I struggle with summer. I don't need to see my legs every day—a constant reminder that they see about as much sunshine as the people who plan to troll this article.

Then, around late October, things are definitively chillier—and hence, chiller. It's time for bomber jackets, long-sleeve button downs, fine-fitted jeans and bulky socks with big personalities. But, there's shopping big, and then there's shopping smart.

People put down too much money on expensive fall clothing, when they can usually find the same thing for much cheaper elsewhere. A good winter jacket can set you back $200, but it can also be $30 if you know where to look. Below, we go over some of the best looks that you can definitely achieve for a fraction of the price.

Olrek Men's Autumn Collar Outerwear Jacket Coat
Look like you're in fall—and low-key in a marching band—for $39.98.

Our writer GUARANTEES you will get laid if you wear this jacket!! (Amazon)
Our writer GUARANTEES you will get laid if you wear this jacket!! (Amazon)

Here we have a Member's Only jacket without the douchiness of the Member's Only patch. If you think of it like this, this jacket is not only fashionable—it's innovative. If you buy this in red, somebody will want to see you naked.

Men's Hooded Packable Down Puffer Coat
Fuck you, Patagucci, for $29.99.

Two red jackets in a row. (Amazon)
Two red jackets in a row. (Amazon)

You see all those yuppie dudes in The Pearl with their $200 nylon shell jackets, right? Yeah, they do look pretty good, but they're doing this whole buying clothes thing totally wrong. This European-inspired windbreaker can cost a tenth of the price, and you can still look like a hot douche about the town on a Friday evening.

Wrangle Waffle Henley
Look like the 90s for $14.99.

A look both classic and on brand. (Wrangler)
A look both classic and on brand. (Wrangler)

Henley's are straight outta Dawson's Creek, and that why we'll always love them. If you don't know what Dawson's Creek is, shame on you—I was born in the 90s, too. One thing we can all agree on: Portland loves the 90s. Wear this, and you'll be showered with compliments for a mere $15.

Dockers 5-Pack Cotton Socks
Stop paying $7 for one pair of socks at Urban Outfitters that are "on sale," and pay $12 for 5 pairs instead.

This is as autumnal as it gets. (Amazon)
This is as autumnal as it gets. (Amazon)

I love socks. Good socks are collectible, but starting at $7 per pair for cheap ones, and a zillion dollars per pair for expensive ones, they can start to seem like Beanie Babies for adults, and we all knew those were overpriced (it just took us 20 years to say it.

But, you can still get good, fashionable socks for cheap if you look in the right place. This $12 pack of 5 Dockers socks are 70% cotton, which means they’re thick and snow boot friendly. Take these on a ski trip! But what’s most cool about these is all the different color variations you can purchase. Don’t just order all white; go for the rainbow. They’re might just be a pot of gold at the end.

ToBeInStyle Men's Beanies—6 Pack
6 for the price of (at least) 1 at any bougie men's store for just $16.99.

I'll let you in on a little secret about beanies: nobody can tell if it cost you $2.83 or $17, or $60. This is why you should buy 6 beanies for $2.83 each. You get every shade under the sun, and it doesn't matter if you lose one. Not only are these cheaper than what you'll find at H&M, they're sure to last you several falls.

(Cool Stuff is a new feature at Willamette Week where we feature product reviews, roundups, sales and other commerce and shopping-oriented content. All Cool Stuff reviews are editorially independent, meaning we provide honest reviews and aren't paid by the brands we write about. If you do choose to purchase something after following one of our links, Willamette Week may receive a commission, which helps fund our journalism.)