How to Be Stylish: The Ultimate Guide to Dressing with Intention

tyle in the clothing sense is defined as “a manner of doing something” or “a distinctive appearance.”  It seems to be this elusive thing that people can see and point out to others, but have a hard time incorporating into their own daily lives.  Style makes you stand out from the crowd-- perhaps that’s why so many people shy away from it, or lose confidence in their ability to accomplish it.  

We’re here to help you adult your way through this dilemma.  You need style-- why?  Because you’re an adult, and you owe it to yourself to put your best foot out the door every single day.  Because humans are visual creatures who-- for better or for worse-- make first impressions and carry them with us the rest of our lives.  Because employers understand that a person who curates their look with intention will bring that same level of oomph to their work.  But ultimately?  

Because you matter, and putting intention into your appearance shows both yourself and the world that you understand and accept your self-worth.  

So… ready to create some style?  Here’s how:

• Clothes that fit well & flatter
• Colors, textures, and patterns
• Accessories
  

By the way-- these suggestions are for anyone, including guys!  Style has no gender.  

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Stylish clothing fits well + flatters your shape

The first key step-- the one that you should do no matter what-- is to make sure that your clothing fits well.  So many people get confused by this step, but it’s really quite simple.  All it takes is some attention to the feel vs. the look of your clothing when it’s on your body.  To save yourself some hassle, be sure to try on your clothing before purchasing whenever possible-- and have the name of a good tailor handy.  

Jackets and blazers add style very quickly, and in office temps that can plummet to 9th-circle-of-hell they’re also practical.  No matter if you’re masculine or feminine, you want to make sure that your shoulders fit.  When you try on a jacket or blazer, button it.  If the cuff hits your wrist or a little over, that’s a good sign-- now try hugging someone (even just pretend).  Can you?  If not, size up until you can.  Then look at the sleeve and torso length.  Longer sleeves can be tailored up, so don’t worry about that.  But look at where the bottom hem hits-- if it’s bunching or pulling in odd directions because of your hips or tush, it’s too long.   This rule applies for any gender.  

Button-down shirts can be a frustration for both genders, too.  But it doesn’t have to be-- generally speaking, if the buttons pull or the fabric bunches, it doesn’t fit.  Size up.  Once you find a shirt that has no gaps or pulls in the button area, try doing some motions that you do all of the time.  For example, reach out to shake someone’s hand or hitch your purse over your shoulder.  Any gaps or pulls?  It doesn’t fit.  (Side note for women who have issues with that ONE pesky button-- if the gap is small and not too tense, a tailor can put a snap in the problem area to keep your modesty.  New York & Co already has them in some of their shirts.)  

Another problem area for most people is the waistline.  No matter where the waistband of your pants or jeans hits, you should be able to put two fingers inside without trouble.  Try sitting down in the dressing room or lowering yourself into a half-squat.  It may feel weird, but if the waistband digs in-- don’t buy it.  Size up or find another cut to try.  And don’t worry about pant length too much-- a good tailor can fix that, or check to see if the same cut of pant is available in different lengths.  

Speaking of lengths… there’s a difference between deliberately cropped pants and riding high-water pants.  A cropped pant will expose the ankle with the hem about an inch above it.  You can fold it for extra flair.  Cropped pants are also usually quite fitted in the leg-- sometimes even a legging fit.  They’re also usually labeled as “cropped.”  If your pants are not that type of fit, and they’re riding high-- get rid of them or don’t buy them.  You’ll look like you’re trying to wear kids’ clothes.  This is especially true for professional clothes!  

Likewise, if your pockets are flaring… the pants don’t fit.  

Let’s take a second and talk about underclothing.  It doesn’t matter who you are-- if your underclothing doesn’t fit right, your clothes won’t fit right.  

Underwear should fit like a second skin, not loose.  It shouldn’t bunch or move around, but neither should it dig in and create bulges of skin.  There are a variety of styles to choose from, and we encourage you to have a few of each on hand because different types of clothing require different kinds of underwear.  

Suits-- for example-- should be fitted and tailored to your body.  That means that your underwear should be, too-- so no boxers or granny panties.  Stick with boxer briefs, briefs, bikini cuts or thongs.  Again, if it moves around and either bunches up or wedges into crevices, it doesn’t fit right.  If you have VPL-- Visible Panty Lines-- change either your pants or your underwear right away.  

