9 Perfect Outfits to Wear on a Second Date

Look up "what to wear on a first date" and surely you'll find hundreds of outfit ideas to draw inspiration from. Thanks to your incredible first-date look and your charming personality, more importantly, you scored a second date. Things are looking up until you remember you need an outfit for that too. Why does no one talk about second dates? They really are just as important as the first if not more important, and we want to make sure you have the ensemble to prove it. 

To help us out a bit, we gathered some second date-outfit inspiration from a handful of our beloved bloggers. On a second date, you can really let your true colours shine, especially if you played it safe on date number one. If you are a T-shirt–and-trousers kind of girl, wear that, but if you want to pull out all the stops and wear a bright floral dress and satin platforms, there's no time like a second date to do it. At the end of the day, wearing what makes you the most comfortable and confident is the right choice, date number aside. 

Ahead, shop the second-date outfit ideas straight from some of our favourite bloggers. 

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T-Shirt + Checked Trousers + Strappy Sandals
(Image credit: @lifeofboheme)

Style Notes: If you love jeans but want to go one further for your date, try a checked trouser. Take your styling cue from Marta Cygen and add a basic white tee, block heel sandals and a mini bag.

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Printed Shirt + White Skirt + Sneakers
(Image credit: And I Get Dressed)

Style Notes: Swap darker tones for a white midi skirt and add a classic Breton striped top and trainers for an impossibly chic off-duty outfit.

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Summer Dress + Block Heel Sandals
(Image credit: @wishwishwish)

Style Notes: Trousers not your thing? You can't go wrong with a pretty sun dress. Carrie Santana da Silva opted for a mid-length iteration, finishing her date-ready look with ankle-tie sandals and a matching tan bag.

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Matching Set + Suede Mules
(Image credit: Happily Grey)

Style Notes: Make a statement and go matchy matchy. Mary Seng gave us all a lesson in styling such a standout look, pairing her punchy two-piece with muted accessories and fuss-free hair.

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Leather Jacket + Black Shirt + Black Trousers + Mules
(Image credit: @beautyrewritten)

Style Notes: Not sure what the weather has in store? If in doubt, sling on that hero leather jacket. Nitsan Raiter wore her biker style draped over her shoulders and completed her easy look with black suede mules.

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Floral Dress + Low Pumps
(Image credit: Song of Style)

Style Notes: A floral dress will always be a winning option. To avoid looking too dressy, simply style your fail-safe frock with mid-height heels.

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Slip Dress + Blazer + Statement Sandals
(Image credit: @damselindior)

Style Notes: The slip dress has made an unexpected return to the spotlight, and according to Jacey Lenae Duprie, and the majority of influencers on our Instagram feed, this silky separate is surprisingly versatile. For evening, just add sky-high heels, and for a day date, dress your new slip down with a blazer and slides. 

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Ruffle Blouse + Jeans + Statement Shoes
(Image credit: @emilisindlev)

Style Notes: Sometimes a button-down shirt just feels too formal. So why not try a ruffle top, instead? Team with high-rise jeans, green flats and a top handle tote like Emili Sindlev for maximum impact.

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Midi Dress + Platform Sandals
(Image credit: @natalieoffduty)

Style Notes: This is a no-brainer. Wear your printed midi dress for date two, three or four—you'll get so much wear out of this wardrobe staple. Zimmermann's iteration is our top pick (up next), and we think its worth every single penny.

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Opening Image: Getty

This post originally appeared on Who What Wear U.S.

Editorial Director

Lauren Eggertsen is currently the editorial director of Who What Wear and has worked at the company for over eight years, where she started as an associate editor and has since worked her way up. Lauren has over 10 years of experience in the fashion editorial space, starting her career with internships at Marc Jacobs, Marie Claire, and The Zoe Report, where she was later hired as their editorial assistant. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. It is here where she leads and manages Who What Wear's fashion team and oversees all day-to-day editorial content and large tentpole moments. This includes all of the runway, trend, and shopping-driven content that ultimately helps to build a strong brand reputation within the industry. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many of the celebrity cover shoots, including big names like Kaia Gerber, Normani, and Kristen Stewart.

She has also attended multiple fashion weeks, including New York, London, Milan, and Paris, where her personal style has been featured on sites such as Vogue, Harpers Bazaar, and Elle. She prides herself on discovering and supporting small brands and on her knack for a good vintage shopping find. When she isn't working, she enjoys researching and dining at reputable restaurants around both her neighborhood and the globe.