January 31, 2025
How to Wear Booties: The Do’s and Don’ts for Flawless Style
If you could only pack one pair of shoes, what would it be? For us, it’s booties. When you need a year-round staple that works for any season, booties are the obvious answer. They’re the shoes you grab without a second thought and still look perfectly styled. Plus, they look great with jeans, shorts, skirts, dresses and everything in between.
The thing about booties, though, is that how you style them can make or break the look. The right combination pulls your outfit together, making it feel chic and intentional. But the wrong one can leave the whole look feeling just a little bit off. So, if you’re in the market for a new pair or just looking for fresh ideas on how to style ankle boots you’ve owned for years, you’re in the right place. Not only does TOMS have booties that fit every mood and outfit, but we’re here to help you style them like a pro, too.
Here are 10 outfit ideas when you need some inspiration on how to wear short boots that give big style!
1. Black Ankle Boots with Distressed Jeans
When people ask us how to style black ankle boots, one of our top tips is to pair them with distressed jeans. This duo is a classic, versatile option that can take you from a sleek, clean-girl look to edgy, bold vibes. The contrast between black boots and the worn texture of distressed denim creates a balance that can be dressed up or down. Keep it casual and trendy with an oversized graphic tee or dress it up a notch with a fitted turtleneck or blazer. Don’t forget to cuff your jeans slightly if you want the boots to stand out, or let the denim hit just above the top of the boot if you’re looking for a more relaxed feel.
Styling tip: Add a belt with a bold buckle or layer on chunky rings and bracelets to give the outfit a little extra oomph.
2. Natural-Tone Booties with a Maxi Dress
For those months when it’s too cold to wear shorts or a skirt but too warm for heavy layers, neutral-toned booties and a maxi dress can be the perfect fit. Ankle booties in this color are great with maxis or long skirts because they anchor the flowy silhouette of the dress while complementing even the boldest of maxi skirt patterns. Pair your booties with a floral maxi and a denim jacket during the day, or, if the plan involves dinner or a night out, go for a fitted dress and add a leather jacket for contrast.
Styling tip: Choose a skirt with a slit to show just a hint of the boot and dimension and movement to the whole look.
3. Wedge Booties with Flared Jeans
When it comes to what jean styles to wear with ankle boots featuring a wedge heel, flared jeans are always a great choice. The wedge bootie combo works because the wider leg of the jeans complements the height and structure of wedge booties, which creates a look that feels balanced and lengthened. For a retro vibe, pair them with a tucked-in turtleneck or a cropped sweater. Or, for something more relaxed, go with a loose button-down or boho-style blouse. Prefer a different style of denim? Read our blog on how to wear ankle boots with jeans to find more style inspo!
Styling tip: Make sure the hem of your flared jeans hits just above or grazes the ground — too short, and it can cut off the lengthening effect of the wedges.
4. Suede Ankle Booties with Shorts and Blazer
Who doesn’t love the soft feel of suede? Not to mention, there’s just something about this texture that effortlessly elevates any outfit. If you’re not sure how to style short boots with this unique material, suede booties work well with almost everything. For professional-chic, you can’t go wrong with jumpsuits and skirts, but a tailored short and blazer situation with suede ankle boots strikes that perfect balance between structured and casual.
Styling tip: Choose ankle boots in a neutral suede to keep things versatile. Complete the look with a tucked-in tank or tee to maintain clean, flattering proportions.
5. Heeled Booties with a Slip Dress
This combo is the ultimate blend of ultra laid-back with a little bit of edge. Heeled booties give you a little lift while still keeping the dress from feeling too formal with a more casual vibe. If you’re going for a relaxed outfit, layer with an oversized cardigan or denim jacket. If you’re dressing up for an evening out, throw on a cropped leather jacket or a sleek coat.
Styling tip: Opt for block-heeled booties — they’re comfortable, stable and add just enough height to complement the flow of the dress.
