Embracing 40 with a Wardrobe Revolution - Seeking Style Guidance

[surf2japan]

Today marks a milestone for me - I've turned 40! This birthday prompted me to scrutinize my wardrobe, which, let's say, is in dire need of an overhaul. I've primarily been a t-shirts and chinos guy, but now I aspire to be someone people regard as a "good dresser." There's something empowering about wearing clothes that exude style and confidence.

However, living in Tokyo, my options are limited due to my stature (95kg, 189cm), a far cry from the average here. I'm considering having clothes shipped from the States through a friend who's visiting soon. It's not the most practical long-term solution, but it's a start.

I'm curious - has anyone faced similar challenges? How do you manage to find clothes that fit well and suit your style? Also, for those who've had a style transformation at 40, what advice do you have? I'm all ears for brand recommendations, styling tips, or even personal anecdotes.

Let's make this a discussion about embracing personal style at any age and size, especially in a place like Tokyo where the fashion landscape might not always align with our body types.

Looking forward to your insights and stories!

 

[SteveMc]

Your situation isn't out of the ordinary. Many guys, when reaching a certain age feel that they need to redefine their style. I recommend that before you shell out any hard-earned dollars, take some time to figure out what style exactly you aspire for?

Do you plan wearing a suit and tie for the whole week? part of the week? perhaps a sport coat and slacks? even more casual? or a mixture of everything aforementioned? Budget is also a consideration.

Start by scouring IG and other places and notice how men that *you* consider well-dressed are dressing. It takes time and effort to develop a sense of style.

Just my two cents.

 

[TheIronDandy]

I found myself making the style change around 40 as well. It can be both exciting and scary, especially when you realise that you're at the point where you can afford to make really bad mistakes!

I think @SteveMc really nails it in the advice above: figure out what style you like, or "who do you want to dress like". Be honest with yourself, both with what you WANT and what you think you will actually be wearing regularly!

I guess it's also worth considering your budget; Tokyo has bespoke makers (expensive) that will make things to any size, and (relatively) nearby so does Hong Kong. The Seoul bespoke scene is supposedly reasonably priced - but even reasonably prices bespoke gets extremely expensive when compared to what most people spend on clothes.

If you're not looking for tailoring, the easiest solution is to find a brand you like, order some things online, and take the hit in import duties...

 

[GaiusM]

I was in a similar position, decided to dress better at 37 or so in Tokyo. At 90kg 180cm I just squeak by LL sizes for the most part. You might have a trickier run at it.
What style are you going for? For suit, sport coats, tailored trousers etc. there are plenty of bespoke and MTM tailors who can accommodate larger sizes, though they come at a price. For OTR check out Sakazen. It is a big 'n tall men's shop with lots of options and a few shops in Tokyo.
For a more casual yet put together look workwear and Amekaji (American Casual) might suit you as well. Often those styles have larger sizes available. Look up Hinoya and Americaya, both in Ameyoko in Okachimachi/Ueno. Brooks Brothers, J Press, Papa's, Paul Stuart, Scotch House etc. might have things that will fit you as well.
For basic shopping and inspiration Hankyu Men's in Ginza and Isetan in Shinjuku are musts. They may have a small selection of bigger sizes but they can point you in the right direction style-wise.
Some online shops are great once you know your measurements. I like Trad House Fukusumi - they definitely offer larger sizes.
If all else fails shop online and import. Be aware that Japanese customs levy heavy fees on some types of goods, particularly leather.
Main thing is to learn what style you are going for, what works for you. That might involve some mistakes. Learning process and all.

 

[justkwan]

Interesting thread as I also approach this milestone of 40.

First step would be to find some style influencers that you like--perhaps even some influencers that have a similar physique. Then those said influencers just might lead you to brands that work for them, or try to find a local tailor to help you recreate the style that catches your eye.

 

[ValidusLA]

Surprised now one has mentioned Ring Jacket before.
I was in their Osaka branch a couple weeks ago and they didn't have much in my size (I am a 56 shoulder), I'm betting w/ your #'s you're maybe a 54 or 52?
52/54 you might find at Ring, and they offer a very good and well priced MTM service.
I would suggest starting there and not going straight to looking for bespoke.