The Best Shoes & Boots From The 2019 Anniversary Sale

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Hey there! I know we’re entering the final weekend of the Anniversary Sale…which is when I typically make my final selects (and try to panic-exchange sizes that didn’t fit, colors that don’t actually work with my existing wardrobe, etc.,). You too? Anyway, I realized that, in the last several weeks, I’ve tried on almost all the shoes and boots in this darn sale. So. Here’s a quick rundown of the styles I like (that are still in stock) and a few tips on styling the trickier styles.

And while Linz refuses to take my idea of “comfort shoes” seriously (I mean….girlfriend swears by Danskos), I was the original creator of the TME Comfort Score system. (Hmmm…should we do annual shoe/boot awards? Like the Allure beauty issue — snort — but for comfortable shoes?)

In any case, if you are new to this party, here’s our TME Comfort Scoring system: 

TME Comfort Score For Shoes & Boots

TME Comfort Score 1 – You can walk — like really walk, not hobble — for at least several hours in this shoe. It doesn’t rub, it doesn’t pinch, yet it meets (or exceeds) our minimum quality control for cool and chic. (If you are only looking shoes in this category…check out Linzi’s article – she covered a ton of the comfort shoes in the Nordstrom Anniversary Sale there.)

TME Comfort Score 2 – It still meets our baseline for cool, but there’s something wrong: the heel is slightly too high, or maybe it’s comfortable only in small doses, etc.

TME Comfort Score 3 – BOOO we hate it. Buy at your own risk.

The Best Shoes & Boots In The Nordstrom Anniversary Sale

1. Everyday Boot In The #NSale

Let’s start with the stuff we’ll wear the most, right?

A. Dolce Vita Sher Perforated Bootie

TME COMFORT SCORE: 1

Dude. I do NOT understand the negative reviews on this bootie. I love them. The heel height is walkable, and the inside bit near your heel is lined in really soft leather. Nothing rubs. I suspect that a tricky fit might be the culprit. I’m normally closer to a 6.5…and ended up being much happier with the 6. The upper did need to break in a little bit…but I had already walked over a mile before I realized that some breaking-in was needed. A few days later they were fine.

My favorite is obviously the snake print (a new neutral, I promise) but the taupe and the light tan are both gorgeous, too. You can’t go wrong with any of them.

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).Dolce Vita Sher Perforated Bootie (Black/White Snake Print)

B. PAIGE Willa Studded Chelsea Boot (Taupe)

TME COMFORT SCORE: 1

I have these boots in snake print. Because of the western styling, they can get narrow near the toes (especially with thick socks like I do), but the leather is high-quality and will eventually stretch into perfection. These boots are also available in black…but I’m a big (huge) fan of the taupe. (Also, I put together a little video showing how best to pair these with jeans.)

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).

I already know how versatile the snake print version is (see them styled (here and here)…but I wanted to put the taupe through its paces as well.  
Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).BOOTS: PAIGE Willa Studded Chelsea Boot (Taupe) 

TOP ROW: sweater | black jeans | peasant top | similar shorts

BOTTOM ROW: denim jacket | dress | sweater | jeans

C. Aquatalia Tilly Waterproof Bootie

TME COMFORT SCORE: 1

These are REALLY GOOD. The heel is barely there — it’s literally just enough to give your legs that ‘high heel look’ — and these boots are soft and comfortable. The shaft is nice and high and narrow enough to slide under all manner of skinny jeans, mom jeans, straight leg jeans, etc.,  

Also? Freaking WATERPROOF. (And comes in a bunch of colors…ummm…check out the chocolate suede.)

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).Aquatalia Tilly Waterproof Bootie (Black)

D. BORN Meggs Bootie

TME COMFORT SCORE: 1 (Linzi) or 3 (me)

Here’s the thing: these boots *can be* insanely comfortable. If you (like Linzi) have what we are going to call “strong ankles” than this is your boot. They looked insanely cute on Linz (see here), are walkable and comfortable and YAY: deserve the comfort score of 1.

If, however, you are more of the scrawny, weak-ankled type…these boots will fit your ankle more like a comfortable old sweater (leg warmers?) and your feet will swim in the pool that is the knit of the boot and you will lose them right off your foot should you ever need to do a high kick. (And you never can tell when you’ll need to do a high kick.) BE WARNED, YOU SCRAWNY-ANKLE PEOPLE. BE WARNED.

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).BORN Meggs Bootie (Gray) 

E. Sam Edelman Welles Bootie

TME COMFORT SCORE: 2

These boots are very cute, and, with socks, would be comfortable enough (the upper is a bit stiff). I much prefer the tan pair, but only the red are left. However….the red is a really dark, pretty red (nothing at all like the product photo) so I thought it was worth playing around.  

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).Sam Edelman Welles bootie (spice mahogany suede)

In general, I find that deep red booties work really well if you are a big wearer of black jeans. Obviously they make black jeans + dark tops more interesting, but the real win was the black jeans + light top. This combo can sometimes look jarring with black jeans and boots, but the red softens it up just enough (without disrupting the long leg line).

