crown vintage Crown Vintage Pimmy Bootie

Why These Booties Became My Fall-to-Winter Essential (And Why They Should Be Yours Too)

I remember the first time I spotted them across a crowded department store. The supple leather caught the light just so, and the perfect stacked heel seemed to whisper promises of comfort without sacrificing style. That was three years and four pairs of Crown Vintage Pimmy Booties ago, and I’ve never looked back. If you’re considering adding these versatile boots to your collection (which, spoiler alert: you absolutely should), I’ve compiled everything I’ve learned about these magnificent booties from countless hours of wear, research, and yes, occasionally obsessing over new colorways at midnight.

After years of trial and error with footwear that either looked good but felt like torture devices, or felt amazing but looked like something my grandmother would wear to garden, I’ve found that the Crown Vintage Pimmy Booties strike the perfect balance between style, comfort, and versatility. They’ve become my go-to recommendation whenever friends ask about reliable, stylish boots that won’t break the bank or their feet.

The Distinctive Design: What Makes Pimmy Booties Stand Out

Let’s talk aesthetics first, because let’s be honest—that’s what initially draws most of us to a shoe. The Crown Vintage Pimmy Bootie features a distinctly vintage-inspired silhouette with modern touches that keep it from feeling costumey. The ankle-height design hits at just the right spot to elongate your legs while providing that classic bootie profile.

What I particularly love about these booties is their understated detailing. The subtle stitching around the upper adds just enough interest without being overwhelming. The rounded toe gives your feet breathing room (goodbye, squished toes!) while maintaining a sleek profile. And can we talk about that stacked heel? At approximately 2.5 inches, it provides just enough lift to feel feminine and dressed up without veering into “I can’t walk more than a block in these” territory.

The side zipper detail isn’t just functional—it adds a modern edge to the vintage-inspired design. Some colorways feature contrast stitching that really makes the craftsmanship pop, while others maintain a monochromatic look for more versatility. Either way, these boots manage to be distinctive without being trendy, which means they won’t look dated after a season or two.

Unlike many booties that seem designed more as statement pieces than functional footwear, the Pimmy balances aesthetic appeal with practical design. The slightly weathered finish on many of the leather options gives them that perfectly broken-in look from day one, which only gets better with age and wear.

Comfort Level: Can You Really Wear Them All Day?

Let’s get down to brass tacks—how do these booties perform in the comfort department? After wearing my first pair to navigate cobblestone streets during a weekend getaway, stand through an entire outdoor wedding, and power through holiday shopping marathons, I can confidently say: these boots were made for walking, and that’s exactly what they’ll do.

The cushioned footbed is the unsung hero here. Unlike many stylish boots that seem to consider comfort an afterthought, the Pimmy Booties feature memory foam insoles that mold to your feet over time. The first time I wore mine, they felt good. By the fifth wear, they felt like they were custom-made for my feet.

The heel height deserves special mention. At around 2.5 inches, it’s the sweet spot where you get enough elevation to feel dressed up but not so much that you’re teetering. The stacked design distributes weight more evenly than a stiletto would, reducing pressure on your forefoot. After a full day of wearing these, I don’t find myself desperately kicking them off the moment I get home.

The ankle support is another comfort factor that’s easy to overlook until you’ve spent hours in shoes without it. The Pimmy Booties hug your ankles just enough to provide stability without restricting movement or causing chafing. The slight padding around the ankle opening prevents that dreaded digging-in that many booties are guilty of.

That said, they do require a brief break-in period. My first pair felt slightly stiff for the first two or three wears, particularly around the ankle and toe box. But the quality leather softened quickly, and by the end of the first week, they felt like old friends. If you’re planning to wear them to a special event, I’d recommend breaking them in with a few shorter wears first.

For those with specific foot concerns, I should note that while these booties offer more arch support than most fashion footwear, they might not be sufficient for those with pronounced arch issues. In that case, you may want to consider adding your own inserts—the removable insole makes this easy to do without compromising fit.

