When I did some “shop my closet” posts a few months ago, I got requests from you guys to style one piece of clothing three ways so I decided to go for it and start with the cutest little houndstooth skirt that I bought for one event and have now worn three times already. It is a classic print with a flirty little flounce, and goes well with anything from button downs and heels for work to a sweater or even fleece, apparently. When it cools down a little more, I plan to wear it with black tights and booties.

For now, this is how and where I rocked this little cutie pie (and scroll down for some big sales!)

Outfit 1: I wore this for a lunch out in Nantucket. Remember this bow sweater from last year? It’s back and comes in both white and grey and is super cute for fall and holiday. This outfit is easy, comfy, and perfectly preppy.

Outfit 2: That same night, it was super chilly but I wanted to wear it again so I threw on with a green Dudley Stephens (they’re restocking in the next week or so so stay tuned for that!) and tucked it in with a pair of statement earrings.

Outfit 3: Last week I went to an event at Blue Hill at Stone Barns and wanted to wear my Hunters but also look cute so she came out to play again with a bodysuit, blazer, and my go to everyday cross body bag.

J.Crew Factory: 40-50% sitewide + up to 75% off clearance through 10/8.
J.Crew: 40% off sitewide through 10/8 including new arrivals and sale (OMG).

PS Head over to Instagram where I’m doing a giveaway for a $150 gift card to J.Crew Factory! If you win, you could buy the skirt and a whole look to go with it. Note, this post isn’t sponsored. I bought everything you see here unless noted, but Factory is gifting the winner of the Instagram giveaway a gift card!

Skirt: J.Crew Factory
Outfit 1: Bow Sweater / Leopard Flats
Outfit 2: Fleece / Tuckernuck Earrings c/o / Leopard Clutch / Leopard Flats
Outfit 3: Old J.Crew Bodysuit (Similar) / Blazer / Hunter Boots / Cuyana Bag

Photos by Julia Dags.