9 Essential Summer-to-Fall Style Swaps for Men

As the seasons change from fall/winter to spring/summer, updating your wardrobe is generally simpler. Warmer weather often means a streamlined selection of clothing, which, while less inventive, clears up the usual outfit dilemmas. However, transitioning back to cooler temperatures can be more complicated.

With the onset of autumn, your clothing choices expand significantly. Casual items like shorts and camp-collar shirts are no longer sufficient; you need to curate layered ensembles that balance warmth and style. While the task may initially seem overwhelming, a few strategic swaps can make this transition smoother and more enjoyable.

What should you be switching out? From light-wash denim to darker shades and moving away from linen in favor of heavier textiles, we’ve got some suggestions for seasonal alterations you shouldn’t miss.

Swap Your: Light Jacket

Light outerwear certainly has its place in a fall wardrobe, but primarily as a layering piece. With temperatures dropping, you’ll want greater insulation to stay warm, as most basic overshirts and windbreakers often don’t cut it.

What you need is a jacket that wraps you in warmth. A cozy fleece jacket can deliver just that.

For A: High-Pile Fleece

The coarser and more textured the fabric, the better. Look for options that will effectively trap heat while also adding a tactile element and visual depth to your outfits. Patagonia’s Retro-X jackets set a high standard in this regard, but affordable alternatives can often be found on the high street or at thrift shops.

Swap Your: Linen Shirt

While linen is a fantastic fabric for surviving the sweltering summer heat, its advantages are limited in the fall. As temperatures cool, that breathability, once desirable, becomes a significant drawback.

At this time, your goal is to warm up, not cool down.

For A: Heavyweight Flannel

In addition to having a few well-tailored Oxford shirts, a heavyweight flannel is essential as the weather changes. The brushed cotton material serves as an excellent insulator, and opting for vibrant colors can add a refreshing touch to your autumn attire. A classic red-black buffalo check is a timeless choice, but be cautious not to veer into full-on lumberjack territory.

Swap Your: Lightweight T-Shirt

In summer, a T-shirt’s main role is to keep you feeling cool. Thin, lightweight, and breathable, these qualities are essential when temperatures are high, but can become problematic as the weather turns.

For A: Heavyweight Long-Sleeve

What you need is a solid base layer that reflects the cooler climate and provides suitable insulation. A heavyweight long-sleeve tee made from thick cotton serves as an ideal alternative. It retains the simplicity and versatility of its lightweight short-sleeve counterpart but is far more fitting for the season.

Swap Your: Linen Shorts

Linen shorts offer unparalleled comfort. Their lightweight and airy nature makes them feel almost invisible. Unfortunately, they are unsuitable for anything but hot and sunny conditions.

For Some: Drawstring Pants

Fortunately, there is a comfortable alternative to linen shorts that is better suited for the fall—drawstring pants. Opt for a relaxed fit and a slightly heavier fabric, such as cotton twill or corduroy.

Swap Your: Light-Wash Jeans

If you’ve been wearing jeans throughout the summer, it’s likely that they’re of the light-wash variety. While dark denim can feel weighty and constrictive during warm months, it becomes a go-to style as temperatures drop.

For Some: Raw Denim

Now is the ideal moment to start working on your fades again. Bring out your heavier denim and wear it often while the temperatures allow.

Swap Your: Leather Sandals

Regardless of the time of year, having versatile leather footwear is essential. In summer, leather sandals fit the bill, but it’s best to retire styles like Birkenstocks as temperatures drop.

For Some: Chunky Derbies

We recommend opting for chunky Derby shoes this year. Look for styles that diverge from the traditional round-toe design without straying too far into the unconventional.

Paraboot’s iconic Michael moc-toe Derby is an excellent example—versatile and seasonally appropriate without feeling dull.

Swap Your: Suede Loafers

Soft suede shoes that can easily transition between formal and casual settings are essential year-round. However, ensure that the shoe shape is compatible with colder conditions.

This isn’t to say loafers can’t be worn in the fall, but opt for footwear that delivers more coverage in chilly weather.

For Some: Soft Suede Chukka Boots

Much like loafers, suede chukka boots provide a comfortable and versatile option that works well with both jeans and tailored jackets. Clarks excels in this category with timeless styles such as the Wallabee and Desert boots that remain hard to beat.

Swap Your: Linen Cap

While it’s not quite time for beanies, consider having a more substantial cap than a lightweight linen option to complement your autumn outfits.

For A: Corduroy Alternative

Corduroy makes for a perfect substitute, offering warmth and texture that enhances visual interest. Choose a cap in a rich autumnal color, such as burnt orange or maroon.

Swap Your: Summer Fragrance

While fresh and light fragrances are ideal for summer, they may get lost in cool air, making it wise to switch to something deeper and richer.

For: Something Heavier