How to Dress Classy
Is it time for you to change up your style? Add a bit of sophistication and class to your everyday outfits? Maybe you have a new job and need some new classy business casual attire, perhaps you’ve moved to a new city, or maybe you just need a change to represent who you have become. Are you wondering how to make that transition and how to dress classy? I’ll walk you through the ins and outs of styling yourself with a more sophisticated, chic, and classy style that you can wear for years to come (or the rest of your life!).
Classy styling is timeless. The navy shift dress and camel-colored pumps you buy today will still be wearable ten years from now. Buying one good pair of pearl stud earrings outweighs the 10 pairs of trendy statement earrings that will be passé a year after you buy them. Having a sophisticated and classy style means that you can wear your outfits to work, Sunday brunch, a city shopping trip, or traveling the world. You can even go sailing while rocking a classy look!
Creating classy outfits is about putting together crucial elements and making sure your style and confidence also shines through. So if you are ready to delve into a new classy look and answer the question of how to dress classy, let’s get started.
Define and Know Your Personal Style
Personal style is something that each of us has; we just have to identify it, understand it, and then live it. It projects your mood, personality and you as a whole, reflecting your interests, lifestyle, inspirations, and your past.
When you find your personal style you know you look great and feel confident when you leave your home. Whether you prefer bohemian, street, high fashion, minimal or classic, you can make your style look classy when the occasion calls for it.
I hear many women say that they don’t have a personal style or they don’t know what their own style is. Whenever I hear this, I recommend that they take a look at their closet. If you’re trying to find your personal style here is a quick tip that you can do right now. Take out your favorite pieces from your wardrobe. Lay on your bed the clothing you wear over and over again and look for patterns. Is it mainly solids or patterns, bright or neutral colors, dresses or pants, flirty or conservative?
Which category do you see your clothing fitting into? Is your clothing learning towards more free-spirited, maybe bohemian? Or is it filled with solids in black, white, and navy in sleek lines and perfect fits? Then it could be minimalistic.
Typically, classic and minimalist styles will look classy all the time. Classic and minimalist styles usually learn towards neutral color palettes, shapes, fabrics which make it easier to put together classy outfits. But don’t think just because you prefer bohemian or street style that dressing classy is out of the question.
Let’s see what it takes to elevate your style to a more sophisticated level.
The 7 Basics of Classy Style
#1 Wear Items that are Made of Classic Fabrics
Classic, timeless clothing made of materials that will last well into the next decade is what you should be looking to add to your essential wardrobe. Think cotton, wool, linen, and silk. These four basic fabrics will stand the test of time if cared for properly. Cleaned and pressed, items made of these fabrics tend to give off a classy vibe all on their own.
These fabrics also have variations that allow you to expand on your wardrobe. Denim is one example of a cotton fabric that cuts across all style lines, from street to boho to minimalist. Similarly, chino cotton works excellent in pants, blazers and even moto jackets (for the street style in you!). Then there is cashmere, a type of wool that feels heavenly against the skin and doesn’t pill with age. Cashmere sweaters, whether they are cardigans, V-necks, or crewneck pullovers pair perfectly with those denim jeans, as well as tailored pants and skirts.
A word to the wise with these fabrics: Read the labels and care for them properly to make them last. While wrinkle-free cotton has become more available, most cotton items will need to be ironed. (Classy outfits are not wrinkly!) Wool, linen, and silk often have to be dry-cleaned or hand-washed. Make a mistake, and you may have to give your 6-year-old-niece that wool cardigan that was a staple in your wardrobe but shrunk in half thanks to your dryer.
#2 If in Doubt Wear Solid Neutrals
Bold patterns and prints can definitely work in a sophisticated and classy look, but you may not be comfortable with such patterns if you are just beginning on your classy style journal. Neutrals are your friend in this case. Solids are plentiful in the stores (and probably your closet), easily combined, and help to stretch your wardrobe.
Typical neutrals are white/beige/cream, navy blue, black, and gray. Now, don’t think you have to dress head-to-toe in black (or other neutral). Monochromatic (different shades or tints of the same color) allow you to vary a color but remain classy. Or you can add small accents that can transform a solid into something eye-catching, like a skinny burgundy alligator belt, a paisley scarf, or a pair of red pumps. Want to know more about monochromatic dressing? Make sure to read What is Monochromatic and How to Wear a Monochromatic Outfit.
