My Favorite and Most Worn Shoes + How I Take Care of Them

October 29, 2018

My Favorite and Most Worn Shoes

After the popularity of sharing my favorite and most worn jeans recently, I thought I’d do the same for my shoes! I am a shoe gal through and through. They can truly make an outfit and as a New Yorker I put my shoes to work so I’m also sharing in this post how I take care of my shoes + protect them.

My Favorite and Most Worn Shoes + How I Take Care of Them

My Favorite and Most Worn Shoes and J.Crew Sweater Blazer

White Sneakers

I was convinced to buy these Common Projects sneakers after seeing my friend Jenny always looking so casually cool and put together in them. They are perfectly slim + sleek meaning they literally go with everything I own. I love these sneakers and have worn them an almost embarrassing amount of times since getting them in March to wear on my trip to Copenhagen and Stockholm. I now bring them on pretty much every trip since they are so versatile. (And I wore them a lot with dresses while in Lisbon!) A head’s up that the sizing on the sneakers is funny – I took them in a size 36 when I’m usually a 37 in European shoes. A full review of them is here.

Plaid Blazer + Gucci Loafers I wit & whimsy

Gucci Loafers

This Fall I caved and bought these Gucci loafers. I had looked at them for nearly two years and even bought the Steve Madden look alikes last year instead. But after I wore those to death (which, because they were Steve Madden didn’t take too much) I decided getting the real deal would be worth it. Now I wear these once a week and love that they are so simple to slide on and instantly elevate an outfit. Better yet? They go with pretty much every one of my favorite pair of jeans. I sized up to a 37.5 in these.

Meghan Donovan of wit & whimsy wears the Reformation Persimmon Dress

Nude Sandals

I really love the Stuart Weitzman Nudist sandals and they’re usually my go-to for weddings and fancier events during warm weather. But after experiencing some low back issues earlier this year, I started wearing my Nearly Nude sandals with a stacked heel pretty heavily. I wore them to every wedding I went to this summer and with countless other dresses for more casual affairs. These shoes are so comfortable. They’re the perfect height, they are great to walk in and they come in loads of colors. I can’t say enough about these as a worthwhile investment for a comfortable heel.

Styling Classics I wit & whimsy

Chanel Slingbacks

Every year for my birthday I buy myself a gift and this year it was the Chanel slingbacks. I thought about these shoes for several years, tried them on several times and never bit the bullet. Now, I can’t imagine my shoe collection without these because I wear them so much! They elevate every outfit and can go with jeans just as easily as they can a pretty summer midi dress. They’re comfortable because of the low, stacked heel and can put up with the many steps I take in them running around. If you like the style and not the price, Sam Edelman makes a similar pair.

Teddy Coat and Kick Flares on Meghan Donovan of wit & whimsy 3


These booties were the best pair of shoes I bought in 2017. I can go for miles and miles without any issues with these little booties and I love styling them with both jeans as seen here or with dresses. I get compliments on them whenever I wear them and truly find myself reaching for them in Fall + Winter at least twice a week.

Elevated Basics

Chanel Ballet Flats

These Chanel ballet flats were another investment pair of shoes I thought about for a long time before I actually bought them in 2016. I treasure these shoes and the sentiment they hold as I bought them while in Paris just before I started my self employment journey. They remind me of a time where I was full of hope and excitement and they always remind me of one of my most special trips to Paris. These flats are so comfortable, have the prettiest design that goes with so much and make any outfit look a bit more dressed up.

Leather trimmed coat on Meghan Donovan of wit & whimsy

Over The Knee Boots

Ever since getting these boots in 2014 I have worn them non-stop through Fall & Winter. They also are great to travel with because they collapse down easily. The quality and comfort makes them worth the splurge. They stay up over the knee (a lot of inexpensive brands will constantly slouch down taking away from the elongating illusion over the knee boots are good for) and they’re great over jeans or with dresses.

Meghan Donovan of wit & whimsy discusses affordable wardrobe essentials

M. Gemi Flats

Whenever you guys reach out to ask about comfortable flats, the M.Gemi Stellato is always my first recommendation. I’m almost due for a new pair because I have worn these so, so much. They are especially great for trips because, once broken in, they are wildly comfortable and great for walking. These flats are just so, so chic in a sea of blah flats in my opinion. M. Gemi really focuses on craftsmanship of their shoes, too so every pair I’ve tried I’ve has proven to be worth the price.

Meghan Donovan of wit & whimsy styles a trench coat

Black Pumps

I included these heels recently in my Fall capsule wardrobe post as I think they personify the perfect black pump which I believe every woman should have in their wardrobe. Better yet is that this is a pair you won’t mind wearing for long haul events or work days because they are so comfortable! I am always reaching for these heels when I have to go to events or be trekking around the city. They’ve totally held up to a bunch of wear + tear, too.

The perfect outfit for brunch

Classic Converse

The classic Converse sneakers are a longtime favorite of mine and I wear them often in Spring + Summer with jeans and with little dresses. In the Fall I think they look so great with sweater dresses.

Vince Coat I My Favorite and Most Worn Shoes

Errand Sneakers

On weekends I live in these sneakers. They’re more stylish than a pair of Vans, they’re super comfortable and they’re great with jeans or, let’s be honest, leggings. They’re my go-to for going to/from my workouts and running errands in my neighborhood. They also come in white, pink, grey and a crazy chic velvet that I have my eye on.

My Favorite and Most Worn Shoes


These comfortable espadrilles look just as good with jeans as they do with dresses and skirts. I’ve worn them so much in the Spring and Summer.

