10 Favorite Fall Transitional Outfits That Never Fail

09/12/2023

I was thinking about fall inspiration and my fall wardrobe at large and thought back (10 years plus) on the transitional outfits that never fail me, year after year. Taking the look back left me feeling inspired for fall transitional dressing, and made me think ahead to what pieces I might want to add in to give the rotation a little update.

Here are 10 favorite Fall transitional outfits that never fail:

I love a full 90’s throwback with fresh basics. This cropped white tee, clean straight leg jeans, topped with a neutral coatigan (this is the best one ever and it’s on sale) and oval tortoise frames is just that.

For the days when it’s cold in the morning and hot by noon, only a suede motorcycle jacket, a tank bodysuit, statement jeans and a tweed bag will do.

A band tee, flares, a cozy cardi and a colorful bag are always a casual fall day home run ensemble.

A cozy sweater set is easily dressed up to go out with a pair of mules or dressed down with sneakers for a lazy Sunday. I ordered this one and it’s so comfy; I can’t wait to style it for the season. I also have this set on my wish list in Minked.

I adore a flowing maxi skirt with a fitted tee and motorcycle boots.

Leather jacket season is short lived over here, and I love pairing one like this (which I’ve heard great things about but haven’t tried) with heels and a mini dress for warm days that turn to cool evenings.

A cream bag with booties and a bell sleeved mini dress is a go-to transitional fall outfit that’s ready for anything.

A sleeveless ribbed midi dress is chic (and bump friendly) under a moto jacket and short studded boots.

I’ve been wearing my vintage pilot suit for over 10 years now and I will never be over it. The ways to wear it are endless. I love this Frame version, which is currently on sale.