Ask LH: How Can I Learn To Dress Better?

Ask LH: How Can I Learn To Dress Better?

Dear Lifehacker, I admit that I’m not the snappiest dresser. I know how to keep my clothes clean and ironed and whatnot, but I don’t always know what I should wear and I don’t look quite as neat and professional as my friends and coworkers. How can I learn to dress better? Sincerely, Schlemiel in Seattle

Dear Schlemiel,

This is one of those things many people learn growing up. If you missed out on that exposure, learning later in life isn’t as easy and straightforward. The upside is that most of what you need to learn is observational, and you have hundreds of examples around you every day to learn from. Before you start looking at other people’s clothing choices, start by looking at your own.

Perform a Wardrobe Audit

Before you go out to buy anything new, the first place you should go shopping is your own closet. If you’re an adult with a job, you’re probably covered for at least three situations: work, social outings and lazy home clothes. Some of your clothes may serve multiple purposes (for example, the jeans you go out in may be comfortable enough to watch Netflix in), but you can probably put together outfits for at least these situations.

Being well-dressed starts with being prepared for a situation. Few people you see who look great in their outfits started by hitting the store right before they arrived. Do a review of your closet. Ask yourself if you would be ready, right now, to dress for the following type of events:

  • Weddings

  • Funerals

  • Job interviews

  • Black-tie events

  • Dressy restaurant outings

  • Birthday/graduation/anniversary parties

This list is by no means comprehensive, but as an adult (particularly if you’re young), you can probably expect to be invited to at least a couple of the things on this list — if not all of them — in a given year. Do you have clothing appropriate for each of the events? If not, start picking out specific events you want or need to be prepared for and start there.

Learn the Basics For Specific Situations

There are certain basics that apply to any situation. Here is a non-comprehensive list of the basics you should cover:

  • Buy clothes that fit. Often, it can feel better to wear clothes that are a bit bigger on you than you would normally wear. However, if you wear pants with a 36-inch waist and you get something with a 38-inch waist, it will look loose and frumpy.
  • Wear things that you’re comfortable with. Part of the reason you wear nicer clothes, aside from fitting in with your current event, is to boost confidence. If you can’t enjoy how you look, or your clothes don’t feel natural, you’ll fidget, squirm and grimace your way to undoing all your hard work.

Once you’ve narrowed down which occasions you want to focus on first, you can start tracking down outfits for specific events. Is a suit overkill for a job interview? What type of dress should you wear to a wedding? How much do you have to spend on dinner before jeans are no longer OK? Ask these questions on a case-by-case basis.

Once you narrow down which situations you want to dress for, you can start searching for appropriate looks. The sources for these won’t always be the same. For example, you can find advice on how to dress for work right here on Lifehacker, but you may have to turn to other sites for the perfect dress to wear to the club.

Over time, the skills and tricks you learn for one outfit will carry over to other situations. Don’t overwhelm yourself by trying to buy hundreds of dollars worth of clothes for every possible event that you don’t even know you’re going to yet. Get clothes for the dinner date you’re going on next week, and the experience you get there will inform what type of shoes you should wear to the office.

Find a Mentor or Group of People to Provide Feedback

No amount of Googling will tell you that you look good. Your body is unique, and there are dozens of factors that can make an outfit that looks fantastic on one person look horrible on another (or vice versa). Your best shot at looking great is to have someone personally look at how clothes fit you. The more experience that person has with making fashion decisions, the better.

If you can’t find someone to help coach you, there are still options. Reddit has dedicated subreddits devoted to helping both men and women get their questions answered, as well as post pictures to ask for feedback. There are also apps and sites like Fashism that exist solely to share outfits and get opinions or inspiration.

If you’re not comfortable with sharing pictures of yourself online (and have some cash to spare), you can hire a personal shopper. In some cases, their whole job is to find the clothes you’re looking for and bring them to you, but others will walk you through the process and provide feedback. Alternatively, if you want to save that money, you can ask employees at clothing stores for feedback.

Read Fashion Sites (and Keep Reading)

Once you’ve got the basics down, you can start getting into the nuance of your wardrobe. This is where specialised sites and publications for men and women can be useful in keeping up to date on style changes over time. While you may have been able to get with wearing overalls with one strap unbuckled in the ’90s, you couldn’t pull that off today. Fashion evolves over time. Keeping up with current trends — to a certain extent at least — is just another part of the process.

Also keep in mind that every publication you subscribe to will have its own particular style. Check out a few magazines and sites, and see how much their style relates to your own. Don’t just dive in to the first publication with Robert Downey Jr on the cover (mostly because you can’t pull off what he can… he’s Iron Man), but instead find something that offers tips in the style you’re looking for.

More importantly, find resources for a style you like and can be comfortable in, and continue in that vein. Don’t just grab the first copy of GQ you can find and buy whatever Bryan Cranston is wearing. Your wardrobe needs to be a reflection of your personal style, as well as being something that you can feel good in.

Also, remember the cardinal rules in any kind of etiquette: follow the host and don’t deviate too much from the crowd. If you’re looking to dress for work, find out how your boss dresses (as well as seasoned coworkers who are on your level). If you’re going to a wedding, you don’t want to upstage the bride and groom, but you should fit in with most of the guests. When you’ve got that down, and you can be happy with what you see in the mirror, you’re already ahead of the curve.


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Photos by Magnus D, Lee Haywood, Orin Zebest.


  • I would second the suggestion of ‘Style Girlfriend’. Megan Collins’ blog dedicated to men’s style was an invaluable resource for my recent wardrobe makeover. I would also recommend ‘the Effortless Gent’, Dappered and Primer Magazine.

  • Stop listening to yourself, start listening to your sister or girlfriend or similar. Who cares if you think it looks good.. you want chicks to think it looks good, am I right? So get their opinions.

  • Next time you go on a holiday to Asia (Thailand, Singapore are good example), stop and get a tailored suit made. You’ll get something that fits perfectly for a couple of hundred dollars.

    You get to pick the fabric and style, plus there are always people to help out. Personally, I go for a grey, single-breasted, three-piece suit (but that’s just my style) 🙂

    Oh, and always get a couple of extra pairs of pants while your at it. You’ll have those cleaned, much more often than you will the suit jacket.

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