I hate wearing shorts. Part of the reason is that my skinny legs look like two spaghetti noodles hanging out of a box; part of the reason is that I find them uncomfortable. Nevertheless, when the weather dips below 65 degrees, I am giddy to throw on my jeans and prepare myself for autumn. When the leaves start dropping from the trees, you’ll want to think about acquiring these next four items for your autumnal closet.  

Crew neck sweatshirt

Coming home after a long day working at my internship or doing a class presentation, taking off my button-down and throwing on an XL crew neck sweatshirt is a top-five feeling for me. They are one of the most comfortable items in my wardrobe, and I often find myself sleeping in them.

Another amazing quality is that there are so many design options. I don’t think you can go wrong with either a simple one-color sweater, or an extravagantly designed one. Even though it makes me a total Ivy League wannabe, I really love my University of Pennsylvania crew neck sweatshirt, and I don’t think there’s anything wrong with wearing some non-University of Maryland college apparel once in a while.

Crew necks are also perfect for layering, so throw on a North Face vest or an unbuttoned peacoat overtop on a sub-50 degree day.

[Read more: Thrifting tips from a fellow thrifter]


While the crew neck sweatshirt is good for layering, a trusty fleece can stand on its own — in both a fashion and a function sense. They look good by themselves, plus they’ll keep you warm even if you’re only wearing a tee underneath.

You’ll always have a large price range to choose from when it comes to fleeces. Uniqlo and Engineered Garments teamed up to deliver an affordable and stylish collection. You could also go with the classic Patagonia fleece, an industry standard for fall weather. If your bank account is feeling particularly strong and you’re willing to drop upwards of $300, I’d recommend any Aimé Leon Dore fleece outerwear item.


Dad caps and flat brims just don’t do the trick once the November wind chill starts hitting — you’ll need a beanie. A nice, cozy beanie will protect you from a bad hair day and keep your ears warm when it’s chilly.

Stylistically, I’d shy away from the pompom variety and move toward the knitted ones, maybe even a reversible one. Carhartt is one brand to trust with cold weather gear and their beanies are no exception, plus they’re usually under $20. Adidas and The North Face (my personal beanie brand) make really simple and high-quality ones as well.

Wear it hanging off the crown of your head or Anderson .Paak-style — tight on your head and rolled up a few times. 


You might forget about them until the first rainy day of the season comes along, but boots are an absolute fall weather staple. Even though I am a frugal fashion guy, I’d encourage you to follow the “Don’t be cheap when it comes to stuff between you and the ground” rule when buying a pair of boots. Footwear isn’t usually the best place to cut corners. Your feet will thank you later.

As far as what kind of boots to choose from, you have a few options. Timberland work boots are a safe bet and can be worn with a variety of outfits — I had a boss who wore them with sweatpants every day to work. Definitely go with the lighter shade of brown for Timbs.

Even though you might associate them more with the winter months, there’s nothing wrong with busting out the L.L. Bean boots on a cold and rainy day. I’m also really partial to the Chelsea (leather not suede) and Chukka style of boots, because they’re a bit more dressy. If you have more of a Vigilante Coffee and WMUC Radio aesthetic, go with some all-black Doc Martens.

[Read more: 8 fashion influencers to follow for fall inspiration]