There are those pieces in our closet that we know really shouldn’t be worn past a certain time of year, but we throw caution to the wind and stretch those boundaries because we KNOW that look is fabulous! The Nautical (long sleeve) T is one of those pieces this year. It really should have been retired in the fall, but we’re seeing it worn this winter. Like the Sperry Topsider, this is a fashion trend that is signature to the spring/summer and those Indian Summer days of fall.

Shall you dare to push the seasonal line, which honestly, is possible in temperate climates like Maryland, where we experience winter by Sybil, 30 degrees one day, 50 the next; please, for the love of Vogue, do not American Apparel your Nautical T. Do not wear your T over a pair of jeggings tucked into some cheap faux-leather camel color calf-high flat boots. It’s not a good look. Horizontal stripes with a bottom that shortens the body rather than lengthens it? I think you can see where this dumpster fire is going.

To rock the Nautical T in all it’s winter splendor this season, pair it with a classic high waist wide leg pant (Banana Repubic/Victoria Secret); either a deep navy, to bring out the color in the T, or a charcoal or black to add some drama. If you’re going for a more relaxed look, a nice wide leg jean (Levis) will look great. Depending on the shape of the shirt, either tuck in, or leave out. If you have a more fitted T, tuck it in for a flattering shape to the waist. Finish the look with a black wedge bootie (Sam Edelman) or a nice grey shade desert-style boot (JCrew).

Audrey Tautou, Coco before Chanel

Banana Republic Heritage modern wide-leg in navy

JCrew McAlister wedge boots