How to look ageless in boots

Invest in great classic boots

Boots are a great investment in your wardrobe from both a style and price point of view. You don’t buy them every year, but rather when you need a new pair either because the old ones need to be retired or a life event has changed the size of your feet. Since their tenure in your closet will be several years, your best bet is to go for an ageless design, i.e. a classic style that can’t be pin-pointed to the year you bought your boots.

Invest in a pair of classic tall boots as your workhorse. #agelessstyle Click To Tweet
#fashionover40 midlife woman looking chic in slouchy boots
Vince Camuto slouchy boots with GNW tight, Eddie Bauer skirt, striped sweater, DIY statement necklace (all own) and layering top c/o Adea

Tips to find the right boots

Here my tips what to look for when you buy boots.

  1. Skip styles that end at the widest part of your calves. Remember that any horizontal line draws attention to the point where it occurs. The widest part of your calves is surely not where you want the attention.
  2. Stay away from boots that are too wide at the top unless they are slouchy. You should be able to put two fingers into the top of the boot when you intend to wear them also over jeans. Otherwise one finger is enough for comfortable fit and style. Great fit at the leg is important to avoid a cold gap. You also do not want to look like you are “standing in your boots.” You are not Grandma Duck. That look is reserved for wellies and rain boots.
  3. When the boots are the only pair you will own, go for sturdy heel leather boot in a neutral color and classic style. This design will work for the commute to the office, visiting clients/customers, having a work lunch with your boss and walking on snowy sidewalks.
    1. Let the colors of your wardrobe be the lead in the choice of the neutral.
    2. Go with black or gray when cold colors dominate.
    3. Tan or brown are good options when most of your clothes are in warm colors.
    4. Only go for a statement color or style, when the pair is your second pair, i.e. not your work horse.
  4. The fit on your feet is critical. Your toes should not be squeezed to avoid cold feet. Recall air is a good insulator. Thus, you want a thin air layer between any winter footwear and your feet.
    1. When you live in a cold climate region, there should be enough room for wool socks and a shearling or foam insole for insulation.
    2. Waiting for the bus or tram can be uncomfortable when due to lack of insulation to the ground your feet get cold. A thick sole is also a factor to consider.
    3. On very cold days, you may consider to add boot toppers as they elongate the boots and close the gap between the leg and the boot. See this post for how to style boot toppers over 40.
  5. In cold climate regions, over-the-knee boots are great to keep your knees warm. When buying OTK boots look for a classic style with sturdy heel and stir away from patent leather (wrinkle alert) and stiletto heels (pretty woman alert, dangerous on ice). Leave stiletto patent leather OTK boots for exotic dancers like Jasmine Dubrow in Independence Day and women in the horizontal profession like Vivian Ward in Pretty Women.
#bootsover40 details of slouchy boots
Zoom-in on details of the work outfit with slouchy boots


When buying OTK boots look for a classic style with sturdy heel. #OTKboots #agelessStyle Click To Tweet

Styling boots over 40

Here are a couple of styling ideas, dos and don’ts for work appropriate looks with boots.

  1. Unless the 70s are a trend, avoid to wear a midi skirt that covers the upper part of your boots. Well, this look is so 70s and ages every woman over 40. Thus, if you go for the trend keep everything else modern.
  2. It is so much sexier to show some skin between the boot and the hem of the skirt. However, be aware that this glimpse of skin – even when covered with tights – is a cold gap. Thus, make sure to wear a long coat.
  3. When wearing a leather skirt go for suede boots.
  4. Over-the-knee boots look great with skinnies under a long tunic length sweater or a tunic dress.
  5. Going for a riding-style or over-the-knee boots are other great option. Pair them with slim pants (skinnies or riding pants), a button-down shirt, blazer and scarf. Add a pearl necklace and diamond studs for a posh casual business winter outfit.
  6. When your legs are your favorite/best feature try knee-high tall boots with an above the knee-skirt. Don’t go shorter than 4 inch (10 cm) above the knee. You don’t want to be mismatched from behind with your daughter. 😉

Here are some outfits with boots for visual inspiration.

#bootsover40 #tallboots woman in tall boots with boot toppersExample: Tall heel boots (own) with boot toppers c/o My Top of the Boots
#fashionover40 woman in stylish slouchy boots Example slouchy Vince Camuto boots (own)
#fashionover50 styling over-the-knee boots in a posh mature way Example Dior OTK boots with long Orvis chunky sweater (all own)
#styleover40 woman looking chic in rainboots Example Hunter rain boots (own)
#midlifestyle East European look
Example East European style
#fashionover50 equestrian style with skirt for work Example equestrian style with skirt
#styleover40 American West equestrian way Example American West equestrian look with Dior OTK boots (own)
#maturefashion calf high lace-up booties Example Double-H lace-up booties

You can find further details and inspiration on styling OTK boots over 40  and how to wear boot toppers over 40.

How do you style your boots? What kind of boots do you need? Let me know, I am curious.

When you think this post was helpful please tweet your friends have a look at these great styling tips and inspirations for outfits with boots.

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Photos: G. Kramm

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