Buying clothes

Every now and then someone asks me for help dressing better. I tend to give variations on the same general answer, so I thought I’d write it down in case anyone else is interested in how I think about it.

I generally don’t like to shop very often, nor do I like spending a lot of money on clothes, but I do like variety and novelty in how I dress. I have the advantage of having built up a wardrobe over several years that makes this easier. For people just starting out, remember that you don’t have to do it all at once. The pieces and brands I describe here are for my personal style, but I think the approach is pretty generalizable.

I generally divide my shopping into three categories: Basics, Flavor, and Faves.

Starting with Basics at the bottom of the pyramid, I expect to spend more per item and wear less often per item as you go up the pyramid. Basics are the majority of my wardrobe, then Flavors, then Faves.

Basics

Basics are the workhorse of the wardrobe — things like solid color v-neck t-shirts, black skinny jeans, and simple outerwear like cardigans and hoodies. I tend to wear these things all the time, but they rarely define the outfit.

Instead, they’re intended to pair subtly with items from the Flavors and Faves without breaking the bank. Sometimes I end up in a trap because I’ll make an outfit I really like out of two Flavor pieces: maybe a blue button-down with a white pattern and white pants — but then I feel like every time I wear the shirt I have to wear the pants and vice versa, and it’s so distinctive that I can only wear the outfit every so often. By having a handful of basics that I can pair those pieces with, I get to wear each piece a lot more often without it feeling like I only have a handful of outfits. The white pants get dressed down with a black v-neck, the button-down gets paired with khaki chinos, and wearing the two together stays a special occasion that feels unique when it comes together.

Thankfully, you can get these items for really cheap. A t-shirt from Uniqlo costs $6, so I’ll get a handful of colors and mix and match them with various outfits. It’s an inexpensive way to change up what you wear and get a lot more value out of the other, more expensive items in your wardrobe.

Basics can include: t-shirts, simple Oxford shirts, shorts/pants, basic outerwear

My go-to: Uniqlo

Exception: a nice pair of jeans can be worth spending a lot on if you’ll wear them all the time and they make your butt look good

Flavors

This is where you really get to define your personal style. Flavor pieces are usually more distinctive, and will help you stand out as an intentional dresser. When people picture you and describe your style, they’ll be remembering these pieces when they answer.

It’s because these pieces are more memorable that I tend to wear them a bit less often than Basics. I’ll wear the same pair of black pants three times in a week, but if I wear the same patterned, short-sleeve popover three times a week, people will start to notice. You want people to remember you for having a style, not a uniform.

If you’re just starting out with building a wardrobe, you might only want to buy a handful of things so you don’t break the bank. One simple way to make sure you’ll get a lot of value out of your new clothes is to think of two different basics you can pair a piece with before buying it. For that really cool shirt you’re trying on — what will you wear it with? Can you match it with shorts and pants? Multiple colors? If so, it’s a great piece to start building a collection with.

A fun aspect of defining your style is evolving it over time. Variety will be easier to come by when you’ve been collecting a wardrobe over years.

Flavors can include: patterned button-downs, popovers, textured slacks, nice sweaters

My go-to: J-Crew

Faves

I love this section of my closet, hence the name. Faves are those things that are unique, memorable, and fill you with confidence when you wear them. They’re really distinct, so you can’t wear them all the time, but every time you do is a special occasion. You won’t own many pieces like this, but odds are, you’ll pay a good amount for the ones you have. I have a long sleeve white silk button-down with a mandarin collar and asymmetric button line that I got in Montpellier that I only wear a few times a year — but every time I do is so fun.

My favorite occasion for buying Faves is when I travel. In addition to being special for how the piece looks, I know I’ll also have a great memory to think of when I put it on.

Faves can include: distinctive shirts, a fancy peacoat, unique shoes, anything you like!

My go-to: Travel shopping (other people I know sometimes shop at All Saints or Scotch and Soda for their nicer things)

Brand guide

Once you have your strategy, it’s time to pick where to shop. Below is a handy chart that works for my style. Pick the style and price range that works for you!

Honorable mentions: Everlane, Club Monacco, Selected

If you want to knock out a bunch of shopping at once, don’t be afraid to try a department store. It’s not my preferred shopping experience, but it can be a good one-stop shop for when you want to update a wardrobe all at once. The Rack in particular can be a cheap way to fill out your Flavors.

My go-to: Nordstrom Rack

Closing thoughts

The most important thing about clothes is that you like how you look in them. If for any reason you put on some fancy item and don’t like how you look, then don’t get it. And if you look in the mirror and feel confident wearing a basic t-shirt, then rock it. But be willing to stretch out of your comfort zone over time — it usually just takes one person telling me I look nice in a new shirt I wasn’t sure about to make me really glad I took the risk.

And finally, buy clothes that fit. The best thing anyone can do to improve how they look in clothes is just getting clothes that fit them. With guys, I usually see clothes that are too large. A simple google search for ‘how to tell if clothes fit’ will go a long way!