a normcore hero, be vocal on your profile about your fashion needs. Like many self-improvement quests, it's in months three and four when any initial awkwardness fades and you start to put things together like a champion.