This last paragraph is for bra-wearers.  The statistics on those who wear the wrong-sized bra are staggering.  Do yourself a favor-- GET A GOOD BRA FITTING by a certified bra specialist.  We highly recommend Nordstrom’s for this-- Victoria’s Secret is known for inaccurate sizing despite having recently expanded their size selection.  A good bra specialist will make you take off your shirt (VS doesn’t) and will ask you questions about the types of clothing you wear over your bra-- because push-ups and sports bras are only good for specific occasions.  Get fitted at least once a year, because changes in lifestyle and health affect breast size and shape more than you realize.  Make sure to ask about proper bra care-- handwashing is generally best-- and buy at least four-- rotating your bras increases their life from 6 months to at least 1 year. Lastly, be prepared to spend more than you think.  

It’s worth it-- and SO ARE YOU.  

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Smart Use of Colors + Textures + Patterns = Style

One of the easiest ways to build a stylish wardrobe is to use the capsule method.  The idea is to ruthlessly route out anything in your closet that you’re not wearing and build a “capsule” of clothing appropriate for your needs and loves.  Sometimes this means creating a collection of basic pieces in one or two neutral colors, and then adding on extras in fun colors or patterns.  

Ultimately, you want to create a selection of basics in  your wardrobe that fit you well and flatter your body.  Sticking to neutrals like black, beige, white, navy and olive simply make combining those pieces easier.  If you’re not someone who likes to “dress by the rules” or feels constricted by rules-based dressing-- don’t bother with this method.  Chances are, that urge you feel to mix and match and throw out the rulebook on dressing is all part of your style!  

Think about your favorite colors.  You don’t have to restrict yourself to just one or two or three-- pick as many as you like!  They’re your favorites, after all.  When you find pieces of clothing that fit you well, try to buy two: one in a neutral and one in a favorite color.  If you have to choose, pick the one that you like the best.  If you love it, you’ll wear it!  

Another way to add style with color is to consider it’s “matchiness.”  Colors that contrast-- like white and black or hot pink and olive green-- create interest.  Where you place color on your body versus a neutral shade will draw attention to that area of your body.  Monochromatic looks-- like the traditional all white or all black-- are created by putting together pieces that are all the same color.  Not necessarily the same shade of color, though-- shade indicates the depth of darkness or lightness of a color, it doesn’t define the color itself.  Monochromatic looks are a statement all their own.  

Textures are a fun way to add interest to an outfit.  What is texture?  It’s the feel and consistency of the surface of clothing-- sometimes it’s more visual than sensual, but usually it’s sensual.  For example, a chenille sweater has a much different texture than a cashmere sweater.  They’re all sweaters-- but the visual and sensual feel of the fabric is very different between them.  Texture ultimately comes down to the type of fabric or knit, and mixing and matching them in your wardrobe instantly adds style-- think of the way silk and satin contrast with denim, or the way linen contrasts with knits.  This is an especially great way to add visual interest to a monochromatic look!  

Patterns are repeated decorative designs on fabric, accomplished by the way the fabric is knitted, woven, sewn, or stitched-- or by appliques and beads.  Patterns are often challenging to people.  If you’re scared of patterns, start small with a tie, belt, purse or scarf.  If you’re feeling bolder, try a printed button-down and set it off with well-tailored jeans or corduroy pants.  A dress with a print or graphic design is easily styled with a neutral belt and a killer shoe-- or even keds and a hat.  

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Accessories Amplify Your Unique Style

To be honest, accessories are where great outfits are made really stylish.  If you only follow the first two steps, you’ll always look pulled together and adult.  But accessories make outfits pop over from “nice” to “stylish.”  Take the time to curate a collection of accessories that match your personality and lifestyle needs.  And remember to play-- style is all about having fun expressing your personality through clothes.  

Ties come in essentially two styles: bowtie and straight tie.  The bowtie has a very distinctive playfulness to it that can jazz up a boring suit and look really fun with a button-down shirt and dark jeans.  Straight ties are more popular and elegant, probably because of the clean lines they create with a suit or a suit-like outfit.  Pick a few ties in solids but also try some prints-- and don’t feel restricted to traditional paiselies, dots, and stripes!  Those are neat and can create some super-sleek outfits when paired with heavier textured pants and jackets-- but some cool alternative styles exist with skull and cheeky prints.  

