I was invited to speak at a conference recently, and in the course of planning my outfit, I started looking for shoes that leaned more towards Serious Professional than my usual vibe โ€” I Worked Out And Haven’t Yet Showered. I was looking for pumps, but sharp, boss babe ones. The problem, of course, is that most of these types of pumps are horrifyingly uncomfortable.   

In the end, Linzi saved (ruined??) me. She and her unshakable pursuit of comfort shoes keep brands like Naturalizer and Aerosoles top of mind and…okfine, Linz, you’re right. Comfort shoes today are not like comfort shoes a few years ago.

I managed to find three pairs of sexy, boss babe pumps that also have a cushioned insole AND a walkable heel. And one of those pairs comes in a seriously drool-worthy range of colors, sooo…

Let’s get to it. 

The 3 Most Comfortable (& Sexy) Pumps

1. My Top Pick: Naturalizer Anna Pumps

Looking for pumps, but sharp, boss babe ones? We found 3 pairs of comfy, sexy high heels with cushioned insoles & walkable heels. Drool-worthy options ahead.

These pumps are the ones I ended up keeping. They’re shockingly comfortable, and the prints, patterns and colors are so freaking good. If snake isn’t your thing, check out the leopard print, or some of the beautiful neutral metallics (cocoa pearl is another fav). Plus, there’s a wide range of the usual suspects (black, red, etc.,) Fit is TTS (true-to-size).

Looking for pumps, but sharp, boss babe ones? We found 3 pairs of comfy, sexy high heels with cushioned insoles & walkable heels. Drool-worthy options ahead.

Find the pumps: Macy’s | Zappos | Nordstrom | Amazon

Find the tee: Macy’s | Free People | Nordstrom

Find the jeans: Macy’s (also in plus size) | Zappos

2. Kenneth Cole Riley 85 Pumps

Looking for pumps, but sharp, boss babe ones? We found 3 pairs of comfy, sexy high heels with cushioned insoles & walkable heels. Drool-worthy options ahead.

At the time, I thought these pumps only came in blue snake…but, happily, I was dead wrong. Kenneth Cole’s Riley 85 pumps come in some seriously statement-making options (red snake, silver, leopard) and all have cushy memory foam, a walkable heel, and comfortable leather. Fits TTS. LOVE.

Looking for pumps, but sharp, boss babe ones? We found 3 pairs of comfy, sexy high heels with cushioned insoles & walkable heels. Drool-worthy options ahead.

Find the pumps: Macy’s | Zappos | Nordstrom | Amazon‘s | Zappos | Nordstrom | Amazon

3. Aerosoles Deal Breaker Pumps

Looking for pumps, but sharp, boss babe ones? We found 3 pairs of comfy, sexy high heels with cushioned insoles & walkable heels. Drool-worthy options ahead.

I didn’t find these quite as fashion-forward as the other two…but they’re still a really solid choice. I especially love the plaid (it literally went with EVERYTHING โ€” much more versatile than I realized at first) and there’s a really beautiful red suede, too. The fit on these runs about a half-size big.

Looking for pumps, but sharp, boss babe ones? We found 3 pairs of comfy, sexy high heels with cushioned insoles & walkable heels. Drool-worthy options ahead.

Find the pumps: Macy’s | Zappos | Amazon

Go forth and conquer, Boss Babes.

xo,

S

4 COMMENTS

  1. What constitutes a “walkable heel” on this site? At 3.5″ high, I wouldn’t even consider these if I saw them on Zappos, as sexy as they all are (that blue!!). I need a glossary of TME terms so I can understand how you city-walking gals think!

    • Oooo…this is fair. These are not the same kind of walkable heels as, say, a pair of wedge sneakers or my wedge Sorel boots. They are, however, extremely walkable in comparison to other high stilettos. While I wouldn’t walk from one end of Philly to the other in these…I could likely walk home from a restaurant, or wear them all day at a blogging conference. I mean…they’re still heels, not sneakers, but walkable given what they are.

      But yeah – we need some consistent terms for this, haha. ๐Ÿ™‚

  2. Love the snakeskin! If you work in a warm climate, the Sam Edelman Yaro sandal is extremely comfortable. I live in Hawaii and these sandals are appropriate even in my โ€œformalโ€ workplace.

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