Casual Holiday Party Outfit for Petites: Stewart Tartan and Denim Done Right

Not every holiday party calls for a cocktail dress and heels. Some of the best celebrations are the casual ones—the gatherings where you can actually relax, enjoy good conversation, and not worry about whether your outfit is too formal or uncomfortable. But here’s the thing: casual doesn’t have to mean boring or unfestive.

Today I’m sharing my favorite casual holiday party outfit that perfectly balances festive style with comfort and wearability. It’s built around a Stewart tartan jacket—one of the most recognized tartan patterns for holiday dressing—paired with vintage flare jeans that are having a major moment right now, and topped off with a black cashmere base layer that serves as the perfect neutral foundation.

This is the kind of outfit that works for casual office parties, friends’ gatherings, family get-togethers, or any celebration where the dress code is “come as you are, but make it festive.” And because it’s designed with petite proportions in mind, every element works together to create a flattering, lengthening silhouette.

✨What You’ll Find in This Post:

In this post, I’m breaking down my casual holiday party outfit:

• 🎄 The Stewart tartan jacket that makes a statement
• 👖 Why vintage flare jeans work for petites (and how to style them)
• 🖤 The black cashmere layer that ties everything together
• 👢 The boots that create the perfect leg line
• 👜 A mini crossbody that’s practical and polished
• 📏 Proportion tips for wearing this look when you’re under 5’4″
• ❓ Your questions about casual holiday dressing answered

1. The Jacket: Stewart Tartan That Makes a Statement

Let’s start with the star of this outfit—the J.Crew Bridgette Lady Jacket in Stewart Tartan. This jacket is everything a casual holiday piece should be: festive, comfortable, and instantly elevating.

Stewart tartan is iconic. The classic red, green, white, and black plaid pattern is instantly recognizable and unmistakably festive. It’s one of those patterns that says “holiday season” without being costume-y or over-the-top.

The Bridgette style is particularly flattering for petites. It’s a lady jacket, which means it has a slightly shorter, more cropped silhouette that hits right at the hip. This length is ideal for petites because it doesn’t overwhelm your frame or cut you off at an awkward spot. It creates definition at your natural waist while still providing coverage and structure. I am wearing a regular size 0, and it fits true to size.

The Bridgette Lady Jacket in Stewart Tartan is lined, and the fabric has a wonderful texture—it’s substantial enough to feel like a real jacket (not flimsy or cheap), but it’s not stiff or uncomfortable. You can move, sit, eat, and enjoy yourself without feeling restricted.

✨ Kelly’s Petite Style Tip: When wearing a statement jacket like tartan or plaid, keep everything else simple and neutral. The jacket should be the focal point, with your base layers and accessories supporting rather than competing with it.

2. The Denim: Vintage Flare Jeans for Petites

Here’s something that might surprise you: vintage flare jeans are incredibly flattering for petites when styled correctly. The key is all about proportion and how you wear them.

These vintage flare jeans create a retro-inspired silhouette that’s trending heavily right now for 2024-2025. Unlike the super-wide flares of the 1970s, these have a more moderate flare that starts at the knee and widens gently toward the hem. This creates a balanced, elongating line rather than overwhelming your frame.

My original Patch Pocket Vintage Flare Jeans are sold out, but J.Crew’s New Vintage Flare Jean is the perfect current alternative with the same flattering fit.

The high-waisted design is crucial for petites. When you tuck your top (or in this case, layer a cropped jacket over a tucked base layer), you’re creating a clear waistline that makes your legs look as long as possible. High-waisted jeans are one of the most flattering styles for shorter frames because they eliminate the torso-shortening effect of low-rise styles. I am wearing Petite Size 25, and the fit is true to size.

The patch pockets add visual interest without bulk. They’re functional but also decorative, giving the jeans a vintage, authentic feel that works perfectly with the heritage look of Stewart tartan. The medium-wash denim is versatile and casual. It’s dark enough to feel polished but light enough to read as relaxed and approachable—exactly what you want for a casual holiday party.

