How To Dress Soft Chic

You Can Dress Soft and Classic and Still Look Put Together


You’ve seen this woman before. She is lovely, elegant, and regal. She moves and speaks with authority, but there is also a grace and softness to her that she embraces. She makes you want to stare, and if she catches you, she will be startled, and possibly freeze momentarily before continuing on her way, just like a deer. She probably doesn’t recognize herself in this description, but the rest of us do. She’s classic with a dose of softness. She is serious with a soft, romantic side.

If you’ve been following along with the classic closet style series, first we covered how to dress classic without looking dated. You can also read about Edgy Chic StyleMinimal Chic StyleCute Classic Style and Sporty Classic Style.

I hope you read all of the versions because sometimes wearing the wrong details is as big as wearing the right details. If you’re not sure what your Chic Style Twist is, take the quiz to find out!


I have a friend who is soft and classic, and she is quiet. And so still. You could mistake her for a statue when she is sitting in a chair. And she has a deep, intense gaze that makes you feel naked as she peels back the layers of your soul with her eyes. She has a quiet, but powerful voice. She is the most reliable and trustworthy person I know. She has such deep feelings that sometimes she can’t keep the tears from spilling over, but she is horrified if someone sees her cry. She is a vault, and extremely hard to get to know, but if you manage to crack the code, she is one of the greatest, most devoted friends you will ever have. 


If you want your outfit to say classic and soft, it’s the subtle details that will tell the story. Look for touchable fabrics, smaller prints, soft florals, lace, ruffles, soft edges, neutrals, soothing colors, subtle details, simplicity, length. That sounds like too much, doesn’t it? Keep reading. I’ll show you how to make it perfect for you.

Touchable fabrics can include chiffon, velvet, knits, silk, cashmere, shearling, things you want to wrap up in.  You are particularly sensitive to things that are too tight and restrictive, scratchy, uncomfortable, itchy, or stiff. Ponte knit is stretchy but very structured. Ask yourself, “Would I want to hug someone if they were wearing this?” 

Small prints and soft florals Think wild flowers and watercolors. Even though the colors are pure and vibrant, the edges of the print might be blurred. If the print is too large it might feel overwhelming. 

Lace is about as soft as it gets. It’s typically a floral pattern, has soft undefined edges in the pattern, and generally comes in neutral colors.

Ruffles flow and have soft edges to them. Being classic means you probably don’t want them too big or wavy.

Other soft edges could be the corners of your hemline, like in a jacket, or the lapel of your jacket might have a shawl collar, sleeve hems might be flared and wavy.

Neutral colors are probably your favorite. When you add a bold color, it’s usually no more than one per outfit, and might even be limited to your lip color sometimes. So black, white and 1 bold color is often your limit or you can feel overwhelmed.

Soothing colors are comforting, like green, blue, purple, and navy.

Subtle details are key. Nothing in your look is overpowering or jumps out. Your look is very cohesive, and not overwhelming. 

Simplicity is your mantra. Not too much of anything or you will feel lost in the noise of too many details.

You are more likely to prefer some length in your tops or skirts. A straight maxi skirt without too much flare or swish, a long straight cut jacket that still has structure, a tailored tunic top, or a longer pendant necklace, but not all of them in 1 outfit.

Straight black and white might feel too stark sometimes, so adding an additional color like blue, purple, or green can give you an added layer of soothing color that is calming. If black feels too stark, try replacing it with navy.

Sometimes you like a sheen like in silk, but not always a shine like high-shine metallics. 

Check out Jessica Alba’s outfit below. The base layer of the outfit is very structured, tailored, neutral, and her soft detail comes in the shape of the trench coat. It’s longer, and has a softness to it, and is also a neutral color. Her jewelry is minimal, and her makeup is very natural and flattering with a soft smokey eye and a neutral lip. Her hair is in soft curls, and very touchable, but in a contained hairstyle.

Soft and Classic Style

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Look for dainty, delicate, and soft edges in your jewelry. Pearls, pendants, soft patterns, and possibly matching sets can work great for you. Also look for filigree or scroll type patterns. Nothing so long or heavy that it gets in your way or swings around too much. Studs are a great earring option for you. Typically if you go long in the necklace, stick to stud earrings, and vice versa.

