Dear Avery,
I’m going on a date soon with this girl I’ve liked for a while. I need to look nice but not too fancy, and I can’t spend a lot of money. What’s a good first date outfit for a guy that will cost around $100?

Just to be clear, I’m not the kind of girl who thinks the clothes make the man. And you’ve already accomplished the hardest part, which was convincing this girl to go on a date with you in the first place.

A great outfit does help, however, especially if your typical sense of style isn’t exactly top-notch — but wear the perfect thing and she’ll definitely be glad she agreed to that date. Sure, she may originally have said yes out of boredom, pity, etc., but show up looking fine and she may re-evaluate whether or not she’s going to kiss you at the end of the night.

First things first, make sure you have a versatile, stylish pair of shoes that can go with pretty much anything — brown is usually a safe bet. A great outfit paired with ugly or beat-up shoes ranks very high on my list of pet peeves. I don’t know if my mother was the only one who ever said, “no one even looks at your feet,” but it turned out to be a nasty bit of reverse psychology. Now I can’t help but check out the kicks first, outfit second. That might just be me and my obsessive need for coordination and my deep and undying love of footwear, but I think we can safely assume my tastes align with most girls. Moral of the story: buy nice shoes.

Secondly, don’t stress out about looking underdressed or overdressed. A guy who wears a pair of pants that fit and don’t look like he changed the oil in them is already on the right track. I don’t know if guys realize this, but girls don’t really set the bar that high for them, fashion-wise. We all pretty much assume it’s a challenge to dress yourself and are pleasantly surprised by a guy who owns anything other than sweatshirts and sports jerseys. So stay calm.

Thirdly, just because you don’t have a ton of cash to spare doesn’t mean you can’t dress to impress. But because I’m guessing you’re one of those guys who struggles to get his shirt over his head in the mornings, I took the liberty of picking out a few options for you.

Option No. 1

You can’t go wrong in a flannel. I may sound like the ultimate hipster, but I don’t even care. I think it’s pretty much a fact that girls go crazy for flannels and every guy should own one or five. Paired with a shawl-collar sweater and slim-fitting, black jeans, you’ll look like every girl’s dream date. Just don’t forget to leave the shirt un-tucked so it hangs out the bottom a little and leave the top few buttons un-buttoned — don’t try to turn a flannel into something it’s not.

Sweater: ASOS, $35.61
Shirt: Target, $22.99
Jeans: Gap, $44.99

Option No. 2

Now, not every guy can rock a henley. Take a long, hard, shirtless look in the mirror before you deem yourself fit enough to reveal your pecs to the world. Ordinarily, a henley is super-casual, but with a nice pair of chinos — daring color choices are encouraged — and a belt to tie the whole look together, you’ll be just the right mix of dressed up and dressed down. If you happen to have a leather jacket, feel free to throw that on top. I won’t be mad about it.

Shirt: J. Crew, $59.50
Pants: H&M, $29.95
Belt: Kohl’s, $19.60

Option No. 3

I struggled to accept denim jackets back into my heart after I permanently banished them in the early-2000s. I woke up one morning and suddenly realized that wearing my Gap Kids jean jacket with my Gap Kids flare jeans really wasn’t cool anymore — not that it ever was — and that I was officially off jean jackets for life. Well, it turns out I totally love them again, so buy a jean jacket, wear it with a pair of khakis and a crewneck sweater and call it a night. Just don’t forget to pick up the tab and give this girl a proper goodnight kiss.

Jacket: ASOS, $42.39
Sweater: Gap, $30.99
Pants: Urban Outfitters, $39

Photo courtesy of Facebook.