10 Transitional Pieces to Wear Now and Into Fall

collage of Transitional Pieces from summer to fall

1. Floral Tiered Ruffle Midi Skirt | 2. Check Newbury Blazer | 3. Floral Puff Sleeve Blue Blouse | 4. Floral Shirred Blouse | 5. Hutton Blazer | 6. Floral Shirred Blouse | 7. Diamond Jacquard Jacket | 8. Plaid Jacquard Cardigan | 9. Flutter Sleeve Wrap Dress | 10. Plaid Bedford Blazer

Several years ago, I had a year long partnership with Ann Taylor, and to this day, it is still one of my favorite projects I’ve ever worked on (some of my old posts from this partnership here, here and here!). I came to love Ann Taylor as a retailer for unique pieces that could do double duty for work and play. Recently, I have been falling for their collections all over again. They’re a good mix of quality basics and fun, patterned pieces that give life to your wardrobe and add touches of femininity to any work outfit.

Yes, I know it’s still only August, but it’s hard not to start thinking about fall—literally my favorite season to dress for, especially when brands are starting to share their end of summer collections that have pieces that work for both summer and fall.

How to Wear Transition Pieces for Summer & Fall

You may have noticed, but one of my goals here is not to just convince you to buy more stuff, but to buy clothing intentionally and be able to wear it multiple ways to truly get the most out of your wardrobe. So, I highlighted a few items from above to give you ideas on how you can wear these pieces now, and also into fall:

woman wearing camel blazer, printed top, and jeans

Camel Blazer

This color is a classic! So beautiful and so versatile!

Summer: Pair it with white pants or jeans and a white top for a chic all-neutral look. Don’t be afraid to wear a detailed white shirt, like this one that gives it just a little bit something extra!

Winter: I love tone on tone in the winter. This would be gorgeous with a camel sweater with jeans or black pants and a simple pair of mules or booties. I would also pair it with white pants in the fall with a black top or sweater and sneakers for a more casual look.

Floral Tiered Ruffle Midi Skirt

Summer: These colors and ruffles are gorgeous! Throw on a pair of sandals like these or these and a dainty white cami (I LOVE this one) tucked in.

Fall: The length of this is great for fall! Pair it with brown booties and a chunky knit sweater, tucked in at the front. For chillier days, through a long camel coat over it! If it’s not too chilly where you live, opt for a thinner white or ivory sweater and a leather jacket.

woman wearing transitional pieces floral skirt
woman wearing floral blouse and jeans

Floral Blouse

Summer: I love how this pops against crisp white pants or the office or evening out, or with a pair of paper bag shorts like this cute pair. For a night out, pair it with heels, and for something more casual, slides like these would be perfect.

Fall: Pair this rusty red top with dark skinny jeans and flat mules or booties! This color is one of my favorites for fall.

These ideas would work perfectly with this blue or pink floral blouse as well!

Plaid Cardigan as Transitional Pieces

Summer: I love the colors in this cardigan. For warm weather, pair it with white paper bag shorts and sandals. I also love it worn backwards so the v is in the back tucked into white pants with sandals or heels like these braided ones.

Fall: Wear it as a shirt, tucked into mom jeans in the front and through on a long camel coat and suede mules. Or, dress it up a bit and wear with skinny jeans, black booties and a black coat.

woman wearing plaid cardigan as transitiona pieces
woman wearing red flutter sleeve wrap dress as Transitional Pieces

Flutter Sleeve Wrap Dress

Summer: Make it easy—just put on your favorite sandals, or even white sneakers for an easy outfit.

Fall: Pair with brown booties, like shown here and a leather jacket. For the office, swap the leather jacket for that that gorgeous camel blazer!

Blazers

I love the camel one for year round, however, I do find the other two to be better for fall, but they were both so cute, I wanted to include them! Also, I love the camel and black check one, so chic for the office and the white one is so fun! I think you can easily wear this to work, but also pair it with a cami, jeans and heels for a night out.

Ann Taylor Sizing

A quick note about sizing! In general, I find that Ann Taylor runs big! I have always ordered a size down from what I normally get, and sometimes. I’ve even ordered my normal size, but in the petite and find that’s a good hack too.

BTW, bell sleeves two ways, and what to wear to a baby shower.

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