Insomniac Sale Picks: Boots with Chunky Heels

*In this late-night feature – which will run on Tuesday and Thursday of each week – I’ll gather up three fun items that are currently on sale online and share them with you! I would LOVE suggestions: Stylish wide-width pumps? Classic v-necked sweaters? Chandelier earrings? Petite dress slacks? What would you like to see featured?*

Marje requested a few picks for boots with chunky heels, so here we go:

clarks jolissa lapis

Clarks Jolissa Lapis – was $230, now $89.99 – $179.99

Burgundy. YUM. This pair sports a sturdy block heel at 2.75″ and a tough-but-classy wraparound buckle detail. And they’re a great option for folks with narrow calves, since they’ve got a 13.5″ circumference. Available in this burgundy and in black in sizes 6 – 10. Size availability and price vary by color. Also over on 6pm in sizes 9 -10. This pair has a shorter heel, but comes in burgundy with a 17.25″ calf circumference.

born shaylee

Born Shaylee – was $200, now $83.16 – $199.95

If you’re looking for a shorter chunky heel, this Born pair fits the bill. With a 15″ calf and 2.25″ heel, it will be as comfy as it is cute. Available in this gray-tan as well as weathered black leather in sizes 6 – 11. Size availability and price vary by color. This similar pair has a 16″ calf.

timberland stratham heights

Timberland Earthkeepers Stratham Heights – was $200, now $120

I own these and will continue to recommend them until there are no pairs left on earth. You can see how much I love my pairs here. These boots are comfy, cute, versatile enough for work or play and – wait for it – waterproof. YES! These have a 14.5″ calf and 3.5″ chunky stacked heel. Available in this cognac as well as black or chocolate brown in sizes 6- 11. If that calf is too narrow or heel too high, this style also comes in an ankle boot with a 2.5″ heel.

miz mooz noa

Miz Mooz Noa – was $220, now $145.94 – $219.95

Miz Mooz is an underrated brand that consistently churns out comfy, stylish shoes and boots. This cool pieced boot is a perfect example – such fun details and interesting construction. This style has a 2″ heel and 14″ circumference and gets high marks from customers. Available in this black as well as whiskey brown in sizes 6 – 11. Also available in wide calf.

Other not-currently-on-sale resources for boots with chunky heels:

  1. Clarks – Stylish, well-made options including booties and tall boots with chunky heels.
  2. Born – Short, mid-calf, and tall in gorgeous colors and all with walkable heels. These stacked-heel cowgirl-influenced boots are calling to me.
  3. Rieker – Comfortable, edgy designs including these badass lug-sole ankle boots.

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

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Dressed for: Girls Night

Already Pretty outfit featuring camel sweater, leather pants, Rebecca Minkoff Logan, black ankle boots

Sweater – BR via Twice
Pants – Not Your Daughter’s Jeans (last year’s so a few sizes left) – similar
Booties – Steve Madden (no longer available) – similar
Bag – Rebecca Minkoff Logan (no longer available) – similar
Earrings – Target (no longer available) – similar

Wore this for a night at my gorgeous friend Michelle’s gorgeous apartment (photos on Instagram), and at the bar near her place. Even though we’re having a surprisingly long and pleasant fall, I’ve been totally freezing lately – possibly due to this ridiculously prolonged cold/cough – so it felt great to be moderately bundled up. I’m sure I’ve mentioned this, but if my neck is cold, I’m cold. If my neck is covered, I’m toasty. Clearly, my personal thermostat is inside my neck.

Also these pants are so glorious. All leather/faux leather pants can be tough to fit and sometimes uncomfortable. Leather front/ponte back? THE BEST.


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**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

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Reader Request: When to Cuff Jeans

cuffing jeans

left | right

Reader Andrea e-mailed me this question:

I wondered if you would do a blog post about when and when not to cuff jeans. I think doing so would add a little something to my limited casual wardrobe. But I can’t figure out what where to use it. Or maybe it is to be done with a certain jean style. I feel like I’m missing something with this look.

