3 Transitional Fall Outfit Ideas

I’m feeling very inspired by all the new arrivals for fall. J.Crew and J.Crew Factory especially nailed it this year, and I’m looking forward to finally being able to wear some of those pieces in the next month. For now, I’m brainstorming some transitional fall outfit ideas that will carry me through the changing seasons and temperatures. Over time, I’ve found the key to styling transitional outfits is picking pieces that you can easily layer. You get double the wear out of the pieces in your closet, and it saves you from buying a whole new wardrobe every season. I’m a big advocate for wardrobe staples, and these versatile pieces are exactly that!

Everyday Lady Jacket

This is a wonderful transitional outfit idea and one you can wear from work to weekend. It includes a tan tweed jacket with the most beautiful white trim and gold button details. I styled it with a basic white crewneck tee and wide-leg jeans. For shoes I went with an affordable pair of cap toe ballet flats that look so much like designer styles but are a fraction of the cost. And I tied this look together with gold knot earrings and a black crossbody bag.

Tan Tweed Lady Jacket / White Crewneck T-Shirt / Colette Wide-Leg Jeans / Gold Knot Stud Earrings / Black Leather Crossbody Bag / Cap Toe Ballet Flats

This is a wonderful transitional outfit idea and one you can wear from work to weekend. This tan tweed jacket is one of my favorite new arrivals from J.Crew. The white trim and gold button details are so beautiful. Style it with a basic white crewneck tee and jeans. The Colette wide-leg jeans are my current favorite pair; they are so flattering. They run a little big, so I recommend sizing down. I’m also obsessed with these cap toe ballet flats. They look so much like designer styles but are a fraction of the cost, coming in at under $70. They are incredibly comfortable and run TTS. Finally, tie this look together with a few accessories like gold knot earrings and a black crossbody bag.

Versatile Black Midi Dress

This outfit starts with a classic black midi dress that you can easily style from day to night. I love that it has long sleeves, so you'll get the most wear out of it. I paired it with Veja white leather sneakers and a small ecru woven tote bag. Lastly, I accessorized with black sunglasses and silver huggie hoop earrings.

Black Puff Shoulder Midi Dress / Black Sunglasses / Silver Huggie Hoop Earrings / Ecru St Barths Mini Tote Bag / Veja Campo Leather Sneakers

Start with a classic black midi dress for a tried-and-true simple outfit idea that you can easily style from day to night. This midi dress is under $100. I love that it has long sleeves, so you’ll get the most wear out of it. To style it into late fall or winter, throw on a jacket and swap the Veja Sneakers for boots. You can’t go wrong with a simple Naghedi tote for a casual look, but feel free to dress it up with a leather crossbody bag for an evening outfit. Lastly, accessorize with black sunglasses and silver huggie hoop earrings.

Fall Skirt Outfit Idea

Skirts are another great transitional wardrobe staple for fall. For this outfit I styled a brown houndstooth skirt with a cream rollback cable-knit sweater. For shoes, I paired it with brown leather Chelsea boots. And to complete the outfit I accessorized with gold hoop earrings and a woven leather bucket bag.

Cream Cable-Knit Rollneck Sweater / Houndstooth Mini Skirt / Gold Hoop Earrings / Woven Bucket Bag / Brown Chelsea Boots

Skirts are another great transitional wardrobe staple for fall. This houndstooth skirt is one of my favorite fall basics for under $45. Style it with a cream cable-knit sweater, and feel free to layer a mid-length wool coat when the temps drop. As for shoes, I love pairing skirts with boots like these Chelsea boots or taller riding boots. Finally, complete the outfit with gold hoop earrings and a woven leather bucket bag.