If you are looking for winter clothing styles to take you through to summer here are a few suggestions.
First off try buying a pair of cargo pants. Get them in a neutral color that works for both summer and winter like bone white, khaki green or tobacco. The best types have cuffs that can be rolled up and buttoned. Layer this look with high boots, a heavy sweater and a scarf. As summer approaches you can then replace the heavy sweater for a lighter one or a t-shirt and switch your shoes to canvas running shoes, rubber boots and then sandals. The good thing about some styles of cargo pants is that you can button them so they are a shorter pant.
Another thing to remember about cargo pants is that the less military they look the more versatile they are going to be in your wardrobe. Look for classic styles with minimal pockets and less brass fittings and buttons unless your other clothes suit the military look.
Another versatile item is a pretty button down shirt. In the winter you can wear it under a tailored suede or leathered jacket and keep toasty and warm. As Spring and Summer approaches you can pair it with a skirt or lighter pants and top it with a denim jacket or a light sweater. If you buy a cargo jacket you can wear it as a suit with the cargo pants throughout the winter and into the summer only in the summer just wear it with a T-shirt or camisole, bare ankles and sandals.
A short sleeved dress in basic black or another neutral color is also a good winter-to-summer purchase. It looks good with a turtleneck beneath and a pair of tights. You can trade in tights and boots for bare legs and sandals as Spring approaches.
If you buy a camisole be sure that it can translate easily into a summer top that can be paired with a breezy cotton summer skirt. In the winter, the same camisole can serve as a flirty undergarment that is much more comfortable than wearing a bra.
Believe it or not you can also wear shorts in the winter as well. You can pair an elegant pair of longer suit shorts with tights and boots. A turtleneck and blazer tops off the look. Then, as summer approaches you can wear the shorts only and dispense with the tights and boots. A pair of wedge sandals looks good with these shorts.