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What to Wear to Work this Fall

by habituallychic

09 . 12 . 19

My friend Stacey used to work in finance in New York but moved to San Francisco a few years ago to work in the tech world. Her last two jobs were in very casual offices but she just started a job at a new startup with “a kickass female CEO who would never be caught dead in a hoodie”. She asked me for ideas on what to wear to work that included comfortable blazers that can be worn with jeans. I decided to put together some mix and match ideas that can help anyone looking to update their fall work wardrobe. I’ve styled some of the outfits with skirts and pants but you could easily swap them out for jeans. You could also mix in any of the pieces from my How to Style White Jeans for Fall post and The Best Shoes and Boots for Fall post.

In my past life, I worked in corporate offices and creative design spaces so I understand what works well when you want to make a good impression. Since I’ve gone out on my own and often work from home, I am allowed to dress more casually but I still always want to be pulled together which is the basis for all of these outfits.

I’m loving double breasted blazers for fall. This double-breasted checked woven blazer has so many different colors that you could wear it with almost anything in your closet.

You know how I love ivory silk blouses and I own many from Sézane. This Charlotte Shirt might be the one I add to my closet this fall. They are always great for dressing up jeans and if you get hot and want to take off your jacket, you will still look pulled together.

If you are allowed to wear jeans to work, I would keep them dark and without rips in case you have to meet a client or have a last minute meeting pop up. These high rise toothpick jeans are 30% off right now with the code SHOPNOW.

These leopard calf hair flats are my new favorite shoes for fall and could be worn with jeans, black pants, and even skirts and dresses. They are also 30% off right now with the code SHOPNOW.

Tote bags are to New Yorkers what cars are to Angelenos. Totes carry our extra shoes, umbrellas, gym clothes, make up, and more each day. This tan leather tote is one of the nicest I’ve seen at a reasonable price. It’s an even better price because it’s 30% off right now with the code SHOPNOW.

On cold mornings on your way to work, wrap your neck in a Heidi Wynne cashmere scarf. It’s also great for overly air conditioned offices.

Celine sent many houndstooth pieces that look similar to this down the fall 2019 runway. A much less expensive option is this chic houndstooth tweed blazer.

I promise this is the last ivory silk blouse I’m going to post but I love the covered buttons on this one. It’s also available in four other colors and 30% off right now with the code SHOPNOW.

Celine also sent many below the knee 70’s inspired skirts down the fall runway. This corduroy midi skirt is much more budget friendly and comes in five colors. You could also style it with a chambray shirt now and a fair isle sweater later when it gets colder. I also think longer midi skirts are more appropriate for the office than mini skirts.

I love the low walkable heel on these python-effect leather knee-high boots. If snakes aren’t your thing, they are also available in burgundy and black leather.

If you plan to treat yourself to one splurge item this fall, make it this Celine Triomphe bag in textile and natural calfskin. It’s at the top of my fall wish list.

Celine also styled their fall 2019 looks with patterned scarves. I love the pop of orange in this printed silk-twill scarf mixed with tweed for autumn.

I’ve already been wearing my grey flannel double breasted blazer with jeans and a blouse on cooler days. I love the covered buttons on this double-breasted wool blazer. Pair it with jeans for a more casual look or with the matching pants for a more professional style.

You know I would pair the grey flannel blazer with an ivory blouse but I also like it paired with this grey cashmere crewneck sweater for a less dressed up look. And since I never met a grey sweater I didn’t like, I just ordered this merino wool boyfriend crewneck sweatshirt for more casual days. You could also pair the suit with a thin sweatshirt for another option or pair the pants with a sweater with a shirt or blouse underneath. I love how many ways you can mix and match the suit. I like the grey tone on tone look but almost any color sweater or blouse would work.

The matching wool tapered trousers are cropped so you could pair them with heels, flats, or sneakers.

I actually own these Zespa sneakers with snakeskin. I found the brand in Paris and love the minimal look of their sneakers. Stacey is allowed to wear sneakers to work so I’d recommend staying with simple styles and nothing with too much pattern or color. I always wear mine for traveling too.

I prefer to pair grey with tan or burgundy over black. This burgundy large textured-leather tote looks chic enough to help get you promoted at work.

Any color Heidi Wynne cashmere scarf would go with this outfit.

I like this lighter colored blazer in rose plaid for those of you who live in warmer climates. It’s also 30% off with the code SHOPNOW.

Throwing a plaid blazer over a floral midi dress is a great way to transition to fall in warmer weather and climates too. It’s also 30% off with the code SHOPNOW.

Another way to transition your summer pieces for fall is pairing them with heavier fabrics and materials like these suede perfect pumps. They are available in 12 different colors and three heel heights.

If you can’t afford Celine, this Ferian tan leather shoulder bag is a great alternative.

You can wear an Apple Watch like everyone else in the tech world or you could differentiate yourself with this chic Cartier Tank Watch. You can also find vintage options for much less online.

I really love silk scarves lately whether tied around my neck or on my bag like this Dutch floral silk scarf. It’s another great option for warmer weather.

Stacey told me she likes knit blazers because they are comfortable. This gilded button tweed jacket is a chic option for fall that would work with jeans, pants, and skirts. You could even throw it over a black shift dress. It’s also 40% off right now with the code FRIENDS40.

The gilded button tweed jacket is a great day to night option. Pair it during the day with a green silk blouse and at night with this black silk tank top or this black camisole. You could also pair it with a black cashmere turtleneck.

I’d pair the gilded button tweed jacket with these cropped wide-leg pants or a black pleated midi skirt. Or you could pair it with my favorite pants, the Cameron slim crop pant in four-season stretch. They are all 30% off with the code SHOPNOW.

You could coordinate the green in the gilded button tweed jacket with these green suede tassel loafers. If that’s too matchy matchy for you, there is a black option. They’re both 40% off with the code FRIENDS40.

I can’t think of any woman who couldn’t use this chic black leather tote for work or travel. It’s 30% off with the code SHOPNOW.

I live in my tan and black Heidi Wynne cashmere scarves all fall and winter. They especially great for traveling.

I think it’s nice to have neutral nails for work since they don’t show chips. My favorite pale shades are Deborah Lippman Gel Lab Pro Nail Polish in baby love and naked. It’s safer than salon gel polishes and doesn’t require UV light.