Guys' Guide to Fall Outfits for a First Date

Guys' Guide to Fall Outfits for a First Date

Picking an outfit for a first date is no easy feat. You have to consider the weather, the activity, and what outfits look best on you. You want to dress to impress, and for some of us, some extra stress may come with deciding on the perfect outfit. We’re here to help you come up with the perfect outfit for your fall date, and we can guarantee that you probably already have what you need to look fashionable in your closet already. And if you don’t, there are easy and practical pieces to get.

Okay, guys, here’s how to dress for a fall first date.

Classic Flannel

Flannel is a fabric that goes hand-in-hand with colder weather, making it a great option for those fall first dates. Men’s flannel shirts are the perfect mix of casual and buttoned-up, making them ideal for a date night, whether you’re heading to a movie, happy hour, or out for a walk. Get yourself a flannel shirt in a color pattern that compliments your natural features — so, if you have blue eyes, go for a flannel with blue detailing. Or, if red is your color, get a flannel with shades of red.

Once you have your flannel top, you can wear it tucked into a pair of men’s jeans or wear it unbuttoned over a crewneck t-shirt with a pair of jeans. The unbuttoned option is decidedly more casual, so it works best for a first date that doesn’t have as much of a dress code — like a walk or a visit to a brewery.

A Sweater

Sweaters are another item that is synonymous with fall. Whether a V-neck sweater, a crewneck, or a turtleneck, a sweater is a great outfit option for a fall dinner date. You’ll look instantly put together, and you can dress your sweater up or down with your choice of pants and shoes. For something more casual, wear your sweater with a pair of dark, well-fitting jeans and fashion sneakers like low-white sneakers or a pair of lifestyle shoes from your favorite brand (not athletic sneakers—athletic sneakers will make this look too casual for a date). This casual look is great for a quick date-night drink or a first date at the movie theater.

For a dressier option, wear your sweater with a pair of your men’s chinos, a leather belt, and a pair of men’s leather boots or dress shoes. The dressier option can easily take you from work to your fall date night, too — so you don’t have to worry about running late for your date after stopping at home to change.

A Button-Down Shirt

Men’s button-down shirts are a tried-and-true closet staple for every man. They’re great for family gatherings, work, and date night, too. Break out your favorite button-down shirt, one that you’ll feel comfortable in, for your upcoming fall first date. If you aren’t sure which shirt is your favorite, wear a classic button-down in white or light blue.

Wear your button-down with a pair of black jeans for something different and a pair of leather boots or leather dress shoes... either way, you can’t go wrong. Make sure your button-down shirt is ironed and wrinkle-free before your date. You want to make a good impression!

A Blazer

A blazer is certainly not required for all (or even most) first dates, but it can be a nice dressed-up look if your first date plans involve going to see a live performance or hitting up a new, fancy restaurant in town. For a first date, you can wear your blazer without your suit pants to give more of a casual vibe. You can wear a dark blazer over one of your fitted men’s t-shirts and worn with some dark jeans and dress shoes. Your outfit is instantly fashionable and may even make your date do a double take when you enter the room — and who doesn’t want that?

Plus, your blazer will keep you warm on chilly fall evenings, and if you’re a true gentleman, you can drape it over your date's shoulders if they get cold.

Dressing for a fall date night is fun. While it takes planning, fall is a season where so many different kinds of clothing, from sweaters to blazers to flannel to t-shirts, get to shine. It’s also easy to dress these items up or down, making them a versatile choice whether you are heading out for weekend brunch or a walk through autumn leaves on your fall first date.


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