✨ Kelly’s Petite Style Tip: The most important thing when wearing flare jeans as a petite is the hem length. The jeans should just graze the top of your shoes—not drag on the ground, not hit mid-calf. This precise length, combined with heeled boots underneath, creates the longest possible leg line.

3. Keeping It Cozy: The Black Cashmere Base Layer

Underneath the tartan jacket, I’m wearing a simple black cashmere crewneck sweater. This might seem like an afterthought, but it’s actually a critical component of making this outfit work.

Black cashmere serves as the perfect neutral base layer for showcasing festive outerwear. It provides warmth without bulk, creates a clean visual line, and allows the Stewart tartan to be the star of the show. If I had chosen a patterned or brightly colored sweater underneath, the whole outfit would feel busy and overwhelming.

The crewneck style works beautifully with the jacket’s neckline. It provides coverage without competing for attention, and it creates a clean, finished look.

Cashmere is worth the investment for pieces you’ll wear repeatedly throughout the season. A quality black cashmere sweater will last for years with proper care, and it works with virtually everything in your closet. It’s one of those foundational pieces that makes getting dressed easier because it goes with everything.

The fitted silhouette is important when layering under a jacket. You don’t want extra fabric bunching up under the jacket’s arms or around your waist. A fitted base layer creates smooth, clean lines that are especially important for petites.

✨ Kelly’s Petite Style Tip: When layering pieces for petites, always start with your slimmest, most fitted layer on the bottom and build outward. This prevents bulk and maintains your natural proportions. Think fitted base layer, structured jacket, and streamlined accessories.

4. The Boots That Ground the Look

The Franco Sarto Stevie Mid Calf Boots are the unsung heroes of this outfit. These boots do so much heavy lifting in terms of creating flattering proportions for petites wearing flare jeans.

The mid-calf height is perfect for wearing under flare jeans. The boots sit completely hidden under the denim, which means there’s no visual break in your leg line. This creates the illusion of one continuous line from your hips to the ground—incredibly lengthening for petites.

The block heel provides height without discomfort. Mid-calf boots under flare jeans create the most flattering leg line for petites—even more so when there’s a modest heel involved. You get the benefits of added height (both actual and visual) without the pain of wearing stilettos to a party where you’ll be standing and mingling for hours.

The black leather is practical and versatile. These boots work with this outfit, but they also work with dozens of other combinations in your closet. They’re not overly trendy—they’re classic, well-made boots that will serve you for seasons to come.

✨ Kelly’s Petite Style Tip: If you’re petite and want to wear flare jeans, heeled boots are non-negotiable. The combination of the flare opening and the heel creates the longest, most balanced leg line possible. Without the heel, flare jeans can overwhelm petite frames and make you look shorter.

5. The Mini Crossbody That Does It All

The finishing touch is the Kensington Mini Crossbody Bag in black. This little bag is proof that you don’t need a large handbag to have everything you need for a party.

The mini size is ideal for petites. Large bags can overwhelm smaller frames, making you look unbalanced and shortening your overall silhouette. A mini crossbody, on the other hand, is proportional to petite frames and doesn’t compete visually with your outfit.

The crossbody style is practical for parties. You can wear it across your body for hands-free mingling, or shorten the strap and wear it on your shoulder. Either way, your hands are free for holding drinks, appetizers, or hugging friends hello.

The black leather matches the boots and sweater, creating cohesion. When your accessories are in the same color family, they create visual continuity that’s inherently lengthening. Everything flows together rather than chopping up your silhouette with competing colors.

The structured shape looks polished and intentional. Even though this is a casual outfit, the structured bag signals that you put thought into your look. It’s the difference between “I threw this on” and “I’m casually chic.”

The size is surprisingly functional. Despite being called a “mini,” these bags typically fit your phone, wallet, keys, lip gloss, and a few other essentials. It’s everything you actually need for a party without the bulk of a larger bag.

✨ Kelly’s Petite Style Tip: For petites, the rule of thumb is: the smaller your frame, the smaller your bag should be. A mini or small crossbody is almost always more flattering than a large tote or hobo bag, especially for parties and social events.