Finding Your Perfect Fit: Sizing Secrets

Speaking of fit, let’s tackle one of the most common questions I get about the Pimmy Booties: are they true to size? In my experience, Crown Vintage Pimmy Booties run fairly true to size, though they tend to be slightly generous in the toe box. This is actually a blessing for all-day wear, as your feet naturally expand throughout the day.

For reference, I typically wear a size 8 in most brands (occasionally sizing up to 8.5 in narrower shoes), and the size 8 in Pimmy Booties fits me perfectly. If you’re between sizes, I’d recommend going with your smaller size, especially if you plan to wear them with thinner socks. For winter wear with thicker socks, your regular size should accommodate the extra bulk without pinching.

The width is what I’d describe as medium to slightly wide. I have fairly average-width feet and find them comfortable without any pinching at the sides. My friend with wider feet was pleasantly surprised that she didn’t need to size up as she usually does. However, if you have very narrow feet, you might find them a bit roomy—nothing a cushioned insole or thicker sock can’t fix.

As for whether they come in wide sizes—officially, no. Crown Vintage doesn’t offer specific wide-width versions of the Pimmy Bootie. However, the generous cut means many people who typically require wide sizes find the standard width accommodating. If you’re concerned about width, I’d recommend trying them on in-store if possible, or ordering from a retailer with a good return policy.

One thing to note about the fit: the ankle opening is relatively generous. This is great for ease of getting them on and acheter cenforce en autriche off and for tucking in jeans, but if you have very slim ankles, you might notice a slight gap. This hasn’t been an issue for me style-wise, and actually makes them more comfortable for all-day wear since they don’t constrict your ankle movement.

Material Matters: What Are These Booties Made Of?

The quality of materials used in footwear can make or break their longevity, comfort, and overall appeal. Crown Vintage doesn’t cut corners here. The Pimmy Booties are predominantly crafted from genuine leather, which explains both their comfort and their ability to age beautifully.

The upper is made from full-grain or top-grain leather depending on the specific colorway. The black and brown varieties I own appear to be full-grain, which means they include the outer layer of the hide with all its natural grain patterns. This contributes to their distinctive look and also means they develop a beautiful patina over time. After three years, my oldest pair has softened and developed a character that only genuine leather can achieve.

Some of the more specialized colors and finishes might use slightly different leather treatments. For example, the suede versions obviously use brushed leather for that velvety finish, while some of the metallic options incorporate special finishes while still maintaining the leather base.

The lining is where many boot manufacturers cut costs, but Crown Vintage uses a soft fabric lining that prevents internal rubbing and priligy senza ricetta italia helps wick away moisture. This might seem like a small detail, but it makes a world of difference for comfort during extended wear.

The sole is constructed from durable synthetic material with a rubber outsole that provides decent traction. It’s thick enough to protect against pavement heat in early fall and cold in winter, while still remaining flexible enough for natural walking movement. The stacked heel is wrapped in matching material to give it that classic look while maintaining durability.

One thing I appreciate about the materials is their weight—the Pimmy Booties strike a nice balance. They feel substantial enough to suggest quality and provide some warmth, but they’re not so heavy that they tire your feet out by the end of the day. I’d classify them as medium-weight booties.

The Color Spectrum: Which Shade Is Right For You?

One of the reasons I own multiple pairs of Pimmy Booties is their impressive color range. The classic neutrals—black, brown, and tan—are perennial offerings and form the backbone of the collection. These are your wardrobe workhorses that will coordinate with virtually anything.

The black leather version, with its subtle matte finish, has been my most-worn pair. It’s sleek enough for office wear but doesn’t look too formal for casual outings. The cognac brown is incredibly versatile and adds warmth to fall and winter outfits. It also tends to show the leather’s natural grain most beautifully.

