When you’re transitioning between fashion seasons, there are some items that deserve to stay in your closet twelve months out of the year. Here is a list of keepers—those special pieces that are flexible enough to stick with your wardrobe season after season.
Calf-length boots or booties
When it’s colder, you can tuck long pants into boots or ankle booties and your whole body will feel warmer.
When it’s warmer, wear them barelegged with a dress or a skirt.
Jean jacket
When it’s colder, wear a cashmere sweater underneath it. The jean jacket can be the second layer. Add a pea coat or puffer as a third layer as it gets colder.
When it’s warmer, a jean jacket is the perfect layer over a dress. Or for business casual, it can be teamed with a pencil skirt, a striped shirt and pumps or boots.
Slim ankle length or boot cut dark jeans
When it’s colder, wear a riding boot under the boot cut jean or tuck the slim ankle jean into the same boot style. Additionally, you can wear a pump with either style jean for a dressed up casual look, anytime.
When it’s warmer, wear a heeled strappy sandal and a loose top with the slim jean. Or wear a chunky platform with a slim-fit classic tee. Add jewelry.
Lightweight cashmere/wool cardigan
When it’s colder, wear a long-sleeved silk or wool T-shirt under it. Add a heavier jacket when heading outdoors.
When it’s warmer, you can wear it open and loose over a tank and pants. Or on a summer night, drape the lightweight cardigan over the straps of your summer dress.
Long tanks
When it’s colder, wear a long tank under a cashmere crewneck sweater. The longer inside layer can be a color accent to your outfit and add more interest. It also allows you to wear a more cropped outer piece and have the modesty you need.
When it’s warmer, a long tank is a perfect layer for under sheer tunics or paired with a lightweight eyelet or lace jacket.
Lightweight wool scarf
When it’s colder, it’s great to wrap it around your neck and bundle up under a coat, cape or poncho. It can also be a great accent piece if it’s in a patterned print or bright color.
When it’s warmer, it’s a perfect wrap to throw over your shoulders in a chilly restaurant.
Leather jacket
Choose a light weight style that allows just enough room to layer a long sleeve shirt or sweater under it. Get SOFT leather, and get the real thing – the “new” plastic leathers can be too hot in the summer and uncomfortable in the winter!
Jill Swanson, owner of Beauty Made Easy, image coach, style consultant, national speaker, and the author of Out the Door in 15 Minutes, Simply Beautiful Inside & Out, Simply Scarves, and Simply Closets.


It would be easy to believe that Jill was born with exceptional looks and style, but she is living proof that beauty begins within. Underneath her impeccable exterior is evidence of a profound challenge. Jill was born with a rare birth defect. 
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