lace up ankle booties

In the market for the best Lace Up Ankle Booties? Our team has researched and reviewed these lace up booties heels to help you come up with a better decision. We’ve also put up a shopping guide with the features you can consider when buying lace up ankle boots heels, lace up high heel ankle boots, and lace up booties flat picks.

Lace Up Ankle Booties

How to Wear Ankle Boots & Ankle Boot Styles

There are so many ways to wear ankle boots – because there are a number of different styles to choose from. Comfort is important, as is matching the right types of ankle boot to the right occasion. Find out more in our expert guide.

Best Women’s Ankle Boot Styles

Kitten Heel Boots

Best for: work, interviews and everyday casual

Kitten heels tend to be quite thin, but are still stable and easy to walk in – because the heels tend to be under two inches. The small heel adds a touch of elegance compared to flat boots.

Wedge Heel Boots

Best for: everyday comfort and stability

While wedge heels tend to be a little taller than kitten heels, they’re still easy to walk in due to the lack of a gap between the toe and heel of the shoe. Wedge heel boots support your entire foot and give you more contact with the ground, providing more stability.

Chunky or Block Heel Boots

Best for: work and job interviews

Chunky or block heeled boots are also a great choice for comfort, as they give your heel more surface area and protection. While they aren’t as stable as wedges, they’re much more so than, say, stilettos. Because of the elegant look they provide, chunky and block heel ankle boots are great to wear for work or a job interview.

Open or Peep Toe Boots

Best for: weddings, parties and special occasions

When fitted correctly, open or peep toe boots can be super stylish – allowing your pedicure to add a hint of glamour to your outfit. This makes open and peep toe ankle boots perfect for weddings, parties and other special occasions. They pair well with cuffed trousers, skirts and dresses.

Flat Ankle Boots

Best for: everyday comfort and casual wear

When it comes to ankle boot styles, these are by far the most comfortable and relaxed. Flat ankle boots can pretty much be paired with whatever outfit you have on – and are in their element on cold or rainy days.

Lace Up Ankle Boots

Best for: work or special occasions, depending on the style

Lace up ankle boots come in many styles, from flat to peep toe. The laces can be adjusted for the perfect fit. However, be careful how tight the laces are – especially around the ankle area. As the day goes on and your feet swell, tight lacing can cause numbness and pain in your foot. Depending on the style of your lace up boots, they could be a good option to wear to work or to a special occasion. Just check they look right with your outfit first.

Buckle or Strap Boots

Best for: everyday support

Buckle or strap boots generally provide more support to your ankle than slip on boots. Make sure to check the strap can be adjusted to your size, and isn’t too big or too small.

  • Too big won’t provide much support and could hurt your ankles.
  • Too small could lead to numbness in your ankles and feet.

Tassel Boots

Best for: making a style statement

Tassel boots don’t usually add anything to the fit of the boot. However, when paired with the right outfit they can add a stylish detail that completes your look.

How to Wear Ankle Boots Over 40

The key to wearing ankle boots over 40 is finding a boot that suits your shape and sense of style. Make sure:

  • The hem of your jeans is no more than an inch off the ground when wearing them with bootcut jeans.
  • If wearing ankle boots with a skirt, that it’s no shorter than knee length.
  • The colour of your boots matches your outfit. Wearing boots that are the same colour as your tights or skirt will help keep your look understated and elegant.

Need more guidance? Get more detailed advice on how to wear ankle boots over 40.

How to Wear Ankle Boots Over 50

Ankle boots are one of the best pairs of shoes to wear if you’re over 50. There are a range of ankle boot types and styles that could work for you, including:

  • Flat ankle boots – one of the more versatile styles which will go with any look or outfit.
  • Tasselled or buckled ankle boots – these can add an extra detail to a simple, everyday look like skinny jeans and a shirt.

Our comprehensive style guide has all the information you need on how to wear ankle boots over 50.

Men’s Ankle Boot Styles

Lace Ups

Best for: work and special occasions

Lace up boots are a popular choice for men, because they provide a lot of support – especially to the ankle – and are comfortable to wear. Lace up boots can also look refined and professional, making them a great option for work and special occasions.

Chelsea Boots

Best for: work, weddings and smart casual looks

Chelsea boots are stylish and smart pull-on boots. These iconic shoes have been fashionable for decades. They look great with smart trousers for work, interviews and special occasions – and also go well with jeans for more of a smart-casual look.

Desert Boots

Best for: everyday, casual comfort

Desert boots, otherwise known as Chukka boots, are lace up boots usually made of suede or imitation suede. These lightweight, casual boots are great for weekend and light work wear.