#3 Fit is Key
Classy and sophisticated clothing is typically tailored and form-fitting (not too tight, but you can show off your figure). Skirts should hit just above or below the knee, as should your classy dresses. Classic trousers are straight, slightly wide, faintly bootcut, or menswear-inspired and should be ½-inch off the floor in the back. Wide-leg pants and skinny pants in classic fabrics are also acceptable, as are ankle pants (shades of Audrey Hepburn!). Blazers, blouses, and sweaters should follow the curve of your waist.
Do not hesitate to take items to a local dressmaker or tailor to be altered to fit correctly. Love that shift dress at Nordstrom, but it’s too big in the bust? That’s a $15 fix. Are those gray wool pants in your closet too long for classic 3-inch pumps or do you want to wear them with flats? Another $10-15 fix. Remember, good quality clothes will last you for 10+ years, and it is a small price to pay for alterations. Beats having to replace cheap pants every three years.
Not everything you wear has to be perfectly tailored and form-fitting. You can mix in unstructured pieces for a more relaxed vibe. Pair a blue-striped t-shirt with chinos and a denim jacket or a flowy maxi skirt with a crisp white button-down shirt (roll up those sleeves for added panache!).
Here is an example of how to wear a jumpsuit, and in this outfit, I opted for solid neutrals and paired a structured blazer with a flowy jumpsuit.
#4 Never Overexpose
Dressing classy requires a bit of modesty — no midriff-baring tops, revealing low décolletage, or mini skirts.
Necklines are typically collared, boatneck, crew neck or V-neck. For some variety, you can also try square, cowl, and scoop necks. For more formal occasions, asymmetrical, sweetheart and halter necklines work as well. Regardless, keep your cleavage and your belly button covered. Additionally, armholes on blouses and dresses should not reveal your bra.
As noted above, hem length on skirts and dresses should be just above or below the knee for everyday wear, with slightly shorter and full-length appropriate for summer events or classic formal wear.
Here is a classy and professional outfit example that I would wear to a professional event or to the office. And this is a very elegant and classy outfit I wore to a black tie event. Those two outfits are examples that you can look stylish and sexy without showing too much skin.
#5 Don’t Go Overboard with Accessories
Simple jewelry is the best way to go when aiming for a classy and sophisticated style. My recommendations are:
- Earrings: small silver or gold hoops, pearl or diamond studs.
- Bracelet: silver or gold bangles (one heavy or several delicate), tennis bracelet, watch (gold or silver with metal or leather band).
- Necklace: Long pendants, pearls, diamond solitaire, cross.
- Ring: Not necessary, but if you do, go either delicate or statement. Thin bands, diamonds, or heirloom rings are fine, and everyone should have one cocktail ring to wear to events or dress up your jeans. Stick to ring and/or middle fingers only.
- Scarf: Scarves are a great way to add color and visual interest to a sophisticated outfit. Particularly if the scarf is bright or with an interesting pattern, again, cotton, silk, and wool are the best fabric options. Try multiple colors and fabrics, with light silk or cotton for spring and thicker wool ones for winter. Florals, paisleys, stripes, and solids are great options. If you need more outfit inspiration make sure to check out: Ways to Wear a Scarf & How to Tie a Scarf: The Definitive Guide.
And don’t forget your shoes. Yes, shoes are an accessory! Pumps, slingbacks, ballet flats, or boots in solid neutrals, such as cream, navy or black, are your best bet. All go with a multitude of outfits, meaning you won’t need to break the bank for a closet full of shoes.
But don’t think that you can’t be daring with your shoe choices, every woman should own a red pair of shoes, and it never hurts to have an animal print to make an outfit pop a bit. (Think leopard print flats with khakis or denim.)
#6 Style Your Hair
Now that we’ve covered colors, fabrics, fit and accessorizing let’s move on to your hair! I can’t say this goes without saying because I want to include all the basics. Make sure you style your hair. If you’re wondering how to dress classy and give the appearance of sophistication make sure you spend a little bit of time styling your hair.
If you’re short on time in the mornings or don’t like styling your hair opt for an easy haircut or a haircut that you can quickly put up. By stylish and chic hairstyles I mean a sleek bun or ponytail. I have a lot of hair, and it’s pretty long so if I want to look stylish, I know I need to spend at least 30 minutes on it if I want to wear it down. But the hairstyle I turn to when I don’t want to spend a long time on my hair is a sleek low bun.
