12 Tips to Buying the Right Boots and Shoes

3. Keep ankle boots and ankles compatible

Ankle boots are wardrobe essentials, but where the top of the boot hits your leg and how snugly it clings matter. Though the iconic Chelsea boot is still a great buy (see tip number 9), if you have wide, puffy or sensitive ankles prone to irritation try two alternative styles. A boot that dips lower in front and rises higher in back, like the LifeStride Giada Bootie in Black ($75, dsw.com/en/us), or a contoured style with V cutouts at the sides, like the DV Dolce Vita Wendee in Black or Taupe ($69, zappos.com) and Steve Madden Lancaster Bootie in Black Suede ($100, zappos.com), frees up the cling with extra space. Problem solved.

(Left to right) A New Day Woman’s Abril Tall Boots in Black; LifeStride Karter in Dark Chocolate; Trotters Misty in Black

Target; Zappos (2)

4. Look for knee-high boots with a stretch panel

Tall boots with a riding-boot flair are topping the must-have list again. Unfortunately, they can be uncomfortable to wear for hours at a time. To avoid the squeeze and for an easier on/off situation choose styles with a side zip and stretch back panel like A New Day Woman’s Abril Tall Boots in Black or Dark Taupe ($40, target.com), LifeStride Karter in Dark Chocolate ($90, zappos.com) or Trotters Misty in Black ($200, zappos.com). They’re comfy and ideal for layering over tights and leggings.

(Left to right) Journee Collection Shelley Women’s Mid-Calf Boots in Brown; LifeStride Kaden Women’s Slouch Boots in Brown; Sun + Stone Nelliee Lug Sole Slouch Boots in Grey

Kohl's (2); Macy's

5. Treat your calves to mid-calf slouch boots

Some of us think tucking jeans or leggings into tall knee-high boots makes our legs feel stuffed. Others would never wear ankle boots with skirts and dresses. Whether the issue is full calves, leg circulation or personal taste, slouchy boots with a ruched look and a shorter mid-calf shaft are an ideal solution. Try the Journee Collection Shelley Women’s Mid-Calf Boots in Brown ($60–$72, kohls.com), LifeStride Kaden Women’s Slouch Boots in Brown ($80, kohls.com) or the Sun + Stone Nelliee Lug Sole Slouch Boots in Grey ($80, macys.com). FYI: Some mid-calf boots are labeled “tall” so check the photo and the shaft length, which should be 10 to 12 inches — no longer.

(Clockwise from top left) Dr. Scholl’s See Me Slip-On Booties in Black Microfiber; Easy Street Womens Archie Booties Flat Heel in Brown; Skechers Women’s Easy Going Latte Slip-On Shoe in Tan

Macy's; JCPenney (2)

6. Maybe you just need casual sporty shoes

Not everyone gets seriously dressed anymore. Some women happily live in athleisure clothes all the time. Layers of pull-on yoga and track pants, leggings, soft tees and slouchy sweaters don’t require the same footwear as dresses and more tailored items. If this is you, head straight for slip-on sneaker booties like Dr. Scholl’s See Me Slip-On Booties in Black Microfiber ($80, macys.com), sporty booties like Easy Street Womens Archie Booties Flat Heel in Brown or Black ($42, jcpenney.com) or a lug sole clog like the Skechers Women’s Easy Going Latte Slip-On Shoe in Tan ($55, jcpenney.com). All deliver comfort, safe, grippy-soled walking and more of a lifestyle look than your usual sneakers.

(Clockwise from bottom left) Clarks Sharon Dasher Women’s Loafers in Black; Easy Spirit Devitt in Black; LifeStride Zee Slip-On Loafers in Black Croco Faux Leather

Kohl's; Zappos; Macy's

7. Make style with support your loafer goal

Birks and sneakers have trained us to expect no pain from outdoor shoes and boots. You’ve probably noticed that the category of “comfort shoes” is getting bigger every season for that reason and the shoes have gotten more stylish. Loafers are leading the comfort shoe pack now so treat your feet to cushioned styles with a twist like the wedge-soled Clarks Sharon Dasher Women’s Loafers in Black ($95, kohls.com), the LifeStride Zee Slip-On Loafers in Black Croco Faux Leather ($70, macys.com) or the minimalist, elegant Easy Spirit Devitt in Black ($61, zappos.com).

