Knitted Polo Shirt- This is a great transition piece. Retire your cotton polos at the end of summer and switch to these until it gets too cold. You can get them in short sleeve or long sleeve.
V Neck Sweater- Go for ones in high-quality merino wool or cashmere. You can wear this over a tucked in button-down shirt (with or without a tie) for a polished look. Or wear it over a tee for a casual look. Or try it alone under a suit for a fashion forward look.
Crew Neck Sweater- Like the cashmere or merino wool v-neck sweater, but more casual. You can wear it alone or over a tee. You can also wear it over an untucked button-down shirt.
Winter Sweater- This is typically a thick wool sweater that comes textured or printed like jacquard, cable-knit, striped, or fair-isle. This is a go-to sweater to wear during the winter holidays.
Cardigan- This is a stylish way to add warmth over a button down shirt or tee. Make sure you have some in solid colors in cashmere. Button a few buttons around the middle, but not the last button. For a more casual look, try a zip up cardigan.
Shawl-Collar Cardigan- This has a classic gentlemanly vibe. You can dress it up by wearing it over a shirt and tie, or dress it down by wearing it over a tee. Don’t button the first or last button.
Hoodie- Save your cotton sweatshirt hoodies for the gym. Step it up with a cashmere or wool hoodie worn over a tee. Wear this casual look during the day on the weekend, never to work.
Sweater Vest- This is a great layering piece. Wear it over a shirt and tie and under a blazer for a classic look. You can achieve a similar look with a v-neck sweater, but a vest will keep you from burning up.
Turtleneck- Not every guy is going to be able to rock a turtleneck. I think if you are slim and trim, then go for it. Pick one in cashmere or merino wool. If you are wearing it under a suit, pick a thinner one in a solid color like black or grey. If you are wearing it alone, you can go with a thicker one and in some kind of print if you like. If you don’t want to fully commit to a turtleneck, you can try a mock neck.