Find a hairstyle that is easy for you to style every day and one that you love as well!
#7 Makeup Makes a Difference
You’ve made it to the last point on how to dress classy! Yay, thank you for making it here. I left this one for last because, to be honest, it’s the one I have the most trouble with. I don’t often “do” my makeup, and this point is one that I continually work on. If you are like me and don’t spend much time on your makeup focus on these three things that will make a difference in your classy look.
Eyes, checks, and lip should be what you focus on if you only have 5 minutes. Put on some mascara to open up your eyes, add some blush to bring some life and dimension to a face, and wear a bold lip to add a pop of color. These three things are subtle but make a huge difference to the completeness of your classy look.
You Don’t Need a Lot of Money to Dress Classy
Contrary to popular belief, classy outfits don’t have to break the bank. Yes, you can spend $200 on a designer-label button-down shirt, but you can also find one of comparable quality and appearance for $68 at Banana Republic, the Gap or Ann Taylor. And because classic, well-made clothing lasts for years, and even decades, you can often find good bargains at secondhand and thrift stores.
Invest in good quality basics that fit well, and that you can mix and match. Accessories—which are much cheaper than clothing—can help change up your looks and stretch those basics even further.
Like I mentioned on my first point about opting for classic fabrics, also look for classic shapes and forever classic closet staples. Don’t waste money on trendy pieces that you’ll only wear for a season.
Keep a Pretty Mani
Your hands and the jewelry on them are an extension of your wardrobe, and a reflection of the care you take with your appearance, especially if you are wearing a statement bracelet or ring that brings extra attention to those fingers.
Indulge in regular manicures, either at home or in a salon. Keep nails short to medium in length, opting for a nice round or oval shape, with clear or nude polish or a French manicure. Stay away from stiletto nails and bold or neon colors, as well as nail art and jewels.
NOTE: If wearing sandals or peep-toe shoes, a pedicure is a must. I find that a simple clear gloss or nude colors work best, but you can always go with a classic red or pink.
Pay Attention to the Details
They say that the devil is in the details, and dressing classy is no exception. The trick to wearing sophisticated clothing is to keep everything neat, clean, and simple. Make sure that the clothes are flattering on you and colors and patterns are balanced.
All items should be free of wrinkles and color coordinated. Check for holes, loose threads, missing buttons, or a hemline that is frayed. Stick with neutrals with pops of color here and there. Don’t over-accessorize; stick with simple minimal jewelry like a pair of earrings and a watch or earrings and a pendant necklace.
Your hair and makeup also play a role in your overall look. Again, neat and clean. Stay away from metallic eyeshadows in loud colors, be careful not to overdo the blush or bronzer, and stick with a neutral or light lip.
How to Dress Classy and Your Personal Style
Dressing classy doesn’t have to be difficult, but it will take some time to meld your personal style with the new sophisticated way of dressing. Don’t automatically discount the clothing you already have in your closet. You may be able to integrate items in ways you didn’t think possible.
My style is more classic and minimalist but I do like to add color whenever possible. As you can see in this outfit post, I’m wearing a classy dress but with with a pattern that screams personality. The small pops of color don’t overwhelm the dress or me but add to my look.
This dress has all of the details I mentioned above, with the hem ending just above the knees, a crew neckline, and it’s form fitting but not tight. It has that classy shape but with a little attitude.
I’ve paired it with a red handbag, fun metallic pump, and minimal accessories: sunglasses, earrings and a dainty watch. Simple, elegant, sophisticated and this outfit perfectly reflects my personal style.
So take a look through that closet again. Maybe you can let the hem down on your favorite skirt or add a cuff to pants that are too long for your ballet flats. And that floral silk blouse? It will look great paired with a neutral skirt and matching pumps. You don’t have to completely give up your own style to be classy and chic, but it will require some effort and modifications.
Are you ready to make a classy transition? Remember classy doesn’t mean boring or without personality. Dressing classy means dressing elegant and sophisticated. It’s also timeless and elegant.
If you feel like you’re jumping from style to style and don’t have the wardrobe that represents where you are in your life then start integrating the style tips I mention in this post! Shop for pieces that you can wear longer than a season and remember that a good tailor is worth every penny.
I hope I have answered all your classy outfit questions and you now know more about how to dress classy. If I missed something leave me a comment and I’ll answer you directly!
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