Fall Style Roundup: 7 Pieces to Wear into Fall
Here’s What To Buy Now With No Regrets

By Taylor Davies | Last Updated: Sep 14 2021

For anyone who enjoys getting dressed and building up a closet of cool stuff (most of you, right?) post-August/pre-true fall is a weird time.

We’re sweating through the last gasps of high summer temps—all while watching college football and starting to think about buying flights for Thanksgiving.

Plus, all the summer apparel and accessories that looked so good in late May are now on sale!

It’s tempting to snap up deal after deal, telling yourself you’re investing in both instant gratification and your future summer self.

Truly, I love that feeling, too. I won’t deny it.

However, retailers are clearing their shelves and looking forward to fall, and you should too.

Below, a fall style roundup of the 7 pieces to wear now and into fall:

2021 fall style roundup

1. (true) blue jeans


Wear it well: If you’re headed back into an office where shorts aren’t really the move no matter the season, it’s time to upgrade your “nice-looking jeans” repertoire.

Pick up some crisp true-blue jeans (or twill 5-pocket pants) for a shade that works year-round.

2. acetate sunglasses


Wear it well: Sunglasses, never go out of season, but they’re still especially necessary now.

Treat yourself to a new acetate frame style and put a fresh twist on your fall accessories game.

3. crewneck sweatshirt


Wear it well: Okay, okay—so you probably need another crewneck sweatshirt like you need a hole in the head!

But! Well, I’m going to do it anyway.

This French terry pullover in a poppy red color will pair great over your trunks on the weekends and with a nice pair of chinos during the week.

4. clean white sneakers


Wear it well: With clean design and a comfortable sole, there’s nothing a good white sneaker can’t solve in life. Or can’t fix a wayward outfit, at least.

New Republic’s “Kurt” sneaker is one of those modern classics you’ll wonder how you ever lived without.

Just in time for weekend strolls on boardwalks and leaf peeping outings alike.

5. A short-sleeve henley


Wear it well: We’ve already extolled on the many ways a henley is essential to your wardrobe, every day of the week.

This subtle blue-green style, from Marine Layer, can be layered under sweaters and sweatshirts into the colder months to come.

6. A new work (or school) bag


Wear it well: A fall style roundup wouldn’t be complete with a nod to “back to school.” Even if you’re well past your school days, it feels good to psych yourself up with something new to get you through the end of the year.

Every guy and his brother has a Filson bag by now, so why not change things up with a similarly rugged bag with a slightly more refined look.

Since careers don’t really get summer vacations, you’re safe to invest now and use this bag all year long.

7. A belt that falls between fancy and casual


Wear it well: Woven belts have a traditionally summery flair. However, made in rich brown leather, this belt has the potential to extend into Autumn with crisp suits and your usual 9-to-5 grind outfits.