What Should I Wear

One occasion to a page: what to put on, and what to leave at home.

51 pages

0–9, A 9

What Should I Wear in 50 Degree WeatherWhat to wear in 50 to 55 degree weather: for an ordinary day, at school, on a run, on a bike and outdoors all day, and what to leave at home.
What Should I Wear for 50s DayWhat to wear for 50s day at school or a fifties party: skirts, jeans and jackets, shoes, hair and looks from your own wardrobe. Poodle skirt · Felt circle skirt with a record or music notes · Full skirt with a defined waist
What Should I Wear in 60 Degree WeatherWhat to wear in 60 to 65 degree weather: for an ordinary day, at school, on a run, on a bike and in a mild city or on a coast, and what to leave at home.
What Should I Wear for 80s DayWhat to wear for 80s day at school or an 80s themed party: tops, bottoms, shoes, hair, accessories and looks from your own closet. Oversized sweater in a bright color · Jacket with padded shoulders · Blouse with puffed sleeves
What Should I Wear for a BaptismWhat to wear for a baptism or a christening: as a guest, for the baby, and as an adult baptized by immersion, with what to bring.
What Should I Wear for a HeadshotWhat to wear for a professional headshot: tops, colors, jackets, glasses and jewelry, with a row for actors and what to leave off. Your usual work clothes · One notch dressier than your workday · Collared button-down shirt
What Should I Wear for a HikeWhat to wear for a hike, from the first layer to the boots, with a row for a 14er and what to leave at home. Moisture-wicking T-shirt · Wool base layer · Thin thermal top, on a cold day
What Should I Wear to an Indian WeddingWhat a guest wears to an Indian wedding, from the mehndi to the reception, with the colors to avoid. Kurta with churidar trousers · Sherwani · Jodhpuri suit
What Should I Wear to an AuditionWhat to wear to an audition, sorted by kind: acting, a musical’s dance call, a music school and a prescreening video. Clothes you can move around in easily · Tracksuit bottoms · Leggings

B 7

What Should I Wear to a Baby ShowerWhat to wear to a baby shower as the mom-to-be or as a guest: dresses, trousers and shoes, by venue and by season, and what to leave at home.
What Should I Wear to the BalletWhat to wear to the ballet, from jeans at a matinee to a gown at a gala, in the words of the companies themselves. That new cocktail dress · Business casual outfit · Suit you have been waiting to wear
What Should I Wear to a Barn WeddingWhat to wear to a barn wedding as a guest: dresses, suits and jackets, boots and block heels, evening layers and a row for a western wedding. Short or midi dress · Slip dress, dressed down · Dress with sleeves, in fall
What Should I Wear to a Beach WeddingWhat to wear to a beach wedding as a guest: dresses, suits and shirts, shoes for sand, hats and colors, and what to leave at home.
What Should I Wear to Beginners BalletWhat to wear to a beginners ballet class: leotards and tops, tights and leggings, shoes, hair, skirts and warm-ups, and what an adult may wear instead. Leotard, the traditional top · Fitted T-shirt · Workout tank top
What Should I Wear to a Black Tie Optional WeddingWhat to wear to a black tie optional wedding as a guest: the tuxedo, the dark suit that replaces it, long and shorter dresses, shoes and what to leave at home. Tuxedo you already own · Black dinner jacket with matching trousers · Midnight blue tuxedo
What Should I Wear BowlingWhat to wear bowling: tops, bottoms, socks and shoes, with what a league or a school team adds and what to leave at home. T-shirt you can swing an arm in · Relaxed polo shirt · Sweater for a casual night

C–F 7

What Should I Wear to a Celebration of LifeWhat to wear to a celebration of life: how to read the invitation, outfits by venue, a personal touch, and what to leave at home.
What Should I Wear to ChurchWhat to wear to church: come-as-you-are, smart casual and Sunday best congregations, traditional parishes, a famous cathedral or basilica, and what to leave at home. Clothes you already own and feel comfortable in · Polo and khakis · Jeans with a nice top
What Should I Wear to My Class ReunionWhat to wear to a class reunion, by where it is held: a hotel ballroom, a bar or restaurant, a picnic, with shoes and a layer for the evening. Midi dress, for a ballroom · Jumpsuit, for a ballroom · Sport coat, button-down and chinos
What Should I Wear for Cross Country RunningWhat to wear for cross country running: clothes by weather, shoes and spikes, what a race day uniform needs, and what to leave at home. Lightweight running shorts · Top that wicks sweat · Plain T-shirt, shorts and socks
What Should I Wear for Family PhotosWhat to wear for family photos and engagement pictures: a color family first, then clothes that go together without matching.
What Should I Wear Floating the RiverWhat to wear floating the river: swimwear, shoes that stay on, sun cover, life jackets, cold-water layers, and what to leave on the bank.
What Should I Wear to a FuneralWhat to wear to a funeral, a viewing or a memorial service: dark, plain clothes, and what to leave at home. Black · Navy blue · Gray or charcoal

