HOW TO GET THE OLD MONEY AESTHETIC STYLE FOR WINTER
Are you struggling to master the old-money style? I’ve got you covered! This complete guide will help you nail the old-money aesthetic, along with 10 effortlessly chic outfit ideas you can recreate.
The old-money or quiet luxury style has surged in popularity over the past few years, largely due to the influence of TV shows like Gossip Girl, Succession, and various celebrity fashion moments that brought this aesthetic into the spotlight.
This style revolves around high-quality, logo-free pieces, timeless designs, and tailored cuts, often paired with elegant accessories for a vintage-inspired touch. Think tailored suits, trench coats, cashmere sweaters, and monochromatic outfits. In essence, the old-money look is all about well-made, understated, and timeless fashion choices that exude sophistication without being flashy.
To effortlessly embrace this style, it’s important to understand the origins of the old-money aesthetic. It stems from a lifestyle associated with those who have inherited wealth, rather than earning it through work.
Their typical hobbies—sailing, tennis, horse riding, golfing, and attending polo matches—heavily influence the fashion choices. That’s why many of the outfits we’ll be discussing are inspired by the attire worn for these activities, blending elegance with a timeless, preppy charm.
While shows like Succession gave us a glimpse into the old-money aesthetic, I believe the true epitome of elegance is Princess Diana. Renowned for her timeless style and grace, she became an icon in the world of fashion. Her ability to effortlessly exude charm made her a lasting influence, and her outfits continue to represent the essence of old-money fashion. From her power suits to casual polo shirts, Diana’s wardrobe consistently embodied classic, understated sophistication, perfectly capturing that old-money vibe.
HOW TO ACHIEVE THE OLD MONEY LOOK
No need to rob a bank to achieve this style! While the quality of the clothes is important, your personal taste and unique style matter even more. It’s all about how you can effortlessly put together simple pieces to create sophisticated old-money outfits.
To fully embrace the old-money aesthetic, focus on these five key elements:
1. CREATE AN OLD MONEY CAPSULE WARDROBE
An old-money wardrobe is built around timeless staples that never go out of style. By incorporating these classic pieces with your unique personal flair, you can effortlessly create endless old-money outfits. The best part? You likely already have many of these items in your current wardrobe, so there’s no need to splurge. It’s all about mixing and matching these essential old-money staples to achieve the look.
Old Money Wardrobe Includes:
Old Money Wardrobe Includes:
Cashmere Sweaters
Trench Coat
Pair of loafers
Button-Down Shirt
Pair Of High-Waisted Trousers
Blazer
Accessories:
Vintage sunglasses
Pearl Necklace
Hoop Earrings
Silk Scarves
Headbands
Structured Leather Bag
2. QUALITY OVER QUANTITY
Investing in high-quality pieces is key to achieving that classic old-money style, and they’ll last you a lifetime. However, buying quality doesn’t require a huge bank account. There are plenty of affordable options made with premium materials—you just need to know where to shop and carefully check the material list before making a purchase. It’s always preferable to choose pieces made from natural fibers for that refined, long-lasting appeal.
3. PATTERNS
Avoid bold, extravagant prints like animal or floral patterns. While there’s nothing inherently wrong with them, they give off a completely different vibe from the old-money aesthetic. Instead, opt for more understated graphic prints, such as stripes, polka dots, and checks, which align better with the timeless, sophisticated look of old-money style.
4. TAILORING
It’s essential to always tailor your clothes for the perfect fit—never too tight or too loose. Invest in structured, high-quality pieces that are impeccably tailored to suit you like a glove and highlight your figure. Well-fitted clothing is a key element of the old-money aesthetic, adding polish and sophistication to any outfit.
5. COLORS
The old-money style often embraces a neutral color palette, featuring soft, understated tones with the occasional pop of color. To simplify your outfit planning, here are some popular old-money color combinations to keep in mind as you put together your looks:
OLD MONEY OUTFIT INSPIRATION
BLACK KNIT DRESS
A black knit dress is a staple for your winter capsule wardrobe. To elevate the look, you can add tan or brown accessories, or go for classic pearl accents for a touch of elegance.
BLAZER & RIDING BOOTS
Instead of opting for something overly oversized, a classic blazer looks incredibly chic. Pair it with white leggings and riding boots for the ultimate old-money vibe. Don’t forget the accessories! The gold details on the belt add a touch of elegance, while statement glasses and a black headband bring in those perfect vintage vibes.
You might also consider a double-breasted blazer with gold buttons—it’s super chic! A navy blazer paired with neutral colors is another fantastic option to achieve that sophisticated look.
