Written by Brandi Hearn
If you've been meaning to sort through your wardrobe, you probably don't need another reminder that it's time. You need a way to get started without spending a Saturday surrounded by clothes and ending up more confused.
I wouldn't begin by emptying every drawer onto the bed. Start with one section, preferably the clothes you wear most often. Have your usual shoes nearby, leave enough room to try things on, and keep somewhere to write down what you notice.
You're trying to work out what you can wear, what needs attention, and what would make the rest of your wardrobe more useful. Here's how I'd approach it.
1. Think About Where You're Actually Going
Before trying anything on, look back over the last few weeks. Think about work, dinners, weekends, travel, and the occasions that come up less often but still need an outfit.
If you spend most days in a relaxed office, that's a good place to concentrate. If you're traveling twice a month, give those outfits some attention too.
Otherwise, it's easy to spend an hour deciding what to do with an old suit and never get around to the trousers you wear every Tuesday. Your actual calendar gives you a useful starting point.
2. Try It On, Even If You Think You Know How It Fits
There are probably a few things in your closet that fit beautifully in your memory.
Put them on. Button the shirt and jacket. Sit in the trousers. Move the way you would during the day. Include the shoes when you're looking at trouser length.
Notice what feels restrictive, where fabric is pulling, and what you keep adjusting. If the shirt bunches around your waistband or the trousers pull through the calf, write that down. It's more helpful than simply deciding the outfit feels wrong.
Some pieces may be worth taking to a tailor. Others may have a fit problem that can't reasonably be corrected. You don't need to make that call on your own; set them aside for an assessment. The men's fit guide can help you recognize the main things to look at.
3. Take a Closer Look at the Condition
Check the places that show wear first: shirt collars and cuffs, trouser hems and seats, knitwear under the arms, and the heels and soles of your shoes.
A little pilling or a loose button may be straightforward to address. Fabric that's worn thin is a different decision.
As you go, separate the pieces that are ready to wear from those that need tailoring, care, or repair. Keep the things you're considering letting go of together too, so they don't quietly find their way back onto the same hangers.
You can also keep a sentimental piece without treating it as part of your everyday wardrobe. The jacket from your wedding doesn't need to compete for space with the one you wear every week.
4. Make Some Actual Outfits
This is the part I'd spend time on.
Take the pieces you're keeping and try them together for the situations you wrote down. Include the shoes, the belt if you wear one, and the jacket or outer layer you'd leave the house in.
You may discover that a shirt you rarely wear looks good with different trousers. Or that a jacket you've struggled with works much better over a fine knit.
You may also find a piece you like that still doesn't go with much. Before adding something just to make it work, consider how often you'd wear the finished outfit.
Photograph the combinations you like. A few good outfit photos are useful on a morning when you have ten minutes and don't feel like experimenting.
5. Be Specific About What's Missing
Now look at the situations you still can't comfortably dress for.
“I need more trousers” doesn't give you much direction. “I need trousers that work with this navy jacket and these loafers for dinner” gives you something you can actually look for.
The same goes for shirts, layers, and shoes. Think about what the new piece needs to work with before you start browsing.
Also consider what happens when your favorite outfit isn't available. You may own plenty of clothes and still depend on one shirt being clean. That's worth addressing.
6. Decide What to Do First
You should now have a few outfits ready to wear and a list of things to do. Keep that list manageable.
Arrange the cleaning or repairs that will bring useful pieces back into the wardrobe. Take the promising alterations to a tailor. Then look at the additions that would help with the part of your week you dress for most often.
You don't have to resolve the whole closet in one afternoon. If you've found three outfits you like and know which trousers need hemming, you've made a useful start.
You Should Know Your Wardrobe Better When You're Finished
You'll know which pieces fit, what goes together, and why certain things haven't been getting worn. You may need less than you expected. Or you may see clearly where it's time for a change.
If you're still trying to understand why so little of your closet gets used, read Why Your Closet Is Full but Your Outfits Still Don't Work. It looks at the patterns behind those unworn purchases.
BRANDI HEARN
Strategic Wardrobe Advisor · Los Angeles
Brandi Hearn is a Strategic Wardrobe Advisor with more than a decade of experience helping accomplished men build intentional wardrobes around their careers, lifestyles, and how they want to show up.