H–M 9

What Should I Wear to a Hockey GameWhat to wear to a hockey game: layers, long pants, shoes, hats and bags, for an arena, a small rink or an outdoor game, and what to leave at home.
What Should I Wear Horseback RidingWhat to wear horseback riding: helmet, pants, boots and tops, with rows for a first lesson and a trail ride, and what to leave at home.
What Should I Wear to Go Ice SkatingWhat to wear to go ice skating: legs, layers, socks, gloves and helmets, for an indoor rink or outdoor ice, and what to leave at home. Sweatpants or warm-up pants · Leggings you can move in easily · Long pants, whatever the season
What Should I Wear to a Job OrientationWhat to wear to a job orientation by kind of workplace, with the answer for when nobody told you. Whatever your welcome message says · Business casual · The clothes of the job itself
What Should I Wear KayakingWhat to wear kayaking on warm water and on cold, from a swimsuit to a dry suit, with the life jacket rules. Swimsuit · Quick-dry T-shirt · Quick-dry shorts
What Should I Wear in VegasWhat to wear in Las Vegas: for the Strip, a pool or dayclub, a nightclub or lounge, a show and a desert hike, and what to leave at home.
What Should I Wear to a Mardi Gras PartyWhat to wear to a Mardi Gras party: the three colors and what each means, masks, beads and costumes, with rows for a lunch, a parade and a ball. Something purple · Something green · Something gold
What Should I Wear for a MassageWhat to wear for a massage: what to arrive in, what stays on under the sheet, and what to wear for shiatsu, Thai, chair and sports massage.
What Should I Wear to MEPSWhat to wear to MEPS: the processing command’s dress table for women and men, underwear, what may stay on, and what is unauthorized.

O–P 7

What Should I Wear to an Oath CeremonyWhat to wear to a naturalization oath ceremony, by part of the outfit, with what the official notice and two courts say.
What Should I Wear to Officiate a WeddingWhat to wear to officiate a wedding, for women and men: dresses and separates, suits, colors, shoes for standing and what to ask the couple.
What Should I Wear on a PlaneWhat to wear on a plane: layers on top, bottoms, shoes for the security line, a row for a long flight and what to leave in the bag. T-shirt or light shirt as the base layer · Zip-up hoodie · Light jacket that comes off fast
What Should I Wear to an Outdoor ConcertWhat to wear to an outdoor concert, by where you will stand or sit: a lawn, a crowd, a seated hall or a punk or rock show, with shoes. Extra jacket for the late evening · Blanket to wrap up in · Layers to add after sunset
What Should I Wear to an Outdoor RodeoWhat to wear to an outdoor rodeo: jeans and skirts, shirts, boots, hats and buckles, what to add for a hot afternoon or a cool night, and what to leave at home. Bootcut jeans · Dark denim with a pressed western shirt · Jeans with a cowboy hat and boots
What Should I Wear to PaintballWhat to wear to paintball: tops, pants, shoes, gloves and headwear, what the field hands out, what changes with the weather, and what to leave at home. Long sleeves and long pants · Closed-toe shoes with grip · Old clothes you do not mind ruining
What Should I Wear for Picture DayWhat to wear for picture day: tops, colors and the backdrop, layers, hair and glasses, uniform schools and what to leave at home. Solid-color shirt or blouse · Collared shirt, ironed · Whole outfit, in case the pose shows it

Q–W 12

What Should I Wear to a Quinceañera as a GuestWhat a guest wears to a quinceañera: dresses, suits, colors, the Mass and the dancing, and the colors to leave to her. Knee-length dress in a rich color · Midi dress · Floor-length gown
What Should I Wear for Rock ClimbingWhat to wear rock climbing, for a first session at an indoor wall and for real rock, with shoes, hair and rings. Sweatpants · Leggings or tights that stretch · Long athletic shorts
What Should I Wear to a Salsa ClassWhat to wear to a first salsa class: tops, bottoms and shoes that turn, what to bring, and what studios ask you to leave at home. Breathable T-shirt · Fitted tank top · Well-fitted polo shirt
What Should I Wear in a SaunaWhat to wear in a sauna: gym, pool and campus rules, textile-free spas, infrared suites, what to carry and what to leave outside.
What Should I Wear to SchoolWhat to wear to school: tops, bottoms and shoes, PE days, uniform schools, recess weather, hats and hoods, and what to leave at home.
What Should I Wear for Senior PicturesWhat to wear for senior pictures: everyday and dressed-up looks, cap and gown, uniforms, the yearbook portrait, colors, shoes and props.
What Should I Wear SkiingWhat to wear skiing or snowboarding, layer by layer, from long underwear to goggles, with what to rent on a first day. Synthetic base layer top · Thermal leggings · Merino wool base layer
What Should I Wear SkydivingWhat to wear skydiving: tops, pants, shoes and cold-day layers, what the drop zone lends, hair and glasses, and what stays on the ground. Athletic clothes that fit close · Long pants, even on a hot day · Lace-up sneakers, tied tight
What Should I Wear to a Teaching InterviewWhat to wear to a teaching interview: suits and separates, dresses, shoes for a school tour and clothes for a sample lesson. Dress pants · Suit jacket and tie · Blazer
What Should I Wear for a Video InterviewWhat to wear for a video interview: plain tops, colors to test, what goes below the desk and what to leave off. Plain collared shirt · Plain blouse · Blazer over a plain top
What Should I Wear to a Wedding ShowerWhat to wear to a wedding shower as a guest: dresses, trousers, colors and shoes, for a garden or a restaurant, and what to leave at home. Dress of any length · Midi dress, for a dressier shower · Sundress, for a casual shower
What to Wear Whale WatchingWhat to wear on a whale watch, from a warm jacket to rubber-soled shoes, with what to bring and what to leave. Thin top as a first layer · Long-sleeved shirt as a second layer · Sweatshirt

Each page here takes one occasion or activity and answers one question: what should I wear? A list is sorted by part of the outfit or by layer, with a row of things to leave at home, and each thing has one line of advice.

What a list says is right for the occasion is checked against guidance published by the people who run it, such as funeral directors, tour operators, employers and careers services, and every source is named under the list.

0–9, A 9

B 7

C–F 7

H–M 9

O–P 7

Q–W 12

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