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Shoes To Wear With Skinny Jeans In Cold Weather
Best Shoes to Buy Right Now
Have you ever heard someone talk about a “pants-to-shoe ratio?” While this expression specifically speaks to the way your pants hang against your ankle upon first glance, shoes play a huge part in scoring high here. They might be the single-handed, most important part of any first style impression. You can be dressed in a simple jeans and tee, but your footwear will absolutely make or break any outfit.
Now that we’ve put a ton of pressure on you to choose the right shoes (sorry), we’re also here to relieve it! While it’s cool to have an extensive sneaker closet, we recommend starting with modern closet essentials that can mix and be matched with any wardrobe. Each pair on this list is worthy of becoming your go-to kicks for the occasion. We are giving you multiple options for each category so you can choose one tailored to your taste and budget. With these 11 shoes in your closet arsenal, you’ll be ready to take on the world! Even in 2020.
We’re kicking off the list with a category many men are pretty skeptical of. As we like to call it, “the mandal,” these shoes are undoubtedly an essential item during the summer months because who wants to be sweaty in socks in 95-degree weather, am I right?! Take note, as many internet forums suggest, we are not including the flip flop in this category. Feel free to wear the thong slipper as you please, but why choose flip flops when you can dress in more stylish and supportive sandals below?
Read more: The Best Sandals for Men
Birkenstock Arizona Birko-Flor
Once known to be the stereotypical footwear of choice for granola-eating, tree-hugging hippies (hey, we’re here for it!), this sandal has now evolved to become a closet essential for the most fashion-forward of men. We’re happy to live in the middle and advocate for the Arizona Birkenstocks as a stylish upgrade to the pool-slide, offering a better-for-you arched footbed and a more durable lifespan. Note, they might feel a bit off at first, but the more you wear them, the more accustomed they become to your own two feet.
Apl Men’s Big Logo TechLoom Slide
One of the easiest sandals to slip on, these Apl slides are perfect for the pool, beach, and beyond. The best part isn’t how lightweight and packable they are, but the fact that they’re made with a flexible strap and molded footbed with every step. They mirror the comfort of the infamous Apl running shoe but are a much breezier option.
Chaco Men’s Banded Z Cloud
These sandals are sturdy and supportive enough for any summer activity. From hiking to biking and even walking around a city, once you break in a pair of Chacos, you’ll understand why they have a cult following.
Adidas Stan Smith Slip-on Shoes
While this isn’t technically a sandal, but we had to include it as an alternative for anyone uncomfortable with exposing their toes. Mules were a huge trend this summer and this version of the Stan Smith are a great sockless option for the dog days when all you want to do is kick off your kicks (ha) with ease.
Low Top Sneakers to Dress Up
Casual wear is becoming more popular these days. And pairing sneakers with a suit is a modern essential style trick for that effortlessly cool, yet elevated fashion mood. From date-night dinners to casual Fridays in the office, having a crisp and clean sneaker is a major priority on this list (keywords: Crisp and clean).
Read more: The Best Sneakers for Men
Veja Esplar Shoes
Veja makes the perfect white sneaker, subtly showing its logo. Feel proud to rock the “V” because this positive impact brand is completely transparent on what goes on in the shoe industry. By shining a spotlight on this, the brand is encouraging the use of sustainable materials, ethical factories, and fairer wages. Veja means “look” in Portuguese, as the brand aims for their consumer to look beyond just footwear.
Greats Royale Sneakers
A minimalist favorite, these versatile sneakers are made with ultra-soft cowhide leather. The more you wear, the better they get. You can literally wear these with anything in your closet and get away with it. Just remember to wear no-show socks!
Koio Men’s Metro Taupe Sneakers
For the non-minimalist, these tonal, low-top sneakers ooze swagger. The athletic silhouette makes them a bit more casual than the rest in this category, but they are still sleek enough to dress them up for an evening out.
Mobs Design Tread Low
For the guy who’s afraid to wear all-white sneakers but is still seeking a dress-up comfort option, opt for the same vibe but in a color. Mobs Design makes sneakers that naturally become your go-to because of their comfort and breathability while keeping that cool guy aesthetic. If you’re not into the cognac, don’t worry, they carry a wide array of colors.
The Dress Down Sneaker
For the days you’re afraid you might scuff up your “dress-up sneaker,” you’ll need a pair you are more comfortable to get down and dirty with. A dress-down shoe should be hip, yet comfortable enough to skate and walk around in. Take a look at some of the best Black Friday sneaker deals going on right now for potential savings on these types of shoes.
Vans Old Skool
Your pants-to-shoe ratio will always be acceptable when rocking the Old Skool skater shoe from Vans. Pro-tip: You don’t actually have to be a skater to wear these. The Vans lifestyle encompasses a laid-back and casual California attitude.
