Since it’s still going to be super hot outside when school starts, you’re not going to want to break out the riding boots quite yet. Ankle booties will upgrade your look from summer to fall while still keeping you looking and feeling totally cool. 

Women's Geneva Hidden Wedge Booties, $40, target.com

A denim shirt dress is super versatile and can be transitioned from season to season effortlessly. 

Belted Chambray Shirt Dress, $30, forever21.com

Maxi-mize

Even though maxis totally scream “fun in the sun,” that doesn’t mean they can’t be worn well into the autumn months—especially in shirt form. Change up this staple by wearing it alone, over jeans, under a cardi...the possibilities are endless.

Red stripe maxi dress, $36, roolee.com

Keep it simple

2015 has been the year of delicate, simple and classic accessories. We love a good statement necklace every once in a while, but pieces that look polished and effortless are perfect for adding a little sparkle to any outfit.

Double strand necklace, $6, hm.com

Distressed denim gives off an oh-so effortless vibe and can be worn with virtually anything. Pop 'em on to make any ensemble street-chic.

Girlfriend jeans, $40, hm.com