Walking Boots

Best for: outdoor activities like walking and hiking

Walking boots, or hiking boots, are just like normal lace up boots but with more comfort. Designed to protect your ankles and cushion your foot, they also guard your feet against rain and uneven ground.

Finding the right ankle boot type can be a hefty task, so try plenty of different options on before deciding what’s right for you. If you’re still unsure on how to wear ankle boots with your favourite outfits, take a look at our style guide.

The Types of Boots Always Worth Investing In


Street Style: February 28 - Milan Fashion Week Fall/Winter 2016/17


Just like you can never own enough white tees, you can never own enough boots. Before you refresh your fall/winter wardrobe with new footwear, though, check your styles. Do you have all the classic silhouettes, or at least one pair of classics? By this, we mean the kind of boot that stands the test of time. Black Chelsea boots meet this criteria, as do your rain boots, and even your new designer stiletto ankle bootie.

It doesn’t matter if these boots have been given a makeover in trendy colors or different textures—you can still tell they’re classics by the shape and overall fit. Not sure what types of boots you need, or are even out there? We have a short, digestible list of ones to own (or try—no peer pressure here) ahead.

Chelsea Boots

Street Style - Paris - January 2017
Edward BerthelotGetty Images

This classic boot comes in all heel heights and toe shapes, but the most distinguishable feature of a Chelsea boot are the black elastic side panels. The shoes often have a tab on the back of the boot, making it easier for you to pull on. Fun fact: The first of this style was made by J. Sparkes-Hall for Queen Victoria in 1851 because she wanted a pair of non lace-up boots, though the Chelsea boots as we know them today didn’t become popular until the ’50s and ’60s. They were considered trendy and “mod” in the United Kingdom when they first came out, and over time these became a timeless wardrobe staple for both men and women.

Combat Boots

Street Style - Berlin Fashion Week Spring/Summer 2019 - July 5, 2018
Christian VierigGetty Images

The army combat boot was initially designed to be worn by soldiers in combat, as the name suggests. While the style is still worn by members of the military today (soldiers are getting upgrades in the designs), civilians tend to look for more fashion than function (I, personally, mostly wear my combat boots to and from the office). Fashionable combat boots still have the same original army elements, such as a rounded toecap, laces, a chunky sole, and a high collar. But the designs are more flexible, coming in various textures, from faux croc to snakeskin, and in every color imaginable. Some styles even have a four-inch heel for a height boost, which are definitely not appropriate for military drills.


Weather Boots (Rain/Snow)

Street Style - Berlin Fashion Week Autumn/Winter 2019
Christian VierigGetty Images

Speaking of functional shoes, you’ll always need a pair of waterproof boots, whether that be snow boots or rain boots, to carry you through the winter storms. Waterproof footwear, thankfully, has come a long way in terms of stylish designs, with many companies like Hunter giving the shoe a more fashun look. (Just check out the Chanel rain boots in the street style photo above.) You no longer need to choose between an ugly rain boot that leaves your feet dry or a boot that leaves you with soaked socks—you can cover all your bases with the weather-appropriate options below.

Thigh-High Boots

Street Style : Paris Fashion Week Womenswear Spring/Summer 2019 : Day Three
Christian VierigGetty Images

Unlike ankle boots, which sometimes leave parts of your skin exposed to the nippy winter elements, thigh-high boots has you covered—literally. The classic style features a shaft that hits mid-thigh and is often fitted to your legs, leaving no weird ripples and bumps. Thigh-high boots can be worn with tights, jeans, skirts, dresses, and more as you’ve seen on your favorite fashion bloggers and celebrities. Not completely sure how to rock them? Good news: I’ve come up with foolproof outfits for this season here.

Stiletto Heel Boots

Street Style : Paris Fashion Week Womenswear Spring/Summer 2019 : Day Nine
Christian VierigGetty Images

A stiletto heeled boot will never be out of date, even though the kitten heel style has made a comeback in recent seasons. The skinny heel can be included on any shoe style from the Chelsea boot to thigh-high options and look best when worn with tailored pieces. Think of the stiletto heel boot as an alternative to pumps at the office for fall/winter. You still retain that confidence you get from your normal heels as well as the height boost. Be right back, trading in my slingback pumps for one of these picks, below.