I am late to the cuffing game myself, but have really enjoyed playing around with this styling trick over the past few months. One thing that I think makes cuffing tricky is that it looks great when it’s a little messy … but artfully messy can actually be harder to re-create than neat. Here are a few things I’ve learned from my own tinkerings:

Skinnies, straight-legs, or boyfriends

This may seem obvious, but it’s worth mentioning. You want the cuff to be fairly small and close to your ankle/calf, so anything that flares out toward the hem like a bootcut or has a wide leg like a trouser cut won’t work. Boyfriend jeans are cuffed more often than not, but you’ll notice that although the jean is loose-fitting the leg tapers and the cuff is fairly close.

Why we cuff

bad jeans cuffs

left | right

Here are two cases in which I think cuffing would actually improve the overall look. Tucking even the skinniest of skinny jeans into ankle boots looks a bit odd, and can cause uncomfortable scrunching. Skinny jeans that haven’t been hemmed to ankle length will bunch and pool at the ankle – cuffing eliminates this problem.

Cuffs that aren’t quite right


left | middleright

Now, listen: The Cuff Police don’t exist. If you can’t get your cuffs to fall just so, that’s completely fine. The likelihood of anyone doing a trend-focused ankle check is slim to none. But just in case you’ve been trying to cuff and can’t figure out what’s off, here are a couple of examples that don’t quite hit the mark.

To my eye, the pair on the left has been cuffed just a wee bit too high. You want to show the curve of your ankle, but don’t need to get up into calf territory. In the middle, the messiness of the cuff is fine but they look mighty bulky. This is an issue that I have with some of my jeans: Ideally you want the cuff to be narrow and relatively flat. This means that cuffing jeans hemmed long will backfire, and cuffing ankle-length jeans will work better. And on the right, you have a super tall cuff – this is a fringe trend now and may eventually become the norm. But it still looks a little funky to most folks.

Cuffs with ankle boots

ankle boots cuffed jeans

left | right

NOW we’re talking. Personally, this is my favorite look for cuffing – with ankle boots or other ankle-height shoes. Let just a sliver of ankle peek out between where the cuff ends and the shoe begins. My ankles get weirdly cold, so I will sometimes do black booties, black/gray striped socks, and cuffed jeans. You want to see where the ankle curves in, but you can still see that with a close-fitting sock in the mix.

Cuffs with heels and flats

cuffed jeans with heels

left | right

Cuffed jeans and pants can also look chic and fun with low-vamp shoes like pumps and or ballet flats. Again, remember to cuff just above where your ankle curves, no higher. This is especially important since you’re exposing more of the foot with a low vamp, and if your cuff is high it will give the impression of crops or floods. Cuffing with this style of shoe is helpful if you’ve got a pair of skinnies that pools at the ankle, as mentioned above.

Cuffs with sneakers

cuffed jeans with sneakers

left | right

And finally, sneaks – a great match for cuffed jeans. Cuffing creates an instantly casual look, and sneakers are naturally casual so they play well together. In this case, I’d avoid socks. You want a bit of bare ankle peeking out between the high vamp of the shoe and the cuff of the jean. Slip-on sneakers work just as well.

So which shoe styles won’t work with cuffs? Mary Janes look awkward because between the vamp, strap, and cuff, your foot is cut into three pieces. Mules are a bit odd for similar reasons, especially heeled ones. And, of course, anything that reaches above the ankle like a tall boot won’t look quite right, though I’ve seen people experimenting with tall-shaft ankle boots tucked under cuffs.

Kind of a lot, right? Again, these are not rules, merely guidelines. And they’re MY guidelines, so you may hear completely different advice from other folks. In fact I sent Andrea to this post which has some overlap, but also shows a cuff that’s much wider than I’d wear or recommend. This styling trick is very fluid, so don’t be afraid to play. If you find that a higher or lower cuff looks better to your eye, go for it. If you like the look of a thicker cuff, go for that, too. Do whatever feels and looks best to you.

Anyone else playing around with cuffs these days? Where do you like yours to fall? Are you more apt to cuff skinnies, straight legs, or boyfriends? All of the above? Other tips to share?

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

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