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What to Wear on a First Date: Fall Edition

October 19th, 2015

It’s true what they say: you only get one chance to make a first impression. And following our humorous look at first date footwear last week, I thought it would be helpful to share a few outfit ideas focusing on what to wear on a first date this fall.

Here’s some inspiration and a few tips.


Play to your strengths. Double down on colors that work with your complexion. These are the colors that will make you look your best and colors that you’ll likely feel most comfortable in. For me, that’s brown, which also happens to be a great fall hue.

Add interest with patterns and texture. If you choose a monochromatic palate as a foundation, use patterns and texture for a little depth. Plaids and fair isle patterns are perfect seasonal options, while a nice pair of corduroys are a good middle-ground when jeans seem too dressed down or trousers too dressed up.

What To Wear on a First Date in Fall - He Spoke Style

| WEARING | Suitsupply blazer and shirt, Brooks Brothers sweater, J.Crew pants, Oliver Peoples sunglasses, Watch c/o Uniform Wares, Boots c/o Allen Edmonds | PHOTOGRAPHY | by Rob McIver Photo

Add some subtle contrast. Pink isn’t necessarily thought of as a fall color, however, when you’re using brown as foundation for an outfit, pink is a nice way to add an accent. It complements brown in a fresh and unexpected way and is sure to attract all the right kinds of attention.

Layer it up. As you know, fall is prime time for layering. A coat seems more like an evening garment and less appropriate for a brunch date. Not to mention that it could wrinkle your blazer. Instead, layer a thin v-neck sweater to stay warm.

Suitsupply Brown Plaid Wool Blazer and Uniform Wares Watch - He Spoke Style

As mentioned, dress boots are always appropriate and are sure to make a lasting impression. My favorites: dark chocolate brown Allen Edmonds Daltons.

Check out our guide on choosing the right boots for fall.

Dark Chocolate Brown Allen Edmonds Dalton Wingtip Leather Dress Boots - He Spoke Style

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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