This post is in partnership with Walmart
Hosting doesn’t need to be complicated, and choosing what to wear shouldn’t be stressful. In my book Simple Gatherings I shared approachable hosting styles and tips for creating memorable moments. No matter your personality or entertaining style, a few thoughtful touches and comfortable clothing choices can help guests relax and enjoy the time together.
Below I’ll outline four easy gathering ideas and suggest what to wear to each. Scroll down for outfit and gift ideas you can add to your wardrobe for the season.
Which style speaks to you?
Here are four outfits (all available at Walmart) that make it simple to be ready for different occasions. Many of these pieces are affordable gift options too — think a cozy sherpa shacket, hair clip sets, or plush socks for stocking stuffers or a treat for yourself this winter.
Casual Themed Gathering:
A casual themed get-together — like a charcuterie board and game night — gives your event direction without a lot of fuss. A simple theme, a few small details, and good company create the perfect relaxed atmosphere.
What to wear? For a casual themed gathering choose stylish jeans, a bright sweater, and ankle booties — comfortable yet put-together.
- Purple sweater – A soft, bright sweater that adds color to winter outfits. It comes in several colors so you can mix and match with your wardrobe.
- Super High Rise Straight Jeans – These high-waisted jeans have a structured feel and good quality for a great price. They offer a polished look while remaining comfortable.
- Black Ankle Boots – A versatile pair with a supportive memory foam sole that pairs with many looks.
Come As You Are:
This is the most relaxed type of gathering — casual, often impromptu, and very welcoming. Invite guests over with little notice, order pizza or pull snacks from the pantry, and enjoy simple entertainment like a movie or good conversation.
What to wear? Comfort is key. With the right pieces you can be cozy and look cute at the same time.
- Sherpa shacket — The softest, comfiest layer that looks great around the house or out running errands. The classic button details and collar give it a polished feel despite its plush texture.
- Cargo joggers — A cinched waist and tapered ankle make joggers feel a bit more put-together than loose sweatpants while staying cozy. Pockets add practicality and they come in multiple colors.
- Claw clip — An easy, stylish way to pull hair up while still looking cute. Sets come in several color options and sizes to suit different hair lengths.
- Cozy socks — Soft, plush socks perfect for lounging and thoughtful additions to holiday stockings or gift bundles.
Celebration Party:
A celebration often calls for an evening gathering with more deliberate planning — candles, a sit-down dinner or elegant appetizers, and a festive atmosphere.
What to wear?
For a celebration, consider dressing a bit more formally to match the mood. A simple black slip skirt, a fitted top, and a few delicate accessories will help you feel polished without being overdressed. These wardrobe staples make it easy to prepare for special occasions with confidence.
- Black slip skirt — A silky, flowy skirt that instantly elevates an outfit. Pair it with a fitted top or tuck in a lightweight sweater for a cozy yet refined look.
- Black mule dress shoes — Pointed-toe mules with a subtle knot detail and memory foam sole offer style and comfort for evening wear.
- Long sleeve ribbed crew neck shirt — A soft, versatile basic that dresses up well with jewelry or layers.
- Hair clips and simple jewelry — Small hair accessories and delicate gold necklaces or bracelets finish the outfit and add a festive touch.
Meet up for coffee
A coffee meetup is the simplest gathering — low pressure, easy to schedule, and a great way to reconnect one-on-one. No prep, no fuss, just conversation and a warm drink.
What to wear? On a crisp day, be cozy but camera-ready with jeans, a crew neck top, ankle boots, and a sherpa shacket for warmth and style.
- Cozy sherpa shacket — A versatile, comfortable layer you’ll reach for again and again, from running errands to grabbing coffee with a friend.
- Super high rise straight jeans — A flattering, modern jean that pairs well with boots and casual tops.
- Black ankle boots — Comfortable and stylish for walking around town.
- Black crew neck — A simple, dependable base layer for any casual outfit.
A quick close-up shows the soft texture and cute button details that make this shacket a favorite for warmth and style.
Shop these looks (click each graphic for details and more):
See more holiday outfits we recently shared.
Find more at Walmart:
Holiday party styles
Winter styles
Family holiday PJ’s and sleep
Gift ideas