Converse Chuck Taylors
Contrary to popular belief (and the rules mentioned above), white Chuck Taylors look cooler when they are worn and a bit dirty. It’s a grungy, 90s moment that has turned into a fashionably relevant icon. The OG skate shoe even sells a “dirty wash” version of these at a higher price among their custom selection, but we recommend getting there on your own, but we understand if you prefer keeping them clean. For Converse alternatives, check out our guide.
Nike Killshot 2
Nike’s Killshot 2 sneakers mixes leather and suede for a play on texture and sheen. They are inspired by the brand’s original tennis shoe, with the classic Nike logo and typeface on the back as an ode to sporty nostalgia.
The Athletic Sneaker
Men’s shoes in general are an oversaturated market. And even when you narrow it down to the athletic category, the options still feel overwhelming. When you want to get super technical, you’ll have to narrow in on the sport of choice to steer your shopping roadmap. But in the meantime, we’re sharing three of our favorite athletic sneakers, below.
Read more: The Best Athletic Sneakers for Men
Hoka One One Men’s Arahi 4
These road-running sneakers are a bestseller for a reason. Users describe them as “running on a cloud.” While they’re made for mileage seekers, they’re equally as great for running errands around town. You won’t find a softer cushion than these from Hoka One One.
York Athletics MFG The Frank Half & Half
Between the leather and the mesh, these sneakers are the perfect marriage between an athletic and a lifestyle sneaker. They are made to work out in, but look great just hanging out in. This small brand out of Boston is onto something. Consider yourself warned, these sneakers will attract compliments from strangers.
AllBirds Tree Dashers
The latest release from AllBirds is the Tree Dasher style, which is partially made from eucalyptus pulp to ensure a cooling effect with each wear. Made to run, sprint, walk, and hop, the Dasher is super technical, sustainably made, and beautifully designed.
K-Swiss Bigshot Light Tennis Shoe
This reliable pair of tennis shoes does its job on the court and is comfy and durable enough to wear during your daily errands, or your off-trail excursions. (Check out our favorite handmade sneakers here).
Loafers give off a calm, cool, and collected, understated elegance. Many guys are intimidated by the tassels or the shine of a loafer, but you shouldn’t be! The second you put on a pair of great loafers, you will feel (and look) like a million bucks. If you’re not quite ready to channel Lord Disick and take the leap to the to tassels, there are plenty of other options where you can achieve the same style mood in a more subtle way.
Read more: The Best Loafers for Men
Sebago Dan Polaris Black/Blue
With a shiny smooth black leather and moccasin-style stitching, these loafers scream excellence while the pop of color scream fun. The timeless shape and detailed design gives you that luxe look without breaking the bank.
M.Gemi The Filare Loafers
The classic penny loafer got an upgrade with this (literally) modern twist. The twisted band where you would normally find a buckle or tassels is subtle and sleek. It’s an all-in-the-details type shoe, unique enough to make you one All M.Gemi shoes are handmade in Campania, Italy and you can smell and feel the quality with each wear.
Astorflex Patnoflex Loafers
Astorflex shows us that loafers don’t have to be as fancy as we thought. If you were intimidated by the above two pairs, opt for a more casual pair, the perfect match with jeans and button-down.
The Work Boot
Originally made for war and factory workers, the work boot has evolved into higher fashion, but it never lost its function. The options below live up to their name, offering steel shanks, carbon fiber toes, and durability to last. After all, that is the point of any investment, right? Whether you work in the field, or not, every guy should own a great pair of utilitarian work boots.
Read more: The Best Work Boots for Men
Red Wing Heritage Classic Moc
Adopted by fashion retailers like Madewell, Red Wing carries a great heritage. This style in particular dates back to 1952 and since then it’s grown into one of the most popular boot styles in the country. The fit becomes increasingly personalized over time, so expect it to be a bit snug at first with slight breathing room that will eventually relax.
Danner Bull Run Moc Toe
With a steel toe, and snug fit, you can do just about anything in these boots. Born and bred in the USA, Danner promises all-day comfort and long-lasting durability. All of their shoes go through a rigorous testing process. Plus, they are stylish enough to wear in the field and beyond.
The iconic 1460 Leather Lace Up Boots carry great history. Originally made for a more comfortable boot during World War Two and then made famous for factory workers in the 1960s, this shoe has evolved to be a fashion week staple today. Over six decades old, the original Dr Martens boot remains an ever-popular marriage of fashion and function.
The Dress Shoe
Wedding season will return someday, and it’s important that you’re prepared for the influx of post-COVID celebrations when that day comes. From oxfords to brogues and Derbys to monk straps, dress shoes come in many shapes and styles. When you’re building a closet of basic essentials, we recommend staying close to home. Once you build the foundation of your closet with these classics, you then can venture out into more.
Read more: The Best Dress Shoes for Men
Nisolo Travel Derby
The best part of these ethically made shoes from Nisolo isn’t the fact that they are collapsible and less than one pound per half pair. It’s the fact that they have a “zero-break in” soft leather upper. Yes, you read that right. These spring/summer dress shoes have a cushioned insole, bringing you maximum comfort at first wear.
