Look, I’m gonna be honest with you—when I first stepped into the sugar bowl eight years ago, I thought showing up in my best H&M bodycon dress and platform heels from Target was enough. I mean, I looked cute, right?
Wrong.
My first meet-and-greet was at The NoMad Bar in NYC, and the second I walked in, I knew I’d miscalculated. The women there weren’t dripping in logos or drowning in sequins—they looked effortlessly expensive in ways I couldn’t quite pinpoint. Meanwhile, I felt like I was wearing a costume. The guy was polite, but I could tell he wasn’t seeing me as someone who belonged in his world.
That night sent me down a rabbit hole. I started studying what actually made someone look wealthy versus what screamed “I’m trying too hard.” And here’s what I learned: luxury isn’t about price tags—it’s about understanding codes.
Fast forward to today, and I’ve cracked the system. I’ve dated finance executives who’d take me to Per Se, tech founders in San Francisco who valued understated elegance, and Miami real estate guys who appreciated a woman who looked polished without looking bought. Through trial, error, and way too many shopping trips, I figured out how to look like a million bucks on a TJ Maxx budget.
So if you’re sitting there thinking, “I need to attract successful men but my bank account is laughing at me”—I’ve been exactly where you are. Let me show you what actually works.
Why Your Look Matters More Than You Think (But Not How You Think)
Here’s the thing about wealthy men—they’re not stupid. They can spot a fake Chanel from across the room, and honestly? They don’t care if your bag is real. What they do notice is whether you look like you understand their world.
I learned this the hard way during my second year in the bowl. I’d matched with this gorgeous man on Seeking—let’s call him Richard—who owned a string of boutique hotels in LA. For our first date at Catch LA, I borrowed my roommate’s “designer” bag (spoiler: it was a really good fake) and wore this trendy outfit I’d seen all over Instagram.
He never said anything about the bag, but he did mention, almost casually, how he appreciated women who had their own sense of style rather than chasing trends. Translation: I looked like every other girl trying to impress him, not like someone with actual taste.
That comment changed everything for me.
Relationship anthropologist Wednesday Martin, author of “Primates of Park Avenue,” talks about how wealthy communities have visual shorthand for belonging—subtle signals that communicate “I’m one of you” without saying a word. In sugar dating, your appearance is exactly that: a visual shorthand for whether you understand the lifestyle he’s offering.
But—and this is crucial—it’s not about looking rich. It’s about looking like you have taste, self-respect, and an understanding of quality. Those are three very different things than just “expensive.”
The Foundation: Building Your Capsule Wardrobe Without Going Broke
Okay, let’s get practical. When I finally got serious about upgrading my look, I had maybe $300 to work with. Not exactly a Bergdorf budget. So I created what I call my “Sugar Baby Starter Pack”—seven pieces that could mix and match into dozens of outfits.
The Non-Negotiables:
1. The Little Black Dress (But Make It Interesting)
Forget the basic bodycon. Look for something with an architectural detail—an interesting neckline, an asymmetrical hem, or subtle texture. I found mine at a consignment shop in the West Village for $65. It was originally from Reiss, had this gorgeous boat neck, and made me look like I had my shit together. I wore that dress to meets in three different cities, and it never failed me.
Budget hack: Check out Zara’s premium line or COS. Their cuts are sophisticated, the fabrics photograph well, and you won’t see yourself coming and going.
2. Tailored Trousers in a Neutral
This was a game-changer. I bought a pair of wide-leg, high-waisted trousers from Uniqlo for $40, then spent $20 getting them hemmed perfectly. Paired with a silk camisole and heels, I looked like I’d just stepped out of a corner office. With a blazer, I could do business dinners. With a crop top, I could do rooftop bars.
The key? Perfect fit. I don’t care if you’re shopping at Walmart—if it fits like it was made for you, it reads as expensive.
3. One Cashmere Sweater
I waited for Nordstrom Rack’s clearance and snagged a cashmere V-neck for $45. Sounds frivolous, but hear me out—cashmere feels different. When a man puts his hand on your lower back, that tactile luxury registers subconsciously. Plus, it made me feel like the kind of woman who owned cashmere, which changed how I carried myself.
4. Nude or Black Pointed-Toe Heels
I splurged on this—relatively speaking. I saved up $120 for a pair of Sam Edelman pumps because I knew I’d wear them constantly. They elongated my legs, went with everything, and were comfortable enough to actually walk in. (Pro tip: If you can’t walk confidently in your heels, wealthy men notice. They’re used to women who glide.)
5. A Structured Bag (Not Logomania)
This is where everyone gets it wrong. You do not need a Louis Vuitton monogram bag. In fact, in cities like San Francisco or Seattle, that might actually work against you—tech money tends to value subtlety over flash.
