Here You Go: Morgan Stewart Told Me the Shoe Trend Were Wearing With Jeans on a Date

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If Morgan Stewart McGraw gives style tips, you don’t question it. You listen, you follow—the end. So get ready for what’s coming your way. The Renggli founder hosted Bumble’s first live Bee Line episode, where she answered various dating questions alongside Mary Holland Nader and her husband, Jordan McGraw. I sat down with Stewart McGraw to decode date-night dressing—whether you’re heading out on a first date or just refreshing your look for a night out with your long-term partner.

Here is Stewart McGraw’s guide to date-night fashion—including the specific pieces she’d avoid (like when we’re wearing flats, and when we’re not). You’ll also uncover inspired shopping picks based on her recommendations, along with the full episode of her Bee Line episode (it’s so fun). And of course, don’t forget to tune in to her addictive podcast, The Morgan Stewart Show, and shop her wildly popular clothing line, Renggli.

Ep. 9 | Morgan Stewart McGraw LIVE on Exes, Nailing Your Bumble Profile & Dating Dos and Don’ts 📞 – YouTube

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What to wear on a first date (drinks, not super fancy)

“We’re wearing really great-fitting denim and a deep V-neck sweater from Renggli (not even a plug). That’s generally what I would wear. But let’s say Renggli didn’t exist—a fitted, feminine, sexy, but not trying too hard sweater and a good pair of jeans and heels. There’s no outfit that’s ever going to beat that. No flats, though. It’s always heels. Dates are when we’re trying to lead to something, right? I think a flat is too casual. It doesn’t need to be the highest heel, but you need some lift.”

What to wear a couple dates in (casual lunch on a Saturday)

“It’s kind of the same formula. I think it’s a lighter color sweater, depending on where you are in the world. I would even do a pair of corduroys—something a little bit more textured and a little but more daytime that doesn’t serve you at night, but it’s a little dressier. I would even do a brown corduroy with a yummy long-sleeve fitted shirt or sweater. I could also see this with a heeled boot. Another trick is another sweater tied around the neck, so you can take things off—in a very seamless and effortless way.”

What to wear after dating for several months (fancier restaurant in the evening)

“A long-sleeve sheer blouse and a nice black trouser, maybe cropped, a little high-waisted with a cute heel, not too high—streamlined, black, sexy, but also not trying too hard.”

Dresses?

“You know, it takes a lot for me to put a dress on. I would do a mini shift dress with pantyhose, and then, in that case, I would wear a flat boot. But I’m not wearing a dress and heels. Like, I feel like that’s when you’re really, really, really together.”

What to wear when you’re committed and meeting the parents

“We’re wearing a button-down shirt, tucked into good pants, jeans, or cords. There’s a belt, a little pop of the collar, and the hair is back.”

What to wear when you’ve been married for several years

“I’ve been married for six years, and I’m wearing basically a compilation of everything I explained to you. I would also do a chunky sweater, but then do a mini skirt to counterbalance with pantyhose for winter. And then a patent leather pointed heel with a strap—definitely something that makes you feel locked in. You could also do a long trench coat with a beautiful tank top underneath and a high-waisted trouser. Overall, stuff you’re comfortable in that makes you feel chic and put together. The through line is nothing fussy.”