11 Men’s Style Staples to Transition From Summer to Fall

Transitioning your wardrobe from summer to fall calls for adaptations to your style. Refreshing your look with high-quality staples is a great way to ease yourself into the cool autumn weather. Stocking your closet with well-made, versatile basics and luxurious extras can help you look sharp and feel great as the seasons change.

1. Classic Jeans

A pair of mid-weight, relaxed-fit jeans in a medium or dark wash is perfect for the changing weather. You can style them with a short-sleeved T-shirt on a late summer day and dress them up with a merino-wool sweater as the temperature drops. Dark indigo jeans look sophisticated with a button-down Oxford, twill, or all-cotton shirt in a coordinating print. And a medium wash looks chill with a waffle-knit tee or a lightweight cotton flannel.

2. Long-Sleeved Henley

For a laid-back weekend look that plays up your best attributes, you can’t go wrong with a long-sleeved henley in muted green, mustard, burnt sienna, or cream. The buttoned placket on this shirt will draw attention to your chest and your face. Add a Cuban link chain or a simple pendant necklace for an adventurous look. Henleys go well with jeans, especially if you have a lean or athletic build. Larger guys can layer a looser-fitting version under a sport coat or a button-down shirt.

3. Lightweight Bomber Jacket

A stylish bomber jacket in navy, brown, black, olive, or orange is exactly what you need when the air turns crisp. Lightweight nylon, cotton, and suede can get you through a fall outing in town or in the country. You can wear this jacket with everything from jeans and chinos to tees and sweaters. Whether you keep it casual with sneakers or dress it up with boots, you’ll look composed and at ease in this comfortable cool-weather classic.

4. Smart, Stylish Chinos

When you want clean-lined, breathable pants that you can dress up in warm or cool weather, choose chinos in beige, nut brown, or brick red. Cotton chinos are lighter and less fussy than wool trousers and more polished than jeans. They look great with loafers, boots, or a lace-up brogue.

5. Leather Boots

A great pair of leather boots sends a sure signal that you’re ready for autumn. Dress up in a sleek Chelsea boot, or get a little rugged with a lace-up style in chocolate brown. Wear your boots with jeans, chinos, trousers, and tops that share a similar level of formality.

6. Versatile Button-Down Shirt

Button-down shirts are a versatile standby that will take you into fall with panache. Whether you pair your shirt over a tee or wear it under a sweater or blazer, there are endless varieties to choose from. Button-down shirts come in every style, including linen, wool, or corduroy, and board shirts that double as jackets or mid-weight cotton options are great for layering or wearing alone. To celebrate the season, pick shirts in earth-toned plaids and prints or dark colors.

7. Quilted Vest

When you’re out on an early-morning stroll or stepping inside a building that has the air conditioning on blast, wearing a quilted vest with a nylon or cotton-blend shell is a great way to keep your temperature regulated. Choose a style that’s lightweight and packable so you can toss it in a backpack if you get too warm. Layer it over a sweater or long-sleeved knit for a casual Friday or weekend outfit.

8. Seasonal Sweater

For cloudy mornings and chilly evenings, a half-zip, crew neck, or V-neck sweater in a cashmere or merino-wool blend makes for a wonderful layering piece. For a casual yet rich look, try a weighty, textured knit and purl or a fisherman’s rib pullover in burgundy, navy, or deep green cotton with an eye-catching striped detail. If you invest in a fully finished classic design made with high-quality yarn, you’ll have a timeless and durable piece you can wear for years.

9. Quality Accessories

Classic shades with metal, tortoise, or black frames will be great for game day and sunny afternoon drinks. Try coordinating your frames with your jewelry, like these gold rings for men, for a bold, put-together look. When you’re out and about, take along a classic canvas or leather messenger bag to hold your essentials. You can also add polish to your outfit with a classic watch like one of these Rolex watches for men.

10. Haute-Casual Cardigan

For an easy-to-wear vintage look with an edge, channel celebrity style in a throwback cardigan. You can look like a movie star in a gray or navy blue grandpa-style V-neck cardigan over a white T-shirt, tailored trousers, and suede or soft loafers. If you prefer a hipster style, take a cue from Mister Rogers, and pick a zip-up cardigan with cable-knit details in blue, red, or tan.

11. Luxurious Loafers

Trade your sandals or boat shoes for loafers in soft leather or suede that will keep your feet snug but not too hot. You can pair them with jeans for a casual feel or dress them up with chinos. You can even wear them with shorts if the weather is especially warm. When it comes to socks, the choice is up to you. Prioritize comfort and be sure to consider your total look. A badly proportioned sock will not flatter your ankle or leg. When in doubt, you’re better off going sockless if your look is casual.

Transition Into Autumn With the Right Stylish Essentials

The weather can be unpredictable as the seasons change, but with the right essentials, you’ll find it easy to look your best. When you invest in the best transitional staples, you’ll be ready for anything.

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