I bought a structured leather tote from Polene (a French brand that’s stunning but way less expensive than luxury houses) for $280. I saved for two months, and it was worth every penny. It looked expensive without screaming for attention, held all my stuff, and transitioned from day to night.
If $280 is still too much, Mango and & Other Stories make gorgeous minimalist bags for under $100.
6. Classic White Button-Down
I know, I know—sounds boring. But a crisp white shirt is so versatile. Tucked into trousers with a blazer? Professional. Half-tucked into jeans with the sleeves rolled? Effortlessly chic. Worn oversized with heels and nothing else for a late-night hotel visit? You get the idea.
I found an amazing one at Everlane for $68. The key is making sure it’s not see-through and fits well in the shoulders.
7. A Blazer That Actually Fits
This transformed my entire wardrobe. I thrifted a Theory blazer for $40, got it tailored for another $30, and suddenly everything I owned looked more expensive. Blazers are wealthy-people camouflage—they signal that you have places to be and people to meet.
Wear it with your trousers for dinner dates, throw it over a slip dress for gallery openings, or pair it with jeans and heels for casual meets. The ROI on a good blazer is insane.
The Details That Separate Expensive from Expensive-Looking
So you’ve got the basics. Now let’s talk about the subtle shit that actually makes the difference—the stuff that took me years to figure out.
Grooming is Non-Negotiable
I met this gorgeous sugar daddy in Chicago—a derivatives trader who took me to Gibsons Bar & Steakhouse. Everything was going well until he gently mentioned that I should consider investing in regular manicures. It stung at first, but he was right. My chipped nail polish was undercutting my otherwise polished appearance.
Here’s what matters:
— Nails: Keep them neat. If you can’t afford weekly manicures, do them yourself with a neutral shade. Wealthy men notice hands—they’re shaking them, holding them, seeing them across dinner tables.
— Hair: It should look intentional. Doesn’t matter if it’s long, short, straight, or curly—just make sure it looks done. I started getting blowouts before important dates ($40) and learned to maintain them between washes. Total game-changer.
— Skin: You don’t need a 12-step routine, but your skin should look healthy and glowy. I keep it simple: cleanser, moisturizer with SPF, and a good concealer. When I want to look extra polished, I add a tinted moisturizer and cream blush. The goal is “expensive health,” not Instagram makeup.
— Scent: Smell matters more than you think. I wear Le Labo Santal 33 (yes, it’s $240, but I saved up and it lasts forever). The compliments I get are worth it. If that’s not in your budget, Glossier You is $68 and incredibly elegant.
According to biological anthropologist Dr. Helen Fisher, scent is one of the most powerful triggers of attraction and memory. The right fragrance can literally make you unforgettable.
Jewelry: Less is More (But Make It Good)
Early on, I thought more jewelry meant more elegant. Wrong again. I showed up to a date in Miami wearing every piece I owned—earrings, necklace, bracelet, rings—and looked like a Christmas tree.
Now my rule is: Pick two, maximum three pieces.
I invested in:
— Simple gold hoops (Mejuri, $75)
— A delicate gold necklace (also Mejuri, $90)
— A classic watch (I saved for a pre-owned Cartier Tank on The RealReal for $1,200—took me six months, but it’s the most compliment-generating thing I own)
The watch was a splurge, I know. But if you’re serious about this lifestyle, one real luxury piece is worth it. It tells men you understand quality. If a Cartier is out of reach, Tissot or Seiko make beautiful, elegant watches for $200-500.
The Fit is Everything
I cannot stress this enough: Tailoring is the secret weapon of looking expensive.
I have a tailor in Brooklyn who charges $15 to hem pants, $25 to take in a waist, $30 to adjust shoulders. For the price of one mediocre dress, I can make five thrifted or budget pieces look custom-made.
Here’s what I tailor:
— Every pair of pants (length and sometimes waist)
— Blazers (shoulders, sleeves, waist)
— Dresses that almost fit but need a tweak
A $40 Zara dress that fits perfectly looks better than a $400 designer dress that’s pulling in weird places. This is the hill I will die on.