Riding Boots

Street Style - Paris Fashion Week - Haute Couture Fall/Winter 2017-2018 : Day one
Edward BerthelotGetty Images

You don’t need to be an equestrian to pull off a pair of riding boots. This knee-high with a flat or low heel style comes in many colors and finishes, but typically brands will offer them in standard shades like brown, black, navy, or grey. Some riding boots come in suede, others in leather, and overall give off a very posh vibe. For a more classic look, go with an option like Coach below. For a more vintage meets modern minimalism feel, BY FAR’s “Edie” butter-soft leather boot hits the spot.

Cowboy Boots

New York Fashion Week - Street Style - Day 1
Christian VierigGetty Images

The further we move from the past, the more designers are looking back to the archives for shoe silhouette inspiration. One of them is the cowboy boot, which has been continuously remade every season. Cowboy boots now come in all prints, colors, and textures outside of cowhide leather. For this season specifically, you’ll find everything from a kitten heel option to a pointy-toe shape metallic design. Here’s to channeling the Wild Wild West the 2019/2020 way with the Western-inspired footwear picks ahead.


JANUARY 13, 2016

Tis the season.

Winter is a chance for your low-cut footwear to rest and recover while you break-out your boot collection.

Following up on our Guide to Loafers, here we break down the essential boot styles for the curated man’s wardrobe.



Sleek and minimal, the chelsea boot is a slip-on style with a sharp toebox and a slim leather sole. They can work with anything from suits, to chinos, to jeans, but are the best reserved for going out somewhere (or with someone) sexy.

Recommended In: medium brown suede or black leather.



If you’re new to the world of dress boots, aka getting suited and booted, this is a great place to start. A medium height captoe dress boot is smooth enough for your sharpest tailored trousers, and rugged enough for your most beat-up selvedge denim.

Recommended In: dark oxblood leather



The wingtip brogue is another essential that can serve as your stand-alone dress boot. We’ve featured the “Dalton“ style from Allen Edmonds as much as any other footwear in AOS history, simply because of their versatility and how long our pairs have lasted.

Recommended In: chestnut brown leather or dark cordovan.



Similar to the captoe dress boot, just slightly more casual in nature due to it’s shorter height, heavy stitching, and napped suede texture.

Recommended In: medium brown suede



This has been a personal favorite of mine lately. Similar to the chelsea boot, but with a 360 ankle strap rather than the elastic side bellies. This is a sleek European style that’s perfect for trousers with tapered trim or slim waxed jeans.

Recommended In: medium brown suede or black leather.



The chukka is a casual ankle boot with short laces and only 2-3 eyelets. It’s a casual style best reserved for jeans and chinos, but a pair in a rich suede can also be a good match for flannel trousers.

Recommended In: tan or light brown suede.



The harness boot, or riding boot, is an extremely tough style meant to withstand a real beating and protect your feet from just about anything. These are meant for motorcycle riding, or doing some hardcore shit-kicking.

Recommended in: the toughest leather you can find.



A form of Chukka boot designed by the military, with flexible gum soles, for dry dusty terrain. The most popular version of these is by Clarks, due to their affordability, comfort and longevity.

Recommended In: waxed leather.



Whether they’re classic Timberlands or Red Wings, the work boot, as with workwear, will always have a place in menswear. These are steel-toed and cut from a thick cowhide to protect your feet and give you plenty of stomping power.

Recommended In: heavy-duty medium brown leather.



This one is for the rockstars and skinny-jean wearing party animals out there. These are best suited for thin-framed musicians and artists who aren’t afraid of a little androgyny.

Recommended in: black, of course. Exotic skin (like python) if you’re really trying to go all-in.



The cowboy boot is a western style with a long history. They’re not for everybody, but for a Southern Rancher like Alex, they can go from horseback to formal occasion in just a matter of a shine.

Recommended in: a natural, understated, non-embellished leather. Preferably vintage.



This one if for snowy days, ski trips, and fashionable hiking excursions. A sleek enough pair, like the ones above, can also be great for trudging to the office through some nasty conditions.

Recommended in: dark brown or oxblood (although these do look badass in a black)


Thanks, as always, for reading. If you have any questions about our online custom menswear, feel free to contact us anytime. We look forward to serving as your personal tailor and stylist. 

Where to Buy Discounted Shoes

To make buying discount shoes online easy and stress-free, here are the best places to look.

1. Amazon

Amazon makes the top of the list because it has reasonable prices on everything. If you’re one of the more than 90 million Amazon Prime members in the U.S., you’ll enjoy free two-day shipping, too.

Whether you’re looking for low prices on brands big or small, you’ll find something here. You can easily compare Adidas and Under Armor to Sorel and Skechers and get the features you want.

To make finding discount shoes on Amazon easy, shop the “Shoe Discount Warehouse” and  “Shoes Under $25” section of the website.

