How to Dress Like a Boss: 10 Items Every Businesswoman Needs in Her Closet

How to Dress Like a Boss: 10 Items Every Businesswoman Needs in Her Closet

This week we’re going back to basics. Sure, it can be fun to hop on trends and buy whimsical items, but the foundation of every great wardrobe is a closet with the essentials. In this blog, I’m talking about the ten items every businesswoman needs in her closet to dress like a boss.


  1. Tailored Blazer Made to Last

Up first, we have an absolute classic for any closet. A blazer is a staple for business and casual outfits. The classic black blazer like the one on Elizabeth Taylor above is sophisticated, and when paired with a blouse and cigarette dress pants it is a timeless “boss” look. Throw a blazer on a casual weekend outfit to give it polish and elevate your otherwise casual demeanor. I love a blazer with jeans moment. This blazer is made to last, and this is the perfect investment piece. Make sure you get this tailored to your body. Proper tailoring is easy to spot and can make all the difference when it comes to business clothes.


  1. Dress

A work dress is another item that should be tailored properly. Tailored clothing looks more expensive. A dress is also a great choice for the office because it’s a one-piece outfit and easy to style. If you’re running late, you’re one zip away from a sophisticated outfit. I recommend having a solid darker dress and a pattered vibrant dress in your closet.


  1. Power-Suit

It can be solid black, plaid, or a fun color. A well-made and well-tailored power suit will give you the confidence to walk into any boardroom and nail your presentation.


  1. Comfortable Heels or Ballet Flats

Finding work shoes that are comfortable, stylish, and of good quality can be challenging. When I find a pair that I love, I buy them in a few colors. Your shoes are going to get a lot of wear, so look for genuine leather. I recommend having both comfortable heels and ballet flats as part of your work wardrobe, but if you have a hard time wearing heels, ballet flats are a timeless shoe that looks great with dresses and pants. Also check out these kiltie shoes from The Office of Angela Scott which are both chic and cool.


  1. Dress Pants

As easy as the dress sounds, you probably live in your dress pants. Buy from brands that specialize in workwear, so you don’t get something too tight or too informal. You don’t need to wear the same style of dress pants every day; instead have a bit of fun with this staple item. You can try high-waisted flared pants, tailored cigarette pants, or straight-legged. Don’t be afraid to venture away from black and blue by trying plaid or camel.


  1. Quality Work Tote

Everyone needs a great tote for work. Totes are both stylish and functional. Find one with enough room for your computer and files and enough compartments for things like pens, keys, and your ID badge. This is a great piece to make an investment and grab something that is genuine leather. It will be a staple in your wardrobe for years to come.


  1. Neutral Trench

Trench coats are always fashionable and very versatile. There is nothing posher than a beige, long trench. The right trench can make you look polished and sophisticated. This jacket will look great with every outfit, including casual outfits. The great thing about some of these “boss” necessities is that they can be worn down and will get plenty of love.


  1. Nice Blouse

A nice blouse to pair with your pants, suit, or skirt. There are many variations of a nice blouse, and I’m sure you already have some in your closet. Try a stunning silk blouse if you’re looking for a luxurious timeless piece. You could also try a crosscut blouse or fun print to switch it up and add your personality to the outfit.


  1. Pencil Skirt

A pencil skirt is always chic. Sometimes we get into the habit of always reaching for our comfortable dress pants and blouse. A pencil skirt is a great item to shake up your wardrobe a bit but keep the same professional and stylish look.


  1. Button-Up Shirt

Equivalent to a men’s dress shirt, businesswomen should also have this staple in their closets. The classic button-up shirt is an item that will get a lot of weekly wear, so get a few to have a bit of variety. Style this with a pencil skirt for a professional look or tuck it into dark denim and pair it with a blazer for a casual workplace ensemble.


I love the classics, and at Jane Israel, I always make sure that I am designing and making clothes that will be well-loved quality items that make you feel like a boss. What is your favorite business wear closet staple?

PS, For tips on how to upgrade your online look grab our FREE GUIDE on How to Dress for Zoom!


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