MONOCHROMATIC LOOK
I hesitated to include yet another monochrome look in this guide, but the truth is, wearing tonal outfits is one of the simplest ways to achieve that old-money aesthetic. Monochrome ensembles create a polished, sophisticated vibe that effortlessly embodies the style.
TRENCH COAT, JEANS & LOAFERS
This look is more casual, making it perfect for daytime outings. Most of us likely already have these pieces in our wardrobes, but I’ve linked some stunning options for you just in case, including the best Loro Piana dupes!
CABLE KNIT SWEATER & WHITE SHIRT
This look is incredibly easy to recreate, and it’s timeless—you can wear it year after year without it ever going out of style.
WOOL COAT & SILK SCARF
Nothing says old money quite like a silk scarf! It’s a simple yet elegant way to add a pop of color to your neutral outfits. You can wear it with a wool coat, paired with jeans and ankle boots or white trainers for a chic, polished look.
COAT, SHIRT & TURTLENECK
How stunning is this outfit? The colors perfectly embody the old-money aesthetic, and the striped coat adds a super chic element to the look. If you love wearing shirts in winter, layering a turtleneck sweater underneath is a great idea for added warmth and style!
WHITE TENNIS SKIRT & SWEATSHIRT
Remember when we discussed tennis as one of the classic old-money hobbies? That’s why a white tennis skirt is a must-have for achieving the old-money look! Simply pair it with a sweatshirt and knee-high boots for a chic ensemble. You can also opt for a grey or black skater skirt, which is easier to style during winter—just add a pair of leggings underneath for warmth and comfort.
TWEED 2-PIECE SUIT
A matching set is essential for achieving that old-money look, especially in tweed. I believe tweed adds a touch of class to any outfit. Paired with a wool coat, it creates a sophisticated formal look that’s perfect for colder days.
CHECKED BLAZER & KNIT TOP
This look embodies the ultimate Ralph Lauren aesthetic: a checked or houndstooth blazer paired with a cozy sweater. This type of pattern instantly lends a heritage feel to any outfit. For added warmth and a vintage touch, consider layering a white shirt underneath—it’s a classic combination that never goes out of style!
THESE ARE THE 20 BEST SHIRT TO WEAR WITH LEGGINGS
Leggings are a comfy staple in many closets, but figuring out what tops to wear with them can sometimes be a challenge. Can you dress them up? Down? What styles flatter your figure? Fear not, fashion friends! This guide unveils the 22 best shirts to wear with leggings, giving you endless options for creating stylish outfits that suit any occasion. From casual tees to chic wrap tops, sporty hoodies to dressy blazers, we’ve got you covered. So get ready to unlock the full potential of your leggings and take your everyday style to new heights!
A STATEMENT PEPLUM TOP
A statement peplum top can add a touch of fun and flirt to your legging look. The peplum, which is a flounce or ruffle around the waist, cinches your silhouette and can help camouflage your stomach and hips. This creates a flattering hourglass figure. Look for peplum tops in bold colors, prints, or with interesting textures to make a real statement. Pair it with sleek leggings for a balanced look, and accessorize with heels or booties to elevate the outfit for a night out.
OVERSIZED SHIRT
An oversized shirt is a cool and versatile option for pairing with leggings. The loose silhouette creates a relaxed vibe, perfect for casual outings or lounging at home. To avoid looking like you’re swimming in fabric, consider how to define your waist. You can try tucking the front of the shirt partially into your leggings for a more put-together look, or tie the shirt at the waist to create a flattering cinch. Layering an oversized button-up shirt open over a tank top or bandeau adds a touch of effortless style. Play with proportions by pairing a longer oversized shirt with fitted leggings, or balance a shorter, boxier cut with high-waisted leggings.
A CREW NECK PULLOVER
The crewneck pullover is a cozy and classic choice for topping off your leggings. This style sweatshirt features a comfortable crewneck collar and goes perfectly with the casual vibe of leggings. For a laid-back look, choose a plain crewneck in your favorite color and pair it with sneakers. Elevate the outfit for cooler weather by layering a long-sleeved tee under the crewneck. For a touch of texture or preppy style, opt for a cable-knit crewneck. Crewnecks also come in a variety of thicknesses, from lightweight fleece for warmer days to sherpa-lined options for ultimate comfort in the winter.
A HOODIE
The hoodie, a champion of casual comfort, is a natural partner for leggings. Whether you’re running errands, relaxing at home, or venturing out for a casual coffee date, a hoodie offers effortless style and unmatched comfort. Choose a classic zip-up hoodie for a laid-back vibe, or a cozy pullover for ultimate snuggles. While plain hoodies are a great choice, graphic tees or fun prints can add a touch of personality. For a more put-together look, elevate your hoodie outfit with sleek leggings and statement sneakers. You can even layer a denim jacket over your hoodie for an extra layer of warmth and a touch of edgy style.