And as a bonus, if you have a Prime membership, most returns are free.


  • Free two-day shipping if you’re a Prime member
  • 30-day return policy for easy refunds
  • Variety of price points
  • Lots of brands and styles


  • Big marketplace can be overwhelming
  • Different return policies if item not sold and shipped by

2. DSW

Clearance sales and discount prices are where it’s at when shopping DSW. It has a decent selection of shoes in-store but its online shop has even more to choose from.

At Designer Shoe Warehouse, or DSW, you’ll find footwear for all activities, including walking, running, basketball, dancing, work and hitting the town.

Its name-brand selection tends to be higher in price, but they always have sales and clearance shoes to pick from.


  • Massive selection of the biggest brand names
  • Clearance section offers deep discounts
  • Rewards members get free shipping
  • Free exchanges within 60 days


  • Not as many deals as some other sites
  • Can’t exchange purchases by mail

3. Zappos

With a wide selection of shoes for every budget, Zappos has something for everyone. Its easy-to-use search options make finding shoes easy.

There are specialized categories like running, diabetic-approved and eco-friendly, and each item has multiple photos to show you the shoe from all angles.

Zappos is also an excellent place to read reviews that can help you select the right shoe for you. Pay attention to pricing because some styles have different prices for different colors, even if they’re the same brand.

There’s a generous return policy that lets you return your shoes for a full refund up to 365 days after purchase. That’s a whole year!

It gives you plenty of time to try on the footwear in the comfort of your own home, and return them for free if you don’t love your shoes.

Probably the best thing about Zappos is you never pay for shipping, even on returns.


  • Large selection
  • Multiple photo angles
  • Free shipping
  • Full refund if returned within 365 days


  • Never offers coupons
  • Pricing can vary for different colors of the same style shoe


Though most notable for its big selection of home goods, also has great prices on shoes for men, women, kids and every age in-between.

It has a lot of designer brands to pick from and budget-friendly choices, too.

Saving on shipping is easy since orders for $50 or less ship for $2.95; orders over $50 have free shipping. Women especially can save big because most of the footwear for women is less than $30.

Overstock’s selection and sales change daily, and that makes shopping fun because there’s always something new to find on the site.


  • Only $2.95 for shipping every day
  • Free shipping on orders over $50
  • 30-day return policy


  • Partial refund for returns over 30 days
  • Varying return policy from marketplace sellers


If you didn’t already know, is the outlet store for Zappos. It carries a little bit of everything, and it usually has a lower price than what you can find at other online retailers.

Sales on Ugg and Hunter boots are typical, and frequently offer coupons to save you an additional 10% or 15% on your total purchase.

You’ll want to check the site often because its deal of the day can save you up to 70% off the shoe’s already low price.

And their clearance section has a vast selection of brands, so you can always find a discount on a super pair of shoes.


  • Discounts of up to 70% off
  • Numerous brand names to choose from
  • Frequent coupons to save more


  • Return shipping is not free
  • Doesn’t offer exchanges
  • No reviews on shoes they sell


If you’re looking for specialty shoes, has a nice selection of eco-friendly, vegan and diabetic-friendly shoes available.

There are loads of non-specialty shoes, too. The search feature on the site helps you find the exact shoe you’re looking for. You can shop by category, too.

Returns are hassle-free and can be done within 60 days. Plus, the company will send you a prepaid shipping label, so you don’t pay return postage.

The variety includes designer brands and a decent selection for work, play and casual shoes. Shoppers looking for a great place to buy sneakers and outdoor footwear online will find a fantastic number of options here.


  • Free shipping on purchases and returns
  • Great for sneakers and outdoor footwear
  • Eco-friendly, vegan and other specialty options available


  • Doesn’t ship to PO Boxes or APO/FPO

7. Poshmark

Some of my favorite finds are from second hand stores. One of my favorite places to find amazing deals on gently used shoes is Poshmark.

Poshmark offers higher-end designer clothes, accessories and even shoes. Trust me, there is treasure on this site. Especially when a new pair of shoes at a fraction of the cost can be found.

Another bonus feature with Poshmark is you can find a seller that has the same size shoe as you and follow them. I met a clothing line retail manager once who told me she wore something new everyday. Here gently used clothes are sold on her Poshmark page.


  • Fantastic selection of well-known brands
  • Make offers and lower the price


  • Returns are based on seller

8. Foot Locker

As one of the best places to buy discount athletic shoes online, Foot Locker has deals on everything for running, soccer, tennis, general exercise and even cheerleading. What you won’t see is anything unrelated to sports.

