I've been a real estate agent in Manhattan for 8 years. Before that i was in school and working luxury retail. 

So, I have always needed my flats to be both more comfortable and more status-broadcasting than the next person.

Like real estate agents, 75% of shiny new flats that come to work in Manhattan don't make it through their first year, and 90% are gone halfway through the next. 

To give you an idea of how hard I wear my shoes, I often handle 2-3 appointments per day, showing 6-12 apartments per appointment. If apartments are closer than 5 blocks away, there's no sense in taking an uber so we walk between them. If there's no elevator, we take the stairs. Could you imagine showing 30 walkup apartments or townhouses per day?

I think I've worn most of the classics: Tod's drivers, Gucci loafers, Chanel ballerinas, those Prada and Lanvin elastic bendy-sole ballet flats, Stubbs & Wootton, Manolos, Repettos, Vivier Belles and Chips, Castañer espadrilles . . . I even had Wallabees at one point. 

I enjoyed all these shoes, though remembering them makes me ruminate, recalling that Sex and the City scene where Carrie realizes she could have put a down payment on an apartment with what she spent on Manolos while renting. 

So older, wiser, more frugal, more selective, and (a tad) more arthritic, I thought I'd share with you the shoes I have repurchased, without regret, time and again.

THESE SHOES WERE SO GOOD, I COMPLETELY WORE THEM OUT, and bought another pair.

1. Ferragamo bow flats ($575 and up)

I call them 'bow flats' because the original style with the perhaps 2" heel is Vara; the modern slightly updated version with the very flat heel and slightly wider vamp is Varina; and there are always season-specific versions with special heels or pointier toes, plus sneaker and espadrille versions. 

If memory serves, I have kicked 6! pairs of Ferragamo bow flats: Varas in ivory, navy, black and gunmetal, a pair of Varinas in navy patent, and printed cotton espadrilles. These are simply the most comfortable flashy designer type flats I've come across. The leather is thicker than the Chanel but not as soft, so it molds to the foot better and stretches out less over time. Similarly, the arch is more molded for support, unlike the totally flat and thin Chanel.

They are also the most hardwearing designer shoes I've owned. Even with frequent wear (2+ times per week), the Varas each lasted 3-5 years before they became too scuffed to impress, and I donated them. Worn less frequently (maybe once or twice a week in the appropriate seasons), the Varinas lasted 8 years . . . at the end they became my 'rain flats' for perhaps 2 months before the patent leather started splitting at the heel and I finally threw them away. 

I have had the same experience with other Ferragamo shoes-- I've had a pair of tan suede oxfords for over 10 years now and they are one of the comfiest pairs of shoes I've ever owned.

I just can't recommend Ferragamo highly enough.

In my opinion, they are completely worth paying full retail for,

and they are available in the usual places:

But if you are cruising for a discount, I have frequently seen them here:

2. Toms ($54 and up)

The socioeconomic mission of TOMS makes them acceptable for almost any occasion in Manhattan. My first pair of Toms was the light gray cashmere pair made in collaboration with The Row in 2011; my second pair was a Bergdorfs/Neimans exclusive in red silk in 2013 or 2014. I wore them with a ball gown once and was complemented all around.

I subsequently bought grosgrain versions in navy, black and orange from Neimans, until they stopped carrying them; thankfully Toms has kept the more upscale grosgrain fabric in their own line and frequently collaborates with high end retailers and fashion designers. I'm definitely going to pick up this Zhou Xun pair:

and I'm really excited about the upcoming Clare V. collab!

Worn 24/7, a pair will last 9 months or so, and unlike Ferragamos they are not the type of shoe that can be resoled or reheeled. I stick to the original style in the most expensive textiles or the designer collab pairs, as those are sort of business-casual appropriate. 

3. Sperry TopSiders($95 and up)

Boat shoes speak an international language of preppy. New York (obviously,) London, Hong Kong, Rome, Paris, Istanbul (and that's just where I happen to have travelled in the last 2-3years) . . . preps wear these shoes year round into old age. While they're very casual shoes, they are easily dressed up with a clean pair of deep indigo or white jeans, collared shirt, cashmere sweater and peacoat/camelhair coat/ Barbour, perhaps with a Longchamps nylon tote or ancient Louis Vuitton mono bag.

