How To Wear Ankle Boots Over 40

DO YOU WANT TO DRESS STYLISH, FEEL AMAZING & AGE APPROPRIATE?!

As women, we can limit ourselves when we are getting dressed because of our fears and insecurities. I totally get it and can doubt myself also. I often ask myself, “Does this look too youthful/inappropriate for my age??” I am in my 40’s and I want to share with you what I have learned, so you also will feel fabulous in what you are wearing!!

A victory for me is I chose to confidently wear crop tops over the last few years. Is that the goal?? NO, no it’s not. It’s just a look I am attracted to and did the inside- work to get out of my head and wear what I love— styling it for the decade I am in.

In our 30’s, 40’s, 50’s & 60’s + we want to represent ourselves by exuding confidence with our style. DID YOU KNOW THAT clothing items can ALWAYS be tweaked to suit our style and age!?!!!

I encourage my clients to do their inside work to build up their self-love and surround themselves with like-minded women. We all need that friend who will be honest with us about what we have put together & whether it looks good or not! With their assurance added to us trusting ourselves is an amazing feeling!

In this article, the looks I have prepared for you are from dresses & skirts to trousers & jeans. I’ll share style tips & where you can wear these looks. YES, we can boldly wear our dressier skirts when casually styled when going to run errands or to ladies’ brunch!

ENJOY! —and remember to always Dress For YOU

FAUX LEATHER PIECES ARE PERFECT FOR FALL WITH ANKLE BOOTS

Faux Leather pieces are for all ages!

Have fun shopping and try on these faux-leather options: leather leggings (you can pair them with an oversized sweater + white sneaker), leather trousers (pair with heels/ loafers + graphic tee), shorts or skirts (style with Over-the-Knee: OTK Boots, tights and textured sweater). These options are an excellent addition to your wardrobe making you look polished no matter how they are styled!

I styled this dress with Dr. Martens from DSW Canada (link below)

STYLE TIPS:

1. Wear this casual look above running errands. If you get cold just add your tailored oversized jacket or long cardigan.

2. If you do not like Dr. Martens boots then choose a Chelsea Boot

FLAT ANKLE BOOTS ARE A CLOSET ESSENTIAL!

That’s right…You need a pair in your closet!

Before I begin: What are FLAT Ankle Boots???

In case you have not heard this reference before they are ankle boots that do not have a heel.

STYLE TIPS:

1. If you are petite, the key when wearing a flat ankle boot, is to wear them with skinny jeans, cropped jeans, or leggings. Leaving a finger with of space between the top of your boot and the bottom of your pant. A visual of the complimenting distance is shown above with my midi-skirt as an example of when you choose to wear a skirt.

2. Elongate all body types by buying ankle boots that hit just below your ankle or a little above your ankle. When the mouth of the boot is at the narrow part of your ankle it compliments your legs!

3. A classic look is an ankle boot with cutouts. They are in style and look amazing when that peek-a-boo of skin is showing.

4. Curvy women can wear flat boots! If your legs are short or thick choose a pair with a notch in the shaft & a pointed toe. If you prefer a rounded toe, just look for a narrow rounded toe (like what I’m wearing). — this adds length to your legs and draws the eye up. Knowing this tip helps you to know what to look for when shopping! There are lots of round-toe-boot options out there to suit your personal taste!

NOTE: I found this fabulous tulle midi-skirt at a boutique and sadly it was the last one or I’d link it for you! I chose this look for you so you can see how you can casually style a “dressy skirt” with a flat ankle boot.

PAIR YOUR SWEATER DRESSES WITH YOUR COMBAT/FLAT BOOTS

Slits in skirts are happening! If you are 50+ I suggest you just have your slit slightly above your knee. Don’t rule them out!!!

I scored this Aritzia sweater dress on consignment. If you do not have a sweater dress in your closet I encourage you to be on the lookout for one. They are everywhere and are as comfortable as sweatpants.

VERY IMPORTANT STYLE TIP:

If you want/need shape-wear bring what you own when you go shopping!!

This is SO important. If you need more shape-wear options in your closet, bring the dress with you to the lingerie store.

