Classic fall outfits

I always look forward to the fall season because fall fashion is chic, warm, and comfortable. If you want a bulletproof fall wardrobe, there are several ways to create classic fall outfits that stand the test of time. Most importantly, these outfits can help you transition to the colder winter months. As a personal stylist, here are my go-to wardrobe items for that chic and classic fall look.

High-Quality Layering

Fall fashion is about keeping warm as the weather cools down. Since this time of year can go from cool to warm depending on the time of day, layering is important. I’m not talking about wearing cheap-looking sweaters and frumpy layers. Your classic fall outfits must be of high quality items.

I’m talking about classic investment pieces that you will wear for many years to come! These layering pieces can also be mixed and matched to create new outfits through the fall and yes, winter season. Here are my recommendations for classic fall layering pieces:

1. A High-Quality Plaid Blazer

plaid blazer

Whether it is a bold or subtle plaid pattern, you can’t do wrong with this classic fall outfit staple. Wear it with skirts and tights, leggings and dress pants. Layer it over a t-shirt, turtleneck, or cashmere crew. A high-quality plaid blazer is essential in pulling together classic fall outfits.

2. Trench Coat

trench coat

A light trench coat is the perfect layering piece in your fall fashion wardrobe. It’s chic, light and classic. Invest in one in a neutral color that fits well. Wearing tailored clothing during the fall with help you look chic and classic.

3. Lightweight Cashmere Sweaters

grey cashmere sweater

A high-quality lightweight cashmere sweater is the perfect fall outfit booster. It’s warm, cozy and chic. I suggest a lightweight cashmere sweater. Get them in colors that are flattering to your skin tone.

Classic Fall Outfit Basics

I have invested in these classic fall wardrobe basics and have been wearing them for years. I love pulling them out of my closet every fall season. Here are the must-have basics for your classic fall wardrobe.

4. Light-weight Turtleneck Sweater

short sleeve turtleneck sweater

Light-weight turtlenecks are versatile and the perfect classic base layer for fall weather. They are also great transition pieces for winter outfits. Invest in high-quality turtlenecks made of natural fibers, which help regulate body temperature.

I like getting them in different sleeve lengths and even have some that are sleeveless. This adds to its versatility!

5. Tailored Trousers

plaid trousers

Classic tailored trousers must have a place in your fall wardrobe. This chic, warm, and sophisticated fall wardrobe staple will instantly elevate your fall style. They are versatile, warm and comfortable. Get them in cotton and wool. This will be a foundations piece for your classic fall outfits.

6. Tweed Skirt

tweed skirt

The tweed skirt is an iconic and classic staple to add to your fall wardrobe. This classic staple will help you create fashionable and chic outfits that are effortless. Wear them with your cashmere sweaters, turtlenecks, and even high-quality tee shirts.

Classic Fall Accessory Staples

These fall accessories are a must-have for classic fall styles. Elevate your fall outfit this season with these tried and true classics:

7. Classic Fall Riding Boots

black riding boots

I recommend getting both a black and brown pair of classic riding boots to elevate your fall wardrobe. These classic boots can be worn with skirts, leggings, and under wide-leg pants. This is a chic fall staple accessory that will level up your fall style. Here is a great video on how to choose the perfect riding boots:

8. Classic Fall Tote Handbag

black leather tote bag

No classic fall wardrobe is complete without a high-quality neutral-color tote bag. Get on in classic, leather, suede, or durable nylon. This will be your workhorse bag from fall through winter.

Classic Fall Outfits Are an Investment

You won’t regret investing in your fall wardrobe. These high-quality layering, basics, and accessories will be the foundation for your classic fall wardrobe. These items are easy to mix and match to create a classic fall capsule wardrobe. Choose natural fibers, earthy neutral colors, and tailored fitting for a chic and classic fall look in 2024.

More Classic Fall Fashion Inspo

Here are my favorite places to shop for high quality fall fashion:

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