Browse Plus Size Stores in Winter Park, Florida
If you’re celebrating your curves, Winter Park has a vibrant mix of inclusive boutiques and stylish retailers ready to help you find the perfect outfit. From dedicated plus size specialists to well-loved national chains offering extended sizing, there’s something here for every taste and body type. Explore our top picks below.
Monkee’s of Winter Park
What Do They Provide?
Monkee’s brings designer fashion right to Park Avenue with a personalized touch. It’s perfect for trendsetters seeking exclusive pieces and a boutique experience.
What Customers Appreciate The Most:
- Great prices on curve-friendly finds
- Excellent personal styling and customer care
- Intimate, welcoming atmosphere
Louise James Boutique
What Do They Provide?
This boutique blends high fashion with affordability, offering carefully curated European-inspired styles in a pink-floraled setting. It’s best for trend-savvy shoppers.
What Customers Appreciate The Most:
- Unique designer pieces at great prices
- Woman-owned, welcoming environment
- Fast-moving new arrivals
Hemline Winter Park
What Do They Provide?
Hemline brings a city-chic flair with on-trend dresses, tops, and statement accessories. It’s ideal for fashion lovers who want a boutique vibe with big selection.
What Customers Appreciate The Most:
- Wide range of contemporary styles
- Knowledgeable, friendly staff
- Well-organized store layout
Versona
What Do They Provide?
Versona curates accessible fashion at mall prices, from statement jewelry to trend-forward tops. It’s a go-to for gift seekers and everyday style.
What Customers Appreciate The Most:
- Budget-friendly accessories and apparel
- Helpful, attentive service
- Generous loyalty rewards
The Grove
What Do They Provide?
This vibrant lifestyle boutique mixes fashion, home décor, and gifts in a glitter-sprinkled Palm Beach-meets-Palm Springs setting. It’s perfect for playful style hunts.
What Customers Appreciate The Most:
- Eclectic, curated finds for home and wardrobe
- Artful, friendly shopping experience
- Unique gift options
Siegel’s Clothing Co.
What Do They Provide?
Family-owned for over 30 years, Siegel’s offers classic to modern mens and womens attire, plus custom suit fittings. It’s a staple for timeless style.
What Customers Appreciate The Most:
- Expert tailoring and fit advice
- High-quality formal wear
- Personalized, welcoming service
J.Jill
What Do They Provide?
J.Jill specializes in comfortable, versatile pieces with extended sizing up to 24, making it a go-to for easy, everyday style.
What Customers Appreciate The Most:
- Reliable extended sizing and fit
- Soft, timeless essentials
- Consistent, friendly service
Sultre Boutique
What Do They Provide?
Sultre hand-picks everyday staples and designer exclusives for an elevated—but effortless—wardrobe. It’s a must for fashion adventurers.
What Customers Appreciate The Most:
- High-end labels at curated prices
- Passionate, knowledgeable staff
- Inviting, fitted shopping environment
Find A Plus Size Store In A City Near Winter Park, Florida
Orlando, FL Maitland, FL Altamonte Springs, FL Casselberry, FL Winter Springs, FL Oviedo, FL
Tips For Finding And Wearing Plus Size Apparel In Winter Park, Florida
Winter Park is all about art fests, lakeside strolls and sunshine—so your wardrobe needs to keep up. Here are a few easy ideas to stay cool, comfortable and on-point.
- Hit local boutiques along Park Avenue early—they often carry fully figured lines you won’t find online.
- Pick breathable fabrics like cotton and linen to handle afternoon sun and sudden rain showers.
- Play with color-blocking or floral prints to match the cherry blossoms at the Mead Botanical Garden.
- Keep a lightweight cardigan or denim jacket handy for cooler evening boat tours on the Chain of Lakes.
- Invest in comfortable sandals or low-heeled espadrilles—you’ll thank yourself on brick-paved sidewalks.
Sidewalk Art Festival Fashion
- The Winter Park Sidewalk Art Festival draws over 350,000 visitors each March—dress for a day among masterpieces.
- Wide-leg linen pants and a breezy off-shoulder top give you room to browse without feeling boxed in.
- A wide-brim straw hat shields you from the sun and doubles as a stylish prop for candid festival snaps.
- Choose a crossbody bag in a bright hue so you can carry essentials hands-free while you shop art booths.
- Slip into cushioned sneakers or low wedges to wander Park Avenue without sacrificing comfort.
Park Avenue Brunch & Boutique Browsing Outfits
- Brunch on Park Avenue calls for a floral midi dress that moves with you as you hop between galleries.
- Pair a plus size denim jacket with a simple tank and skirt for a look that transitions from day to dinner.
- Cute block-heel sandals give you lift without the ache when you explore local shops.
- Accessorize with a lightweight scarf—you’ll add flair and stay cozy in air-conditioned boutiques.
- Opt for neutral tones with a pop of coral or teal to echo the city’s lakefront sunsets.
Lakeside Leisure & Seasonal Layers
- Summer highs often hit the 90s—go for a breezy sleeveless shirt dress and ventilated sandals by Lake Virginia.
- A lightweight kimono over a tank and shorts keeps sun protection in check without bulk.
- When winter temps dip into the 50s, a plus size utility jacket and dark skinny jeans strike the right balance.
- Layering hacks like a slim fleece vest under a rain-resistant shell are perfect for those surprise showers.
- Keep a tote bag in a fun print on hand to stash extra layers or market finds from the Saturday Farmer’s Market.