How to Figure out What to Wear Wherever You Go

Last Updated: October 23, 2022

While some people have an innate sense of what to wear no matter where they're going, for others, it's a real challenge. If you're in the latter camp and find sorting out the right clothes for each occasion and place a royal pain, you're in need of some quick and easy advice. Perfecting an outfit so that you get it right each time will require some forethought about comfort, suitability and what looks best on you. Once you've worked out these things, you'll be able to apply the method from this point on.

Part 1

Part 1 of 2:

Planning ahead

1
Think about the event before the day or evening it happens. This will help relieve you of those last-minute insane dashes through an entire wardrobe. The things to cover include:
- What is the event? Is it formal, semi-formal, or all-out casual but nice? Is it a formal party or are you just casually hanging with your friends?
- What season is it?
- What will the weather/temperature probably be on the day/night?
2
Consider your trusted confidantes. These might be friends, a spouse, your children, etc. Then make use of them for the following questions:
- What are you wearing? (Only needed if you're in so much doubt, you can't figure out what to choose.)
- Which of my outfits do you think I look great in?
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3
Check the chosen clothes beforehand. Fix up any tears, loose hems, stains, etc. or get them to a dry cleaners.

Part 2

Part 2 of 2:

Choosing the clothing

1
Choose according to season. If it is cold, wear warmer clothing, if it is hot, wear cooler clothing. If you really must wear something you'll freeze in, add a coat or jacket. Do not wear anything you'll boil in, it is nigh on impossible to feel comfortable and you may faint or get heat stroke.
2
Choose by style. It might be fashionable, but does it fit and look great on you? If not, don't force yourself into it. Instead, stick with whatever makes you look wonderful. Gone are the days when only one style ruled the roost. You are liberated enough now to be able to choose what brings forth your best features. It's okay if it's not the textbook outfit to wear, it's more important that you feel confident with what you have on.
- You can give a nod to current trends by adding an accessory that sums up the trend, be it by color, shape or logo.
3
Make sure all of your clothing fits nicely. When everything is popping out or you can't distinguish your frame, the look fails to present you at your best. If something is really great and not in your size, get it tailored.^{[1]
X
Expert Source

Kathi Burns, CPO®
Board Certified Professional Organizer
Expert Interview. 31 December 2019.} A well-tailored outfit is always worth the effort and expense.
4
Consider comfort. Fashion doesn't always care about comfort but you should, especially if whatever you're going to requires you to stand a long time, or sit on hard seats, or be blown about by a cold breeze while pretending to like the weather. Think about the venue too––heels on a lawn party will soon grow really exhausting, while running around in just a bikini at the pool party will be less desirable when it comes time to evening drinks indoors at the bar.
5
Use layers. These are especially useful when you are not sure what the day holds; a cute knee length skirt, layered tanks, and a light jacket will go almost anywhere.^{[2]
X
Expert Source

Kathi Burns, CPO®
Board Certified Professional Organizer
Expert Interview. 31 December 2019.} Peel or add layers to add or subtract formality. At nighttime, add some eye liner, high heels, maybe an over sized accessory and you'll get a whole new nighttime look.
6
Prefer simplicity over all else. Tons of accessories aren't necessary. Stick to your main piece and build around it with things that complement it.
- Remember texture, prints, and colors. Contrast is nice, but when everything clashes, it's going to spoil your whole presentation.
- A scarf is cute, whether it is a silk Hermès scarf or a knitted Burberry scarf.
7
Wear minimal make-up if you're going all out with the clothes and more attention-grabbing makeup if your clothing is more simple (e.g.: red lipstick and eyeliner).
8
Own it. If you show up in a place and realize you're dressed completely wrong, own it. Make it seem like you did it on purpose—people will admire you rather than be embarrassed for you.

Warnings

Don't copy exactly what everyone else is wearing. — Just get a feel of the style that people will be wearing.

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Always ask more than one other person's advice (but make sure you show that you have an idea that you know what you like, so it doesn't seem like you really have no clue at all).

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