Beyond these staples, Crown Vintage regularly introduces seasonal colors that allow you to express more personality. I’ve seen everything from deep burgundy (perfect for holiday season) to olive green (amazing with fall wardrobes) to various shades of navy and gray. There have even been metallics—a subtle bronze was available last fall that walked the line between statement piece and neutral.

The suede versions come in an even wider color palette, including some unexpected options like dusty rose and pale blue. These require more care to maintain (more on that later), but offer a softer look that works beautifully for transitional seasons.

When choosing a color, consider not just what you’re drawn to but what will integrate best with your existing wardrobe. If this is your first pair, I’d recommend one of the neutrals—black if you wear a lot of cool tones, brown if you gravitate toward warmer hues. If you’re adding to a collection, consider a seasonal color that can become your signature piece.

Something to note about the colors: the images online don’t always perfectly capture the richness and depth of the leather in person. The brown tends to be slightly warmer and more dimensional than it appears in photos, while the black has subtle variations in its finish that give it character.

Styling Your Pimmy Booties: From Casual to Dressy

The versatility of these booties is perhaps their greatest strength. I’ve worn mine with everything from jeans and a t-shirt to dresses for semi-formal events, and they never seem out of place. Here’s how I style mine across different scenarios:

For casual everyday wear, Pimmy Booties elevate even the simplest outfit. My go-to combination is straight-leg jeans, a simple tee or sweater, and a leather or denim jacket. The booties add just enough polish to make the outfit feel intentional rather than thrown together. They work equally well with skinny jeans tucked in or with wider-leg styles that fall over the ankle.

For office wear, I pair them with slim trousers or pencil skirts with tights in cooler weather. The professional silhouette of the bootie works beautifully in business casual environments without feeling stuffy. They’re particularly good with cropped trousers that show off the ankle detail of the boot.

For dressier occasions, they complement midi dresses beautifully, adding a bit of edge to feminine silhouettes. I’ve worn my black pair with a floral midi dress and leather jacket for dinner dates, and the cognac version with a sweater dress for fall weddings. The height is just right to elongate your legs without restricting movement on a dance floor.

For transitional seasons, I love them with shorts and a light sweater in early fall, or with a flowy dress in spring. The closed-toe design makes them appropriate even when temperatures are fluctuating.

One styling tip I’ve discovered: these booties work particularly well with outfits that have some contrast in texture. The leather of the boot pairs beautifully with softer fabrics like knits, chiffon, or linen, creating visual interest without clashing.

As for jewelry and accessories, the understated design of the Pimmy Bootie means they don’t compete with statement pieces. I often wear mine with bolder earrings or layered necklaces, using the simplicity of the boot to balance more dramatic elements elsewhere in my outfit.

Seasonal Suitability: Year-Round Potential?

When I first purchased my Pimmy Booties, I envisioned them primarily as fall footwear. Three years later, I’ve found myself reaching for them in every season except the height of summer. Here’s my breakdown of their seasonal suitability:

Fall is undoubtedly their prime season. The ankle height and leather construction provide just enough warmth for cooling temperatures without overheating. They pair perfectly with fall wardrobes of sweaters, light jackets, and transitional dresses. This is when they truly shine.

Winter is more conditional. In milder winter climates or for quick trips between indoor locations, they’re perfectly adequate. The leather provides some protection against the cold, and the rubber sole offers decent traction on dry surfaces. However, they are not specifically designed for winter conditions. They lack insulation for truly cold temperatures, and while the sole provides some grip, it’s not designed for ice or heavy snow. I wear mine throughout NYC winters, but I switch to proper snow boots when serious weather hits.

Spring sees them come back into regular rotation as temperatures warm but aren’t yet hot enough for sandals. They’re perfect with spring dresses on cooler days, and the closed-toe design protects against spring showers (though I avoid wearing the suede versions in heavy rain).

Summer is when they typically stay in the closet, as the leather construction makes them too warm for hot weather. That said, I have worn them on cooler summer evenings with dresses, and they’re perfect for summer nights when temperatures drop but traditional fall footwear would feel too heavy.

