Fashion should be fun, not stressful. If you’ve been wearing the same type of dress for years, it might be time to shake things up. These five dress styles can help you discover new looks that make you feel confident and excited about getting dressed.
Why Try New Dress Styles?
Most women stick to what feels safe. Maybe you always reach for A-line dresses or only wear black. But trying different styles can show you flattering cuts you never considered and help you find your style.
Fashion stylist Sarah Chen, who works with clients in New York, says: “I see women transform when they try something outside their comfort zone. Often, the style they thought would never work becomes their new favourite.”
1. The Wrap Dress – Works for Almost Everyone
What it is: This is a type of dress designed to wrap around the body and fasten at the waist with a tie.
Why try it? Wrap dresses are like the Swiss Army knife of fashion. They work for work meetings, dinner dates, and casual weekends.
The wrap style creates a V-neck that’s flattering on most body types. The tied waist gives you shape, and you can adjust how tight or loose you want it.
How to wear it:
- Choose a solid colour if you’re nervous about patterns
- Choose knee-length or midi styles for maximum versatility.
- Pair with heels for work or sneakers for weekends
Real example: My friend Lisa always wore straight-cut dresses until she tried a navy wrap dress for a work presentation. She got so many compliments that she bought three more in different colours.
2. The Midi Dress – The Perfect Middle Ground
What it is: A dress that hits between your knee and ankle, usually around mid-calf.
Why give it a go? Midi dresses strike the perfect balance—not too short or too long. They’re suitable for nearly any event and can be worn in any season.
If you usually wear mini dresses, a midi gives you coverage without feeling frumpy. If you typically go for long dresses, switching to a midi can offer a stylish and updated change.
How to wear it:
- Try different fits: fitted, flowy, or structured
- Add a belt to define your waist if the dress is loose
- Wear with ankle boots, heels, or flat sandals
Styling tip: Fashion blogger Maria Rodriguez suggests: “If you’re short, choose a midi dress with a higher waistline. It makes your legs look longer.”
3. The Shirt Dress – Casual Meets Polished
What it is: A dress that looks like an oversized button-up shirt, usually hitting at or below the knee.
Why try it: Shirt dresses are comfortable like pyjamas but look put-together.
This style works especially well if you like menswear-inspired fashion or prefer looser fits over body-hugging clothes.
How to wear it:
- Belt it for a more fitted look
- Leave it loose for a relaxed, casual vibe
- Cuff the sleeves to create a relaxed vibe.
- Add a cardigan or blazer when it gets chilly for extra warmth and style.
Shopping tip: Look for shirt dresses in cotton or linen for summer and heavier fabrics like wool blends for fall and winter.
4. The Fit-and-Flare Dress – Classic with a Twist
What it is: A dress that’s fitted at the top (through the bodice and waist) and flares out from the hips.
Why try it? This style is incredibly flattering because it shows your waist while skimming over your hips and thighs. It’s feminine without being overly dressy.
If you’ve avoided fitted dresses because you’re self-conscious about your midsection, the fit-and-flare might surprise you.
How to wear it:
- Choose a length that makes you feel comfortable (mini, knee-length, or midi)
- Try different necklines: scoop neck, V-neck, or off-the-shoulder
- Add a cardigan for work or keep it simple for dates
Body type tip: Personal stylist David Kim notes: “Fit-and-flare dresses work on every body type. The key is finding the right proportions for your frame.”
5. The Slip Dress – Effortlessly Cool
What it is: A simple, usually sleeveless dress that hangs straight from thin straps, inspired by vintage lingerie.
Why try it? Slip dresses are having a major moment. They’re minimal, elegant, and surprisingly versatile.
This style might feel intimidating if you’re used to more structured dresses, but slip dresses can be styled up or down easily.
How to wear it:
- Layer a t-shirt or turtleneck underneath for a trendy, layered look
- Add a blazer for work
- Wear with sneakers for casual days or heels for evening
- Try a midi or maxi length if you prefer more coverage
Styling examples:
- Casual: Slip dress + denim jacket + white sneakers
- Work: Slip dress + blazer + pointed flats
- Date night: Slip dress + strappy sandals + delicate jewellery
How to Choose the Right Style for You
- Consider your lifestyle: If you’re always on the go, prioritize comfort and easy care. If you attend lots of meetings, choose styles that work in professional settings.
- Think about your body: Everybody is different. What matters most is how the dress makes you feel. If you feel confident and comfortable, you’re wearing the right thing.
- Start with one: Don’t feel like you need to try all five styles at once. Pick the one that seems most appealing and give it a real chance.
Where to Find These Styles
Budget-friendly options:
- Target and H&M carry all these styles.
- Uniqlo has great basics, especially shirt dresses.
- Old Navy often has a good wrap and fit-and-flare options.
Mid-range:
- Everlane makes excellent slip dresses
- Madewell has great shirt dresses and midi styles
- Anthropologie carries unique versions of classic cuts
Investment pieces:
- Diane von Furstenberg created the wrap dress (her original designs are worth the splurge)
- COS has beautiful, minimalist midi and slip dresses
Making It Work in Your Real Life
- Start small: If you’re nervous about trying something new, start with a less expensive version. If you love how it looks and feels, you can invest in a higher-quality piece later.
- Pay attention to fabric: The same dress style can look completely different in different fabrics. A cotton shirt dress feels casual, while the same style in silk looks more formal.
- Don’t force it: If you try a style and hate how it looks or feels, that’s okay. Style is meant to bring joy, not cause anxiety.
Quick Summary
These five dress styles – wrap, midi, shirt, fit-and-flare, and slip – offer different ways to look and feel good. Each style has its benefits and works for different occasions and body types.
The best way to find your new favourite is to actually try something different. Pick one style that interests you and give it a real chance. You might discover that the dress style you never considered becomes your go-to choice.
Your next step: Look through your closet and identify what types of dresses you always choose. Then, pick one style from this list that’s different from your usual choice. Try it on, wear it for a full day, and see how it makes you feel.
Fashion is about finding what makes you feel like the best version of yourself. At times, it involves leaving your usual routine and giving something unfamiliar a try.