Sweater dresses can, NOT ALWAYS, show off our warbly bits, and with incorrect shape-wear chosen it can cut you in the wrong places making things worse—so you’ll either give away or sell your dress. With this tip, you will pair the right dress with the required undergarment and look hot AF!

SHORT DRESS AND ANKLE BOOTS

30’s: Go to town— have fun and express yourself

40’s: Still own it! Short skirts do not have to leave your closet!

50’s +: Absolutely you can pull off a short skirt or dress!! Tweak your look by having it 2” above your knee and pair it with a longer or matching hem in your Blazer, Cardi or Jacket!! If you have cellulite, add tights (not the see-through hose)

ANKLE BOOTS + TRENCH COAT ARE STAPLE PIECES FOR 30+YRS OLD

I featured this look so you can see it put together. Sometimes all we need is a visual and encouragement.

STYLE TIP:

Trench coats are a closet must-have and are amazing for layering too. Ex. Wear your favorite jean jacket (pop the collar) underneath your Trench coat, and VOILA- you look so sophisticated!

Note: with this look, I chose a chunky flat Chelsea boot. You can also switch it up with your favorite pair!

CROP WIDE-LEG PANTS WITH ANKLE BOOTS

This look does not suit everyone’s taste but if I was to style you I’d pull some for you and share why they work.

STYLE TIPS:

1. Wide-leg Pants work amazingly on rectangle & triangle body shapes because the cut adds shape to your frame.

2. If you are short this style with a high waist can add height for you. Especially when paired with a heeled ankle boot.

3. Flattering on bodies that are straight, curvy, hourglass, tall, or petite. They are so versatile and add FUN drama pending on the width of the pant leg. Pair them with a classic tee or a printed blouse that represents YOU!

NOTE: featured above is the White MARTA Boot that is currently sold out by ALDO Shoes. *Black is available. White sells out SO quickly so when you love a pair—buy them :)

BOLDLY WEAR YOUR WIDE-LEG JEANS WITH PEEK-A-BOO POINTED TOE

This is a “let’s go for wine’ kinda look!

I encourage all my clients to have these pieces in their closets because you look so damn good wearing them!

STYLE TIPS:

1. Owning a Cognac (Carmel) color boot is a closet staple because it switches things up in your closet expanding your options. Style them with what you’d wear with your black pair. AKA. it’s neutral!

2. Cognac color boot look amazing with medium wash denim.

3. Wear with your black and white pieces AND, your purse does not have to match!!

4. Psst… Long necklaces are back in style for Fall 2022!!! So pull yours out again :)

WIDE-LEG TROUSERS PAIRED WITH COMBAT BOOTS

Some women have told me that Combat Boots seem too youthful… or can be a boot where you would feel silly wearing them because others around you are not gravitating to them. If this is the case and you like them— become a trendsetter or confidently choose them because you like them!

I paired these boots with trousers. I wanted to dress them down to show you how chic this looks. (note: This boot looks like Dr Marten 1460 lace-ups)

STYLE TIPS:

1. Wear combat boots with everything: Dresses (short and long), Shorts. Skinny jeans, Wide-leg Pants. Leather items or your Mom-jean.

2. The Combat boot can be chosen with a platform sole as well if you want more height— this option is totally in!

3. If you have lots of skinny jeans: tuck in your Tee, wear a crop top, and knot your tee under a Blazer for an enviable look.

4. When wearing with Trousers: have the bottom of your pants almost match the bottom of your sole with a bit of a drape. This looks so casual and effortless. If they are short pants follow the rule shared above about ideal spacing so your legs are elongated.

NOTE: Please do not wear this boot with Capris pants. Cropped YES, but not capris!

CASUALLY CHIC & COMFORTABLE

I would bet that most of you have some of these items in your closet: a Blazer, Hoodie, Leggings + Combat Boots.

If you don’t have these exact boots you can choose your Chelsea Boot or Blundstones!

This look does not have to be tweaked for any age!

ELEVATED COMBAT BOOT LOOK FOR YOU

We all exude beauty— we see it in others but can sometimes have a hard time seeing it in ourselves… I felt beautiful in this outfit. I hope you do also if you are inspired to recreate it. I wore an oversized boyfriend blazer, my husband’s cashmere sweater, faux leather mini-skirt, black sheer hose, and Dr. Martens.