I have worn through just three pairs of these in 20 years and consider that an accomplishment. With constant daily wear, a pair can easily last 3 years. And the set of people who appreciate these consider them to look better, the older and more beat up they become. 

Like Toms, Sperry has begun working with designers on limited edition options for each season. They typically choose a hip, masculine label (in the past they've worked with Band of Outsiders, Jeffreys, Gray Malin, Barneys, Jack Spade, Patta, Noah NY and Quoddy). Also like Toms, it's best to not go for the new house designs. I stick to the authentic/original, gold cup, limited edition and designer collab lines. Or I should say I would stick to those lines . . . I've been wearing the same pair of original brown 2 eyes for four years now, with no end in sight. I think these are the most comfortable shoes I've ever worn.

4.  J. Crew Leopard Print Calf Hair Shoes In Almost Any Style ($54 and up)

Around 4 years ago I discovered J. Crew Factory existed and wanted to try it. I waited until a ludicrous clearance sale and purchased sunglasses, PJs, 4 oversized V neck cashmere sweaters, three pairs of cropped cashmere/wool blend pants and a pair of leopard print calf hair ballerina flats.

The shoes looked far better than I expected (especially for the price; CHEAPY CAT PRINTS ARE AWFUL), were incredibly comfy, coordinated with everything, and lasted somewhat over a year with very frequent wear. 

When they were shot, I bought a pair of smoking slippers in the same leopard print calf hair and have been even more pleased with them. They started to bald in places after about a year; while that's unacceptable on a ballerina, it's sort of decadently fab on the more masculine smoking slipper. I think they have a solid 6 months+ left in them depending on how frequently I wear them; when they're put to rest I will definitely sign onto the J. Crew sale section and do it all over again. These shoes are comfy and look much pricier than they are.

5. minnetonka moccasins ($45 and up)

Minnetonka mocs are pure Americana. I have never met a granny who didn't wear white unbeaded leather kilties, nor a little boy who didn't shuffle around the cold Northeast wearing shearling lined softsoles (a style they appear to have named 'Charley'). Old people and kids wear them because they are extreme comfort shoes.

My navy leather boat sole Thunderbird 2s took me seven years to wear out (wearing them once, or rarely twice, a week). My suede kilty hardsoles took almost two years to wear out with very frequent, almost daily wear. And I'm not ashamed to admit that I've worn both the 'sheepskin hardsole moc' and 'alpine sheepskin moc' as outside shoes rather than slippers, and they lasted one winter and 3/4 of a winter respectively, which is not bad for house slippers!

Moccasins can be worn in the same elevated preppy looks as boat shoes, and where Tod's say "I'm an aggressive negotiator!" Minnetonkas say "I will ensure you pass your board interview". 

6. Limited edition Converse Chuck Taylors($125 and up)

Grimey, beat up Chucks are too adolescent for me, but the Converse collabs have made them acceptable sportswear accompaniments. My first pair twelve years ago was, I believe, the first Converse designer collab: red silk unisex low top slip-ons designed by John Varvatos, sold exclusively at Neiman Marcus. It might have been the first time they did the laceless slip-on. I loved those shoes so damn much I still occasionally search for them on eBay, but it was so long ago the internet seems to have no record of their existence. I wore them constantly until they were stinky and frayed; I think I had them a total of three years.

Around 2009 the Play/Comme des Garçons hightops hit and saturated the market; Converse limited editions have been art-and-design-crowd signifiers ever since. There are an insane number of drops every single season, and just trying to keep up got me hooked on HYPEBEAST. My favorites have been Damien Hirst and Missoni, they are great for days when I can't be bothered to wear a look beyond all-black-everything. I don't wear them much, so they're both good as new several years later. 

Chucks and Jack Purcells are not supportive, but are incredibly comfy in the way worn-in slippers are, lightweight and flexible. There are also lots of limited edition One Stars, which are personally nostalgic for me as a kid who wore them in the 90s, but they've got less caché. Did you know Converse has been selling the low-top all stars silhouette for 101 years??? CLASSIC is an understatement for these.

What are your favorite workaday flats?

Right now my wishlist includes: Bass penny loafers, Belgian shoes and *maybe* some red Gucci Jordaan loafers, which is a progression of loafers from sweet schoolboy to banker to bath-house proprietor. 

Any recs for me?