If you’re looking for fashion or dress shoes, DSW is a better place to look, with an excellent selection at low prices.

Foot Locker makes it easy to find the right fit if you have specific needs, such as motion control and stability. You can use filters to narrow down your choices.

They offer free shipping on orders of $75 or more, and returning can quickly be done in-store or by mail.

For bigger savings, sign up for their newsletter to get discounts and coupons sent right to your inbox.


  • Best selection of athletic shoes
  • Can return or exchange in-store or online


  • Orders must be for $75 or more to get free shipping
  • “SmartLabel” fees charged for returns


With free shipping, you can’t go wrong with Even their return shipping is free, which makes refunds a breeze.

There are dozens of different shoe styles to choose from for men, women and children at discount prices. You’ll find brand names at a variety of costs to fit your budget, including work boots, running shoes, sandals and boots.

The site features daily deals and low prices every day, making it an excellent place to buy discount shoes online.


  • Free shipping on purchases
  • Free return shipping


  • No returns accepted beyond 45 days
  • Doesn’t offer product exchanges

10. Famous Footwear

Offering some of the best value when it comes to discount shoes online, Famous Footwear has low prices. It’s a great place to buy shoes, boots and sandals for up to 50% off every day.

Plus, there are additional sales and discounts to save even more.

If you sign up for the rewards program, you’ll get access to exclusive offers and free shipping.

Famous Footwear has a fabulous selection for men, women and kids. The range of children’s shoes isn’t as extensive as what you’ll find on, but you’ll find a decent choice of infant and toddler sizes here.


  • Return in-store or by mail
  • Rewards program for exclusive discounts


  • Exchanges not available by mail
  • Must pay for return shipping
  • Limited children’s shoes selection

11. Zulily

Though the selection isn’t large, you’ll save serious cash with deep discounts on shoes at Zulily. The styles can sell out fast, so don’t hesitate to buy if you see something you love.

You won’t find free shipping here, but you can qualify for free shipping on subsequent orders after you place an order with paid shipping. Just note that the time period when you can add on an additional order for free shipping is limited. If you wait too long, you’ll have to pay to ship your purchase.

If you’re in a hurry to get your shoes, Zulily isn’t the best option. Orders frequently take two to three weeks to arrive on your doorstep, and that can seem like an eternity when you’re used to next-day shipping.


  • Qualifying additional orders ship free
  • Deep discounts on shoes


  • Smaller selection
  • Long shipping times

Tips Before you Buy Shoes Online

When you shop for shoes online, you’ll quickly realize how much lower the prices are, compared to local stores.

Even though you can’t try the shoes on first, buying shoes online is a pleasant experience for many consumers.

“It is the only way that I’ve bought my shoes over the past 15 years,” says Carol Gee, an author in Atlanta. She looks for sales that are at least 35% off the regular price. “That is when I pounce if I see something I have to have,” she says.

To have more confidence when buying shoes from home, here are the best tips:

Shipping – If you can score free shipping and a great shoe price, that’s the ultimate combination. But some stores will give you free shipping only when you hit a minimum purchasing requirement.

Make sure you know the shipping costs before spending too much time browsing the site.

Returns – Your life is busy and sometimes it’s tough to meet a 30-day return window if you don’t like the shoes you ordered. Look for a store that offers you at least 60 days to save yourself some stress.

Pricing deals – Comparing prices from different sites is easy when you’re shopping online. And there are tons of options for discount, clearance and coupon savings, especially if you sign up for the company’s email newsletter. Save even more by using a coupon app.

Search options –A deep discount isn’t any good if you can’t find the shoe you want. Being able to filter by price, style, brand, size, width, heel height, color and more will help you find your perfect shoe faster.

Images – Since you can’t physically hold the shoe in your hand, find a retailer that has large enough images to see the details. Having multiple pictures from different angles and a zoom-in option can help you decide if you like the shoe or not.

Don’t wait to try them on – When you get the shoes, try them on right away without removing any of the labels. Even though some stores offer generous return policies — Zappos gives you 365 days! — if you miss the window to return the shoes, you may not get a full refund.

Test them indoors – Before removing the labels or price tag, spend some time wearing your shoes inside. If you wear them outside, you risk damaging them, and that makes it impossible to return. Remember to walk around carefully, so you don’t accidentally remove the labels.

Sell older shoes once you’ve used them – You’ve bought a great shoe, worn it for a while, and then feel it’s time to get rid of it so you can make room for a newer style. You don’t have to throw the shoes away. Try selling your used shoes, either online or in person.

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