8. Know how trendy you can go

Every fall there are a couple of statement shoes that scream “I am super-cool and fashionable.” This year it’s cowboy-inspired boots, believe it or not (along with all those loafers and lug soles). Not every new trend will appeal to you. However, when you find one that does, don’t just jump into the most extreme version … unless of course you’re one of the rare 50-plus fashionistas who dresses that way. Instead choose a moderate version with just enough trendiness. Take a look at modified home-on-the-range styles like the slouchy Universal Thread Adaline Western Boots in Taupe ($40, target.com), rustic Zara Cowboy Split Leather Ankle Boots in Brown ($119, zara.com/us/en) and Scoop Women’s Studded Faux Suede Booties With Stacked Heel in Tan ($40, walmart.com). Urban cowgirl.

(Clockwise from bottom left) J.Crew Emma Haircalf Boot in Rich Mahogany; Franco Sarto Waxton Chelsea Boot in Black Snakeskin; Naturalizer Henry in Green Multi Tonal Snake Leather

6pm; Nordstrom; 6pm

9. Have at least one attitude boot

It’s the pair you wear with the edge and confidence of a black leather jacket. Though lug sole moto and combat boots are trendy, too, they’re not for everyone over 50. Instead try an ankle boot in snakeskin or leopard (because we can never resist a good animal print) like the Naturalizer Henry in Green Multi Tonal Snake Leather ($34, 6pm.com), J.Crew Emma Haircalf Boot in Rich Mahogany ($62, 6pm.com) or Franco Sarto Waxton Chelsea Boot in Black Snakeskin ($150, nordstrom.com) to boost your style and mood. You’ll walk taller and feel grounded and ready to tackle anything. Just add your sassiest jeans.

(Left to right) Simply Vera Vera Wang Madisonn Women’s Chelsea Boots; LifeStride Simone Women’s Boots in Taupe; Worthington Women’s Brighton Booties Block Heel in Black

Kohl's (2); JCPenney

10.  Update, don’t repeat, your favorites

We make repeat purchases of basic shoes or boots simply because we know they work or are reluctant to attempt new styles and brands. Don’t get stuck in that rut. Footwear designers are always sneaking in improvements along with style updates. You might, for example, update your usual Chelsea boots this time around with the addition of a a comfy sock-like collar and stable lug sole like the Simply Vera Vera Wang Madisonn Women’s Chelsea Boots ($60, kohls.com) or Worthington Women’s Brighton Booties Block Heel in Black ($45, jcpenney.com), or opt for a style with a casual ribbed-knit collar like the LifeStride Simone Women’s Boots in Taupe ($90, kohls.com). Change is always good.

(Clockwise from top left) Walking Cradles Henrietta Pump; Journee Collection Womens Isobel Kitten Heel Booties; H&M Faux Suede Slingbacks

DSW; JCPenney; H&M

11.  Change your idea of fancy shoes, too

Not long ago high-heel pumps were it. The stiletto — still a favorite of royals and movie stars — has become as useful and desirable to everyday women as a pushup bra or industrial-strength shapewear. That said, now our social lives are picking up so put a pair of “dressy” shoes on your to-buy list. Choose low-heel black slingback pumps like the Walking Cradles Henrietta Pump ($95, dsw.com/en/us) or H&M Faux Suede Slingbacks ($25, hm.com/en_us) or a kitten heel bootie like the Journee Collection Womens Isobel Kitten Heel Booties ($80, jcpenney.com). Two of the hottest after-5 looks to snap up now.

(Left to right) Josmo Outdoor Women’s Waterproof Chelsea Rain Boot in Black; Chooka Women’s City Solid Tall Waterproof Rain Boot in Black; Cougar Firenze Waterproof in Black Gloss

Walmart (2); Zappos

12. Buy a pair of grownup waterproof boots

This is one of the most essential fall buys, but it’s often overlooked. Make your rainy-day boots a dupe of your favorite everyday style so you’re not stomping around in old galoshes with an otherwise great outfit. I know rain boots in a bright turquoise, stripes or polka dots look appealing but stick with neutral black. Choose a Chelsea ankle-boot style like the Josmo Outdoor Women’s Waterproof Chelsea Rain Boot in Black ($30, walmart.com) or the Cougar Firenze Waterproof in Black Gloss ($70, zappos.com) or a knee-high riding-boot style like the Chooka Women’s City Solid Tall Waterproof Rain Boot in Black ($80, walmart.com). All look sophisticated with a trench now, parka later and everything from a wrap dress or midi skirt to joggers and jeans. Don’t even hesitate.

Lois Joy Johnson is a beauty and style editor who focuses on women 50 and older. She was the beauty and style editor at Ladies’ Home Journal and a founding editor of More magazine. She has written three books: The Makeup Wakeup, The Wardrobe Wakeup and The Woman's Wakeup.