A CABLE KNIT SWEATER
A cable knit sweater adds a touch of cozy sophistication to your leggings. The textured knit creates visual interest and elevates your outfit beyond just casual wear. Cable knit sweaters come in a variety of thicknesses, making them perfect for layering on chilly days or wearing alone in cooler weather. Choose a chunky cable knit for a more dramatic look, or a finer knit for a more polished feel. Pair your cable knit sweater with leggings and booties for a fall weekend brunch, or throw it on over a fitted turtleneck and high-waisted leggings for a wintery chic look. This timeless combination is both comfortable and stylish, making it a perfect choice for the cooler months.
MONOCHROMATIC LOOK
For a sleek and sophisticated look, consider a monochromatic outfit with leggings. This means dressing head-to-toe in one color or a gradient of similar shades. Not only is it incredibly chic, but it also creates a streamlined silhouette that can be very flattering. Leverage the power of neutrals like black, grey, or beige for a timeless look, or make a bold statement with a vibrant color like emerald green or cobalt blue. Play with textures to add visual interest – pair a matte legging with a shiny satin top, or a chunky knit sweater with smooth faux leather leggings. Don’t forget accessories! A pop of color with a bag or statement earrings can elevate your monochromatic look from simple to stunning.
A TUNIC-LENGTH TOP
A tunic-length top offers a comfortable and versatile option for pairing with leggings. Unlike shorter tops, tunics provide extra coverage, making them ideal for those who want a bit more modesty or prefer to camouflage their hips and thighs. The longer length also creates a balanced silhouette that flatters many body types. Tunic tops come in a variety of styles, from flowy and drapey to structured and tailored. Choose a lightweight tunic for warmer weather or a thicker knit for cooler days. Dress your tunic up with heels and a statement necklace for a night out, or keep it casual with flats and a denim jacket for weekend errands. Tunic tops offer endless possibilities for creating comfortable and stylish looks with your leggings.
SILK BLOUSE
A silk blouse adds a touch of unexpected luxury to your leggings. The soft, lustrous fabric creates a beautiful contrast to the matte finish of leggings, instantly elevating your outfit from casual to chic. For a balanced look, pair a fitted silk blouse with flowy leggings or a relaxed-fit blouse with slimmer leggings. Play with proportions by tucking the blouse partially in for a more defined waist, or leave it loose for a more effortless vibe. Silk blouses come in a variety of styles, from classic button-downs to feminine blouses with ruffles or ties. Choose a neutral color for a timeless look, or embrace a bold print or pattern to add personality. Accessorize with delicate jewelry and statement heels to complete this dressy look, perfect for a night out or a special occasion.
A TURTLENECK CROP TOP
The turtleneck crop top is a trendy and unique option for pairing with leggings. It offers a surprising mix of cozy comfort and edgy style. The high neckline adds warmth and a touch of sophistication, while the cropped silhouette shows a hint of midriff for a contemporary vibe. This top works best with high-waisted leggings to balance proportions and create a flattering silhouette. Choose a fitted turtleneck crop top for a sleek look, or a looser knit for a more relaxed feel. Play with textures by pairing a chunky knit turtleneck crop top with smooth faux leather leggings, or a fine-gauge knit with a cotton blend legging. Accessorize with a statement necklace or bold earrings to draw the eye up, and complete the outfit with sneakers for a casual vibe or heels for a dressier touch. The turtleneck crop top with leggings is a perfect choice for the fashion-forward individual who wants to create a stylish and unexpected look.
BOMBER JACKET
Bomber jackets and fleece leggings are a match made in comfy-cool heaven. The bomber jacket’s sporty silhouette with ribbed cuffs and hem adds a touch of structure to the cozy softness of fleece leggings. This combination is perfect for casual outings, errands, or even travel. Choose a classic bomber in olive green or black for a timeless look, or embrace a bolder shade or fun print to add personality. Play with textures by pairing a smooth satin bomber with fleece leggings, or a matte bomber with fleece that has a fuzzy, sherpa-like texture. For footwear, sneakers are a natural choice, but you can also elevate the look with booties or ankle boots. This outfit is all about effortless style and everyday comfort, making it a perfect choice for relaxed yet put-together vibes.
