Here is my attempt at listing my essentials.

Now revised with the feedback.

T Shirts in Earth Tones such as Brown, Olive Green and Cream
Long sleeved for colder weather
3/4 sleeved for in between
short sleeved for warm weather

Button Up Shirts

Denim Shirt
Chambray Shirt

Blue Jeans

Straight Legged Mid rise Blue Jeans
Slouchy Skinny Mid rise Blue Jeans
BF Blue Jeans

Summer Bottoms

Denim Skirt

Linen Pants - Wide Legged with draw string waist, neutral colours (Joe Fresh, Emmy Pants)

Toppers

Cardigans in earth tones. Waist length with buttons (cashmere for winter, cotton for warmer weather)

Denim Jacket

Brown Leather Jacket - Waist Length - Blazer Style

Footwear

Birks

Finn Comfort Sandals

Walking Shoes

Winter Boots - Neutral Colour - Upscale Snow Boot

Chelsea Boots

Frye Boots

Handbag

Vintage Coach Bag

Jewellery

Wedding Rings - Gold Band - Gold Engagement - Gold and Rose Gold Band (Right Hand)

Watch - Usually mix of Stainless Steel and Gold

Bracelet - Bangle - Silver or Gold

Outerwear

Olive Green Puffer

Burberry Trench Coat