For those in more moderate climates without extreme seasons, these could genuinely be year-round footwear with the right styling adjustments.

Caring For Your Investment: Maintenance Tips

Quality boots like the Pimmy are an investment, and proper care will significantly extend their lifespan. Here’s my care routine that has kept my oldest pair looking great for years:

For leather versions, I apply a leather conditioner every few months to keep the material supple and prevent cracking. Before the first wear and at the beginning of each season, I use a waterproofing spray designed for leather. This provides protection against light rain and accidental splashes without changing the appearance of the leather.

For suede versions, a suede protector spray is essential before the first wear. I refresh this protection every month during regular wear. I also keep a suede brush handy to lift the nap and remove any surface dirt before it can set in.

For all versions, I wipe them down with a slightly damp cloth after wearing them in inclement weather or on salted sidewalks in winter. Salt can be particularly damaging to leather, so prompt cleaning is important.

I use shoe trees when they’re not being worn, which helps maintain their shape and absorbs moisture. If you don’t have shoe trees, stuffing them with acid-free tissue paper works as an alternative.

For scuffs on the leather versions, a matching shoe cream applied with a soft cloth can work wonders. For more significant scratches, a professional shoe repair shop can often restore them to near-perfect condition.

One maintenance tip that’s saved my boots multiple times: addressing any heel wear immediately. The heel cap can be replaced inexpensively by a cobbler if you notice it wearing down, preventing damage to the structural heel itself.

I also recommend rotating between multiple pairs if possible. Wearing the same boots day after day doesn’t allow them to fully dry out between wears, which can shorten their lifespan. This is my justification for owning multiple colors, and I’m sticking to it!

Where To Buy: Finding The Best Deals

Crown Vintage is a brand that’s primarily associated with DSW (Designer Shoe Warehouse), so this is the most reliable place to find the full range of Pimmy Booties. They’re typically available both in physical DSW stores and on their website. The benefit of shopping in-store is being able to try them on, especially if you’re new to the brand and unsure about sizing. The website, however, often has a better selection of colors and sizes.

Beyond DSW, you can occasionally find Crown Vintage Pimmy Booties at other retailers like Famous Footwear and department stores such as Macy’s, though the selection is usually more limited. Online marketplaces like Amazon sometimes carry them as well, but be cautious about authenticity when purchasing from third-party sellers.

As for pricing, these booties typically retail between $70-$90 at full price, which I consider extremely reasonable given their quality and versatility. However, with a bit of patience, you can often find them on sale. DSW regularly runs promotions that bring them down to the $50-$70 range, particularly for seasonal colors as the season ends.

If you’re a DSW rewards member (which is free to join), you’ll occasionally receive special offers specifically for Crown Vintage products. I’ve purchased pairs for as low as $45 during these promotions. The best sales typically happen at the end of each season (late fall/early winter for most colors, late winter for winter-specific shades).

For those who don’t mind gently used items, resale sites like Poshmark and Mercari often have Pimmy Booties available at significant discounts. I’ve seen barely-worn pairs listed for $30-$40, which is an absolute steal for this quality.

One shopping tip: if you fall in love with a particular color, don’t wait too long to purchase, especially if it’s a seasonal shade. Crown Vintage tends to rotate their color offerings, and while the classic neutrals remain constant, the more unique colors may not return in subsequent seasons.

How They Compare: Pimmy vs. Other Crown Vintage Booties

While the Pimmy is my personal favorite from Crown Vintage’s lineup, the brand offers several other bootie styles that might better suit certain preferences or needs. Here’s how the Pimmy compares to some of its siblings:

The Crown Vintage Tabitha Bootie features a similar silhouette but with decorative strap and buckle details. It’s slightly more rugged-looking than the Pimmy, with a more pronounced western influence. If you’re looking for something with a bit more visual interest, the Tabitha might appeal to you. However, I find the clean lines of the Pimmy more versatile for diverse outfits.

