One of the biggest problems I had when I first decided I wanted to dress better was finding information relevant to me, a beginner and — perhaps more significantly — an undergrad without an unlimited budget for high-end clothes. There was so much information out there, but I didn’t really know where or how to start. So in the interest of helping out our fellow fledgling menswear enthusiasts, the following are some tips I wish I had when I first started.
1. Think about your lifestyle/job/what you do on a day-to-day basis and whether there are any specific factors that might limit what you can or can’t wear. A college student won’t be going for the same look a corporate attorney or physician will be. A key part of being well dressed is being properly dressed for the occasion — you want to look good without being out of place.
2. For inspiration, find someone whose style fits what you envision yourself looking like. Whether this is a character in a TV show/movie, a celebrity, a blogger, or someone you know in person, study them. Figure out what it is you like so much about their style. Examine how they dress to accommodate or accentuate certain body features. You certainly won’t want to just copy someone’s style directly, but use it as a guide when you’re thinking about what you want to wear. Similarly, find brands that make clothes similar to those that you want to wear. Browse stores, lookbooks, and catalogs and figure out which companies and styles appeal to you the most. By no means should you get all of your clothes from one place, but when you don’t know exactly what you’re looking for yet, exploring different brands will help you find a look that suits you.
3. Start with the basics. Simon Crompton once said, “It’s always worth starting with something quite normal because you’ll get the most wear out of it and once you’ve got it you can get something else next time … You learn that actually the kind of things you love most and use most are quite ordinary” (emphasis ours). Fight any impulses you might have to get clothes with complex patterns or loud colors, and acquire basic shirts in simple colors such as blue and white or some combination of those (oxford cloth button downs — commonly referred to as OCBDs — characterized by the casual, woven oxford cloth and button down collars, are a great choice) first. Maybe add some striped shirts or a subtly checked shirt as you progress. Especially as you’re just starting out, you shouldn’t be buying individual “outfits” or “looks”. Rather, you should be getting clothes that harmonize with everything else you have.
4. Know that it’s a slow progression. It takes a directed effort to get to where you want to be. Get your feet wet and try things out. You may screw up. You may even look a little funny at times. But you may also discover something that revolutionizes the way you dress. You’ll never get there if you don’t try. That being said, it’s much easier to introduce one major change at a time. Make sure you’re comfortable wearing button-up shirts before you start adding a blazer.
5. Carry yourself with confidence. No matter what you do, you’ll look immeasurably better if you are confident.
6. Read this blog. You’ll thank us later (just buy us a drink). We certainly don’t know everything, but we’ve been where you are before.
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