Sarah Flint Perfect Pump My Favorite and Most Worn Shoes

The Perfect Pump

One of the most comfortable pairs of heels I own = the Sarah Flint Perfect Pump. Expertly crafted with comfort in mind, the soles feel like little clouds which makes scooting around town easy, breezy in these. I also love that they come in three heel heights and multiple colors. I own the Black, Taupe & Red.

The London Eye I wit & whimsy

Kitten Heels

These little kitten heels allow me to feel put together and dressed up but don’t sacrifice comfort. I size down to a 6.5 from my usual 7.

Sarah Flint Natalie Bow Flat in Nude I wit & whimsy

The Sarah Flint Natalie Flat is a go-to shoe for me for its feminine silhouette and comfortable design. I own this shoe in multiple colors and have blogged about this great shoe here, here & here.

Weekend Casual Athleisure Outfit I wit & whimsy

These APL Techloom sneakers were a best buy of 2019 and I haven’t stopped loving wearing them. They are so comfortable and I love that I don’t have to wear socks with them. They are the shoe I reach for every time I am heading out for a long walk, going on a light hike or want to be extra comfortable in a sneaker that doesn’t sacrifice style.

Barbour Icons Collection I 125th Anniversary I wit & whimsy

These heeled Marc Fisher boots are so good for Fall and Winter that I now own them in two colors.

A Guide to the best of the Vail Valley I wit & whimsy

My favorite boots for Winter, these Marc Fisher boots are as stylish as Winter boots come. They are warm, so chic and crazy comfortable. They sell out every single season for good reason.

Inez Boot Review I wit & whimsy

These Inez booties are so comfortable and I love the perfect neutral color of them. A full review can be found here.

Plaid Blazer + Distressed Denim I wit & whimsy

My favorite sporty-chic sneaker. These Golden Goose sneakers are so easy to slip on and I love how they look with everything from skirts to dresses to jeans and leggings.

. . .

Now, onto the care of my shoes as I get asked about this a lot over on Instagram! As you can see, I buy rather nice (and therefore pricey) shoes and I do this because of comfort and because of longevity of wear. If I’m dropping a lot of $$$ on my shoes I need them to last – a long, long time. And, living in New York City, I walk a ton. I really put a lot of miles on my shoes – particularly those showcased above.

When I was first introduced to the concept of adding a protective sole to my shoes before I wear them it was a game changer for me. I’ve been taking my shoes to Firm Shoe Repair in Union Square for almost as long as I’ve lived in New York and upon repairing a few pairs of my shoes the guy told me I really needed to be getting protective soles put on before wear not when the sole starts to have already worn down. He told me most shoe manufacturers don’t put proper soles on the shoes so that they wear down faster and have you purchasing more. Adding a protective rubber sole protects the actual sole of the shoe and will allow for you to really get a lot more use out of the shoe.

It is insane how much this piece of rubber helps.

Now I get the rubber sole added immediately when I buy a nice new pair of shoes and have faith afterwards that I can walk a ton in them. It’s what has allowed me to keep wearing shoes like my Rag & Bone Newbury boots for years and years. (I’ve had two protective soles put on at this point and owned the shoes for six years and they’re still going strong. This would have never been possible without the protective soles.) Protective soles also help when wearing your shoes out in less than desirable weather like rain and snow. If you don’t have a protective sole the water can seep in through the stitching and cause damage and break down threads and leather.  The $10-$15 addition of the soles will save you a lot of money in the long run.

If I buy suede shoes I often ask the cobbler to weather proof them as well while I’m in getting the protective sole. Alternatively, I’ll use something like Scotchguard or a spray like this at home to further protect the fabric and ensure I’ll get longevity out of the pair. (Weatherproofing your shoes will go a long way in easing any anticipated anxiety of being stuck commuting when the skies suddenly open up with rain or it begins snowing before you do, in fact, make it home.)

Other helpful tips for longevity on your shoes?

I keep my investment shoes in their boxes to avoid dust getting on them and when I travel with them I always pack them in their duster bags and keep tissue in the shoe so they don’t get smashed and out of sorts.

In short, all these extra steps are worth it. More than half of the shoes shown above I have owned for more than 3 years and they still look rather close to brand new. (I was prompted to share all these things after someone remarked on how my Chanel ballet flats looked brand new still when I was wearing them in Paris the other week!) Good thing, too, because I love wearing each and every pair ;).

I do these days miss my former affinity for stilettos that I used to wear way more often but these days I choose comfort and function over fashion. (My mother always told me this day would come…!)

Shop the Post:

p.s. my idea of the perfect capsule wardrobe and why I’m looking forward to the next few months.

8 comments on “My Favorite and Most Worn Shoes + How I Take Care of Them”

  1. Girl, your shoe collection is to die for! I love the outfit with the Kate Spade pumps, they just make everything look so chic!!!!!!

  2. Hi! I love your style – very similar to mine. Classic and the perfect capsule wardrobe for a New Yorker. Can you also do a post on your favorite pairs of sunnies you own? I love each pair you wear! Thanks! Best, Christine

  3. Totally needed this post! I recently moved to DC and have been forced to swap to flats with how much I walk now. I’m spending decent money on new flats and want them to last!

  4. Absolutely LOVE this post and every description – plus the way you care for them! It must have taken you awhile, and I just wanted to say THANK YOU! Adding every single pair to my wish list. I do own those Vince sneakers and am totally obsessed. Do you happen to know if Chanel shoes are cheaper in Paris?

    1. Thank you so much for your sweet appreciation, Sam!! For Chanel shoes – it depends on the exchange rate when you go but they do generally tend to be a bit less because you can get the VAT on them. You’ll get about $90 back on the Chanel flats if you purchase them overseas. Hope that helps!

Leave a Reply

Your email address will not be published. Required fields are marked *