Stylish pieces to seamlessly take you from fall to winter

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We are well into October and I'm wondering if Fall is ever going to stop by and hang out for a little bit. This weekend was a teaser but since temperatures are supposed to be hovering somewhere near 90 degrees today, I'm wondering if we're going to be forced to skip fall and jump right into winter. Let's all do some sort of dance to the pumpkin spice latte gods or the people controlling that weird PSL (hate myself for using that acronym) Snapchat filter that this isn't the case.

Since the budget isn't allowing for a ton of new clothes this season, I'm hunting down pieces that can transition easily and that I won't grow tired of after a couple wears. I'm also looking for pieces that work with stuff I already have in my closet. Basically, I know everything below – with the exception of the dress – can be worn with a striped t-shirt. And since that's the essential building block of my wardrobe, it means these all get the stamp of approval.

1 | 2 | 3 | 4 | 5 | 6 | 7a + 7b | 8

Sale Alert: This J.Crew button down is 30% off right now along with this vest – which I own in three colors – and all outerwear. Makes it a great time to snag a new coat. Plus, this Old Navy dress and Gap sweater are both 40% off along with everything else there and Banana Republic. Oh and here's a more budget-friendly pair of gray slip-on sneakers. I WANT the Vince pair but my wallet says get the Vans.

The only thing that may be a little out of my comfort zone are these slip-ons. I've been wanting both a pair of casual ones for weekend running around and a sleek pointy pair as an alternative to heels with cropped work pants. I've been lusting over the Everlane flats but saw these and thought they were a dead ringer. You will NEVER guess who makes them.

Last but not least, lately I'm using a bold lip color as a way to distract from an otherwise simple outfit. I've recently tried out this exact shade (Rouge Zinnia – 734) of the Dior Rouge lipsticks and it gets two very enthusiastic thumbs up from me. Goes on smooth in one coat and give you that, "oh I just found this in my bag and threw it on" look. Chic but not like you're trying too hard to make fetch happen.

p.s – if you're wanting to do a little more fall shopping, here's my top 10 picks for under $50.

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