Casual Fall Dressing

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Which season is your favorite to dress for? For a lot of people, it’s fall. Because there are so many things to love about fall clothes. Cozy sweaters, cute booties, great jackets – and those amazing fall colors. And all the fall layers.

But one thing that trips up a lot of people is the layers. You may not be sure what to layer under what, which jacket to wear over – and when (and how) do you add a layer? And then there’s the question of accessories.

So, in order to make getting dressed in cold weather just as simple as it is in warm weather, I wanted to share an easy way to create outfits this fall. Actually, it’s probably the easiest way to make some cute fall looks. Here’s the breakdown:

  • Start with a simple sweater and a pair of jeans.

  • Add a third piece.

  • Finish with intentional accessories.

And the best thing is that you don’t need to start from scratch every time you get dressed. Because you can take the same sweater and jeans and make a bunch of different looks – it’s really all about how you finish them off. So, here are a handful of fun and stylish fall outfits to take you from weekend errands to holiday lunches (and everywhere in between). And they all start with a sweater and jeans.

A few of my friends helped me out with these:

Take a look at the outfits, ask me any questions in the comments – and check out Kim in a few of these outfits at the end of this article!


A v-neck sweater is a perennial favorite and pale blue jeans are timeless – which makes them perfect as the basis for a bunch of easy fall outfits.

When in doubt, keep it simple for a day of running around – add a denim jacket (in a different shade than the jeans), fun sneakers and a pop color scarf.

To amp up your style for a girls’ brunch, grab a velvet jacket, standout booties and a scarf that ties all the colors together. (And check this out for all the different ways you can wear a velvet jacket this season.)

For lunch or work or casual date night, toss on a blazer and loafers – there’s nothing more classic than that.

When it’s time to be holiday festive (but still casual), add some shine! Then click here for other ways to dress festive when your holidays are casual.


When fall turns to winter, it’s all about being cozy. So, a turtleneck sweater (with dark blue jeans) fits the bill perfectly.

Brrr, it’s cold outside – and sometimes inside, too. Which means it’s time for a fur vest, suede boots and a stellar scarf.

When you’re in the mood, play with menswear influences with a navy pinstripe blazer and metallic loafers. And read this article for a few more ideas on adding menswear influences to your style.

Add some feminine color for an evening out with a lavender leather jacket and floral print booties – this outfit is sure to turn heads.

When you’re in the mood to grab the spotlight, an embellished jacket and white booties are all you need to sparkle all night.

And, as promised, here is Kim in a few of these outfits. Doesn’t she look great?

Don’t forget to check out my friends:

And if we’re not already friends on social media, let’s fix that. Follow me here on Instagram and Facebook. And check me out on Pinterest to see what inspires me!


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