There’s no question about it. Fall is my favorite season to dress for. Layers, tartans, knits, and suedes make up the sartorial climate as the actual climate transforms into one big cozy hug.

Candles are lit, days are shorter, meals taste better, and friends come to call. And before all my loyal-to-summer friends dismiss my love of these approaching chilly days, remember there’s no fall like a New England fall and my childhood story is set in a small Connecticut town – not unlike the Stars Hollow of Gilmore Girls. I was born to love fall.

But beyond being an ode to Autumn, I wanted this post to outline the items that will be and have always been in my fall wardrobe.

Fall Spice Outfit 8
Fall Spice Outfit 6

Outfit 1: Workplace Casual

About as classic as you can go with a fall look, I wear a look like this on repeat the days I’m not shooting new blog content.

Let’s Break It Down

  1. Crewneck Sweater – Rust. Spice. Caramel. Camel. Tan. Brown. No matter your preferred hue, it’s all about the warm tones in the fall. Choose a crewneck sweater with a more relaxed fit for a little more comfort.
  2. Medium or Dark Wash Denim – Save your light washes for the spring and summer. Fall is all about depth and layers so reach for or invest in a good pair of dark wash jeans to last you throughout the cooler months.
  3. Block Heels – I love them for two reasons: they’re easy to walk in and elongate your legs while wearing denim. Pick them up in tan or brown for a comfy yet glamorous look.
  4. Tan Trench – There’s nothing more classic than a tan trench. If you don’t have one in your closet already it’s time to invest. Take the time to find a style that you’re comfortable with and pull the trigger.
  5. Hair Scarf – Unlike a trench coat, hair scarves are not about investment and more about $4 well spent. I love adding them for a Parisian touch to my ponytails on days when my hair is misbehaving.
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Fall Spice Outfit 4
Fall Spice Outfit 9

Outfit 2: Plaid Perfection

Haven’t you heard? Blazers are in. Chances are you have a blazer or two skulking around the back of your closet. It’s time to pull them back out and pair with everything from dresses to denim.

Let’s Break It Down

  1. Little Black Versatile Dress – Everyone knows the golden rule of fashion is to pull out the LBD whenever things get tough. One of my favorites is a long sleeved shirt dress that pairs with everything from leggings and boots to heels and pearls. While fancy is fun, versatile is much more cost-effective. I find my favorite dresses like these at Banana Republic.
  2. Plaid Blazer – To my surprise Target has a great collection of workwear items via their A New Day line. They’re chic and snappy and on-trend without being trendy. This blazer was a $30 steal right off the rack.
  3. Brown Belt – If I’m wearing pants I’m likely wearing this belt. Do yourself a favor and buy a last-a-lifetime leather option like this.
  4. Chelsea Boots – I’ve waxed on about the joys of these boots before and I’ll say it again… I’ve never put anything comfier on my feet. I walked both Seattle and Portland in these boots without breaking them in and not a blister in sight. The style of a chelsea boot is also very flattering and perfect for toning down a business casual ensemble.
Fall Plaid 1
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Fall Plaid 4

Outfit 3: Casual

Perfect for travel days, coffee shop days, and weekends, this look is all about balancing lengths and layers without being constricted. The classic denim jacket gets an upgrade with an oversized fit and comfort becomes chic with a pair of seriously sporty sneakers.

Let’s Break It Down

  1. Oversized Sweatshirt – If you have yet to discover the immense joy an oversized sweatshirt brings, it’s time to introduce to your new best friend: the Aerie Desert Sweatshirt. Perfectly oversized and slightly distressed it’s the perfect compliment to leggings in the winter, skirts in the spring, and lounging anytime of the year.
  2. Oversized Denim Jacket – An affordable option to the fuzzy and puffy coat craze, a denim jacket will never go out of style. And with the resurgence of 80s fashion an oversized jacket is perfect. This was an Amazon find for me and at $38 I thought it was a good deal.
  3. Black Leggings – Effortless and slimming, I wear black pants 80% of the time. These suede-leggings from Banana Republic lets me get away with wearing supremely comfortable pants to meetings.
  4. Chic Sneakers – It’s Adidas all the way around here. This is my second pair of NMD shoes with the first ones lasting me at least 3 years. You might balk at the price, but sometime you just have to pay for style.
Fall Sporty 3
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Fall Sporty 2
Fall Sporty 4

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Emily Lewandowski @emilyjlewandowski