How To Be Stylish: A Beginner’s Guide

So, you want to up your style game? Perhaps you need help dressing for an interview or you’ve decided that now you’re a little older, you’d like to try dressing a little smarter? Or maybe you’re like me, a mild eccentric interested in style, utterly seduced by the thought of enjoying a cigarette in a silk smoking jacket while reclining in a deep oxblood chesterfield, surrounded by hardback books?

Whatever your reason, there are a few simple steps to becoming better dressed. It’s not as simple as throwing on some expensive clothes though. Far from it; it’s a way of life that you need to commit to. It takes time, effort and yes, money. It’s not particularly cheap to dress well although with some thoughtful, versatile purchases and prudent sale shopping, you can garner a stylish wardrobe on a sensible budget.

The following are the top ten ways to get you started:

1. Figure out your own personal style

How do you want to dress? Do you want master tailored separates or go with a more utilitarian, work wear inspired look? You need to be comfortable in what you’re wearing. When you feel that you look good, you’ll carry yourself with confidence. If you’re wearing clothes that you’ve bought because of the advice of an online blog, even if they’re not “your style”, you’ll be uncomfortable and that will show in your body language. Find your own style and tweak it from there.

2. Ignore trends

Style and fashion are two very different things. If you try to keep up with trends, you’ll be constantly updating your wardrobe. Ralph Lauren once said “Style is very personal. It has nothing to do with fashion. Fashion is over quickly. Style is forever” and it’s true. If you keep trying to be fashionable, you’ll never be stylish.

3. Accrue the basics

I’ll cover this more in a separate, dedicated post but you need to start by nailing the basics. Basically, the building blocks of a wardrobe that will always be in style. Think minimalist white trainers, dark denim and navy polo shirts. The pieces that will work year-after-year-after-year.

4. Buy with versatility in mind

You’ll be amazed at how many outfits you can make by picking up a few well-considered pieces. The right navy blazer for example will pair with chinos, jeans, trousers, shoes, and trainers, allowing you to dress it up or down as necessary.

5. Find a good tailor

Unless you are the luckiest man on the planet, clothes will not fit you perfectly off the rack. You’ll need to invest some time and money in going to a tailor. The good news is that most alterations are fairly inexpensive. A decent tailor or seamstress can hem a pair of trousers for as little as £6. It really does make the world of difference too. There’s nothing worse than seeing three inches of excess fabric pooling over somebody’s shoes or baggy shirtsleeves. It looks sloppy.

6. Learn how to care for your garments

Good clothes require good care. There’s no point in investing money in clothing, then getting them altered to fit to then not look after them properly. Buy yourself a clothes brush, shoe brushes, creams and polishes (I swear by Saphir’s shoe care products), decent hangers for hanging blazers and coats with shoulder support and garment bags to keep suits and coats fresh. You’ll really elongate the lifespan of an item by taking care of them.

7. Find “your” shops

With globalisation and fast fashion, no two stores offer the same sizing. In some cheaper stores, two of the same item, in the same size can sometimes fit differently. You’ll need to shop around to find a store that suits your frame. I tend to buy my blazers from Suitsupply, my shirts and trousers are usually from Reiss, swimwear and polo’s from Orlebar Brown and basics like sweaters and t-shirts from Uniqlo.

8. Invest in quality accessories

Don’t be the guy that wears a black belt with brown shoes, it looks odd. I try to keep my shoes, belt and watch strap in complimentary colours; the devil is in the details after all. Pick up a decent quality belt from somewhere like Suitsupply and you’ll be set for years. They even offer a free in-store shortening service. Likewise, invest in a decent quality pair of socks with hand stitched toes and wave goodbye to your socks rubbing across the knuckle of your toes.

9. Don’t over-accessorise

The old adage of “less is more” is very much true when it comes to accessorising an outfit. Ideally stick to 3 accessories maximum including a watch. Also, don’t accessorise for the sake of it. A tie bar is used to keep a tie in place. If you’re wearing a waistcoat, it performs the same job; drop the tie bar.

10. Buy better shoes

If you take nothing else away from this article then please pay attention now, this is the most crucial point. It is impossible for a man to be well-dressed in bad shoes. You could be wearing a beautiful bespoke suit from Savile Row and it will be completely spoiled by a shoddy, unkempt pair of shoes. Invest in quality footwear. They’ll last you for years and your feet will be grateful.

These ten tips will get you started on the road to being better dressed but it’s not an over-night process. A well-rounded, stylish wardrobe can take years to curate. The key is to invest in quality pieces that won’t go out of style. The most important thing to remember though, is to have fun with it. The clothes you wear are an extension of your personality and a means of self-expression. Wear what you like and what makes you feel good, even if it goes against societal norms. That’s what it means to have a sense of style.

I’ll be posting more in-depth articles on some of the above points soon. Subscribe to my feed to get updates when they go live. Finally, feel free to leave a comment below, I’d love to hear your thoughts.

Thanks for reading,
Terry