Reinventing Yourself – The Starting from Scratch List

Paul Smith London – The Byard Solid Wool Suit ( $837) via Park & Bond

Six years ago I put together a starting from scratch list.  The idea was to reinvent myself, and the quickest way was with a new look.

The idea of reinventing myself, wasn’t a new thing for me and I’m sure you’ve all had a similar experience at some point in your lives. But I had never made a list and put time into thinking what exactly I needed to change.

It’s been awhile since I’ve gone through that process and I’m thinking of refreshing and replacing some of the items on my list. I’ll share that shopping list with you soon. First, I thought I’d share the basic elements of that original list along with some style tips.

The Basics:

Socks – I go through tons of socks… I’m really not sure why.

Bold colours! Let a bit of personality peek out with every step you take. (Calvin Klein 3-pack non-binding dress sock $23 CAD)
Corgi Striped Knitted Sock – $30 (

Underwear/Undershirts – I like to have fresh new underwear in the drawer.  So I’m always throwing out the old and replacing them.

Hot, cold, no matter the weather… I always wear a v-neck undershirt with my dress shirts. But that’s just me. (I prefer Hanes. 3-pack $20 CAD)
Silk with a mesh front… these Joe Boxer Tech boxer/briefs are Project 40 approved! (A little pricey  at about $20 but worth it.)
  • H&M is a great place to load up on underwear. Good quality at the right price.


Black Loafers – these are simply essential.

Must have – black loafer that holds a shine. (the Colebrook – $180)

The Double Monk – Okay, the double monk isn’t essential but  a brown loafer is.

What more can I say?
John Lobb – Truro Tasselled Leather Loafers – $1,360

Brown/Blue Saddle Shoes – I love saddle shoes. Comfortable and stylish. A nice casual shoe rounds out the starting from scratch shoe list.

I have a pair of Florsheim that I bought at a DSW in Buffalo for $75. I love them!
  • I love shoes! I’m sure you can tell. I believe good shoes and a good haircut are the foundations of men’s style.

Four Season Suits:

If you’re starting from scratch I would suggest a slim fit, single breasted, two button navy blue suit, followed by a nice four season grey suit.

Here’s an example –

Blue – Burberry London $1,695
Grey – YSL $1,495

  • The corporate uniform. These are your go to business suits. They can be worn several times a week and no one will notice.
  • Make sure the jacket fits for shoulders, chest and length. Everything else can be altered.
  • Here is a hint when you are buying off the rack. Always buy one size smaller than you think you are.
  • Final rule of thumb, just do one button on your suit jacket. On a two button, single breasted suit, just do up the top button. On a three button, single breasted, do up the second button.


Build your personal shirt wardrobe with Bespoke Online Tailors.

  • My closet is full of custom-made, french cuff dress shirts. I shop primarily at Maxwell’s. They are a Hong Kong based travelling tailor. Get measured up once in person or send your measurements in and you can shop through their online catalogue.  Eight to ten weeks later you have custom-made dress shirts delivered to you home (3 shirts for $150).
  • You’ll also need a casual button down shirt to wear with jeans and a blazer. I’m thinking the classic Ralph Lauren Oxford:
Polo Ralph Lauren Oxford Shirt – $95 (
  • Make sure the collar and shoulders fit and the arms are the right length. The rest can be altered. Yes… you can have you shirts altered too. I didn’t realize this myself until a few years ago. For the longest time I wore off the rack shirts with a bunch of extra material at the waist. I didn’t know that for a few dollars, a tailor could make this problem disappear. Now you know.

Sports Jacket/Blazer:

I have the need for tweed –

Okay, a blue blazer, if you don’t have one should be your first buy. But take a moment and just look at this jacket… now imagine all the things you could do with it. It’s a must have also.

But, a blue blazer is a closet essential. Dressed up with grey pants or worn a little more casually with khakis, it’s a versatile item. Then, there is my personal favorite, a blue blazer with jeans and a white shirt.

  • Choose a dark navy blue to increase its versatility.
  • To save some money, your blue suit can also be broken up with the blazer worn separately with jeans, textured trousers or khakis.


I have more jeans in my closet now than I care to mention. But here’s a good starting point –

Levi’s 1967 505 Washed Slevedge Denim Slim Jeans – $250
  • If you are starting from scratch, look for a slim fit dark jean. It can be dressed up or down and will work perfectly with the new blue or tweed blazer in your wardrobe.
  • When you get your new jeans altered, make sure the hemline will work with both a loafer or a lace-up shoe.

The Accessories:

The Watch- You need a grown man’s watch.

Uniform Wares – 150 Series Slim Steel Wristwatch – $310 (
  • Never trust a man who doesn’t wear a watch. If he doesn’t care about his own time, he won’t care about yours.
  • Your grown man’s watch doesn’t need to be expensive. Classic styles are available at all price points.

Travel Bag/tote – I know, I’ve been talking about this forever… I still don’t have one!

Aubin & Wills – Tote Bag $120 (

Cuff Links – It’s the little details that complete the look. French cuffs and understated cuff links are favorites of mine.

Tiffany 1837™ cuff links – $525 CAD
  • The finishing touch to your French cuff shirt.
  • Simple and classy is my preference. Not too big, not too small and avoid the novelty cuff links.

Wallet – I may be in the market for a new wallet. I’m still undecided on this one. I like the one I have but since I’m starting my 40’s fresh it feels like a new wallet would signal a fresh start.

Prada men’s credit card holder – $133 CAD
  • The thin card holder wallet (combined with your new money clip) is definitely an essential. Replace the filing cabinet wallet with a sleek look.
So there it is, my starting from scratch list.
I’ve come a long way since I put together the original list. I hope sharing this  helps you as much as creating it helped me.


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