It’s a common misconception that, barring a visit to a country bar or a horseback riding trip, cowboy boots are an unforgivable fashion faux-pas. Most fashion lovers who want to keep up with ever-changing current trends steer clear of cowboy boots to avoid looking old-fashioned or reminiscent of the starring actress in an old Western film.
However, the stigma against wearing cowboy boots has begun to shift during the past few seasons. Prominent celebrities like Reese Witherspoon and Miley Cyrus have been spotted rocking Western footwear as a part of their everyday look. Contrary to popular belief, it actually is possible to create a cute, trendy look that includes cowboy boots. In fact, cowboy boots have the potential to add an interesting focal point and whimsical finish to a wide range of looks.
Use the Cowboy Boots outfit ideas in this post to learn how to incorporate cowboy boots into your outfits without looking dated or cliché.
1. With a Sundress
A sundress and cowboy boots is a classic pairing. It’s easy, balanced, and a feminine sundress effortlessly counteracts the rougher vibe of cowboy boots. However, be careful with this combination. Wearing the wrong sundress with your cowboy boots can turn your look from cute and trendy to prim and dated.
Avoid wearing floral-printed sundresses with cowboy boots. This pattern pairing is overdone and tends to make your outfit look old-fashioned and off-trend if you’re not strolling through a field with a guitar slung over your shoulder. Instead, stick with simple dresses with one solid color or a basic pattern. If your dress isn’t fitted by design, cinch a belt around your waist to emphasize your figure and add a modern finish to your look.
2. At a Festival
Cowboy boots as music festival attire was pioneered by Vanessa Hudgens, the Coachella queen herself. Known for her extravagant and effortlessly stylish festival looks, Vanessa wore cowboy boots to a recent Coachella festival and has also been spotted wearing similar Western-style boots while out on an average day in LA. Since Vanessa paved the way, other style-conscious celebrities–model Kendall Jenner included–have opted to rock cowboy boots at music festivals.
You can pair cowboy boots with just about any festival outfit. Wear them with denim shorts, gypsy shorts, rompers, sundresses, etc. A modern, artsy festival outfit with classic country-style cowboy boots is an unexpected pairing that gives your look a unique, whimsical finish.
3. With Denim Cutoffs
Like a sundress, denim cutoffs paired with cowboy boots is a classic look that is complementary but also has the potential to come off as cliché.
Avoid looking like you’re channeling your inner Daisy Duke by creating a look that is undeniably modern. Pair high-waisted denim shorts with a crop top to stay in line with current trends. Add a longer cardigan to balance out your look. Or, pair frayed or flare cutoff jeans with your cowboy boots to put a trendy twist on the tried and true shorts and boots combo.
4. Over Distressed Jeans
It can be risky to pair cowboy boots with full-length jeans if your destination for the day does not include a horse ranch. It’s impossible for an outfit to look trendy if it also makes you look like an aspiring cowgirl.
However, that doesn’t mean that you can’t wear jeans with your cowboy boots. In fact, denim and cowboy boots complement each other very well. An effective way to pair cowboy boots and jeans together without looking dated is to wear distressed jeans. Destroyed jeans are inherently a modern trend that automatically modernize any piece, including cowboy boots.
5. With Detailing
When you picture cowboy boots, the first images that come to mind are likely pairs of boots in varying shades of brown and black. However, cowboy boots are available in countless different colors, patterns, and styles. Wearing these untraditional boot styles helps modernize your outfit and erase the old-fashioned connotation of cowboy boots.
Try pairing colorful cowboy boots with a basic, neutral outfit. Use them as the eye-catching focal piece of what would otherwise be a dull look. If you want to be able to match your boots with more pieces you already have in your closet, stick with a neutral color. Instead, find black or brown boots embellished with embroidery or other detailing that adds interest and style to the boots.
6. Under a Maxi Dress
Cowboy boots complement dresses of any length, from short sundresses to full-length maxi dresses. Wearing cowboy boots with a maxi dress creates a look that is simultaneously casual, carefree, and stylish.
Avoid pairing cowboy boots with a long dress that extends all the way down to the floor. At least a few inches of your boots should show underneath your dress. Go with heeled boots instead of flats if your dress hits the ground. High-low dresses that show off your boots in the front are also a trendy choice. You can also wear a maxi skirt with your boots. Pair your skirt with a fitted crop top or tied T-shirt to maintain balance in your look. Any long dress or skirt that you pair with cowboy boots should have a simple pattern and a loose fit to create a streamlined finish for your look.
7. With Something Simple
When you wear cowboy boots, they should be the clear focal point of your look. Pieces with bright colors and busy patterns have no place in a look that also includes cowboy boots.
Stick with neutral colors and simple patterns instead. Cowboy boots clash with most complex patterns. Take extra care to avoid classic patterns like flannel that not only clash with cowboy boots but make your outfit look more old-fashioned. Keep accessories to a minimum and make sure that your cowboy boots are the most eye-catching piece in your look.
Cowboy boots aren’t something to fear. Wearing your own pair of cowboy boots is definitely a fashion risk, but it’s a risk that’s worth taking if you want to shake up your style in an unexpected way.
