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The Most Stylish Men’s Finds in the Zappos Birthday Sale

You won’t find me putting this in their birthday card, but let’s just get this out of the way now: Zappos is not cool. They’re massive, yes. Great customer service? Absolutely. But for a retail site where you can find Salvatore Ferragamo crown bit loafers next to a pair of Skechers, the quantity-forward selection can feel overwhelming to shop. They’re selling everything they can get their hands on, and it shows.

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Now, don’t get me wrong. I’m not saying I’m cool. Just this morning, I made a “Cash me...inside this bed!” joke because I was supposed to go on a run while it poured outside. It was not well-received.

But I know how to edit! So the team and I did the work of digging through hundreds of pages of product to find you not only the best deals from Zappos’ 20th birthday sale, but the most stylish ones too.

Looking for the best buys for women? Check out our picks here.

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Steve Madden Adoro slip-on sneakers, $64

Steve Madden Adoro slip-on sneakers, $64
Graphic: Shep McAllister
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With a woven leather upper, these Steve Madden sneakers already look more expensive than they actually are. At 29% off, they become even harder to resist. So just give in already!

CARLOS by Carlos Santana chelsea boots, $59

CARLOS by Carlos Santana chelsea boots, $59
Graphic: Shep McAllister
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Here’s a sentence I never thought I’d write...but don’t sleep on smooth jam master Carlos Santana’s casually elegant footwear. He’s like the celebrity men’s answer to Jessica Simpson (true story: every woman you know owns a pair of her shoes and is obsessed with how comfortable they are, even if she’s not willing to admit it).

Magnanni Ezra double monk straps, $252

Magnanni Ezra double monk straps, $252
Graphic: Shep McAllister
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When a luxe as hell pair of dress shoes like this is half off, well, you buy them.

Canali suede loafer, $223

Canali suede loafer, $223
Graphic: Shep McAllister
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Ahem….ditto.

Athletic Propulsion Labs Techloom Breeze, $60

Athletic Propulsion Labs Techloom Breeze, $60
Graphic: Shep McAllister
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If you’re not afraid of a little hi-vis color for your feet, you really can’t beat this deal. 70% off the Techloom Breeze from cool kid sneaker brand APL. The style runs a bit narrow, but once your foot’s in, the snug feel is surprisingly comfortable.

Kenneth Cole stacked dress shoe, $86

Kenneth Cole stacked dress shoe, $86
Graphic: Shep McAllister
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This navy pair of dress shoes with a rubber sole may be a little more trendy than what you’d usually go for, meaning when they’re on sale is the perfect time to pull the trigger. Wear them with a pair of charcoal trousers with no break (and sans socks) and a knit polo for a stylish end of summer vibe.

Polo Ralph Lauren pool slides, $43

Polo Ralph Lauren pool slides, $43
Graphic: Shep McAllister
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You may remember this tartan pair of pool slides from a roundup back in June and now here they are. On sale. We’re going to take it as a serendipitous gift to you, the reader, from the universe, rather than a negative reflection on our taste level.

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Bugatchi swim trunks, $53

Bugatchi swim trunks, $53
Graphic: Shep McAllister
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Don’t forget that Zappos sells more than just shoes. This pair of Bugatchi swim trunks would be a perfect purchase to distract yourself from the sad fact that summer’s more than half over. Oh, now you’re thinking about that, aren’t you? Yeah, sorry. My bad...

Richer Poorer grey crewneck sweatshirt, $48

Richer Poorer grey crewneck sweatshirt, $48
Graphic: Shep McAllister
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Team SG has opined on our love of grey crewneck sweatshirts before. If you’re ready to drink the crewneck Kool-aid with us, this Richer Poorer style is ringing up at under fifty bucks during Zappos’ birthday sale. Its garment-dyed French terry cotton lends a super-soft, broken-in feel you’ll love.

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Nike SB anorak, $55

Nike SB anorak, $55
Graphic: Shep McAllister
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As someone who always wanted to be that girl from the episode of MTV’s Made that became a skateboarder, I’m a totally (lame) fan of the Nike skateboarding line. Thankfully, you don’t have to learn how to bust a kickflip (lol please don’t let me know if that’s even a thing or not) to sport this anorak with style.

Joe’s Jeans Brixton Straight and Narrow jean, $98

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At nearly 50% off, this pair of designer denim will convert you to jeans that (generally) ring up at three figures.


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About the author

Megan Collins

Megan Collins started Style Girlfriend to help guys look and feel their best. Today, she and her team share tips, tricks, and shortcuts to a closet that inspires confidence.