denim skirt outfit

6 Classic Outfits You’ll Want To Add to Your Fall Outfit Rotation

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Fall feels like the best of both worlds in the fashion world. The weather can be warm enough to rock classic summer fashion pieces like denim skirts and crisp white shirts, but it’s also brisk enough to start layering on cashmere sweaters and blazers. If you’re stumped on what to wear this fall, look no further! I have compiled 6 classic outfits that can easily be recreated. With everything from lug sole boots to silk scarves, keep scrolling for looks you’ll want to add to your outfit rotation.

1. turtleneck + dress pants + camel coat + silk scarf + tote bag + loafers with socks

This classic look offers a little bit of everything: a wearable color palette of beige and white, classic shapes, and an elegant style. The long coat paired with the white turtleneck sweater makes the outfit feel modern and sleek, while the loafers and socks give this classic style a cozy and chic touch. Finish off your outfit by accessorizing with a silk scarf for extra style.

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2. denim jacket + wide-leg pants + loafers + jewelry

Even the most casual denim jacket can get a chic fall update with beige wide-leg pants. The pair of pants offers a great style and a relaxed silhouette that can be worn to the office and beyond.

When it comes to a great fall shoe option, no outfit can’t benefit from loafers. In fact, it is a closet staple that is the perfect piece to wear all season. A great way to finish a timeless style is with gold hoop earrings and layered necklaces for a statement look.

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3. button-down + sweater + denim skirt + blazer + socks with loafers + silk scarf

When the fall weather is indecisive, a good style tip to follow is to wear a denim skirt. Style it as you would with your go-to straight-leg jeans with pieces like a cashmere sweater and a button-down shirt layered with a black blazer.

For a slightly relaxed office look, round off your outfit with socks and loafers. To add more warmth to your ensemble, accessorize with a silk scarf.

shop similar: button-down | sweater | denim skirt | blazer | loafers | scarf

Related: Fall Monthly Outfit Calendar | 30+ Outfit Ideas

4. striped button-down + trench coat + jeans + crossbody bag + socks with loafers

Are you getting frustrated trying to create stylish looks this fall? A simple way of achieving a great style is with classic pieces. Building your outfit around a trench coat is never a bad idea!

The best thing about a trench coat is that you will get a lot of use from it this season. Even better? The styling possibilities are endless with a trench coat. Consider pairing it with a striped button-down for a seriously chic look. This combo can be worn as one of your everyday outfits this fall.

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5. turtleneck + shorts + lug sole boots + blazer

Break out your white summer shorts if bearing a little bit of leg is still an option for you. But instead of dressing them up with knee-high boots, wear lug sole boots instead. Though they started off as a trend, these boots are going to stick around for a while. They are practical and edgy and give an outfit a high fashion and trendy touch.

Style them with a turtleneck and layer on a black blazer for a professional look. Consider wearing this outfit for a date night or everyday wear.

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6. t-shirt + matching suit set + trench coat + loafers + crossbody bag

This final look is a great choice for fall. As many fashion lovers may know, a trench is a staple in a classic wardrobe. It offers a versatile and iconic silhouette that can easily turn basic items like t-shirts into a high-fashion look.

Pair your trench coat with other timeless garments like a matching suit set. A coordinated suit never misses; it is a surefire way to always look chic. Round off your look with black, polished loafers and a crossbody bag for maximum chicness!

shop similar: t-shirt | matching suit set (pants, blazer) | trench coat | loafers

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Classic items like blazers, loafers, and trench coats are the best investments you can make for your capsule wardrobe and fall outfits. However, if you feel a little stuck putting those pieces together, use this style guide to find classic outfits to wear this season.

To make sure your fall closet has everything you need, find out what pieces you need in your closet: Classic Fall Capsule Wardrobe (Shopping List, Outfit Ideas, & More!)


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.