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).BOOTS: Sam Edelman Welles bootie (spice mahogany suede)

sweater | black jeans | peasant top 

F. Dolce Vita Cotelyn Bootie

TME COMFORT SCORE: 2

These are just tons of fun. If you’ve never dabbled in the world of statement booties, or want an easy way to upgrade your denim, try these. (And if you’ve been considering — but are scared of — a lighter boot…these also come in zebra. Both are pretty amazing.)  Basically a complete outfit upgrade for $109. (Buy big enough to wear with thick black socks — it’s OK if they peek out from under jeans, and they’ll be totally comfortable for walking.)

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).Dolce Vita Cotelyn Bootie (Tiger Print)

G. Sorel Cate Waterproof Lace-Up Boot (Only Black Available)

TME COMFORT SCORE: 1

Only the black version of this boot is left, but the vibe is decidedly more combat boot than rugged librarian, which frankly, I wasn’t sure about to begin with. (Combat boots, however, will be having a huge moment this winter.) Bottom line is that these Sorels are waterproof, comfortable, and walkable. So very tempting for this city girl, who will have to routinely brave slushy school-drop offs.

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).Sorel Cate Waterproof Lace-Up Boot

F. UGG Kristin Waterproof Bootie

TME COMFORT SCORE: 1

There’s nothing super-special about these boots. They’re cute (would actually look good with leggings), waterproof and comfortable. Practical and boring. Linzi prob loves them.

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).UGG Australia Kristin Waterproof Wedge Boots (black or olive green)

G. UGG Melrose Bootie 

TME COMFORT SCORE: 1

I really wanted to bring these home. I did…not. I see these UGGs as a very slippery slope…I mean…if you basically own outdoor slippers would you ever wear anything else? And then the same argument can be made for giant sweatpants and my husband’s old sweater and then maybe I’ll add a big scarf because…chic? 

Actually….just add a ‘Supreme’ hat and call it streetwear.

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).UGG Melrose Bootie (Chestnut) 

2. Heeled Boots In The #NSale

A. Jeffrey Campbell Raven Bootie

TME COMFORT SCORE: 2

These are some of my favorite booties from the Nordstrom Anniversary Sale. They come in both snake print (shown) and a black neoprene fabric. I’ve actually owned the black neoprene for months now (you can see them here, with a dress + tights) and the fabric version is the more comfortable of the two. The snake isn’t bad either, but the boot upper is stiffer (and not nearly as comfortable on bare legs). That said, given the height of the heel, these boots are surprisingly walkable. Date night only, but still RAWR. I mean….SSSSSS.  

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).Jeffrey Campbell Raven Bootie (Snake) 

B. Sam Edelman Leahla Slouchy Midi Boots

TME COMFORT SCORE: 2+

These boots are gorgeous and comfortable and much more walkable than most of the truly heeled boots in this category. I reallllly like these. But…they’re a bit tricky to style.  

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).Sam Edelman Leahla Slouchy Midi Boots (taupe)

Cam also tried these boots on (here) and they were much more midi on her. Which I loved. On me, they hit a bit higher than midi but I’m calling it close enough. I haven’t decided if I like them over skinny jeans but…maybe? Maybe I’m willing to go there? The shorter length feels more modern than tall boots and I REALLY like what these do for dresses. Hmmmm…..

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score).BOOTS: Sam Edelman Leahla Slouchy Midi Boots (taupe)

TOP ROW: tee | jeans | scarf | dress (xs)

BOTTOM ROW: dress (xs) | green jacket (xs) | denim jacket (s) 

C. Louise Et Cie Sid Bootie

TME COMFORT SCORE: -2

These are, annoyingly, mostly sold out. The reason I’m still talking about them is because they’re also available in red (and a few sizes left in black or white croc). I have last year’s version and they’re a seriously sexy boot. The kind that makes jeans-and-a-tee date night ready…or livens up a boring black dress (even with tights). I think it’s because the stiletto heel isn’t quite as high as it looks. (And while the website says it’s 3.5″ heel….I actually think it’s lower than that. I’ll double-check mine.)

Gang, we tried on MOST of the shoes & boots in the Anniversary Sale. PAIGE, Sam Edelman, Dolce Vita, Sorel, UGGs, Vince….Here are the best (+ a comfort score)Louise Et Cie Sid Bootie (Zeopard)

D. Vince Havana Notch Bootie (Only Black Available) 

TME COMFORT SCORE: 1-2

These are on the hairy edge of being able to walk around all day. Office environment? Absolutely. Date night? You betcha. Walking hard around Philly, covering miles in a typical day of school drop-off/pick-up/ to the office/to lunch/back home again? Maaaayyyybe not quite. But they’re freaking fabulous and go with everything and are just comfortable enough. 

Sizes are almost completely sold out, but every time I check, different sizes are back in stock so there’s hope.  