Where to Actually Shop (My Real Sources)
Okay, you want the tea on where I actually shop? Here’s my rotation:
For Basics:
— Uniqlo (their tailored pieces are shockingly good)
— COS (minimalist, architectural, Scandinavian elegance)
— Everlane (quality basics, transparent pricing)
For Statement Pieces:
— Zara Premium / Massimo Dutti (same parent company, elevated aesthetic)
— & Other Stories (French-girl vibes, unique but wearable)
— Reformation (more expensive but worth it for dresses, especially on sale)
For Designer on a Budget:
— The RealReal (authenticated pre-owned luxury)
— Vestiaire Collective (European luxury resale)
— Poshmark (if you’re patient and know what to look for)
— Gilt / Rue La La (flash sales, but move fast)
For Accessories:
— Mejuri (fine jewelry that’s actually affordable)
— Polene (stunning French bags)
— ATP Atelier (Scandinavian minimalist shoes and bags)
Thrift/Consignment IRL:
— Buffalo Exchange, Beacon’s Closet (if you’re in NYC)
— Crossroads Trading (West Coast)
— Local consignment shops in wealthy neighborhoods (this is KEY—go where rich women donate their closets)
Pro tip: The best thrifting is in affluent suburbs. I’ve found Burberry trench coats and Vince sweaters in Greenwich, CT consignment shops for a fraction of retail.
Putting It Together: Outfits for Every Type of Date
Let me walk you through real scenarios I’ve navigated:
The First Meet & Greet (Coffee or Drinks)
Goal: Approachable but polished. You want him to see you as someone he could introduce to his friends, not someone who’s trying too hard.
My go-to:
— High-waisted jeans (dark wash, no distressing) from Madewell
— White button-down (half-tucked, sleeves rolled)
— Nude heels or ankle boots (depending on season)
— Structured bag
— Gold hoops and watch
— Natural makeup, hair down and loose
This outfit says: “I have my life together, I value quality, and I didn’t agonize over this for three hours” (even though you totally did).
The Upscale Dinner Date
This is where you get to dial it up. I wore a version of this to Le Bernardin in NYC and felt like I belonged:
— That little black dress with the interesting neckline
— Black pointed-toe heels
— Simple gold necklace (delicate, sits at collarbone)
— Small structured clutch or evening bag
— Hair in a low bun or sleek ponytail
— Classic red lip or nude gloss (depending on your vibe)
This is elegant, sexy without trying too hard, and photograph-ready (because these men love showing off beautiful women in nice restaurants).
The Daytime Activity (Museum, Brunch, Shopping)
You want to look effortless but chic:
— Tailored trousers (cream or camel)
— Cashmere sweater or silk camisole with a blazer
— Loafers or minimalist sneakers (if you know he’s casual)
— Sunglasses (this is important—good sunglasses elevate everything)
— Tote bag
— Minimal jewelry
I wore this to a Saturday afternoon at the Broad Museum in LA, and my date kept saying how “put-together” I looked. That’s code for “you look expensive.”
The Weekend Getaway
If he’s taking you to Napa or Miami or the Hamptons, you need versatile pieces:
— A breezy midi dress (I love Reformation for these)
— Linen pants and a matching top
— That white button-down (for casual dinners)
— A swimsuit that looks expensive (high-cut, solid color, good fabric)
— Comfortable but chic sandals
— Oversized sunglasses and a straw tote
The goal is looking like you vacation often and well. Even if this is your first time flying first class, you should look like it’s routine.
What Rich Men Actually Notice (From Conversations I’ve Had)
Look, I’ve had the privilege of asking dozens of successful men what they actually pay attention to when they meet a potential sugar baby. Some of their answers surprised me.
Things They Notice (Good):
— Clean, maintained nails and hands
— Hair that looks intentional and healthy
— Clothes that fit properly (not too tight, not too loose)
— Good posture (confidence is everything)
— A signature scent
— Quality over quantity in accessories
— How you carry yourself entering a room
— Whether you look comfortable in upscale environments
Things That Turn Them Off:
— Obvious fast fashion worn badly
— Overly trendy outfits (they want timeless)
— Excessive makeup or fragrance
— Uncomfortable shoes that make you walk awkwardly
— Visible tags or price stickers (yes, this happens)
— Anything that makes you seem insecure or try-hard
— Logo-heavy pieces that scream “I want you to know this is designer”
One Manhattan real estate investor told me: “I can tell within 30 seconds if a woman understands elegance or is just wearing a costume.” That stuck with me.
The philosopher Alain de Botton writes about how we’re attracted to people who seem to inhabit their world naturally, not perform in it. In sugar dating, your appearance should feel authentic to who you are, just elevated.
The Mindset Shift That Changes Everything
Here’s what nobody tells you: You can have all the right clothes and still not look expensive if you don’t feel it internally.
The biggest transformation in my sugar journey wasn’t buying better clothes—it was believing I belonged in these spaces.
I used to walk into The Polo Bar or Nobu Malibu feeling like an imposter. My posture would shrink, I’d fidget with my bag, I’d scan the room nervously. And guess what? People picked up on that energy.
Everything changed when I started doing this mental exercise before dates: I’d imagine I was already a successful woman in my own right—someone who’d earned her place at that table. Not because of a man, but because of who I was. That shift in internal narrative changed how I walked, talked, and carried myself.
