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The Only Five Shoes You Need

In the post-pandemic world we now live in, it’s safe to say that function and comfort have supplanted style and form in many ways — most particularly, for me, in the choice of footwear. I have given up the ghost on high heels, preferring flats and lug soles. Also, with the concerns over the environment and the effects of fast fashion, many folks have been paring down their wardrobes and their consumption.

So, I recently questioned how many pairs of shoes does a middle-aged woman actually need, wear, and can consciously own? The answer (give or take) is five. Yep, at least for this working mom who gets out and about every couple of weeks, five shoes are all that is needed. Well, sort of.

First, a retro sneaker. Not the sneaker you exercise in, but a mid-to-thick soled sneaker with throwback flair that you can wear with non-athletic clothes to put a sporty spin on everyday style. Puma’s Palermo Sneakers will fill the brief in either black/gray or white/gray. For a true 80s vibe, check out Reebok’s Club C 85 Sneaker in chalk/green. Sure, you can wear either pair with jeans or sweatpants, but the key to this shoe is contrasting the aesthetic and styling with unexpected pieces like wide-leg trousers and midi-skirts.

For occasions where you do want a bit of classic feminine footwear, look no further than the pump. Of course, there are so many variations of pump-style heels. You have your ankle strap pumps, slingbacks, Mary Janes, pointy toe, round toe, square toe. And once the toe shapes and the strap styles start intermixing, the pump variants out there can become overwhelming. What I found works best is having a signature heel shape/height, toe shape, and strap situation. For me, that’s a mid-height square heel, rounded toe, with no straps. This style admittedly is not currently on trend, but luckily, I have a go-to pump from Nine West purchased in 2017. I was able to find a similar version available at Nordstrom, Anne Klein’s Castana Round Toe Block Heel Pump, in nude or navy. I may be tempted to add a second pair of pumps to my roster when reading about these and their iFlex cushioned footbed. Regardless of temptation or signature pair style, wear pumps with jeans and blazers or shift dresses and trench coats.

Moving onto boots. There is a boot type I find myself reaching for multiple times a week when putting together daily outfits: The good old everyday ankle boot! Considering how often ankle boots can be worn, it’s very much worth making sure you have a pair you love and a pair that lasts. LL. Bean’s Teva Anaya Booties are waterproof and rugged but stylish. In either black or brown, these boots can be both functional and fun when worn with jeans or cropped trousers. Plus, their rubber outsole and microfiber lining make them perfect for the upcoming season. If you’re interested in something with a bit more gloss, check out Vince Camuto’s Viltana Bootie with a squared-off toe and sculptural block heel. This pair is less weather-resistant than the LL Bean option but brings a bit of glamour to your everyday look.

Next, we have riding boots. Ironically, you want to stay away from anything too equestrian in nature, as that style has less versatility. Instead, look for knee-high flat boots that can be worn either over a skinny pant as well as under a long dress or loose trousers. Sam Edelman’s Made Knee-High Boot in black, cognac, or brown fits the bill, or should I say foot, with their sleek design and minimal hardware. These boots can be worn with leggings, a sweater dress or culottes, and a turtleneck. For something a bit more budget-friendly, there is Kelly & Katie’s Sion Riding Boot from DSW.

Lastly, there are functional flats. Whether in a ballet style, loafer, or brogue style, a sturdy flat will take you a long way in a lot of looks. Like the pumps, you have to find the best flat style for you and your feet. I get a lot of wear from Allbirds’ Tree Breezers, which are woven, machine-washable ballet flats that nicely hug and conform to the foot, versus their more uncomfortable leather counterpart from the 90s’. This casual shoe is great with loungewear and athleisure looks. For an androgynous, loafer take on flats, check out G.H. Bass’s line of Weejuns that can be dressed up, down, and eccentrically, depending on which shade and sheen you pick up. I love their suede version in teal for holiday festivities, the leather metallic pink version for girls’ night, or the Whitney Weejun in wine for a day at the office.

Do I now only have five pairs of shoes? Of course not! I have twenty years’ worth of heels, flats, loafers, sneakers, mules, boots, clogs, etc. But for my life now and for the foreseeable future, the five styles above are what I’ll be wearing most often, if not exclusively. These five styles, in addition to all-terrain sneakers, hiking boots, snow boots, and, of course, the various sandals styles come summer.