What wardrobe items are really worth investing in?

You want to dress like a boss, but you’re operating on a non-boss income level. How do you determine where to invest so that your wardrobe presents your best you, while not going into debt or having a closet full of “stuff” that you don’t really need?

It’s a pressing issue for many of us. We’ve surveyed a number of boss women, and also reflected back on our time in board rooms and corporate settings, and we’ve come up with this short list of 12 investment-worthy items. We think these are no-regrets purchases that – when made after careful consideration and thought – will serve you well for a decade or more.

Think of them as foundations for a wardrobe – start with the right base, and everything else will fall into place.

1. Black basics. If you find a great black skirt, dress, or pair of trousers that fit well and are easy to dress up or down, definitely buy them – even if you have to stretch to afford it. You can live in them for days, just switching up the tops and accessories you pair them with. Dolce & Gabbana has fantastic basic black skirts, dresses, and pants, particularly in their pre-fall collections. Dior, Derek Lam, Theory, Prada, Gabriela Hearst and Givenchy are also reliable sources. You might not believe it, but the maximalist Gucci also almost always has great classic skirts in neutral colors that are really flattering. Try to get these basic pieces in jersey – maybe with some stretch – and you won’t regret it.

2. A white shirt. A crisp white shirt is just always a good idea – when we need a photo taken, or just don’t want to think too much, we reach for one of these. Anne Fontaine has demonstrated that a white shirt can take an infinite number of forms – but if you only buy one, make it a simple architectural silhouette (probably with long sleeves). Theory makes excellent ones, sometimes with a bit of stretch in them, which makes them even more flattering and comfortable. So does Veronica Beard.

3. A great pair of jeans. Our go-to jeans are dark navy. But one of our chic friends lives in black ones. White jeans look crisp all year round. Your call.

4. A leather jacket. You need one, and if you choose well, you can wear it to work, out on the town, for a dinner date, or for brunch with friends. Rick Owens is the master of the cool-girl leather jacket. Vince makes lightweight colored leather jackets that travel really well.

5. A trench. When we travel, we almost always bring a trench – and we’re almost always really glad that we did. Burberry’s has what you need, and in our experience the brand’s products are durable, easy to clean, and also easy to dress up or down as needed.

6. An overcoat. If you’re living or working in a cold climate, you need one go-to overcoat. Depending on your style and preferences, it might be a classic wool or a long puffer. Moncler, Chanel, Dior, Bottega Veneta, Altuzarra and Louis Vuitton almost always have terrific investment outerwear as part of their pre-fall and fall-winter collections. If you shop carefully, you’ll be able to score one on sale in late autumn.

7. A bag for work. Way back in the day, boss women actually carried dark brown or black rectangular briefcases, the better to fit in with the boys. Happily, those days are long gone. Invest in a bag that will hold what you need without weighing you down too much. Having easy access from the outside to your phone, laptop, keys and other necessities is a must. We’ve been carrying a black patent Louis Vuitton bag for lo these many years, and it still looks like new. We’ve found that LV, FENDI, Valentino, Gucci and Prada – while expensive – tend to be experts in luggage and leather goods. If you’re making an investment in a bag, you aren’t going to go wrong with any of those. You can of course do Chanel. That’s a given.

8. A bag for play. A clutch or a small cross-body for black-tie events or just a fun night on the town is really the only other bag you need. Sparkly black or metallic silver would be our choice if we could only have one of these. Saint Laurent Paris has incredibly chic patent and sequined black evening bags that will take you anywhere you need to go. Balenciaga, Chloe and The Row have great ones, too.

9. Heels that you can walk comfortably in. Whatever heel height works for you is the one you should choose. We live in a pair of round-toed black platform pumps from Christian Louboutin because they’re chic, comfortable and serious. There are fantastic kitten heels in the market right now, too. Other brands we have never had a bad shoe experience with? Prada, Saint Laurent and Chanel. We love Valentino Rock Studs, Gianvito Rossi and Aquazzura, too. If you don’t work in an environment that requires a formal shoe, invest in a pair of great black boots, booties, or sneakers that make you feel like a boss.

10. Classic ballet flats. If you can spring for it, a pair of Chanel ballet flats are going to last you basically forever. The secret of many a boss woman is their go-to pair of two-toned flats in black and “nude.” They’ll coordinate with every single thing in your wardrobe, and they are nearly indestructible.

 11. Two pairs of earrings. One traditional – like pearl, diamond, silver or brushed gold. And one that’s just crazy-fun and that makes you feel happy. If you’re lucky, you’ve inherited the traditional pair from your great-grandmother. If not, the Style Council loves Cartier and Van Cleefs. We love Ippolita earrings – they’re not inexpensive, but we reach for them every time, and they’ve never let us down, never needed repair, and always make us feel great. Ditto Marni, Jennifer Fisher, and Dinosaur Designs.

12. A statement belt. It’s amazing how a belt can catapult you into an entirely new level of chic. We still remember when former First Lady Michelle Obama was spotted wearing an iconic Alaia belt soon after her husband declared his candidacy for President. The fashion world instantly took notice – she was there to win. That’s the power of a great accessory. Have a look at Gucci, Alaia and Alexander McQueen if you want to follow suit.

You’ll get bored with these items long before they’ll wear out, and that’s OK. As your income rises, you can have fun building on the strong foundation you’ve created.

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