Welcome to Gentleman Within’s second edition of Styling Cinema™, a series where I attempt to refresh/modernize stylish outfits from the movies.
Part 2 features the quintessential romantic comedy (rom-com) — When Harry Met Sally — and 8 hand-selected, versatile looks from Harry Burns (Billy Crystal). If I had a lady friend to style Sally Albright’s (Meg Ryan) outfits I’d have her on, alas it’ll just be me!
The premise of this series is to put my spin on my favorite looks from classic movies using garments and accessories that I have in my own closet. And more importantly I want the outfits to be wearable.
When Harry Met Sally has some iconic moments, after all who can forget this scene? It’s often regarded as the original rom-com that birthed thousands more. While watching it for the nth time (usually around New Years), I started analyzing Harry’s outfits and how — with some modifying — could lead to tremendously stylish looks. And so the idea for part 2 of this series was born.
Without further ado, Styling Cinema Pt. 2. Enjoy!
When Harry Met Sally Outfits (Lookbook)
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Here’s my take on 8 hand-picked outfits from When Harry Met Sally. Keep in mind, it was released in 1989, and so, many of these looks — while still wearable today — are in need of a fashion refresh. As always, I’ve provided links to all the pieces I’m wearing below, so feel free to shop the looks.
Outfit 1: The Vintage Athleisure
We’re starting things off with a little vintage athleisure. This outfit is anchored by a two everyday basics, from the athletic grey zip hoodie to the faded light wash jeans (you’ll be seeing a lot of these as it was essentially a late 80s trend).

I decided to stay mostly true to the original look with a gray zip hoodie from one of my favorite broadway musicals, Hamilton. But instead of light wash denim, I opted for a mid-wash slim jeans with subtle distressing details. Underneath, I’m wearing my trust Uniqlo Supima Cotton Tee in white overtop a performance undershirt for that contrasting collar.
And instead of the golden, leather strap watch, I went for a vintage resin black Casio watch with a white dial — equally as classic IMO. For shoes — in keeping with the athletic tones — I chose the Everlane Court Sneaker in white with a blue tab accent detail. And just for fun, I threw on a stylish puffer vest from Outerknown to add variety to this otherwise understated, simple look.
Outfit Details
- Hamilton Zip Hoodie: gray zip hoodie
- Supima Cotton Tee: Uniqlo
- Summit Puffer Vest: Outerknown
- AirFlex+ Slim Jean: American Eagle
- The Court Sneaker: Everlane
- Classic Quartz Watch: Casio
Outfit 2: The Relaxed Vintage
For look 2, Harry continues with the vintage theme of slim, light wash jeans, what looks to be a lightweight, heather gray crewneck and a pair of retro white kicks which add on those athletic undertones.

I decided to put on the lightweight merino Active Tee in charcoal gray from Ministry of Supply and layer the heavyweight overshirt in a darker gray from Under 5’10, keeping things ultra-relaxed and casual.
For the jeans, I remained faithful to Harry’s look, buy opting for what seems to be his favorite, light wash jeans. Alternatively, you could go mid-wash or even dark wash slim jeans and it would make for a solid everyday look.
Sneaker check — again I went with the popular Everlane Court Sneaker in all-white for this fit, complemented by the oatmeal colored merino wool socks. And finally, since this is a decidedly casual fit all around, I opted for a cordovan belt with antiqued gold buckle to contrast against the overall look. It works if you ask me.
Outfit Details
- Heavyweight Overshirt: Under 510
- Composite Merino Active Tee: Ministry of Supply
- Slim Fit Light Wash Jeans: Peter Manning
- The Court Sneaker: Everlane
- Merino Wool Calf Socks: Bombas
- Full-Grain Leather Belt: Anson Belt
- Antiqued Gold Belt Buckle: Anson Belt
- Silver Cuff Bracelet: Oliver Cabell
- Silver Ring: Oura
Outfit 3: The Smart Casual
This third fit from Harry isn’t my favorite, but I like what he’s attempting with the smart casual aesthetic. While I love the textured sport coat and the layering up top, he missed the mark with the v-neck sweater, light wash straight-fit jeans and white sneakers. There’s just too much dissonance between the ensemble, like he went for a high-low approach, but took it too far.

And so to correct and modernize this fit, I took some liberties with my outfit details. For one, instead of the professorial blazer, I went with a slicker, yet still smart Comfort Jacket from Uniqlo, paired with a refined brushed heather button up from Ash & Erie, and the more accessible crewneck sweater in classic cashmere from Everlane.
Next, I finally dropped the vintage light denim and went with the tried and true white sneakers from The Perfect Jean to add some finesse to what would’ve been too relaxed. To finish off the looks, I went with the white leather low tops with a suede trim from Veja, a more elegant footwear option than the tennis sneakers Harry has on. Overall, these changes make this fit more modern and elevated, IMO.
Outfit Details
- Comfort ‘Jersey’ Jacket: Uniqlo
- Brushed Heather Shirt: Ash & Erie
- The Grade-A Cashmere Crew: Everlane
- Slim Fit Dark Blue Jeans: The Perfect Jean
- Esplar Suede-Trim Leather Sneakers: Veja
» Related: Check out Styling Cinema Pt. 1 featuring the indelible Back to the Future.
Outfit 4: The Hipster Throwback
Harry was channeling some serious Pinocchio vibes with outfit 4. I’m calling it the Hipster Throwback. Like the previous fit, this one could use some refreshing too.

