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7 Fall Outfits that Will Never Go Out of Style

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Happy first day of fall! I thought I’d celebrate by sharing 7 fall outfits that will never go out of style. Being trendy is fun and certainly something cool to experiment with, but there’s something to be said about the classic fall outfits. I’m not shy to try out the trends (I just bought a belt bag aka fanny pack everyone haha #notashamed #wellkinda), but I like to have a good amount of classic fall looks to ~fall~ back on too! 😉

7 Fall Outfits that Will Never Go Out of Style

1. checkered pants + loafers + basic tee
Why it will never go out of style:
This checkered print has been a classic for so long. And yet, a trend. So double whammy. I’ve reported it as a trend for a couple years now and it’s still going strong so I’d say this is pretty timeless! Oh, and loafers. Or in the words of my husband, “grandma shoes” 😉  But if looking like a grandma is wrong, I don’t want to be right. Related: Staples You Need to Prep Your Wardrobe for Fall

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shop similar: pants | loafers

2. striped top + denim skirt + mules
Why it will never go out of style: Because stripes. I know, I know, I talk about stripes all the time. Sorry, not sorry! But I wouldn’t talk about them so much if they weren’t so important. Denim skirts are a great transitional piece too, so it’s extra versatile for fall!

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shop similar: striped sweater | denim skirtscarf | straw bag

3. olive pants + denim shirt + leopard booties
Why it will never go out of style: Olive is one of those colors that always comes back as a staple for fall. A denim shirt is super versatile. And if you believe that leopard is a neutral like me, well then enough said!

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shop similar: denim shirt | olive pants | leopard booties

Related: 5 Fall Must Haves

4. denim dress + silk scarf + white boots
Why it will never go out of style: Whenever you see fall back to school styles being advertised, denim is always included in those styles. Why? It’s a foundation to pretty much any look! Whether it’s a denim skirt, a great pair of jeans, or this denim dress, it’s something worth having in your closet. And a lot of it too!

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shop similar: denim dress, similar here and here |  white boots

Related: 6 Stylish Ways to Wear Your Silk Scarf

5. check blazer + basic tee + denim skirt + slides
Why it will never go out of style: Classic print (just like outfit #1) and a classic denim foundation. And these mules/slides are a spin on the classic “Grandma” shoe! Now how many times can I say classic!?

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shop similar:  blazer | denim skirt 

Related: How to Wear Your Favorite Summer Pieces in Fall

6. striped top + checkered pants + leopard print blazer
Why it will never go out of style: I can hear what you’re thinking. “But Carolyn, this outfit looks so crazy, how is that a classic fall look?” Valid question. Answer: classic prints! If I were mixing some tribal with chevron and tie-dye, then maybe I’d be deserving of that side eye. But I’m not. Oh, and if you’re reading this and like to dress that way, that’s totally cool. You do you, boo.

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shop similar: blazer | pants

7. black tank + utility jacket + white culottes + leopard heels
Why it will never go out of style: Neutrals are always a yes and this pairing is different than your classic black and white but definitely fall appropriate. This utility jacket is a fall staple, and you usually see it in casual looks, but I wanted to dress it up a bit with the leopard heels. Oh and don’t worry, no white after labor day isn’t a thing!

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shop similar: utility jacket | culotte jeans | leopard heels

I actually already had my first pumpkin spice latte and after doing a sugar detox for a while, I found it to be way too sweet haha. So that won’t be how I ring in the new season officially, but I’ll for sure think of something!

What are you going to do to welcome fall?

Related Fashion Posts:

fall style


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.