HOW TO WEAR BOOTS – THE MANY OUTFITS

2In preparation for fall and the gorgeous, cozy fall outfits, I wanted to share with you 20 stylish ways to wear boots. (Fall, the best time of the year!) The outfit possibilities with boots are endless. This should give you style inspiration for the fall season so here is a collection of my favorite boot outfits that I’ve worn on the blog.

Boots are my preferred footwear during the fall. With the so many options available: over the knee, flat, heel, wedge, pointed toe, ankle, etc. there is a boot to go with every outfit style. There are boots for casual outfits, dressing up and work professionally.

Depending on your style and your personal preference a classic black or brown riding boot might just be the only boot you need this fall. But if you’re a boot enthusiast, like I am, then you’ll want to wear flat embellished ankle boots, heeled ankle boots in black and brown, of course some furry boots for the snow and so on.

In the fall boot outfits below you’ll see a variety of outfits with a variety of boots. You’ll also find a list with an outfit explanation and a link to more photos.

I turn to Sole Society when I need a new pair of boots or booties! I highly suggest you check them out if you’re looking for a pair of cute and affordable boots!

Wearing neutrals and cozy knits with brown ankle boots
One of the most popular outfits on my blog features a pair of gorgeous and perfect brown ankle boots from Sole Society. I wore an oversized turtleneck, matching blazer, belt and distressed jeans. Overall this outfit is very cozy and can be worn on a casual date or walk along the park.

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Tips and Tricks That Will Change Your Life

101. Despite what it says on the tag, cashmere is best washed by hand. To dry it, use a salad spinner, which releases excess water in seconds.
100. Use white wine to remove red wine stains.
99. Wash new jeans twice before taking them to the tailor. Why? Because jeans will always shrink in length when washed.
98. To stop angora or mohair from shedding, fold the garment and place it into a zip-top bag and freeze it for at least three hours.
97. Remove odors from vintage or thrift clothing by spritzing them with a mixture of one part vodka, two parts water.
96. “Remove white deodorant marks from a garment by gently rubbing the protective foam used on hangers against the fabric.” — Jonathan Simkhai, designer
95. If you get an oil stain on your favorite handbag, coat the mark with baby powder and let it stand overnight. By morning, the stain should be gone. If a bit still remains, repeat the process until the stain is completely gone.
94. The best at-home method to keep diamonds sparkling: liquid dishwasher detergent and an old toothbrush.
93. The secret to well-fitting everyday clothes is Lycra. The formulas to look for: 95% cotton/5% Lycra spandex for T-shirts, and at least 2% Lycra for jeans to hold their shape.
92. “Always organize your clothes going light to dark from left to right in your closet. Your eye will follow the color and thus help you stay organized.” — Melanie Charlton Fascitelli, Founder, Clos-ette and Clos-ette Too.
90. Wondering about the quality of your cashmere? Gently stretch the body of the garment to see if it snaps back. A lower-quality cashmere won’t.
fashion tips
J. Crew
89. “If you don’t have time to try on jeans in the store, try the Neck Method: You can determine your size by placing the waistline of the jeans around the diameter of your neck. If the waistline of the pant comfortably meets at back of your neck, then the jeans will fit.”— Sarah Ahmed, Creative Director, DL1961 Premium Denim
88. Cut down your closet by 25% by asking yourself this one question: “If I were shopping right this second, would I buy this?” If the answer’s no, out it goes. — Melanie Charlton Fascitelli, Founder, Clos-ette and Clos-ette Too.
87. “Never put your swimwear in the washing machine, and always hand dry. The machine will damage the suit and it will lose its elasticity. The only exception: At the end of the summer or vacation, wash your swimwear in lingerie washing bags on the gentle cycle with a bit if Drift or Woolite. But only after many wears.” —Shoshanna Gruss, Designer
186. To drop bloat five days before a big event, stay away from dairy and whole grains, which can do a number on the digestive system.
85. A useful style tip: While fake designer bags are a huge don’t, fake diamond studs are a huge do. Faux stones are hard to spot to the untrained eye.
84. Dressy occasions aren’t the time to play with trends, so know your silhouette and stick to it to always look your best. Perfect example: Sofia Vergara knows she looks good in mermaid dresses, and always chooses variations of the shape on red carpets.
83. “Never put a garment on immediately after ironing, as this can actually cause new wrinkles to form. Instead, let it sit for five minutes to set the press.” — Althea Harper, Designer and Rowenta Brand Ambassador
82. The best way to de-fuzz a sweater: use a pumice stone.