Jack Erwin Clarkson
If you only can afford one dress shoe, go for an all-black cap-toe oxford. You can’t go wrong in this timeless classic. It will go with almost any suit and even a tuxedo.
Cole Haan Original Grand Short Wingtip Oxfords
Every guy should own a pair of Wingtip Oxfords. In this category, we suggest staying between black and brown leather. Cole Haan should be your go-to for affordable, yet high-quality dressy footwear.
The Chelsea Boot
Chelsea boots are the perfect city boot, especially transitioning into fall. They are elevated and streamlined but give off that bad boy, downtown attitude for major sex appeal.
Read more: The Best Chelsea Boots for Men
Thursday Boots Cavalier Boots
Don’t be afraid of the lighter suede. These are made with a “WeatherSafe” suede upper that will actually get better and look ruggedly seasoned with age. Thursday Boots are known for high quality and style, without looking too stuffy.
R.M. Williams Classic RM Leather Chelsea Boots
As the brand’s most timeless design, these deep brown leather boots are any city dweller’s dream. The deep brown goes with just about anything and the soft leather will keep your comfort levels high.
The Frye Company Paul Chelsea Boots
There is nothing like the quality and comfort of a pair of Frye boots. They use the softest leather, built to last. These boots will take you from the workday to the weekend without question.
The Driving Shoe
Ah, a classic Italian staple: the driving shoe. With the rise of automobile ‘driving culture’ in the 1960s, this moccasin/dress shoe hybrid derived from the demand for a comfortable option to wear on the road. It became a status symbol of the rich, for those who had a nice car to drive, who also had exclusive shoes to wear while driving it.
Driving shoes are typically made of soft Italian leather with rubber nubs or pads covering the soles. This construction allows for durability and comfort with a distinctive traction for stability while driving. Nowadays, sure they can be worn for driving but they also serve as a great slip-on shoe for around the house and casual outings. The driver has become a staple of well-dressed men for decades.
Read more: The Best Driving Shoes for Men
Wolf and Shepherd Gunner Driver
These sleek gratin leather slip-ons are made with memory foam and extra cushioning, so they literally feel like slippers. They come in seven different colors.
To Boot New York Palo Alto Driving Shoes
Trust us when we say, if you’re going to get a driving shoe, you’ve got to go for Italian-made leather … because, well, history! These driving shoes will make you want to buy a vintage Italian car and drive along the coast.
Aurelien Light Blue Suede Driving Shoes
Made for leisure and luxury, these Ultramarine driving shoes are thoughtfully designed for comfort every step of the way. They are the perfect Mediterranean vacation shoe.
If you’re going for a quick daytime hike, you might think sneakers will suffice. But why dirty your great trainers and when you can grab a pair, made specifically for the lakes, valleys, and mountains? If you’re hiking a rigorous mountain, you’ll definitely need something more technical, but the sporty hiking sneakers below offer non-slip treads and great support, so even if you’re not a seasoned hiker, you can at least look the part.
Adidas Outdoors Terrex Free Hiker Blue Men’s Hiking Boot
The rubber, suede, knit mixed media material makes these hiking shoes modern and sporty enough to wear around town. Even though it’s a major fashion trend this season, the knit built-in-sock serves the purpose of sealing away dirt and gravel.
Merrell Altalight Shoes
The Altalight shoes are the lightest pack hiker Merrell has ever built. They promise to keep your feet on the trail, even when it’s wet. They are complete with the same high-tech features from some of their other famous hiking boots with a cult following, but they aren’t as intense-looking.
Teva Gateway Low
The Gateway Low is best for day hikes. These shoes are made with 55% recycled polyester and leather sourced from sustainably-minded tanneries. The Teva brand is more a lifestyle, that inspires outdoor adventures and is on a mission to protect the Earth. These treads will repel water and feel cool and comfortable – a pretty technical hiking shoe with a sneaker-like vibe.
Danner Mountain 600 Hiking Boots
Leave it to Danner to take hiking to the next level with these comfortable boots that feature Vibram technology and construction that has more in common with your favorite sneakers than with clunky hiking boots of days gone by.
Where to Buy Discounted Shoes
To make buying discount shoes online easy and stress-free, here are the best places to look.
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 Amazon.com
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
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, Overstock.com 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, 6pm.com 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 6pm.com 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, Shoes.com 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
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 Onlineshoes.com. 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 6pm.com, 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
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.https://64f9cdf444b59d0a64d1a26509b2a0d0.safeframe.googlesyndication.com/safeframe/1-0-37/html/container.html
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.
Buying shoes online is a quick and easy way to save big. Amazon is probably the go-to choice because it has a huge variety of items for sale, but the best overall for online shoe shopping I have experienced is Zappos.
With Zappos, you get free shipping on a fantastic selection of discount shoes, with lots of images and information about the shoes. Plus, the return shipping is free and you have 365 days to return your shoes if you decide they’re not a good fit.
Really, you can’t go wrong shopping at any of these stores. They all offer super discounts and have brand names and styles that fit every budget.