To modernize things a bit, I chose a white slim fit performance dress shirt from Everlane. Slim fit anything will always feel more contemporary. As for the pants, I like the pleated trousers and so I upped the ante with a pair of my own with side tabs instead of belt loops. The braces here are redundant, but I’ll play along and keep them since it’s a major piece of this overall look.
Moving on, I have no idea what the shoe situation is here, but I picked what I thought would complement the look. And so look no further than my dependable Fifth Avenue cap-toe oxfords from Allen Edmonds in the dark chili colorway. Classically modern in the best of ways if you ask me.
Outfit Details
- Performance Dress Shirt: Everlane
- Pantaflat Cotton Trousers: Loro Piana
- Fifth Avenue Cap-Toe Oxford: Allen Edmonds
- Suspender Braces: Amazon Fashion
- Silver Cuff Bracelet: Oliver Cabell
- Silver Ring: Oura
Outfit 5: The Cozy Athlounger
For outfit 5, I love oversized cable knit mockneck sweater Harry’s got on here. Unfortunately I don’t own an oversized mockneck, but I do have a handful of rollneck sweaters and so I’m going with that in a similar color of beige with a more refined body fitting aesthetic. Not quite as comfy, cozy, relaxed as Mr. Burns, but still picks up a similar mood.

Onto the pants, I wouldn’t have thought to pair a turtleneck sweater with sweatpants, but if you think about it, they’re match made in sartorial heaven. One is comfortably refined while the other is comfortably casual, leading to a great high-low balance. I kept true to the original fit with a pair in heather gray.
On his feet, the socks are looking quite cozy as well, I imagine they’re some sort of woolen fabric and so I opted for a thick gauge pair of socks in merino wool. And as for the book, I’m not sure what kind of reads Harry is into, but the one I’ve got right here is David Coggins’ Men And Style, a must have for any menswear enthusiast.
Outfit Details
- Cable Knit Turtleneck Sweater: Amazon Fashion
- Gray Sweatpant Joggers: Adidas
- Merino Wool Heavy Expedition Socks: Fits
- Men And Style: Essays, Interviews & Considerations: Amazon Books
- Silver Ring: Oura
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Outfit 6: The Cozy Casual
IMHO, the classic white trainer is an ultimate forever piece, that should have a stranglehold on your closet for at least 3 seasons out of the year, if not year round. Harry sure loves his trusty white kicks as he’s wearing a pair in scene after scene. Can’t blame him really. He also loves jeans of the light wash variety (told you we’d be seeing ’em plenty). Can’t knock him though since it was a sign of the times.

Outfit 6 is essentially the same as the previous fit, but instead of sweats and socks we’ve got denim and sneakers which is out of home appropriate attire while still keeping it casual, cool.
I’ve kept the rollneck sweater from the last look and decided to recycle the Court Sneakers from Everlane and the AirFlex+ slim jeans from AE, one of my favorite pair of jeans to wear.
Outfit Details
- Washable Mock Neck Long Sleeve Sweater: Uniqlo
- AirFlex+ Temp Tech Slim Jean: American Eagle
- The Court Sneaker: Everlane
Outfit 7: The Winter Classic
Now onto outfit 7. If you want to lend instant elegance to any outfit, pick up an overcoat (topcoat) in camel or charcoal gray for maximum versatility. Harry is donning an oversized overcoat here that’s sure to keep him warm, but the early-90s NFL linebacker shoulder pads are stunting his style a bit.

Though he’s on trend for the era, I refined the look with a slightly shorter, much more slim fitting topcoat in a similar grey color. This fit is much more modern while keeping true to the original. Next, I decided to throw on a black cable knit turtleneck to complement the coat along with a charcoal gray ‘tapered’ wool trousers (tapered being keyword here) with a herringbone pattern that’s elevated as ever.
Finally, if you want to add a fashion forward edge to your winter outfits, do yourself a favor and throw on a few trusty accessories like a cashmere scarf and leather driving gloves to instantly add a dash of style and sophistication that’ll show that you’re serious about style.
Outfit Details
- Wool Overcoat: Asos Design
- Cable Knit Turtleneck: Amazon Fashion
- Tapered Italian Wool Perfect Pant: Banana Republic
- Micah Wingtip Dress Boots: Idrese
- Cashmere Scarf: Peter Manning
- Leather Driving Gloves: Amazon Fashion
Outfit 8: The Home Team
And last but certainly not least, outfit 8…”The Home Team” is anchored by one of my fall favorites that casually adds a laid-back spin to your off-duty look — the field jacket. Go for olive, tan or navy — olive being my favorite of the trio.

We’re back where we started, and there he goes with the light wash jeans again, not only that, his best friend is twinning with him. As much as I respect the light wash, I opted for a more versatile mid-blue, slim fit pair from Mott & Bow with distressing details at the ankle opening for a dash of additional style.
It looks like he’s got a grey turtleneck on and so I went with my lightweight Uniqlo HeatTech turtleneck with more a performance fabric. For the shoes, I went with the original Tread by Everlane trainer in an olive colorway to match the olive field jacket. And lastly, Harry is a New York Yankees fan, but I’m not and so I went instead with a Temple University (my alma mater) New Era cap. Fit checked!
Outfit Details
- Tribeca Field Jacket: Peter Manning
- HeatTech Turtleneck: Uniqlo
- Slim Fit Jeans: Mott & Bow
- The Trainer Sneaker: Everlane
- Fitted Ball Cap: New Era Cap
Conclusion
There you have it, my 8 recreated and refreshed outfits from the archetypal When Harry Met Sally. While none of these hand-picked looks are a serious sartorial statement, they are wearable and stylish as they come (with a little modernizing).
I won’t spoil the movie for anyone who hasn’t seen it (you’ve had 32 years lol), but I do want to mention that it’s a feel good, heartfelt film that any rom-com lover is sure to enjoy. And that they sure could’ve used 21st century technology, haha.
What should be the next installment of this Styling Cinema series?
Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.
Looking forward to seeing you in there.
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