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  • Writer's pictureBest Damn Things

Best Damn Casual Clothing Items Every Man Needs for Fall (And how to wear them)

We are all ready for cooler weather but is our closet? Have you forgotten how to layer clothing? I mean, summer is easy, throw on a t-shirt and some shorts. But when it comes to fall clothing and a new season, we all need reminders of how to wear certain items AND desperately need to freshen up our style with some new pieces. Men, here are some fall clothing ideas to get you started and some suggestions on how to wear them.

I have two teenage boys and a husband. I keep up with trends (by default) and I know how to answer, "What do I wear with these pants? Can I wear brown shoes with this?" Here is a list of items that are essential as cooler weather comes sweeping in. You will need layers for chilly mornings and when the sun goes down. I got you covered - literally.

*Disclaimer: Please note that some of the links are affiliate links and I may receive an affiliate commission. These are my opinions and are not representative of the companies that create these products. My goal is to recommend quality products from my own personal experience and research.

Two Pair of Jeans

Jeans might be one of the hardest things to shop for. There are skinny, boot cut, straight leg, slim fit, plain pocket and embroidered pocket jeans. Most everyone already knows the style and fit of jean they prefer. My suggestion is to find a pair you love and buy two. Buy one pair in a lighter wash and one pair in black / dark wash.

Dark wash / black jeans are easier to dress up. Lighter wash jeans tend to be more casual. It's good to have a casual pair and a more dressy pair.

Jeans are extremely versatile. You can pretty much wear them with anything; a t-shirt or a tucked in button down shirt or blazer and loafers to dress them up.

The main thing is to find a pair that fits you well, fits your style (not everyone can pull off skinny jeans), and you feel comfortable in.

Jeans are an essential part of any wardrobe. And are an essential piece of clothing for fall.

Graphic Tees

T-shirts are a vital part of layering. Should you have plain short sleeve t-shirts and long sleeve t-shirts? YES. You can find those here. But, it's also important to show your style and personality. Graphic tees are a great way to show off your personality under a plaid shirt or light jacket.

If you are looking for great graphic tees, or other artist designed items, to fit your style, I suggest looking at Redbubble. They have SO MANY graphic tees to choose from; music, band, movies, superhero, sports, games, hobbies, anime, animals, cinema, patterns, culture, and trendy to name a few.

The really cool thing about this site? Everything is created by artists and then placed on different products. This means their items are unique. Unique items means you get to show off your own personal style. That's a good thing.

Plaid Twill Shirt

It isn't officially fall until you get out the plaid. Please don't think that plaid only means the checkered red and black pattern - it doesn't. Plaid is actually the type of fabric and how it is woven together. You can buy plaid shirts in an array of patterns - including the classic red and black.

Plaid shirts are GREAT for layering. Plaid is versatile which is why it is a fall staple. Here are some different ways you can wear a plaid shirt:

- Unbuttoned with a graphic long or short sleeve tee underneath and a pair of light wash or dark wash jeans and your favorite sneakers or boots (casual).

- Buttoned up and tucked into a dark pair of jeans or light pair of jeans (dressier).

If you button up and tuck in, remember to wear a belt!

-Un-tucked under a light fall jacket

-Tucked into a pair of khakis with a light jacket over it (dressier option)

-Un-tucked under a light vest

Field Jacket

A lightweight jacket is a must have for fall. A jacket is one of the easiest ways to put on an extra layer. I like this one because of the stylish features of the chest zipper and the straight cut. Try to choose a neutral color to compliment other pieces. Navy, sand, or grey would be my top choices.


Boots are a must have for fall and winter when you need more protection from cooler weather, rain, snow, sleet.

A good pair of brown leather lace up boots is a great purchase. You can wear them with light wash jeans, dark wash or black jeans or khakis. Yes, you heard me correctly. You can wear

brown shoes with black jeans/khakis.

Simple Zip Up Hoodie

The zip up hoodie is a timeless classic. There are so many different styles available now. Look for a style you like at an affordable price so you can buy a couple of them. I would recommend to buy one solid color and one with a pattern.


There you have it, your fall essentials to get you started this season! Have fun shopping for items that make you feel good and show off your personality.

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