How to Dress Well

Co-authored by Christina Santelli

Last Updated: March 6, 2024 References

Ready to upgrade your wardrobe? Dressing well will make you look and feel confident and energetic. No matter what your budget is, you can take steps to upgrade your appearance. Note: this article is aimed primarily at women. Tips on how to dress well for men are available here.

Part 1

Part 1 of 3:

Knowing What Flatters

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1
Focus on fit. If clothes fit poorly, no matter how attractive or fashionable you will not look well-dressed.^{[1]
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Christina Santelli
Professional Stylist

Expert Interview. 22 April 2019.} Tight clothes look cheap and make you look heavy. Clothes that are too large will make you look sloppy.^{[2]
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- Just because you can get into the clothing does not mean it necessarily fits properly.
- How an item is supposed to fit depends also on styling. For instance, urban style clothing for men in the United States are often very loose fitting compared to a pair of conservative khakis.
- Dresses can be difficult to fit properly because most women wear different sizes in tops and bottoms. A dress fits well if the neckline lies flat whether you are sitting or standing. All seams should lay flat and straight (unless perhaps the styling is purposefully not in that way). The material shouldn't pull or pucker around the chest or hips. The garment should fit snug but not tight.^{[3]
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- If you’ve gained or lost weight recently, evaluate your wardrobe. Discard or alter clothes that no longer fit correctly.
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Each individual is different, but most women fall into the apple, pear, banana, or hourglass categories.^{[4]
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- Apple-shaped women carry weight around their middles. These women look best in A-line dresses and clothing that emphasize the bust and legs while de-emphasizing the waist.
- Pear-shaped women are smaller on top and larger in the hips and thighs. They look best in A-line dresses, layered tops, and simple, darker-colored bottoms.
- Banana-shaped women are slim all over. These women look good in most clothing. They can highlight their shape by wearing clothes that create curves: Flared pants, cinched waistlines, and tapered jackets accomplish this feat.
- Hourglass-shaped women have slim waists and full hips and breasts. They look great in tailored pieces and wrap dresses.
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Learn which colors look best on you. Look at the veins inside your wrist. Do they look green or more blue?^{[5]
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- If they look green, you have a skin tone with a yellow base. Warm colors will look better on you. Try off-white, red, yellow, orange, and brown, as well as yellow-tinted greens and blues. Avoid pastels.
- If they look blue, you have a skin tone with a pink base. Cooler colors will look better on you. Try white, pastels, and jewel tones.
- When in doubt, stick to mostly neutral colors. Black, gray, and brown look fabulous on nearly everyone. Add pops of brighter color here and there – a bright blue necklace or a deep red belt, for example – to make outfits look interesting.
Many women have areas that they do not really like to show off--even fashion models have this issue! Also, if you are following a modest dress code or prefer to do so, buy items that do not bring focus to areas that you would rather not. For example, if you are uncomfortable showing your legs, avoid buying mini-skirts.
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Focus on classic, rather than trendy, styles. Dress your body in attractive, flattering clothes that work for your figure. Sometimes today's trends will do this, and sometimes it is wiser to not do so. Forcing yourself into certain colors, cuts, and styles because the fashion magazines are featuring them will not make you well dressed. Wear what suits you best.
- But be willing to experiment! You may be surprised by how a new style may flatter your appearance.
- Be careful about taking fashion magazines at face value. Very often, they are trying to "sell" you on certain styles, brands, and so on more than they are actually reporting on what is fashion.
- Fashion can also be very regional. What is in style in the US may not be what is cool in Brazil.
Your efforts to look good will be undermined by uncomfortable shoes that make you teeter around in pain or constrictive clothes that you’re constantly shifting and adjusting. Wear clothes that make you look and feel sublime.^{[6]
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Christina Santelli
Professional Stylist

Expert Interview. 22 April 2019.}
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Take care of your clothes. Always read labels and follow the instructions for laundering clothes properly – this will make your clothes look good for a long time.
- Iron your clothes if necessary. No one looks well-dressed in wrinkled clothes.

