Mainstream media tends to show Sugar Babies in an almost cookie-cutter-like uniform: a tight, skin-baring dress and heels. While there’s nothing wrong with this classic sexy look, let’s face it—it may not be the most comfortable option, or the option that would be everyone’s go-to. What’s really sexy? Being confident. How do you feel confident? When you are comfortable (literally & figuratively) in what you are wearing. And if you’re teetering on uncomfortable heels, in a dress where you are constantly having to pull down your hem for fear of exposing yourself—you’re probably not comfortable. So how do you pull off a drop-dead look that you feel wonderful in, without pain or self-consciousness? Well, there are plenty of options for the three outfit staples!

The Right Heels

High heels may be one of the most confidence-boosting inventions of mankind, but not all are made equally. Super-snug toe boxes, mediocre-quality leather, a less-than-perfect fit—these are all culprits of high-heel pain. When it comes to heels, you want quality: the best materials, the best fit and the best construction. The investment is more than worth it, ladies.

Manolo Blahnik, a godfather of shoe design, very purposefully designs his heels to be comfortable so women will hang on to them for years. His ultra-classic BB pumps are not only a must-have for any woman, but they are extremely well-balanced in construction (taking pressure off the balls of your feet) and roomy from front-to-back, making them perfect for wider feet.

With its spacious toe-box in a deceptively comfy point shape, Valentino Rockstud pumps are another must-have. Also, don’t be worried by the strappy styles—they’re made with sumptuously soft leather that softens rather than pinches.


Handbags are easily one of the most expressive parts of your style. Whether you’re a girl who loves the legends like the Birkin and the Chanel Double Flap, or ornate bags covered in studs & chains like Stella McCartney’s Falabella—you can’t help but feel confident when carrying your belongings in these pieces of art! Plus, they come in just about every color on the spectrum, with patterns and new materials each season, so it’s practically impossible to not find one to fall in love with.


Let’s all collectively take a moment to thank Coco Chanel for womankind’s most-coveted piece of clothing: the little black dress. It flatters every woman, matches every bag, makes your jewelry pop and, ultimately, lets your beauty take centerstage. The LBD should be any Sugar Baby’s wardrobe staple—the thing she reaches for first and has no doubt it’ll make her Sugar Daddy’s jaw drop. You can choose from a massive variety of silhouettes—a slinky minimalist look, a fitted mini, an embellished attention-grabber, a bold Saint Laurent romper (rompers count as LBD’s!)—the options are simply endless.

But what if it’s winter and it’s simply too cold to bare your legs? Or what if you are just one of those women who isn’t the biggest fan of dresses? Cue the jumpsuit. A black jumpsuit can also be of “LBD caliber”—equally sexy with plunging necks and/or backs and chic with impeccable, curve-hugging tailoring. A Givenchy jumpsuit is simply stunning with its beaded, low neck, while a Alberta Ferretti design radiates a sultry yet sophisticated vibe with a sheer bodice that overlies a deep-V front & back.

Jumpsuits like this Givenchy (left) and Alberta Ferretti (right) look just as sexy as any LBD.

Ultimately, every Sugar Baby should wear what makes her feel like a goddess. Don’t feel limited to a certain look. Express yourself. Being your most-confident, authentic self is what is sexiest in a woman, and ultimately, it will attract the Sugar Daddies you are most compatible with. Feel good, look good, play good!