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The Hiking Boot

6Hiking boots vary widely in appearance, but the key to sniffing out this shoe is a relatively rigid structure that provides support for the ankle without restricting movement. The first hiking boots were likely birthed in the 1870s in response to the emergence of mountain climbing as a sport in Europe, but it took over a century for the shoe to evolve into the all-purpose outdoor recreation hiking boot we recognize today. You’ll likely find a beat-up breed on the feet of the tree-hugging, granola-chomping set.

How to wear them: Fortunately, there are now more refined kinds that retain the function and feel of the original without the need for a fleece and a flashlight. Our take is best worn with rolled corduroys (a single cuff will do) and a shawl collar cardigan or fitted Fair Isle sweater.

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How to Wear Ankle Boots with Jeans

10If we had to pick one outfit to wear every day for the rest of life, it would most likely be ankle boots with skinny jeans.
MORE: A 7-Day Diet to Burn Belly Fat That REALLY Works
Our love for these wardrobes staples is unwavering. It’s the ultimate pull-on-and go winter outfit that will never let you down, whether you’re heading to the office, running errands, or keeping it casual for dinner.
What to wear with boots, however, can get a little tricky. Here we’ve rounded up some handy tips to make sure you know exactly how to wear boots with jeans.
1. Roll the cuff of your jeans just above your boots to show them off.
If you tend to reach for your skinny jeans every time you’re in the mood to wear ankle boots, it’s time to change things up. Cuffing denim above the ankle (rather than trying to tuck jeans into your boots) allows you to wear straight leg or boyfriend jeans, too. Just think of all the possibilities! This pairing works best when you’re working with a pair of high-heeled booties—added height offsets the tomboyish look of baggy cut jeans.
To cuff your jeans, simply fold the hem of your jeans about two-inches, and then fold a second time to get the desired length. A little tip: it’s often easier to cuff your jeans before putting them on, and then just adjust afterwards as needed.
How to Wear Ankle Boots with Jeans: Our Top 5 Tips For Nailing This Pairing
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How to wear jeans and boots.
Photo: Tuula Vintage

If we had to pick one outfit to wear every day for the rest of life, it would most likely be ankle boots with skinny jeans.

MORE: A 7-Day Diet to Burn Belly Fat That REALLY Works
Our love for these wardrobes staples is unwavering. It’s the ultimate pull-on-and go winter outfit that will never let you down, whether you’re heading to the office, running errands, or keeping it casual for dinner.

What to wear with boots, however, can get a little tricky. Here we’ve rounded up some handy tips to make sure you know exactly how to wear boots with jeans.

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How to wear jeans and boots.
Photo: Imaxtree

1. Roll the cuff of your jeans just above your boots to show them off.
If you tend to reach for your skinny jeans every time you’re in the mood to wear ankle boots, it’s time to change things up. Cuffing denim above the ankle (rather than trying to tuck jeans into your boots) allows you to wear straight leg or boyfriend jeans, too. Just think of all the possibilities! This pairing works best when you’re working with a pair of high-heeled booties—added height offsets the tomboyish look of baggy cut jeans.

To cuff your jeans, simply fold the hem of your jeans about two-inches, and then fold a second time to get the desired length. A little tip: it’s often easier to cuff your jeans before putting them on, and then just adjust afterwards as needed.

2. Fold the hem of skinny jeans inward.
If your jeans are too long to really show off your boots in the best light, fold the hem inwards and tuck them in, so that the fold is invisible. This works best on skinny cuts and will look like you’ve had your jeans tailored to the perfect length, rather than cuffed. Do this before you actually pull the jeans on, and iron the cuff to make sure the crease stays sharp and flat all day.

3. Rip your hem.
Pull out a pair of scissors and snip your skinny denim to crop them at the perfect length to show off your ankle boots. We recommend that you use a tape measure and pencil to mark exactly where you would like to cut, and then use a sharp pair of fabric scissors to cut along the outline. Leave them un-hemmed for an intentionally distressed finish. Try this trick to give your tired skinny, boyfriend, or straight jeans a fresh attitude.

