How to Dress Classy Without Looking Like You’re Headed to a Job Interview
Photo Credit:@jastookes
I used to think dressing classy meant looking… well, kind of boring. Crisp button-downs, sensible heels, head-to-toe beige—basically the fashion equivalent of elevator music. I’d see someone in a perfectly tailored outfit and think, Sure, she looks polished—but does she look like she’s having fun?
Here’s what I realized: looking polished doesn’t have to mean looking predictable. You can be polished and interesting at the same time. The trick is mixing classic pieces with modern touches—because no one wants to look like they’re trying too hard (or worse, not trying at all).
Need Help Building Your Wardrobe?
Want to see how to style these pieces? Check out our Classic Style Outfit Guide for easy outfit ideas using classic pieces.
Not sure if classic style fits your personality? Take the Fashion Persona Checklist to find your signature style.
Ready to upgrade your entire wardrobe? Learn how to do it step-by-step with our How to Build a Classic Style Wardrobe guide.
Take your favorite pieces to a tailor
Nothing says “effortless class” like clothes that fit properly. Even the most expensive dress can look sloppy if it’s too loose or too tight.
Italian Cotton-Blend Houndstooth
$595.00
Add a pop of color with a statement bag, bright
Neutrals like black, white, camel, and gray always look refined—but a head-to-toe neutral outfit can feel a little flat.
Italian Full-Grain Leather
$675.00
Focus on quality over quantity
Trendy pieces come and go, but a perfectly fitted white button-down or a classic trench coat will last you years.
Cheesecloth Shirred Zip Top
Cotton Cheesecloth
$125.00
Wear a Blazer With Jeans Or A Slip Dress
Minimalism doesn’t have to be dull. Clean lines and structured pieces create a timeless foundation.
Contrast Bound Crop Jacket
Italian Textured Cotton Blend
$545.00
Try pairing a chunky knit sweater with satin trousers
A monochrome outfit in all cotton? Yawn. But mixing silk, wool, and leather? Instant interest.
Merino Stretch Rib Two-Way Zip Sweater
$195.00
Layering 101
Layering isn’t just practical—it’s a styling trick. A long coat over a turtleneck, paired with straight-leg jeans? Chef’s kiss.
Slouchy Long-Length Jean
Cotton Denim
$315.00
Add a belt over a blazer or a slip dress
A belt isn’t just functional—it creates shape and makes an outfit feel complete.
The Work Appropriate Utility Dress + Belt
$425.00
Wear a sheer blouse under a fitted vest
Soft, flowy fabrics look romantic; structured fabrics feel powerful. Combining both? That’s where the fun happens.
Ultrafine Luxe Merino Button Sweater Vest
Superfine Merino Wool
$185.00
If you’re going bold with jewelry, keep the rest of the outfit simple.
A simple gold chain or chunky hoops can make even a jeans-and-tee combo feel put together.
Classic Huggie Earrings
$240
Structured Handbag > Slouchy Bag
A structured bag makes everything feel more intentional.
Twist Lock Tote
Soft Tumbled Italian Leather
$825.00
Cat-eye, oversized, or square frames always feel timeless.
A good pair of sunglasses can instantly make you look more put together.
D Frame Sunglasses
Acetate Renew
$245.00
Pointed-toe flats elongate the leg and work with almost any outfit.
Round-toe flats can feel a little too youthful, but pointed-toe flats? Sophistication.
Pointed-toe flats elongate the leg and work with almost any outfit.
The Bow Point II
$165
Ankle Boots Over Knee-High Boots
Ankle boots feel more modern and versatile. Knee-high boots can easily cross into costume territory.
Chiselled Toe Leather Ankle Boot
Soft Italian Leather
$750
Try wearing loafers with cropped trousers
Loafers give that cool-girl vibe while still feeling polished.
The Double Bit Driver
$199
A low heel in patent leather or suede feels chic without the pain.
High heels aren’t always practical—but a kitten heel or block heel? That’s the sweet spot.
The Knot Sandal
$189
Try stacking gold and silver rings
Forget the old rule about matching metals—mixed metals feel fresh and intentional.
Athena Sculptural Ring Stack Silver
$380
Black and Navy Can Coexist
Yes, you can wear black and navy together. It’s a subtle and sophisticated color combo.
Mixed Media Shirt Collar Short Dress
Mixed-Media Jersey
$275.00
Wear White Year-Round
Who made the rule that white is only for summer?
Cheesecloth Drawstring Hem Pant
Cotton Cheesecloth
$165.00
Leggings and hoodies don’t have to look sloppy.
Pair leggings with an oversized trench or a hoodie with structured trousers.
Merino Cashmere Relaxed Zip Hoody
Italian Merino Wool + Cashmere
$465.00
A slip dress is one of the most versatile pieces in any wardrobe.
Layer it under a sweater, throw on a leather jacket, or wear it with heels for a night out.
No outfit works if you’re not wearing it with confidence.
Stand tall, own your look, and remember—you don’t have to follow every rule to look fabulous.
Bouclè Textured Crop Top
Textured Jersey Tailoring
$185.00