Part 2

Part 2 of 3:

Developing a Personal Style

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Indulge your own special, personal style.If you’re a girly girl, feel free to wear dresses every day. If you are more of a tomboy, choose jeans. If you are preppy, dress that way. If you like bohemian, dress that way. Authenticity is attractive.^{[7]
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Add interest with accessories. When you have a sense of what looks best on you, you can enhance your look with fun choices that express your individuality.^{[8]
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- If you like bright colors, wear them! Wear your charcoal skirt and cream-colored top that looks fabulous and work-appropriate, and add red kitten heels or a multi-colored bracelet.
- If you like bold jewelry, wear something amazing every day! Big hoop earrings can add interest to jeans and a t-shirt. A statement necklace can quickly make a basic work outfit fabulous.
The point isn’t to pick an image and emulate it. It’s to compare the tremendous variety that is available, and to discover inspiring looks. If you consistently like certain styles or colors, then you’ll know what to look for – you just need to adapt whatever you like to suit your figure and coloring.^{[9]
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Christina Santelli
Professional Stylist

Expert Interview. 22 April 2019.}
Having a repertoire of outfits that fit well and suit your style will serve you well. Develop a rotation of looks for work, for the weekend, for dressy events, and for anything else that you need regularly. Then you’ll be able to approach all these situations with confidence.
Women who dress too old or too young look inappropriate. Whatever you age, embrace it! Instead of aiming to look older or younger, aim to look like the most fabulous you.
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Take calculated risks. Don't mix all kinds of crazy patterns and colors into a single outfit. But remember, it’s fine to try something new and different. The key to dressing well is to wear your clothes with confidence.
- Try, for example, combining neutral colors with one animal-print item -- something like a bright leopard-print blouse under a black cardigan.
- Alternatively, you can try wearing a risky-seeming, fashion-forward item, but keeping the rest of your look comparatively understated. If you're in love with the enormous shoulder pads you saw featured at fashion week, try them! Just pair them with something slim and neutral on the bottom, and stay away from bold accessories.

Part 3

Part 3 of 3:

Updating Your Wardrobe

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1
Clean your closet. Toss anything that doesn’t fit, clothing you haven’t worn in two years, and anything else that’s in poor condition. Doing so will free up space for new, more functional pieces.
- Don’t toss those clothes into a dumpster. Donate them to charity or give them to friends or relatives. If they are in decent condition, consider trying to sell them.
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Figure out what you need. After you’ve gotten rid of the junk, evaluate your wardrobe clearly and identify what’s missing. Your needs will depend on your individual lifestyle, but in general, you want to make sure you have:^{[10]
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- blouses and casual shirts
- button-down shirts
- pull-over sweaters
- pants – at least one pair of jeans and at least one pair of trousers
- casual dresses
- casual skirts
- a jacket for cool weather (and one for even colder weather, if you live where it gets cold)
- at least one or two semi-formal or formal dresses
- shoes – at least one pair for workouts and one or two each for casual, business, and dressy outfits
Once you know what you need, it’s time to shop! But don’t just rush to the mall. You'll save time if you research some popular online stores first. If you don’t see what you like, move on – save time by shopping at stores that fit your lifestyle.
It’s tempting to simply order clothes online, but you’ll have better luck if you head out to the stores that seem promising and try clothes on. Sizes vary considerably from retailer to retailer, and it’s hard to know what will flatter you without seeing a garment on your body.
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Spend your money wisely. If your budget is smaller, start browsing at lower-priced retailers. There’s no reason to spend too much – as long as a garment is well made and fits properly, you will look fantastic. That said, you don’t necessarily want the cheapest clothing available. If it wears out after two weeks or falls apart in the washing machine, it’s no bargain.^{[11]
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- Do some additional research online and try to hit stores when they are having sales. This can allow you to pick up higher-end items for bargain-basement prices.
- Invest in a few key pieces that you will get a lot of mileage from – like a sublime pencil skirt for work or a classic black dress. Spend less on trendier items that you won’t wear for long.
- Don’t be afraid to comparison shop. Before you buy something, see if an online retailer has the same item for a lower price.

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How can I be more stylish?

Christina Santelli
Professional Stylist
Christina Santelli is the Owner and Founder of Style Me New, a wardrobe styling concierge based in Tampa, Florida. She has been working as a stylist for over six years, and her work has been featured in HSN, the Pacific Heights Wine and Food Festival, and the Nob Hill Gazette.

Christina Santelli

Professional Stylist

Expert Answer

Buy clothes that fit the shape of your body well, or else you won't look as comfortable.

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What goes with pink?

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Darker, toned down colors can be great complements to bright colors like pink. Consider pairing it with grey, black, or dark blue tones.

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Can I wear a gray shirt with black and white shoes?

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Yes, you can.

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Feel good about yourself. That way, your inner beauty and confidence will shine through, no matter how you look.

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If you don't know what to wear, consult a close friend or relative. The people who know you best will usually know what looks best on you.

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