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The Winter Boot (aka Cold-Weather Boots)

9This is perhaps the broadest boot group of boots, with styles from military-issue Kevlar lace-ups to suede and shearling-lined slip-ons. What they have in common? They all fit the foot snugly to help retain heat. Born from the simple need for survival, waterproof winter boots made of deer skin and tree bark with bearskin soles are at least 53 centuries old. And while structure and style have thankfully changed, the basic premise of protection against winter’s woes remains the same. No one north of Florida should be without a sturdy pair past December.
How to wear them: We’re currently occupied with technical takes that combine leather uppers with reinforced rubber on the toe. Trust us — they’re nothing short of genius for when snow turns to slush. The combination of materials also allows you to comfortably keep them on throughout the day with jeans, a thermal Henley and fitted puffer coat.

You don’t need to be braving the elements or hoofing around on horseback to buy into men’s boots. Turns out, even if you’re on desk duty, there’s still a way to slip ’em on with style.

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The Cowboy Boot (aka Western Boots)

5They’re exactly as you imagine: A tall boot shaft at least above the middle of the calf, no laces and a heel of about two inches (known by footwear aficionados as a Cuban heel). Although similar riding boots have been part of an equestrian lifestyle for centuries, it wasn’t until the 1860s that decorative hallmarks like an angled heel and top stitching came into existence. They’re still the shoe standard with the cowboy contingent west of the Mississippi, but you don’t have to lasso livestock to own a pair.

How to wear them: For city folk, we suggest a more modern take in broken-in brown or tan with a rubber sole. And unless you can actually wrangle something, couple your cowboy kicks with jeans (preferably a dark and slim boot cut), an Oxford shirt and a tweed sportcoat.

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The Chukka Boot (aka Turf Boots or Bucks)

4Like the Chelsea, the chukka is also known for hovering in the ankle area. But the similarities end there. This boot comes with two to three eyelets of lacing and is often outfitted in suede. In the 1940s, chukkas popped up as part of a trend toward casual dressing, and by 1950, the British brand Clarks had invented its iconic desert boots (essentially a chukka with a crepe rubber sole), solidifying the style’s spot in shoe history.

How to wear them: A recent resurgence in popularity has everyone from college kids to soccer dads sporting chukkas. And for good reason: It only takes a solid Oxford shirt and straight-leg jeans with a single cuff that gently covers the boot without breaking (so the pants fall straight over the shoe in a clean line) to do these shoes justice.

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The Military Boot (aka Combat Boots)

8As you might expect, boots made for the military are designed with one goal in mind: to shield you from an unfriendly environment. As a result, combat boots run the gamut from ankle-high to under-the-knee, and are typically made from technical materials like waterproof leather, Gore-Tex and rubber. The first boots for battle were worn by the Assyrian army as early as 1000 BC. Fast forward a few thousand years, and you’ll find them on the feet of everyone from generals to teenage gothic and grunge types.
How to wear them: Swapping traditional black boots for red ones and donning dark denim (complete with a couple of cuffs or tucked directly into the boot), a vintage tee and a tailored peacoat should keep you clear of counterculture territory.

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The Motorcycle Boot (aka Engineer Boots)

7The height ranges from above the ankle to below the knee, but all motorcycle boots boast a low heel in order to aid in putting the pedal to the metal, as well as heavy-duty leather for protection against an unplanned meeting with the pavement. Engineer boots are the archetypal old-school biking boot (as opposed to the tricked-out racing or motocross kinds) and are speculated to have surfaced during the Depression era when the Chippewa Shoe Company developed a boot based on those used for equestrian sports in England. Hell’s Angels and attorneys who attempt to ride their midlife-crisis Harleys are huge fans.
How to wear them: These days, you can flaunt a pair with all the elements of a true engineer boot without coming off like a costume. Toss them on in your downtime with a pair of black jeans, a relaxed-fit pocket tee and, of course, a leather jacket.

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The Chelsea Boot (aka Dealer Boots)

3Characterized by ankle-high height, a close fit and, most notably, no laces. Instead, the Chelsea boot employs an elastic panel known as goring, which allows the shoe to stretch when taking it on or off. Although Chelsea boots rose to fame in the ’60s mod scene (the Beatles booted up in a similar eponymous style), the shoe first came into being over a century earlier during the Victorian era as a riding boot praised for its convenience.

How to wear them: Today, more refined varieties with dress shoe soles are making a comeback at the edgier end of Wall Street. We think it’s proof positive that suits and boots can live in perfect harmony — provided, of course, that the cut complements the Chelsea’s slim, sleek lines. Your shirt collar, tie and, yes, even your briefcase should have an equally trim proportion to the slimness of the boot. We recommend pairing your navy suit with brown Chelsea boots, like the one pictured here.

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