How to Dress for a Staycation: Relaxed and Stylish

A guide on dressing for a staycation.

A staycation is a vacation you take at home or in your local area. It is a time to relax and recharge without the stress and expense of traveling. But just because you are not going far does not mean you should neglect your style. In fact, a staycation is the perfect opportunity to experiment with new looks and create a wardrobe that is both comfortable and chic.

This guide will provide you with all the information you need to create the perfect staycation wardrobe. We will cover everything from loungewear to date night outfits, and we will provide you with concrete examples and actionable tips.

The Staycation Wardrobe: A Core Philosophy

The core philosophy of staycation style is effortless comfort with a touch of intentionality. This isn’t about being in a full-on sweatpants-and-old-T-shirt slump. Instead, it’s about curating a collection of pieces that feel good against your skin, allow for easy movement, and still make you feel put-together. The goal is to feel like you’re on a true getaway, even if you’re just on your couch. Think of it as an upgraded version of your everyday casual wear.

Building Your Staycation Capsule Wardrobe

A capsule wardrobe is a small collection of versatile clothing items that can be mixed and matched to create a wide variety of outfits. For a staycation, a capsule wardrobe is essential for keeping your options open without feeling overwhelmed. Here’s how to build one:

  • Foundation Pieces:
    • The Perfect T-shirt: Invest in a few high-quality T-shirts in neutral colors like white, black, gray, and navy. Look for fabrics like Pima cotton or modal for a soft, luxurious feel. Example: A white, slightly oversized Pima cotton tee from Everlane.

    • Versatile Bottoms: A pair of well-fitting, comfortable jeans (stretch denim is key), some relaxed linen trousers, and a pair of chic joggers are your workhorses. Example: A pair of medium-wash Levi’s 501 ’90s Jeans for a classic look, or cream-colored linen pants from J.Crew for a breezy feel.

    • A Comfortable Dress: A simple, midi-length dress in a breathable fabric like cotton or Tencel is perfect for everything from lounging to a backyard dinner. Example: A simple black A-line midi dress with a V-neckline.

    • The Go-To Sweater or Cardigan: A soft, oversized cardigan or a crewneck sweater is essential for cool mornings and evenings. A cashmere blend or a chunky knit cotton works well. Example: A beige, chunky-knit cotton cardigan that can be thrown over a T-shirt or dress.

  • Statement and Accent Pieces:

    • A Silk or Satin Camisole: This adds a touch of elegance and can be worn with jeans or trousers for a simple, chic look. Example: A charcoal gray silk camisole from Vince.

    • A Patterned Scarf: This can instantly elevate an outfit, whether tied around your neck, in your hair, or on your bag. Example: A colorful silk scarf with an abstract print.

The Ultimate Guide to Staycation Outfits

Now, let’s get into the specific outfits for different staycation scenarios.

Scenario 1: The Lazy Morning and Coffee Run

This outfit needs to be effortlessly comfortable but still presentable enough to grab a coffee without feeling underdressed.

  • The Formula: High-quality loungewear + stylish outerwear + chic sneakers.

  • Actionable Steps:

    1. Start with a pair of matching loungewear separates. Think a soft hoodie and joggers set in a muted color like sage green or oatmeal.

    2. Layer with a long, wool-blend overcoat or a structured trench coat. This instantly elevates the look and makes it feel more intentional.

    3. Finish with a pair of clean, minimalist sneakers (like white leather Common Projects or Veja’s) and a simple tote bag.

  • Concrete Example: An olive green, fleece-lined crewneck and matching joggers. Layer a camel-colored wool coat over it. Complete the look with white leather sneakers and a large canvas tote. You look comfortable, but the coat and sneakers make it clear you’re not in your pajamas.

Scenario 2: A Day of Reading, Cooking, and Relaxation

This is about maximum comfort without sacrificing style. The key is to choose fabrics and silhouettes that feel good.

  • The Formula: Relaxed-fit basics + elevated accessories.