Suddenly, men started treating me differently. Not because my clothes changed (they didn’t), but because my energy did.
So yes—invest in the wardrobe pieces I’ve mentioned. Get the tailoring. Learn the codes. But also do the internal work of believing you deserve to be there. That’s the real luxury no one can buy.
Common Mistakes I See (And Made Myself)
Mistake #1: Thinking “Sexy” Means “Revealing”
Early in my sugar dating journey, I thought showing more skin would make me more desirable. I’d wear bodycon dresses with plunging necklines to first meets, thinking that’s what rich men wanted.
What I learned: Wealthy men are surrounded by beautiful women showing skin. What stands out is elegance, mystery, and sophistication. The most memorable outfit I ever wore was a high-neck, long-sleeved midi dress that showed zero skin. I got more compliments on that than anything low-cut I’d ever worn.
Leave something to the imagination. Allure is often more powerful than explicit sexuality.
Mistake #2: Wearing Trends Instead of Classics
Biker shorts and oversized blazers might be trendy, but they date you and your photos immediately. When you’re building an arrangement, you want to look timeless—like you could belong in any era of elegance.
Stick to classic silhouettes and add personality through subtle details, not viral TikTok trends.
Mistake #3: Neglecting Shoes
Men notice shoes more than you think. Scuffed heels, worn-down soles, or cheap-looking materials undercut everything else.
You don’t need twenty pairs. You need three really good pairs that you maintain religiously: nude heels, black heels, and either ankle boots or elegant flats. Invest here—it pays off.
Mistake #4: Over-Accessorizing
More jewelry doesn’t mean more elegant. I see this constantly—women layering every piece they own and looking cluttered instead of curated.
Pick your statement: earrings OR necklace. Add a watch and maybe one ring. That’s it. Clean lines, simple elegance.
Mistake #5: Ignoring Undergarments
This is unsexy to talk about but crucial: visible panty lines, bra straps that don’t match, or ill-fitting undergarments ruin an otherwise perfect outfit.
Invest in seamless underwear, nude bras that actually fit, and shapewear if needed. The foundation of your outfit matters just as much as what’s visible.
Building Confidence in Your Look
The best piece of advice I can give you? Curate a “confidence outfit”—something that makes you feel absolutely unstoppable.
Mine is: black tailored trousers, a silk camisole, my Theory blazer, nude heels, gold hoops, and my watch. When I wear this combination, I feel like I could walk into any room and own it. I’ve worn versions of this outfit to first dates, allowance negotiations, and even regular job interviews. It’s my armor.
Find yours. Build it intentionally. Wear it when you need to feel powerful.
And remember—you’re not dressing to become someone else. You’re dressing to become the most polished, elevated version of yourself. There’s a huge difference.
The Real Secret Nobody Talks About
You want to know the real secret to looking expensive?
It’s not the clothes. It’s not even the grooming or the accessories.
It’s looking like you don’t need him.
The most attractive thing you can project is self-sufficiency wrapped in grace. When you look put-together, it signals that you take care of yourself, that you have standards, that you’re choosing to be there—not desperately hoping he’ll choose you.
That energy, combined with the right wardrobe, is absolutely magnetic.
I learned this during a dinner at Carbone in Miami with a private equity guy. I’d spent the day at the beach, then carefully put myself together for dinner—nothing overdone, just polished and intentional. At one point, he said, “You know what I love? You look like you have your own life. Like this is just a nice addition to your world, not your whole world.”
That’s the energy to cultivate. And your wardrobe is just the external expression of that internal confidence.
Your Action Plan (What to Do Right Now)
If you’re reading this and feeling overwhelmed, here’s where to start:
This Week:
1. Go through your closet and pull out anything ill-fitting, visibly cheap, or overly trendy
2. Identify gaps in your wardrobe using my essentials list
3. Research tailors in your area (ask in local Facebook groups for recommendations)
This Month:
1. Buy ONE foundational piece from my essentials list (start with the black dress or tailored pants)
2. Get it tailored if needed
3. Practice styling it three different ways
4. Invest in proper undergarments
Next Three Months:
1. Slowly build out the rest of your capsule wardrobe
2. Start following elegance inspiration accounts (not influencers, but accounts focused on timeless style)
3. Visit consignment shops in wealthy areas
4. Practice going to upscale venues in your elevated wardrobe to build comfort
Remember: This is a process, not a overnight transformation. But I promise you, when you show up to your next meet looking polished, feeling confident, and projecting that “I belong here” energy—everything shifts.
You’ve got this, babe. Now go build that wardrobe and step into the arrangement you deserve.
—Victoria