Would you agree as we grow we see how much time we’ve wasted comparing ourselves to others? I was so confident in this look, I didn’t even think twice. That’s what I desire to give to you if I style you or through my articles. That you feel so good in what you wear you are excited to get ready because you know how to put looks together that complement you.

STYLE TIP:

If you are 50+ just add a non-sheer hose to this look. Not leggings, please. Leggings and skirts do not complement, it takes away…IMO.

OR, if you are not comfortable wearing a short skirt— choose a pencil, long, or midi-skirt to execute this look!

PRINTED ANKLE BOOTS

Prints are an amazing way to express our personalities. When wearing a printed ankle boot keep it simple with your look. Let your boot be your style statement!!

Pair your printed boots with a plain tee, fun accessories EX, hat and bracelets, and your favorite jeans.

TIMELESS-CHIC LOOK

Never feel underdressed when you choose this look!

With your favorite ankle boots + jeans and any tee, you will look polished, and a lot of thought was put into an effortless look.

This combination is timeless and needs to be your “go-to look” when you don’t know what to wear!!!

SLEEK TROUSERS AND A BULKIER SWEATER

PSST: This look works across the board! Ages 30+ can successfully pull this off.

STYLE TIP:

The main thing to remember no matter what size/shape you are when re-creating this look is: If your top piece is bulky/oversized— then wear a fitted/sleek bottom. & if your pants are loose/baggy then choose a more fitted top. DO NOT wear baggy on both top and bottom. Remembering this rule will be a huge benefit when getting ready.

LET ME SHARE WHY A BODYCON DRESS + ANKLE BOOTS IS FOR ALL SHAPES

The Bodycon dress looks best on the hourglass shape BUT, with style tips, you too can rock this style of dress…. Here’s how:

1. Pear Shape: add a jacket or blazer where the hem of the coat lands at the small of your waist. This will make your legs look longer and even out your proportions because you are fuller at the hips. OR, reach for your long cardigan.

IMPORTANT: please stop dragging and pulling your layering pieces across your body to cover you up. Trying to close your garment adds bulk. Leaving them open created a center line down the middle of your body that compliments you making you look confident and taller. Pair your dress and chosen layering item with a cut-out ankle bootie= so sexy!!

2. Can I wear a Bodycon dress with a belly?

YES, choose a thicker material, a darker color, or a print you love or a vertical striped print to disguise your tummy. Invest in shapewear and also, choose a bold earring that draws the eye up.

3. Added Bonus: They feel like loungewear & look CHIC AF.

KNIT SKIRTS, HAT + ANKLE BOOT

Add this look to your memory for a Fall, Winter, and early Spring Go-to look.

STYLE TIP:

When wearing a midi-skirt have the length of your skirt and the shaft of the ankle boot meet at the calf area of your leg— the smallest part of your leg. This will also elongate your look because a knit skirt is typically high-waisted making you look taller no matter your shape. Knit Skirts come in all styles— they are a DFY Styling closet must-have.

WHYY THE WRAP-DRESS SUITS EVERYONE

Wrap dresses are amazing because they stand the test of time and trends and define everyone's waist. The tie at the waist can either be built in, stitched in, or created with the belt you choose. The tie waist cinches the slimmest part of your torsos giving you an ultra-slimming effect. Paired with a v-neckline, the dress enhances your bust and slims over the hips.

STYLE TIP:

1. This dress is a great option for those with a pear shape or those looking to add curves.

2. Don’t limit yourself to the belt given with the dress. Some are built in but when they are not get creative and switch up the belt with a wide belt, scarf, or thin belt.

MIXED PRINTS + ANKLE BOOTS

This is an outfit combination that suits any age!

A STYLE TIP when you are mixing prints is to choose one color that matches two pieces and VOILA, they can be worn together.

My ankle boot is a bit higher but, because of the scoop at the neck of my boot it still features the small of my calf so it compliments my legs

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styles featured in this post:

**Please note links are CAD$ and I only recommend products I would use myself and all opinions expressed here are my own.  

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