A Guy’s Guide: How to Transition Your Style From Summer to Fall

by Ethan More

As the seasons change from summer to fall, it might be tempting to pack up the summer gear and invest in a brand-new fall wardrobe. Before you begin the seasonal overhaul, though, take a look at what you already have in your summer wardrobe that you can comfortably use as you head into autumn. As you take inventory, remember these tips for an effortless transition.

1. Keep Thin, Minimal Garments Close

If fall temperatures reach the 80s and 90s, thin layers are the most comfortable and appropriate. When the temperatures drop, don’t pack up the thin layers just yet, though. In fact, keep an option like a slim-fit tee around because it’s not uncommon for the temperatures to fluctuate throughout any given day in the fall. During seasonal transitions, it’s not unusual for the weather to feel brisk and cold in the morning and sweltering hot in the afternoon.

You can put on a turtleneck for those chilly autumn mornings. This sweater could even work while you’re in an office that’s blasting the air conditioning. However, if the temperature skyrockets in the afternoon, you’ll feel uncomfortably hot as you commute home. There’s nothing wrong with a turtleneck as long as it’s paired with a thin t-shirt underneath. Wearing a thin garment helps when you need to peel off a layer or two.

2. Incorporate Heavier Fabrics

For many people, fall is the favored season for fashion. Fall fashion incorporates rich colors, chic details and interesting layering. Since there’s room for them in this fashion-forward season, keep heavier garments in your arsenal.

Pair your thin layers with a stylish blazer or cardigan. If you’ve loved wearing white t-shirts throughout the summer months, simply add a few men’s hoodies to look and feel seasonally appropriate during the fall. A graphic t-shirt can easily look more sophisticated with a well-fitting navy-blue blazer. As you begin to shop for fall, incorporate garments that have some weight involved. A denim jacket is a classic staple to consider. Collect a few blazers and cardigans in colors like black, navy blue and olive or dark green.

3. Wear Leather Shoes and Boots

As summer comes to a close, you won’t be able to comfortably transition your flip-flops into the next season. However, if you’re looking to rock a comfortable look for a low-key day, try wearing socks with Birkenstocks. If you own a pair of Birkenstocks or a similar style, there are ways to wear them well into the fall.

If you plan to dress up a bit more, swap out the sandals for leather shoes and boots. Keep an eye out for leather shoes and boots in classic colors like cognac, black and gray. While suede boots are nice, they’re more suitable for the transition from fall to winter. In the meantime, leather boots and shoes are easy to dress up or dress down. If you’re unsure what type of leather shoe to try, loafers are ideal as they can be worn with a pair of shorts, jeans or slacks.

4. Look for Interesting Layers

Button-down shirts are versatile in any season. They also work particularly well when they’re paired with thinner layers underneath. If you’re heading to a fall festival, a plaid button-down works well with a graphic t-shirt underneath. When you’re headed to a dinner date, a blue button-down shirt looks nice with a navy-blue blazer.

In addition to button-down shirts, don’t forget about sweaters and sweatshirts. To make your look versatile, try a range of sweatshirts with different necklines. For most men, crewnecks and v-necks tend to be the most flattering choices.

5. Add Accessories

Sunglasses are certainly the most iconic accessory of the summer as people spend more time in the sun. However, your eyes still need protection throughout the entire year. If you’ve purchased a great pair of sunglasses for the beach, it’s OK to continue rocking them through the fall months. An all-black pair is the most versatile and classic option.

If you’d like to quickly make a button-down shirt look more formal, wear a bow tie. When you’re heading to an evening bonfire, in addition to layering well, wrap a scarf around your neck. To keep your pants up and provide a polished finish, wear a leather belt in a color like navy blue or brown.

Source: Maridav/

As fashion evolves, it’s becoming increasingly popular for men to add unique bracelets, rings or necklaces to their look. Along with a long-sleeved henley and classic timepiece, add a quirky yet interesting bracelet to make the look more rugged and stylish.

6. Make the Switch From Shorts to Pants

Wearing a comfortable pair of shorts is fine as the warm temperatures linger. As it gets colder, though, it’s best to wear more options like khaki pants and denim jeans. Look for khakis and slacks in a range of colors like olive green, navy blue and brown.

When you’re looking for denim options, instead of opting for the classic blue jeans, keep an eye out for black jeans and dark denim jeans. Denim is classic, so it goes well with almost any fall color. It’s also great because denim can be paired with a great blazer and a pair of leather shoes to look effortlessly stylish.

Source: Joshua Aucoin/

Moving Forward Into Fall With Fashion and Flair

As you get excited about adding new items to your wardrobe, remember to take inventory of what’s already hanging in your closet. When you’re able to plan outfits and mix different pieces together, you might find that there’s more to work with than you realized.

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