The Crown Vintage Joelle Bootie has a lower stacked heel (about 1.5 inches compared to the Pimmy’s 2.5 inches) and a more casual appearance. If maximum comfort for extensive walking is your priority, or if you prefer a more understated heel height, the Joelle is worth considering. That said, I find the slightly higher heel of the Pimmy more flattering without sacrificing comfort.

The Crown Vintage Darlene Bootie offers a more streamlined silhouette with a slightly pointed toe, giving it a more formal appearance than the Pimmy. It’s beautiful for office wear and dressier occasions, but the pointed toe can be less comfortable for all-day wear compared to the Pimmy’s more rounded shape.

What sets the Pimmy apart in the Crown Vintage lineup is its exceptional balance of style, comfort, and versatility. It’s neither too casual nor too formal, neither too plain nor too embellished. This middle-ground positioning is precisely what makes it such a wardrobe workhorse—it can effectively adapt to nearly any situation.

In terms of cost, most Crown Vintage booties fall within a similar price range, so your choice really comes down to style preference and specific needs rather than budget considerations.

The Verdict from Real Wearers: Reviews and Feedback

I’m clearly a fan, but don’t just take my word for it. The Crown Vintage Pimmy Bootie consistently receives strong reviews online, typically averaging 4.5 out of 5 stars across various platforms. Here’s what other wearers frequently mention:

Comfort is a recurring theme in positive reviews. Many reviewers express surprise at how comfortable these booties are right out of the box, with several mentioning that they wore them for entire days of sightseeing or shopping without discomfort. The cushioned footbed receives particular praise.

Versatility is another commonly cited advantage. Reviewers appreciate being able to wear them with multiple outfit types, from jeans to dresses. Several mention owning multiple colors for this reason.

Durability gets high marks, especially given the price point. Many reviewers report their Pimmy Booties holding up well for multiple seasons without significant signs of wear, even with regular use. The quality of the leather and construction is frequently mentioned.

On the more critical side, some reviewers with narrow heels mention experiencing slight slippage at the back of the boot. This appears to be less common but might be something to consider if you have particularly slim ankles.

A few reviewers with high arches or specific foot conditions mention adding their own insoles for additional support, though they still rate the boots positively overall.

Regarding sizing, the vast majority of reviewers find them true to size, though there’s a small subset who recommend sizing down half a size, particularly for the suede versions which may stretch slightly more with wear.

Weather resistance receives mixed reviews. While most agree they’re not designed for severe weather, opinions vary on how well they handle light rain and damp conditions. This likely relates to whether reviewers have applied waterproofing treatment beforehand.

Final Thoughts: Are Crown Vintage Pimmy Booties Worth It?

After three years and multiple pairs, my verdict is an enthusiastic yes. The Crown Vintage Pimmy Bootie offers exceptional value for its price point, delivering quality, style, and comfort that rivals booties costing twice as much or more.

What makes these booties stand out in an overcrowded footwear market is their remarkable balance. They’re stylish without being trendy, comfortable without looking orthopedic, versatile without being boring, and affordable without feeling cheap. Finding all these qualities in a single boot is genuinely rare.

If you’re looking for your first pair of quality booties, or if you’re tired of cycling through footwear that disappoints in either the style or comfort department, the Pimmy deserves serious consideration. Their classic design ensures they won’t look dated next season, while their comfort level means they’ll actually be worn rather than languishing in the back of your closet.

For those who already have a robust boot collection, the Pimmy offers something surprisingly difficult to find: a reliable, go-anywhere bootie that can be the backbone of your fall and winter footwear rotation. There’s a reason they’ve become my default recommendation when friends ask for boot suggestions—they simply deliver on all fronts.

Whether you’re drawn to the classic black for maximum versatility, one of the rich brown tones for warmth, or a seasonal color for personality, I’m confident that Crown Vintage Pimmy Booties will become one of the hardest-working, most-loved pieces in your wardrobe. Three years and countless miles later, mine certainly are.