Your shoes should have more round or almond toes and be comfortable. Pinched toes would draw your attention all day and make everything else fade to the background. Shoes are a great place for some color since it’s small real estate and not too much.

Makeup is another way to keep it soft. You probably love not wearing any makeup. To bring some definition to your face without feeling too made up, consider adopting the French makeup aesthetic: Brows, lashes, and a bold lip. Brows and lips frame the face and give just enough definition for a classic without being too much for your soft side. If you have light brows and lashes, and don’t want to feel the weight of brow and lash enhancers like mascara, dying or tinting them is a more natural look that still gives you the face-framing to enhance your features. If you want to wear a soft smokey eye, then go for a light lip color. 

Hair won’t be too severe. You would probably prefer structured hairstyles with softer edges, so instead of a blunt bob, maybe a softer bob with a little curl. Your curls would be loose and wavy, not tight and bouncy. You have the kind of hairstyle that someone could run their fingers through.


There are some brands that were made for you. Soft Surroundings and Garnet Hill can be great if they have the right colors, but you can usually find black, navy, and white there. Chicos, Cabi, Lularoe, Charter Club, CJ Banks, J. Jill, Free People (but they can get a little too soft and swingy, so watch that), Lands End, Liz Claiborne. Sometimes Ann Taylor, Loft, White House Black Market, and Banana Republic. They are all classic, but their undertone can vary from season to season with the trends. 


The classic is in the style and fit of the clothes. Classic includes button ups, dark wash, tailored jeans (look for 2% spandex so they stretch for comfort, but hold their shape), shirt dresses, stripes, chino shorts, pencil skirts, flats, loafers, trench coats, and a very tailored fit. The overall look of the clothing is classic, and you sprinkle in some romantic details to add a whisper of softness.

Your favorite striped Breton tee might have a cowl neckline. Your black pencil skirt might have a slight A-line cut for ease of movement and comfort. Your button ups might have a soft drape to them. You might enjoy a finer stripe in your clothes than a wider, bolder stripe. Add some softness to classic black pumps with a round or almond toe and a medium heel height. Pair a classic shirt dress with delicate jewelry or a scarf. Sticking to more solid colors, and keeping the patterns on a smaller scale also keeps the softness from drowning you. All the details with a lot of pattern would be too much for you.


I just listed a whole lot of options for adding soft details to your outfits, but don’t wear all of them at the same time. The trick is to pick and choose one or two soft details. If you wear a scarf, your shirt needs to be more fitted and tailored, but not uncomfortably tight. If you choose a maxi dress or skirt, keep it classic and tailored in the shirt or bodice – no ruffles, etc. It can be as subtle as a velvet blazer with a rounded lapel paired with structured (but stretchy) jeans and a tailored top. Your favorite pencil skirt probably has some stretch to it. You could wear a kimono with tailored jeans and top, or a dolman sleeve with structured jeans, but a dolman sleeve and cowl neck might feel too soft. Maybe you like scarves as long as they are worn so they don’t fall below your breastbone and everything else is very tailored, and maybe you love a scarf AND a maxi skirt. How much cowl is too much for you?

If you feel dumpy or dowdy, you’ve gone too far with the softness and you need more classic structure. You might be happiest getting your soft details in your layers and accessories. 

Only you will know the perfect balance. Do you feel too rigid in your clothes? Do you feel overwhelmed with too much softness in texture or structure? Is there too much softness in your outfit and you don’t feel authoritative enough? Start with one soft detail in your outfit and see if you want more. Some women feel better in more, and some can only take so much. It’s very personal Also, don’t forget the bold hues. Those say you mean business.

Soft and Classic Style

Jessica Alba is wearing a very classic outfit with tailored top and jeans, classic sandals, a black structured bag, and belt, and matching all her leather accessories. She brought in a bold color with a looser, dolman-sleeve cardigan to bring a soft quality. Her jewelry and makeup is simple and natural. She could have worn a bold red lip.