6. Chelsea Boots with Cargo Pants
Chelsea boots aren’t limited to leggings and skinny jeans. There are several ways to wear boots with dresses as well. But if you’re looking to bring a little bit of attitude, one of our favorite looks is Chelseas and Cargos. It’s all about balancing the structure of the boots with something more relaxed (and who doesn’t love a few extra pockets?). Throw on a fitted top or cropped hoodie to keep it neat, or opt for an oversized jacket for a casual, street-inspired outfit.
Styling tip: Let the cargo pants sit just above the boots or give them a slight tuck — this keeps the silhouette clean and prevents bunching.
7. Metallic Booties with a Little Black Dress
The LBD is a staple in closets around the world — but why not kick it up a notch? Pairing metallic booties with a little black dress creates an effortlessly chic contrast that’s both modern and sophisticated. If you’ve ever wondered whether ankle boots can work with a timeless LBD, the answer is absolutely. A pair of silver or gold metallic booties add just the right amount of shine to elevate the classic dress, making it perfect for a night out, date night or special occasions like New Year’s Eve or Valentine’s Day.
Styling tip: Layer with a cropped leather jacket or a tailored blazer for a sleek, fashion-forward finish that adds just the right amount of edge.
8. Print Booties with a Matching Set
Want to add a little flair to your matching set? Bold print booties are the perfect way to bring personality and contrast to a coordinated look without overpowering it. Whether you choose bold animal print or lumberjack-chic plaid, patterned booties create a dynamic focal point while keeping the overall outfit sleek and polished. A monochrome set — whether it’s a blazer and shorts, a crop top and mini skirt or a tailored co-ord — provides the perfect backdrop for statement footwear.
Styling tip: Keep accessories minimal to let the boots stand out, and consider layering with a structured blazer or sleek leather jacket for an extra touch of sophistication.
9. Chunky Ankle Boots with a Shirt Dress
Ever wondered how to dress booties on the chunkier side? A combo that always works is lug boots paired with a shirt dress, whether that’s in denim, crisp white or a bold print. The unstructured, oversized shape of the shirt dress adds dimension to chunky boots, resulting in an outfit that feels trendy and cool but not too heavy. For daytime, go with soft fabrics like cotton or linen. For evenings, try a structured or belted option to elevate the look.
Styling tip: Cinch the dress at the waist with a belt to define your shape and create balance against the bulkier boots.
10. Western Booties With White Jeans
How do you wear booties with white jeans? Go country! White denim is a year-round staple, but pairing it with classic Western-inspired boots adds a stylish, slightly rugged edge. The contrast between crisp white jeans and the earthy, textured look of Western booties creates a chic, effortless vibe that works in any season. In fall, layer with a cozy knit sweater or an oversized flannel for a laid-back feel. Come spring, switch it up with a breezy blouse or a fitted tee for a fresh, polished look.
Styling tip: Try a slight cuff or cropped white jeans to let your Western booties shine. Opt for a belt in a matching tone to tie the whole look together.
The Do’s and Don’ts of Styling Booties
So now that you’ve got some ideas on what to wear with short ankle boots, let’s go over a few do’s and don’ts to help you pull off each look effortlessly:
Do’s
- Play with proportions to balance your look
- Let booties be the focal point of your outfit
- Experiment with layers like jackets, blazers or cardigans
- Pair bold booties with neutral or minimal clothing pieces
- Make sure your jeans, pants or skirts complement the boots
- Incorporate textures like leather, suede or denim for depth
Don’ts
- Over-accessorize and crowd the outfit
- Stick to one predictable style — mix it up
- Pair chunky or heavy booties with equally bulky clothing
- Ignore fit and length when styling pants or dresses
- Limit booties to fall or winter — wear them year-round
- Neglect proper care and maintenance for your booties
Wear TOMS. Wear Good.
When it comes to what to wear with short boots, the options are truly endless. Pair them with jeans, dresses, or shorts — they’ll fit perfectly into any closet.
At TOMS, we have a wide variety of boots and booties for every style. Plus, each purchase contributes to meaningful change, supporting people and communities around the globe. Learn more about our impact.
Shop our women’s shoe collection to find the perfect pair and step into something good.