Why This Casual Formula Works for Petites

Let me break down exactly why this combination is so successful for shorter frames:

• The cropped jacket length is key. It hits at the hip, which is the most flattering length for petites. It creates definition without overwhelming your frame or cutting you off at an awkward mid-torso spot.
• The high-waisted jeans elongate your legs. When paired with the cropped jacket, you’re showing your waistline and creating the longest possible leg line. This is basic petite styling 101, but it works every time.
• The flare balances the proportions. The moderate flare of the jeans creates a balanced silhouette when paired with the structured jacket on top. You’re not top-heavy or bottom-heavy—everything is in proportion.
• The heeled boots under the flare create magic. This is the secret sauce. The boots sit completely under the jeans, creating an unbroken line from hip to floor. Add in the couple of inches from the heel, and you’ve got serious leg-lengthening happening.
• The monochromatic base is lengthening. Black sweater, black boots, black bag—these create a continuous dark column that visually elongates your frame. The light-wash jeans and colorful jacket sit on top of this lengthening foundation.
• The fitted base layer prevents bulk. By keeping the cashmere sweater fitted and smooth, you avoid the bunching and bulk that can happen when layering, which is especially important for petites.

More Ways to Style Stewart Tartan for the Holidays

Stewart tartan is incredibly versatile beyond this specific outfit. Here are some other ways to wear it throughout the holiday season:

• With black trousers and heels: For a slightly dressier take, pair the tartan jacket with sleek black trousers and heeled pumps or booties. Add simple gold jewelry and you have a polished look for office parties or dinners.
• With a denim skirt: Try the jacket over a black turtleneck tucked into a denim midi skirt. Add tights and boots for a feminine but casual holiday look.
• Over a sweater dress: Layer the tartan jacket over a fitted black or burgundy sweater dress. Add mid-calf boots and you have an instantly elevated outfit for any casual celebration.
• With leather pants: For an edgier take, pair the tartan with black leather or faux leather pants, a simple tee, and ankle boots. This works great for evening parties with friends.
• With cream or ivory: Instead of the black base I’m wearing here, try the jacket over a cream or ivory sweater with dark jeans. The lighter base creates a softer, more romantic take on tartan styling.

More Tartan From Amazon

• Long Sleeve Flannel Pajama Set
• Cashmere Shawl Wrap
• Plaid Crossbody Bag
• Plaid Vest
• Tartan Scarf

The Art of Casual Holiday Dressing

There’s a real art to casual holiday dressing. You want to look festive and polished enough to show that you made an effort, but you don’t want to be overdressed or uncomfortable. This outfit strikes that perfect balance by combining festive elements (the Stewart tartan) with comfortable, wearable basics (jeans, cashmere, practical boots).

More Petite Holiday Styling Inspiration:

• Check Out How I Styled These Vintage Flare Jeans in a Daily Look
• Red Corduroy Pants Are Having a Moment – Here’s How to Style Them
• The Petite-Friendly Suit That Actually Works

Closing Thoughts On Casual Holiday Style

Casual holiday parties are some of my favorite celebrations of the season. There’s something wonderful about gathering with friends and family in a relaxed setting where comfort and conversation take priority over formality. And having an outfit formula like this one—festive enough to feel special, but comfortable enough to enjoy yourself—makes getting dressed for these occasions completely effortless.

The beauty of this outfit is its flexibility. You can dress it up slightly with more polished accessories, or keep it super casual by swapping the crossbody for a larger tote and adding a scarf. You can wear the jacket alone without the cashmere layer if you’re in a warmer climate, or add even more layers if you’re in a colder region.

What I love most is that every piece here earns its place in your wardrobe beyond this single outfit. These aren’t one-hit wonders that you’ll wear once and never reach for again. They’re versatile, well-made pieces that work in countless combinations throughout the season and beyond.

Whether you’re heading to a casual office party, a friend’s gathering, or a laid-back family celebration, I hope this outfit inspires you to embrace the art of casual holiday dressing—looking festive and polished while feeling comfortable and like yourself.