There can be some overlap in cute and soft, like in round-toed shoes or florals, but the execution is different. The difference is cute is youthful and girly, and soft is soft and elegant. Cute and classic women can borrow the looks and ideas from the young girls and elevate them to a grown up version. Little girls play dress up to look like a soft, soft woman. So if it looks at all appropriate for a young girl, you’ve got the wrong item. So a cute and classic will wear a round toed shoe, but may prefer color, shine, bling, or glitter. A soft round toe shoe might have color, but probably not shine and color. Your key words are simple and subtle.


Since I’m definitely not classic and soft, let’s look at someone else, Mary Orton of She is the very definition of stunning, regal, refined, elegant. You can’t help but stare. And she knows and embraces her soft classic so well. I just love her style. I get such style envy and wish I were a classic and soft when I see her. Also, #girlcrush.

Photo credits here.

Outfit #1: Talk about the perfect fall outfit! Mary’s whole outfit is very structured and classic, and she brings in the softness with the dolman sleeve, cowl neck sweater. Notice that her turtleneck layered underneath is a structured fit in the neck. If it were also cowl, it would be too drapey. She’s wearing a long pendant necklace that is simple and structured in design, and stud earrings to compensate. Her almond toe boots with a mid-height chunky heel are sensible but stylish. 

Outfit #2: Her swing top isn’t too wide, and the fabric isn’t too soft, so it stays puts. It’s tailored at the top, so it allows her to wear the scarf in a structured shape that doesn’t fall down to wear the top widens, and doesn’t add bulk up top.  Her wide-legged cropped pants are very structured while being loose and comfortable. She keeps her earrings simple so it’s not too much detail up top.

Outfit #3: I love the elegance of this dress. It’s very structured up top with a soft bow that stays neatly in place. What makes the bow soft instead of cute is that it drapes down in a soft shape instead of standing at attention. The maxi dress flares softly at the bottom making a soft swish instead of a girly twirl. The sleeves puff slightly at the bottom before being reigned in with a tailored cuff. The floral print is small but evenly and uniformly spaced, and the belt highlights her waistline.

Photo credits here.

Outfit #4: This  outfit is straight classic with one soft twist: the lace cardigan. Even though it’s long, it’s straight and structured, and the lace adds a dignified softness. The cardigan is a big detail, so everything else is simple: neutral color palette, simple jewelry, and structured, classic clothes. Her ponytail is neatly done, but not pulled so tight she’s getting a facelift. There is some softness to it.

Outfit#5: We can’t see all of Mary’s outfit here, so I’m going to guess she is wearing all neutrals. Her shearling jacket is structured in cut, but has the softness of the material it’s made of. I mean, who wouldn’t want to wrap up in that? The belted waist shows off her figure.

Outfit #6: Mary’s maxi dress is simple in structure, and fairly straight. Romantic without being too drapey. The fabric is light, but holds its shape. Her shoes are stylish, but comfortable. The color palette is neutral, and her jewelry is subtle but simple. Her hair is soft, controlled waves.

Photo credits here.

Outfit #7: I love this dress. I used to have one very similar in color and style, and I finally realized it was too soft and swishy for my edgy style, but it is glorious on her. Soft and swishy, but not girly and twirly, Even though the top is structured, it’s not too fitted, and it blouses a little over the belt, which gives definition to her waist. The skirt is a midi length, which shows her legs, and keeps the dress from overwhelming her. If it were a maxi length with the fullness of the skirt and the bodice, she might look lost in all that fabric. With that gorgeous watermelon color she is keeping the rest of the color palette neutral. Adding more color would be overwhelming.  

Outfit #8: The stripes, the fit and color of the jeans, the structure of the bag, even the shoes are all straight classic. Mary adds a subtle softness in the cut of the turtleneck. It has a slight dolman sleeve and the neckline is looser, slightly cowl. Her accessories are simple, and the stripes are the star of the show. 

Outfit #9: Once again, this outfit is as classic and structured as it gets. Basic black and white outfit, and she brought in a touch of coziness with a blanket scarf that she belted to give it structure and make a jacket. I love that she buttoned the collar all the way up to contrast with the drape of the scarf. 


As important as it is to add the soft elements you want, it’s equally important to avoid certain elements if you want that soft, soft vibe. I’ve showcased Edgy Classic StyleMinimal Classic StyleCute Classic Style and Sporty Classic Style. Learning about all of them will help you avoid the details that will take away from your soft and classic look.

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