A COLLEGIATE CARDIGAN
Channel your inner campus cool with a collegiate cardigan paired with leggings. This classic knit sweater, often featuring letterman-style patches or embroidered details with a school’s name or mascot, adds a touch of preppy charm to your look. The structured button-up front and ribbed detailing offer a polished counterpoint to the casual comfort of leggings. Collegiate cardigans come in a variety of colors and styles, allowing you to showcase your school spirit or simply embrace the preppy aesthetic. Pair a classic navy or crimson cardigan with high-waisted leggings and loafers for a timeless look, or choose a vintage cardigan with a quirky mascot for a more playful vibe. This combination is perfect for running errands, grabbing coffee with friends, or adding a touch of school spirit to your everyday style.
DENIM JACKET
The denim jacket, a timeless staple, offers endless possibilities for styling with leggings. Its rugged charm adds a cool, casual layer to your outfit. Denim jackets come in a variety of washes, from light and distressed to dark and inky. Choose a classic trucker style for a versatile option, or explore cropped silhouettes, oversized fits, or ones with unique details like colored stitching or embroidered patches.
Denim jackets work well with all colors of leggings, so you can create a monochrome look in denim or add a pop of color with a vibrant pair of leggings. For a casual vibe, pair your denim jacket with a t-shirt and sneakers. For a more dressed-up look, try a silk blouse or a turtleneck crop top underneath. Don’t forget accessories – a statement necklace, a colorful scarf, or a chunky belt can take your denim jacket and leggings outfit from ordinary to extraordinary.
A SHORT-SLEEVED KNIT TOP
A short-sleeved knit top is a versatile and comfortable option for pairing with leggings. The knit fabric offers a step up from a basic tee while remaining breathable, making it perfect for warmer weather or layering in cooler months.
Choose from a variety of knit types, like a chunky cable knit for texture or a fine merino wool for a more polished look. The fitted silhouette of a short-sleeved knit top complements the sleekness of leggings, creating a balanced and flattering look. Play with proportions by pairing a cropped knit top with high-waisted leggings or a longer tunic-length knit top with fitted leggings.
This combination is perfect for casual outings, errands, or even work with a blazer or cardigan thrown over. Dress it up with heels and statement jewelry for a night out, or keep it casual with sneakers and a denim jacket for weekend fun. The short-sleeved knit top offers endless possibilities for creating comfortable and stylish looks with your leggings.
FLANNEL SHIRT
The flannel shirt and leggings combo is a fall fashion favorite that reigns supreme in both comfort and style. Soft, warm flannel adds a cozy touch, while its structured silhouette balances the casual vibe of leggings. This winning duo thrives on its versatility: layer a flannel shirt unbuttoned over a tee for a laid-back look, or tie the tails for a cinched waist. Colder weather? Throw on a thermal underneath for extra warmth. Flannel’s plaid patterns and colorways offer endless options. Go classic with a red and black buffalo plaid, embrace softer hues with a pastel plaid, or elevate your look with a solid-colored flannel paired with black leggings and booties. Best of all, flannel shirts are effortlessly stylish. Throw one on over your leggings and you’re ready to conquer the day, making it a perfect choice for busy schedules or weekend adventures. So, embrace the cozy vibes and fashion-forward flair – the flannel and leggings combo is your one-stop shop for fall style.
A LAYERED BUTTON-DOWN
A layered button-down shirt adds a touch of effortless polish to your leggings. This styling trick offers endless possibilities and lets you play with textures and proportions. For a classic look, try a crisp white button-down unbuttoned over a fitted tank top or graphic tee. The button-down adds structure and a touch of formality, while the inner layer keeps things casual. Feeling bolder? Experiment with color! Layer a brightly colored or patterned button-down over a neutral-colored tee. Play with length too – leave the button-down long and flowing, or knot the hem at the waist for a more defined silhouette. Don’t forget about sleeves! Roll them up for a relaxed vibe or keep them down for a more polished look. Layering a button-down with leggings is a versatile choice, perfect for casual outings, brunch with friends, or even the office with a blazer thrown overtop.
HIGH-LOW TOP
The high-low top, featuring a shorter front hem and a longer back, adds a touch of drama and asymmetry. This creates a striking contrast against the sleek, fitted silhouette of leather leggings. To achieve a balanced look that flatters your figure and elongates your legs, pair your high-low top with high-waisted leather leggings. Play with materials – choose a flowy chiffon or rayon top for a casual vibe, or elevate the outfit with a structured crepe or satin top for a dressier occasion. Keep accessories simple to avoid overwhelming the outfit, but a statement necklace or chunky earrings can add a touch of personality. This edgy combination is perfect for a night out, concert, or any event where you want to showcase your unique style. Remember, balancing proportions and choosing the right materials is key to creating a cohesive and effortlessly cool look.
