Men's Fall Date Outfits: What to Wear

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Get inspired with men’s fall date outfits and shop fall style staples to wear on your next outing…

Last September, I went on an epic first fall date. It began in the late morning and ended in the early evening.

We kicked things off with a walk from the East Village to the West Village here in New York, followed by cocktails before noon and lobster rolls at a charming sidewalk table. Then, a stroll through Central Park, a lingering conversation in the Temple of Dendur at The Met Museum and finally, a long, flirty subway ride back downtown.

You catch all that? It was a marathon meet-up, and the temperature must have swung by about 15 degrees throughout the day. Neither of us had planned to be out for so long, but thanks to some smart layering choices, we were both H-O-T-T-O-G-O from day to night with ease.

How should you dress in the fall for a date?

It depends on what you’re doing! But no matter what the plan is for your next fall date (I really do recommend a walk that ends at a museum, whether that’s Central Park and the Met or whatever’s local to you), you want to be prepared with your look.

If the thought strikes terror in your bones, I’ve got you.

Because here at SG HQ, date outfits are sort of our thing. So, helping you figure out stylish fall date outfits for men is right up our alley.

A good rule to follow?

Make an effort, but don’t overthink it

I get it! When figuring out what to wear for a date, there’s plenty of forces to balance out.

You want to look more polished than usual, but not like you’re trying too hard. Should you bring a jacket? Where will you hold it?! Do you need a backpack?!?

I’ve got you.

Here at SG HQ, we pulled together the can’t-miss guide to men’s fall date outfits.

Check out style inspiration below, for dressy date nights out on the town, coffee dates, and everything in between. Then, shop some of our favorite fashion finds for men to wear on a date this fall.

Below, 7 stylish men’s fall date outfits to inspire you:

Coffee Date Outfit

What makes this a great date outfit: A little bit of flair goes a long way. I’d bet you a dollar that your date will absolutely remark up on a pair of cool sneakers, even if (especially if?) the rest of your outfit is more conservative.

Afternoon Brewery Tour Date Outfit

man in a red button-up shirt, khaki shorts, and brown shoes with white socks — @wears_oli

man standing inside next to a bike, wearing a navy bomber jacket, western-style hat, sweatshirt and jeans — @l.l. wood

What makes these great date outfits: Fall weather can be fickle. Maybe a day date means shorts. Maybe it means jeans and light jacket.

When it comes to a casual day date look, a statement jacket can go a long way to helping you look and feel your best. Meaning? You present your most confident self.

Stroll Through the Park Date Outfit

man standing at a train station wearing a short-sleeve plaid shirt with ankle-baring khaki-colored pants — @jms_hrvy_fits

What makes this a great date outfit: This look says to me, “I know my personal style, and take pride in it.”

And that is sexy! A man with a unique sense of style is attractive, because it means he’s taken the time to think about what he likes, what he doesn’t, and the image he wants to project to the world.

Maybe that’s canvas sneakers and cropped workwear pants. Maybe it’s a natty blazer and Oxford shirt combo. Whatever makes you feel the most you.

Late-Afternoon Drinks Date Outfit

man standing in a corner wearing an orange hat, white shirt, olive jacket, turquoise necklace, dark pants and loafers, men's fall date outfits — @surf_and_tailor_moat

What makes this a great date outfit: The details!

The pop of color in that beanie? So cool. The turquoise necklace? Unexpected and fun!

The moccasin loafers? A noted (and appreciated) finishing touch!

Casual Dinner Date Outfit

What makes this a great date outfit: There’s something about wearing white or off-white pants that says, “I’m a grown man who won’t spill ketchup on myself.”

And I’ve gotta say? That’s sexy as hell.

Dressy Dinner Date Outfit

man standing on a sidewalk in sunglasses, wearing a brown coat with a tan sweater over the shoulders, light-colored pants, and suede shoes — @jhilla

What makes this a great date outfit: These looks are the gold standard in stylish fall date night outfit-dressing.

Sumptuous sweater in a gorgeous fall color? Check. Pants that, just like above, prove you’re a grown up? Check.

For the footwear, it depends on where you’re going. Sneakers could work, or lace-up boots could be the move.

First Date Drinks Outfit

man walking on the street wearing a red short-sleeve shirt over a white tank with olive green pants and high-top nike sneakers — @ryanjhj7

What makes this a great date outfit: An unexpectedly playful statement piece, like the high top sneakers, sets this casual outfit apart.

If you’re wondering what’s best to wear on a first “get to know you” date? This is it.

What to keep in mind when getting dressed for a date

This is not the time to experiment! Let your dazzling personality to do the heavy lifting for now. Experimenting with your style can be fun, but not when you’re mixing a new look with the nerves involved in getting to know someone new. There’s a reason we support uniform dressing here at SG HQ!

Dress for the “job” you want. If this is a first or early in the game date, meeting up with a potential paramour can feel more like a job interview. You want to present your best self, so dress your best! Consider it a perfectly polished resume you wear.

Basic isn’t bad. Wearing elevated basics on a date means that you get to stick in your comfort zone while looking like your best, sophisticated, stylish self. That could mean a cashmere cardigan, or the loafers that make you feel like an off-duty James Bond.

Below, shop fall date style:

close-up of a man wearing a brown v-neck cardigan over a white crewneck t-shirt — J.CREW
Alpaca-blend cardigan, $198

man from the waist up wearing a navy v-neck sweater vest over a white t-shirt with jeans — GAP
textured sweater vest, $49