  • Actionable Steps:

    1. Start with a pair of wide-leg trousers in a soft fabric like Tencel or modal. They offer the comfort of sweatpants but with a more sophisticated silhouette.

    2. Pair with a simple, fitted tank top or a relaxed-fit T-shirt.

    3. Add a cozy element like a chunky knit cardigan or a plush robe.

    4. Keep footwear simple—slippers or barefoot is the ultimate staycation luxury.

  • Concrete Example: Navy blue Tencel wide-leg pants paired with a white ribbed tank top. Throw on a thick, cream-colored knitted cardigan when it gets a little chilly. A pair of sheepskin slippers completes the relaxed, luxurious vibe.

Scenario 3: A Backyard BBQ or Picnic

You’ll be moving around, sitting on grass, and potentially getting a little messy. The outfit needs to be practical yet stylish.

  • The Formula: A simple, breezy dress + practical footwear + sun protection.

  • Actionable Steps:

    1. Choose a midi or maxi dress in a durable, breathable fabric like cotton poplin. A-line or smock styles are great for freedom of movement.

    2. Skip the heels and opt for comfortable, stylish sandals or canvas espadrilles.

    3. Protect yourself from the sun with a wide-brimmed straw hat and a pair of sunglasses.

    4. A crossbody bag is perfect for keeping your hands free.

  • Concrete Example: A floral-print cotton smock dress that hits mid-calf. Pair with brown leather slide sandals. Accessorize with a large straw tote bag and a classic pair of aviator sunglasses.

Scenario 4: A Date Night In or Out (Local)

Whether you’re ordering takeout and lighting candles or heading to a nearby restaurant, this outfit needs to feel special.

  • The Formula: A chic top + stylish bottoms + deliberate details.

  • Actionable Steps:

    1. Choose a statement top. This could be a silk camisole, a lace-trimmed blouse, or a simple top with interesting details like puff sleeves.

    2. Pair with your favorite pair of jeans (dark wash for a sleeker look) or a pair of sleek trousers.

    3. Add a bit of shine with delicate jewelry like a layered necklace or hoop earrings.

    4. For a date night in, go barefoot or with a pair of elegant house slippers. For a date night out, a pair of block heels or sleek flats works well.

  • Concrete Example: A black silk camisole with a delicate lace trim, tucked into a pair of dark-wash, straight-leg jeans. Add a pair of small gold hoop earrings and a few layered necklaces. For a night in, a pair of velvet house shoes is a stylish and comfortable finish.

Maximizing Your Staycation Wardrobe: The Details

The devil is in the details, and this is where you elevate a good outfit to a great one.

  • Fabric is Your Best Friend: Choose natural, breathable fabrics like cotton, linen, silk, and Tencel. They feel great, drape beautifully, and are comfortable for all-day wear. Synthetic fabrics can trap heat and feel sticky.

  • The Art of Layering: A lightweight jacket, a cardigan, or even a chic scarf can completely change an outfit and adapt it to different temperatures. A simple T-shirt and joggers become a full look with the addition of a structured blazer.

  • Footwear Matters (Even at Home): Don’t just settle for old sneakers. A pair of elegant leather slides, minimalist sneakers, or even some plush house shoes can make a huge difference in how you feel and how your outfit looks.

  • Accessories are Key: This is where you can have fun and express your personality.

    • Hats: A baseball cap for a casual walk, a wide-brimmed hat for the garden.

    • Bags: A small crossbody for quick errands, a large tote for carrying a book and a blanket to the park.

    • Jewelry: A few carefully chosen pieces—a watch, a delicate necklace, or a pair of statement earrings—can make you feel polished.

The Power of “Feeling Good”

Ultimately, the best staycation outfits are the ones that make you feel good. They are a reflection of your desire to relax and enjoy yourself, but also to feel a sense of occasion. When you put on an outfit that you love, it changes your mindset. It transforms a regular day at home into a special experience. This guide isn’t about being perfectly dressed for a runway; it’s about being thoughtfully dressed for the ultimate in relaxation and self-care. It’s about showing up for your staycation in style, and that is a truly powerful thing.