Ties aren’t just for men, either!  A woman can wear them, too!  Wear it menswear style like Katherine Hepbuurn, or pair it with a pencil skirt and fitted blouse-- think retro bombshell.  How would Marilyn Monroe or Sophia Loren style it?  The same goes for suspenders.  

Suspenders are definitely retro, and wearing them is a statement-- it doesn’t matter what gender you are.  Suspenders create clean lines that emphasise the shape of the body and draw the eye upwards.  You can get them plain or patterned.  

Belts are a cinch-- literally.  Putting on a belt shouldn’t always be about keeping your pants up, although that function is definitely important!  Belts come in so many colors, patterns, textures and widths-- they pull the eye in at a key point in the body and help create structure to the appearance of the outfit.  Try to wear a belt either at the waistline or above it to create the most flattering shape.  

Belt buckles can almost be considered an accessory all their own, because they can carry a lot of personality!  The key to styling a belt is to think about how much shape you want to create-- if you wear it simply with regular jeans or pants and a shirt, go for a belt that  is about an inch in width.  You want it to fit through the belt loops.  

But what if you’re trying to create structure with a loose dress or a straight shirtdress?  Pick a belt that’s a little wider-- if you’re wearing a shirtdress, pick one that fits the loops-- in a darker or brighter color.  Really loose or bombshell looks can benefit from a very wide corset-style belt, because it really pulls the outfit in at a focal point that’s flattering and creates a highly defined shape.  

If you really want a retro look that’s dressy, add a pocket kerchief in your suit’s breast pocket.  Play with fabrics, colors and patterns.  Or tie on a scarf.  

Scarves are an accessory that’s often overlooked, but they’re also probably the most practical one because they’re multi-functional.  An oversized scarf-- no matter how light the fabric-- can be folded in numerous ways to become a belt or shawl.  Try tying one onto your purse straps or around your wrist as a bracelet.  Bad hair day or third-day hair?  It takes some practice in the mirror, but a headscarf can be wrapped in a multitude of ways to add a retro and colorful flair. Smaller scarves-- kerchiefs-- can be tied around the throat or wrist, or around a ponytail or bun.  In cooler months or atmospheres, a pashmina shawl adds instant warmth and worldly flair to any outfit-- even a business suit or evening dress.  

On a casual day, bandanas look really cool!  Tie them around your head in the traditional biker manner.  Or, if you’re a girl, tie it in reverse like Rosie the Riveter or around your throat like a greaser girl with a cropped jean or leather jacket.  

By the way… leather ANYTHING makes for instant cool factor!  

Cufflinks are another overlooked accessory.  They add sophistication to a suit that a tie cannot replace.  If you really want to dress to impress, add a cufflinks and a tie clip.  When picking cufflinks and tie clips, try to match the metals and keep the design clean with a small stand-out detail-- think a tiny crystal or, for rock’n roll flair, a skull.  Skip the sports-themed ones-- they’re juvenile.  Again, don’t feel restricted by gender here!  Adding cufflinks to a white or black button-down shirt adds instant style for anyone, and adding a tie clip and tie to a bombshell or menswear look really jazzes up the way you put the outfit together.  

Other types of jewelry punch up style, too.  Necklaces, bracelets, and rings don’t have to be pricey.  Perfectly acceptable hoop and dainty stud earrings along with louder pieces can be found at the dollar store just as easily as a higher end boutique.  

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There are lots of other accessories and ways to put outfits together that we haven’t covered here.  There are whole books on the subject-- ones worth checking out include: Accidental Icon by Iris Apfel, Advanced Style by Ari Seth Cohen, The Truth About Style by Stacy London, How to Get Dressed by Alison Freer, The Lucky Shopping Manual & The Lucky Guide to Mastering Any Style by Kim France & Andrea Linett.  

Style is honestly as simple as how you put an outfit together.  It’s about taking that step beyond putting on clothes, and really taking a moment to consider how to express your personality with clothing.  It’s a way for the world to see how well you value the way that you see yourself.  

What are some other style questions that you’d like us to address?