A BOXY BLAZER
The boxy blazer injects a dose of modern style into your leggings look, balancing dressed-up polish with relaxed comfort. Unlike traditional blazers, this style boasts a looser silhouette with sharp lines and wider shoulders, creating a laid-back vibe that complements the casualness of leggings. To avoid a bulky look, balance is key – pair your boxy blazer with high-waisted leggings to define your waist and elongate your legs. Play with proportions! A cropped blazer looks chic with high-waisted leggings, while a longer one can balance shorter leggings. Beauty lies in its versatility: throw it on over a tank top and sneakers for brunch, or dress it up with a button-down, heels, and statement jewelry for work or a night out. Boxy blazers come in various materials and textures – a classic wool blazer offers timeless appeal, while linen or a plaid blazer adds a bolder statement. With its ability to elevate leggings and create on-trend looks, the boxy blazer is a unique and must-have wardrobe staple.
LONG SLEEVE SHIRT
The long-sleeve shirt is a legging’s ultimate chameleon, offering both comfort and a chance to play with style. It’s a workhorse for cooler weather, providing coverage and endless outfit options. Channel a classic and casual vibe with a crisp crewneck or V-neck tee, perfect for layering with cardigans or denim jackets. Want to dress it up? Elevate your leggings with a silky blouse or a button-down shirt, tucked in or left loose for a more relaxed look. Texture plays a role too – a chunky knit adds cozy vibes, while a fitted turtleneck creates a sleek silhouette. Feeling bold? Graphic tees or printed long-sleeves let your personality shine and add pops of color or pattern. No matter your style preference, a long-sleeve shirt is waiting to be the perfect match for your trusty leggings.
A LEATHER SHIRT
The smooth leather adds a touch of sophistication, its inherent coolness perfectly complementing the casual comfort of leggings. To achieve a balanced look, pair your leather shirt with simple, solid-colored leggings in black or neutral tones. This grounds the outfit and lets the leather take center stage. Fit is key – a well-fitting leather shirt elevates the entire look. Avoid anything too baggy or too tight. Choose a moto jacket with asymmetrical zips for an undeniably edgy vibe, or opt for a classic button-down for a more polished take. Keep accessories simple and avoid anything too flashy. A statement necklace or layered bracelets can add personality without overwhelming the outfit. This leather and legging combination is perfect for a night out, concert, or any occasion where you want to showcase your unique style.
A STRIPED SHIRT
A casual striped tee is your everyday hero, perfect with sneakers for errands or dressed up with flats or booties. For a polished touch, partially tuck your tee in. Feeling bold? Wider stripes add a graphic punch. Play with contrasting colors for a statement or embrace monochromatic stripes for a subtler look. When the weather cools, cozy up in a striped sweater. Chunky knits add a stylish touch, while thinner stripes evoke a nautical vibe – pair them with white leggings and boat shoes for a fresh, classic look. Remember, vertical stripes are your lengthening BFF, perfect for balancing proportions with leggings. No matter your style, there’s a striped shirt or sweater waiting to be the perfect partner for your trusty leggings.
A COLOR-BLOCKED
Unleash your inner color enthusiast with a color-blocked top and leggings. This dynamic duo injects a playful dose of color and vibrancy into your look. Color-blocking features contrasting colors in one garment, offering a unique and eye-catching way to elevate your leggings. To create a balanced look, ensure the colors complement each other. Opt for analogous colors (think neighbors on the color wheel) or a timeless combo like navy and white for a polished touch. Feeling bold? Experiment with contrasting colors to make a high-impact statement. When it comes to proportions, play with the color block placement to flatter your figure. Horizontal blocks can add width, while vertical blocks elongate your silhouette. Keep your leggings simple – solid black is a versatile choice, but you can also experiment with colored leggings that complement your top’s color palette. Let your color-blocked top be the star! Accessorize minimally with simple jewelry and a neutral tote bag to complete the look without overwhelming the outfit. This fun and fashionable combination is perfect for casual outings, brunches, or even work with a blazer for added polish. So go forth, embrace the color, and create a unique and eye-catching look with color-blocked tops and leggings.
CONCLUSION
From cozy staples to chic statement pieces, this guide has explored 22 of the best shirts to wear with leggings. Whether you’re seeking casual comfort, effortless style, or a touch of dressy polish, there’s a perfect top out there to elevate your leggings and create endless outfit possibilities. So, embrace your creativity, mix and match these tops with your favorite leggings, and discover the versatility and style potential this wardrobe combo has to offer!
