My fashion neurosis is now in overdrive. I'm leaving for Japan on Friday and after weeks (yes weeks!) of deliberation, I think I've finally figured out what's coming with me.

Usually on a trip like this, I would be very practical and pack what I needed for sightseeing and hiking, and maybe dress it up a bit around the edges. But when I’m heading for world's finest fashion nation (sorry skylurker, even better than France!) I have to bring my A-game.

It starts and ends with the shoes. They need to be comfortable. They need to come off easily indoors. They need to be as smart and formal as possible. I’m packing three pairs.

1. Hiking boots - for outdoors and acting basic.
We're planning a few days hiking between city visits, so they need to come with me. The big challenge is always to work gear into my holiday wardrobe and make them worth their weight without sacrificing style.

I've had these boots for over twenty years and they’re still going strong after walking the Inca Trail and the West Highland Way. The classic leather style (hard to find these days) makes them slightly easier to style. Not easy to take off indoors but I like to think they look pretty smart with bright skater laces, and for this trip I've chosen acid yellow/green (inspired by Angie's genius combination of cognac and citron.)

To go along with these, I am packing:

• Arcteryx hiking pants - Not bad for gear. Nice material, nice cut.
• Two button down shirts one Uniqlo +J, one Paul Smith (not pictured.) A good way to smarten up the hiking pants and boots.
• Mamut Gore-Tex anorak (not pictured) Honestly, I’d rather not take this at all. Velcro! The horror! I can’t be without it on the side of a hill in a rainstorm though, so in it goes.
• Uniqlo compact down jacket - Their best product ever. Incredibly useful and actually rather cute.
• Three stripy long sleeved tees. They can make anything look stylish.

2. George Cox creepers - for urban cool.
These are a cult item in Japan apparently. They tick all the boxes, being smart, comfortable and easily slipped on and off.

These look brilliant with:

• MMM x H&M oversized pants. Wide pants are trending in Tokyo at the moment, according to my sources. Not as impractical as they look. Fab with a stripy tee and...
• Convertible bomber jacket, made by me. A great team player and a good counterpoint to the hiking boots.
• Crash pants ByBrown - My favourite trousers, can wear them cropped or full length. Good with all tops and play nicely with the hiking boots when paired with…
• Leather and wool jumper, made by me. Completes the olive/cognac/citron combo.

3. Trippen Dream booties - for dressing up.
I need something dressier than the creepers and these really up the ante. Not so easy to slip on and off, but not so difficult either. Improbably comfortable, these wear like sneakers even with the platform.

These open up more dressy possibilities such as:

• White shirt dress, made by me after an avant-garde classic by Issey Miyake. Has to come along. Boho-lite with hiking pants and boots, minimal urban cool with all black.
• White plisse midi skirt, vintage. Another item trending in Tokyo. Chic and ladylike with the Trippens and Breton shirt, downtown cool with creepers and leather jumper and surprisingly workable Harajuku style with the Issey shirt, convertible bomber and hiking boots, if I can work up the nerve.
• Multicolour short sleeve knit from Cos. Great with the skirt, in case I want to make like a gangsta and flash some ink.
• Taffeta bomber by Back. Not a duplicate, more of a complement. White needs black and this is dressier than the compact down jacket. Lightweight, packs tiny. I may swap this out for my pagoda shoulder blazer, space permitting.
• Black silk blouse ByBrown, not pictured. Perfect with black pants in case I need to get really fancy.

———
And that’s it. I think I’ve covered all bases, things mix and match fairly well and it should all fit in a small suitcase, along with underwear, socks, swimwear, one or two tees and a couple of scarves and hats. Weather forecast says highs of around 20C/68F, so I'm thinking I'll be warm enough with layering.

Breaks down like this:

• 3 pairs of shoes
• 3 pairs pants
• 3 jackets
• 1 skirt
• 2 mid-layers
• 3 long sleeved tees
• 2 button down shirts
• 1 silk blouse
• 1 shirt dress
• 1 fancy knit

If you’ve even read this far, (thank you for your patience with my overthinking!) I’d really value your opinion. This is a pair of shoes and several garments more than I’d normally pack, but I don’t usually go from very casual to very dressy in a single capsule.

What do you think? Am I being over-ambitious with the dressy choices? Can you spot any gaps? Should I try to make room for the blazer instead of the second bomber?

Thanks for taking the time!