October like May are considered months when people change their wardrobe from the cold season to the hot season or viceversa. During this change, I always ask myself ” how could I have bought something like this shirt?” and the next step is trash can. Seriously I have tried to keep old clothes saying to myself ” I am going to wear it next season” but then it never happens.

Recently my new theory is trash something old to have more space for new clothing. Very few times I have regretted my choice. To be honest I have kept three skirts that I used to wear (many many years ago) only because the fabrics are nice and I wish I could wear them again one day – never say never.

Whenever I clean my closet, I always make a list of things I would like to buy and today I would like to share this wish list with you: my 5 must-have pieces.

1. Little black dress: you might think it is trivial to choose a little black dress as a must-have but it is not. This type of dress is perfect for any occasion: business meetings, ceremonies, and dinners. You may want to consider to have one for fall/winter and a lighter one for spring /summer. I usually don’t wear dresses but I have one too in my closet.

The Bovary Lace Sheath Dress by Tory Burch is a timeless silhouette and a staple for cocktail party dressing. The flattering knee-length is perfect for a day-to-night transition. You can complete the outfit with a woolen coat or with a cashmere shawl.

2. IT Bag: we can discuss for hours about what an It Bag is or which ones are considered IT. For me an It Bag must be quality -made, it does not go out of fashion after one season and can be wore in several occasions matching various outfits.

Luggage mini in pony calfskin white by Celine.

3. Combined look: I could have choosen a tailleur (lady’s suit) with skirt but since I don’t wear skirts, I would rather have a tailored suit but with trousers.

Satin and velvet, lapel collar, button closing, multipockets, lined, high waisted, darts by Armani Collezioni.

4. Black pumps: no other shoes can better complete a lady-like outfit other than a glamorous pair of pumps. The pump is the perfect pair of heels for a cocktail party, dinner date or even to go to work.

Black kid leather pumps with asymmetric cross-over straps, almond toe, signature red soles by Christian Louboutin.

5. Overcoat: overcoats and jackets are my two favourite fall/winter garments simply because they complete every outfit. It does not matter, sometimes, what you are wearing underneath because the attention is captured by your coat. Another reason why I suggest to spend a little bit more on an outwear garment other than on a blouse or a sweater. My latest coat is navy blue.

Woolen coat with asymmetric high-stand collar, slit pockets, patent leather belt, A-line silhouette, back seams for a contoured shape by Cinzia Rocca.