Update your ankle booties. The difference between a look that feels safe but dated and one that feels modern and effortless often comes down to one small swap. These new ankle booties are what the pulled-together version of you would choose - sleek, elongating, and modern. Outfit 1 Velvet blazer xs Everlane tee medium Everlane cashmere sweater xs Madewell 90's jeans. 25, cut hems Madewell Dime booties 5.5 Chanel Trendy CC small YSL sunglasses Quince earrings Outfit 2 AYR Shirt xs Everlane cotton sweater xs Aritzia jeans 26, sized up and cut hems. Staud Wally ankle booties 35 Parisa Wang bag (can't be linked) Celine sunglasses Quince earrings Outfit 3 Banana Republic coat petite xs (old) Everlane cotton sweater xs AGOLDE Relaxed jeans 25, cut hems. Go tts Madewell Dimes booties 5.5 JW Anderson bag Celine sunglasses Outfit 4 Aritzia cashmere sweater xs Everlane tee medium Aritzia jeans 26, sized up and cut hems. Chanel Trendy CC small Madewell Dimes booties 5.5 YSL sunglasses Dorsey James Necklace 15" Outfit 5 Aritzia jacket xs Aritzia tee medium Aritzia jeans 26, sized up and cut hems. Stuart Weitzman sock booties 35 Parisa Wang bag (can't be linked) YSL Sunglasses Dorsey James Necklace 15" LTKStyleTip LTKPetite LTKSeasonal