Gang, we tried on MOST of the shoes & boots in the #NSale. PAIGE booties, EILEEN FISHER pumps, Vince flats, Cole Haan wedges....See how comfy they are.Vince Havana Notch Bootie 

3. Heels & Clogs In The #NSale

A. EILEEN FISHER Rope Pump 

TME COMFORT SCORE: -1

The only reason these get a comfort score of -1 is because after wearing them alllll day (we’re talking one of those epic 12 hour days)…the rope part started digging into my swollen feet. But for date nights, walking around the city, normal work days….they’re amazingly comfortable, and, because of the delicate look of the “straps”….actually read pretty sexy, too. 

Gang, we tried on MOST of the shoes & boots in the #NSale. PAIGE booties, EILEEN FISHER pumps, Vince flats, Cole Haan wedges....See how comfy they are.EIELEN FISHER Rope Pump (Black Suede)

B. Cole Haan Wedges

TME COMFORT SCORE: 1

These shoes were a total surprise. They don’t look like anything special on the shelf (or on the product page), but the cut of the toe box makes them surprisingly sexy. The fact that the ankle strap is lighter means that (on light skin tones) the leg line is elongated. I was shocked by how much I liked these. Truly a heel one could walk a mile (or two) in. (Scotti paired the gray version with boyfriend jeans, here.)

Gang, we tried on MOST of the shoes & boots in the #NSale. PAIGE booties, EILEEN FISHER pumps, Vince flats, Cole Haan wedges....See how comfy they are.Cole Haan Lara Ankle Strap Pump (black)

C. AGL Slingback Pumps

TME COMFORT SCORE: 3

I couldn’t get the fit right on these pumps. I had cinched them down to the last hole, and they still slid off the back of my foot. I suspect I’ll need to size down another half size, and then, like a reviewer mentioned, perhaps stretch out the front.

Or…skip it. WAY too much work.  

However, these pumps are super sexy, have a heel that *should* be walkable (if they didn’t slide off) and buttery soft leather.  On the right foot, these would be amazing.Gang, we tried on MOST of the shoes & boots in the #NSale. PAIGE booties, EILEEN FISHER pumps, Vince flats, Cole Haan wedges....See how comfy they are.

AGL Slingback Pumps (nude, gray, or black)

4. Flat Shoes & Sandals In The #NSale

A. Vince Marley Venetian Loafers

TME COMFORT SCORE: 1 – 2

I am waffling on the comfort score because can “comfortable flats” even exist? I am SKEPTICAL. 

However, this Vince pair is made of insanely soft suede, have super-cushy soles AND the back heel is some sort of engineering genius that is collapsable/foldable and actually molds gently to the heel. Uncomfortable rubbing potential? Literally zero.

I like all of the suede colors, but brought home the bordeaux.

Gang, we tried on MOST of the shoes & boots in the #NSale. PAIGE booties, EILEEN FISHER pumps, Vince flats, Cole Haan wedges....See how comfy they are.Gang, we tried on MOST of the shoes & boots in the #NSale. PAIGE booties, EILEEN FISHER pumps, Vince flats, Cole Haan wedges....See how comfy they are.Vince Marley Venetian Loafers (Woodsmoke and Bordeaux pictured)

B. EILEEN FISHER Asha-Su Flats

TME COMFORT SCORE: 2

I’m struggling to find the right fit…which might be why my comfort score is only a 2. These would flop off of my back heel, so I suspect I’ll need to go down a half size. The back heel part doesn’t have that wonderful engineering of the Vince loafers above….but these shoes are very comfortable.

Bonus? The shape is surprisingly sexy, and that strange mesh part (that EILEEN FISHER shoes often use as a comfort device) isn’t as noticeable, even in the lightest color. These were a happy surprise.

Gang, we tried on MOST of the shoes & boots in the #NSale. PAIGE booties, EILEEN FISHER pumps, Vince flats, Cole Haan wedges....See how comfy they are.Eileen Fisher Asha-Su Flats (taupe suede)

C. EILEEN FISHER Zanya Sandal

TME COMFORT SCORE: 1

Good GOD THESE THINGS ARE COMFORTABLE. And the new knotted detail completely fixes the perceived design problem that one reader aptly named, “bandaged feet”. (Granted, that was directed at this pair in nude, but I love them still.)

Gang, we tried on MOST of the shoes & boots in the #NSale. PAIGE booties, EILEEN FISHER pumps, Vince flats, Cole Haan wedges....See how comfy they are.Eileen Fisher Zanya Sandal (Black)

 

Happy August, everyone! Good luck on the last weekend of the sale, and hopefully this little guide helps narrow things down. Because….summertime. Don’t forget to check out our full NSale coverage here!   

xo,

S

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About Author

Shana founded The Mom Edit in 2008. She lives with the love of her life (his name's Mike) and their two crazy boys in downtown Philadelphia. She loves a good styling challenge (her engineering side shows eventually), appreciates kindness, and usually picks scotch over wine, sneakers over stilettos, and shorts known as denim-underwear, always.

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8 Comments

  1. Love your outfits with the taupe Willa booties! Can you add links to what you’re wearing? You know, because I haven’t shopped enough 🙂

  2. Nope – I got the same size that I get for all boots (but it IS a half size bigger than my flats size). They were a bit tight at first, but stretched out nicely after a couple of wears.

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